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PRE-FEASIBILITY REPORT FOR
Greenfield Multi-Purpose Plant for Manufacturing of Various Technical Grade Pesticides and Intermediates
AT
Plot No. D-3/5/3 GIDC Dahej Phase III, Tal Vagara, Dist. Bharuch, Gujarat
Total Production Capacity Pesticides Technical :26700 MTPA
Intermediate :4400 MTPA Plot Area: 100272.418 sqm (10.02 Ha)
Cost of the Project: 170 Cr [Schedule 5 (b), Category–A as per EIA Notification 2006,
amended till date]
April – 2019
Doc. No: 2018_ECSS_EIAI2_1800019
APPLICANT
CONSULTANTS
Shreeji Pesticides Pvt. Ltd. (Subsidiary of Willowood Chemicals Pvt. Ltd.)
Plot no 69/P Village manjusar Tal Savli Vadodara
PIN: 391775, State: Gujarat E-mail:
saurabh.srivastava@shreejipesticides.com Tel No: +91 2641-256315
Eco Chem Sales & Services Office floor, Ashoka Pavilion ’A’ New Civil Road, Surat, 395001
(NABET Accredited-NABET/EIA/1720/RA 051)
E-mail: eco@ecoshripad.com Tel No: +912612236223
Prefeasibility Report SHREEJI PESTICIDES PVT. LTD.
Eco Chem Sales & Services, Surat Greenfield Technical Grade Pesticides and Intermediates Manufacturing Plant 1
CONTENTS 1 EXECUTIVE SUMMARY ............................................................................................... 5
(i) Introduction ............................................................................................................. 5
(ii) Project Description .............................................................................................. 5
(iii) Environment ........................................................................................................ 6
(iv) Environment sensitivity ........................................................................................ 6
(v) Conclusion .......................................................................................................... 6
2 INTRODUCTION OF THE PROJECT/ BACKGROUND INFORMATION ...................... 7
(vi) Identification of Project and project Proponent .................................................... 7
(vii) Brief description of Nature of the Project ............................................................. 7
(viii) Need for the Project and its Importance to the Country and or Region ................ 8
(ix) Demand Supply Gap ........................................................................................... 8
(x) Import vs Indigenous production .......................................................................... 8
(xi) Export Possibility ................................................................................................. 8
(xii) Domestic/Export Markets .................................................................................... 8
(xiii) Employment Generation (Direct and Indirect) due to the project .......................... 8
3 PROJECT DESCRIPTION ............................................................................................. 9
(i) Type of project including interlinked and interdependent project, if any ................... 9
(ii) Location with co-ordinates ................................................................................... 9
(iii) Details of Alternate Sites Considered ................................................................ 10
(iv) Size or Magnitude of the Operations ................................................................. 11
(v) Project Description with Process Details............................................................ 13
(vi) Raw Materials & Final Products ....................................................................... 130
(vii) Storage and Transportation Details of Raw Materials ...................................... 138
(viii) Resource optimization/recycling and reuse envisaged in the project ............... 142
(ix) Availability of water its source, Energy/power requirement and source ............ 142
(x) Quantity of wastes (Liquid, gas & Solid) to be generated and scheme for their Management / disposal .............................................................................................. 144
(xi) Schematic representations of the feasibility drawing which give information of EIA purpose ...................................................................................................................... 150
4 SITE ANALYSIS ........................................................................................................ 152
(i) Connectivity ........................................................................................................ 152
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(ii) Land Form, Land Use and Land ownership ..................................................... 152
(iii) Topography (along with map) .......................................................................... 152
(iv) Existing land use pattern ................................................................................. 152
(v) Existing Infrastructure ...................................................................................... 152
(vi) Soil Classification ............................................................................................ 152
(vii) Climatic Data from Secondary Sources ........................................................... 153
(viii) Social Infrastructure ........................................................................................ 153
5 PLANNING BRIEF .................................................................................................... 154
(i) Planning concept ................................................................................................ 154
(ii) Population Projection....................................................................................... 154
(iii) Landuse Planning ............................................................................................ 154
(iv) Assessment of Infrastructure Demand ............................................................. 155
(v) Amenities/ Facilities ......................................................................................... 155
6 PROPOSED INFRASTRUCTURE ............................................................................. 156
(i) Industrial Area (Processing Area) ....................................................................... 156
(ii) Residential Area (Non Processing Area) ......................................................... 156
(iii) Green Belt ....................................................................................................... 156
(iv) Social Infrastructure ........................................................................................ 156
(v) Connectivity (Traffic and Transportation Road/ Rail/ Metro/ Water ways etc) .. 156
(vi) Drinking Water Management ........................................................................... 156
(vii) Industrial Waste Management ......................................................................... 156
(viii) Power Requirement & Supply/ Source ............................................................ 156
7 REHABLITATION & RESETTLEMENT (R & R) PLAN ............................................. 157
(i) Policy to be adapted (Central /State) in respect of the project affected persons including home outsee, Land outsee and Landless labourers .................................... 157
8 PROJECT SCHEDULE AND COST ESTIMATE ....................................................... 158
(i) Likely date of start of construction and likely data of completion ......................... 158
(ii) Estimates project cost along with analysis in terms of economic viability of the project ........................................................................................................................ 158
9 ANALYSIS OF THE PROPOSAL (FINAL RECOMMENDATIONS) .......................... 159
(i) Financial and social benefits with special emphasis on the befit to the local people including tribal population, if any, in the area .............................................................. 159
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Eco Chem Sales & Services, Surat Greenfield Technical Grade Pesticides and Intermediates Manufacturing Plant 3
LIST OF TABLES
Table 1-1: Environmental Sensitivity ..................................................................................... 6
Table 2-1: Project Description ............................................................................................... 7
Table 2-2: Manpower Details ................................................................................................ 8
Table 3-1: Co-ordinates of the project ................................................................................. 10
Table 3-2: Details of Proposed Production Capacity ........................................................... 11
Table 3-3: Raw Material details ......................................................................................... 130
Table 3-4: Storage and Transportation Details of Raw Materials ....................................... 138
Table 3-5: Details of Water Consumption .......................................................................... 142
Table 3-6: Power Requirements and Its Source ................................................................ 144
Table 3-7: Fuel details ....................................................................................................... 144
Table 3-8: Waterwater generation details .......................................................................... 144
Table 3-9:ETP details........................................................................................................ 145
Table 3-10: Process gas emission details ......................................................................... 149
Table 3-11: Flue gas emission details ............................................................................... 149
Table 3-12: Details of Solid & Hazardous Waste and its Management .............................. 150
Table 4-1: Site Connectivity .............................................................................................. 152
Table 5-1: Area Statement ................................................................................................ 154
Table 8-1: Capital Cost Projection ..................................................................................... 158
Table 8-2:Recurring/Operating Cost Per Annum ............................................................... 158
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LIST OF FIGURES Figure 3-1: Water Balance Diagram .................................................................................. 143
Figure 3-2: Effluent Treatment Scheme ............................................................................ 147
Figure 3-3 Schematic diagram of Sewage Treatment plant ............................................... 148
Figure 3-4: EIA Purpose .................................................................................................... 151
Figure 5-1: Plant layout ..................................................................................................... 155
LIST OF MAPS
Map 3-1: General and Specific Location Map ........................................................................ 9
Map 3-2: Google Earth Image ............................................................................................. 10
LIST OF ANNEXURES
Annexure 1: Plot allotment letter ....................................................................................... 161
Annexure 2: Toposheet of the Region ............................................................................... 162
Annexure 3: PCPIR Document .......................................................................................... 163
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Eco Chem Sales & Services, Surat Greenfield Technical Grade Pesticides and Intermediates Manufacturing Plant 5
1 EXECUTIVE SUMMARY
(i) Introduction
Shreeji Pesticides Pvt. Ltd. intends to set up a plant for manufacturing pesticides technical grade and intermediate products at Dahej GIDC, Bharuch, Gujarat. The total plot area is 100272.418 sqm (10.02 Ha). The cost of the proposed project is 170 Crores. The proponent proposes to manufacture 26700 MTPA of Pesticides Technical (Fungicides, Herbicides and Insecticides) and 4400 MTPA Intermediate.
Applicability of EIA notification – 2006
The project falls under following Schedule:
“Pesticide Industry and Pesticide Specific Intermediates (excluding formulation)”, Project or Activity 5(b), Category “A” as per MoEF&CC, EIA notification, 2006 and amended till date and it will be appraised at Central level. As the proposed project site falls under PCPIR, Dahej Industrial Estate Zone III, Public hearing will be exempted. PCPIR document is enclosed as Annexure 3.
Justification for the Project
Presently, India is leading in the manufacturing of agrochemicals and is likely to become a world leader very soon. India is having very good engineering & research scientist pool and long proven expertise of producing quality pesticides, insecticides and herbicides. To fulfill the demand supply gap, it is decided by Shreeji Pesticides Pvt. Ltd. to setup a new plant with the state of art technology. For this the company will be adopting modern machineries and equipment and process technologies, with emphasis on waste minimization techniques wherever required. The proposed project for manufacturing of various products is based on the market surveys and in house captive consumption.
(ii) Project Description
Land: The total plot area for the proposed project is 100272.418 sq.m (10.02 Ha) which has been procured from Dahej GIDC, Bharuch.
Power: The power requirement for proposed expansion will be 4550 KWH which will be sourced from DGVCL.
Water: Total water requirement will be 1445 KLD. 1183.4 KLD fresh water will be sourced from GIDC, Dahej, 240 KLD boiler condensate will be recycled back in process and 21.6 KLD will be recycled from Sewage Treatment Plant.
D.G Set: Four D.G Sets of 750 KWH will be used as emergency power back up only in case of power failure.
Fuel: FO/NG/Coal will be used as primary fuel in proposed project. FO (25 KLD) will be sourced from HPCL. Natural Gas (33000 SCM) will be sourced from GAIL. Coal (62 TPD) will be sourced from Indian supplier or Imported. HSD (25 KLD) will be used in D.G.Set and will be sourced from local supplier.
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Manpower: During construction phase, the manpower requirement will be of 30 permanent and 400 temporary. During operational phase, manpower employed will be 150 permanent basis and 400 on temporary basis.
(iii) Environment
Wastewater Generation: Total effluent generation will be 521 KLD and Sewage generation will be 24 KLD. An Effluent Treatment Plant of 625 KLD will be provided to treat the effluent generated and STP of 25 KLD will be provided to treat the sewage. 5 KLD from group company will be treated in proposed Effluent treatment Plant.
Solid Waste / Hazardous Generation: Hazardous/ Solid Waste/ Municipal solid waste for Collection, storage and disposal will be carried out as per Hazardous & Other Wastes (Management and Trans boundary Movement) Rules, 2016. Generated landfilling waste will be sent to BEIL, Ankleshwar/Dahej (common TSDF).
Greenbelt Development: About 8345 Plants will be planted for Greenbelt Development on area of 33379 sqm which will be 33.33 % of plot area.
Air Environment: There will be 5 process stacks, 3 boiler stacks, 1 D.G.Stack and 1 Thermic Fluid Heater. Standard Air Pollution Control Measures will be provided to control emissions.
(iv) Environment sensitivity There is no agricultural, forestry, National parks, Wild life sanctuary, Eco sensitive areas within 15 km.
Table 1-1: Environmental Sensitivity Particular Details Distance with direction
Areas which are important or sensitive for ecological reasons - Wetlands, watercourses or other
water bodies, coastal zone, biospheres, mountains, forests
Narmada Estuary 10.26 kms towards S Water
Bodies/Watercourses 0.55 km towards NE
Coastal Zone Coastal area is located at an
aerial distance of 7.7 km towards W
Reserve Forests Dahej Reserve Forest at 8.6 kms towards SW
Areas used by protected, important or sensitive species of flora or fauna for breeding,
nesting, foraging, resting, over wintering, migration
Afforested Mangroves 8.6 kms towards SW
Nearest habitation Padariya Village 800m in NNE Densely populated or built-up
area Dahej 7.78 km in SW
(v) Conclusion
There is no adverse impact anticipated on environment due to proposed project.
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2 INTRODUCTION OF THE PROJECT/ BACKGROUND INFORMATION
(vi) Identification of Project and project Proponent
Project
Shreeji Pesticides Pvt. Ltd. intends to set up a plant for manufacturing agrochemical technical grade and intermediates products. The proposed plants are meant for Multipurpose products. The plant will be supported with adequate utilities, tank-forms, warehouses etc.
The proponent proposes to establish a pesticide manufacturing unit at Plot No. D-3/5/3 GIDC Dahej Phase III, Tal Vagara, Dist. Bharuch, Gujarat having total plot area of 100272.418 sqm (10.02 Ha) & total investment is ~170 Cr. As the proposed project site falls under PCPIR, Dahej Industrial Estate Zone III, Public hearing will be exempted. PCPIR document is enclosed as Annexure 3.
Project Proponent
Shreeji Pesticides Pvt. Ltd. was established in the year 1989, acquired by Willowood Chemicals (Pvt) Limited in the year 2010, the plant is engaged in research and development, production, application and sales of agrochemicals. The pesticide unit plant is located in the Economic and Technical Development Zone in the city of Baroda, Gujarat, India and its employees includes doctorate and master’s degree holders as well as other experienced workers. The pesticide plant has also received accreditations of ISO9001:2008.
The pesticide plant mainly specializes in the contract manufacturing (Toll formulation) & development of agrochemicals for multinationals companies, and after years of relentless efforts has made great strides in the research, development, production and application of agrochemicals.
(vii) Brief description of Nature of the Project
The proposed project involves manufacturing of various Technical Grade Pesticides and Intermediates. Brief description of the project is given in Table 2-1.
Table 2-1: Project Description
S. No. Details Description
1. Nature Pesticides Manufacturing
2. Product Pesticides Technical (Fungicides,
Herbicides and Insecticides) 26700 MTPA
Intermediates 4400 MTPA
.3 Location Plot No. D-3/5/3 GIDC Dahej Phase III, Tal Vagara, Dist. Bharuch, Gujarat
4. Cost of the project 170 Crores
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(viii) Need for the Project and its Importance to the Country and or Region
Need for the proposed products is based on the demand and supply gap in the current market. With increasing utilization of the current products, in future, to carter the requirement of all the products, it is essential to have the proposed manufacturing unit.
(ix) Demand Supply Gap
Indian Pesticides is one of the rapidly growing markets and has emerged a strong export oriented business. About 6000 MT/Year of Agro Chemical Product are manufactured in INDIA and 5000 Tons/Year sold in India and in others Countries 1000 MT/Year.
(x) Import vs Indigenous production
At present 400 Cr technical grade product is imported from Taiwan,Korea,China. After the proposed project this dependancy will be reduce and it will be boost to MAKE IN INDA campaign.
(xi) Export Possibility
Company may export the products as per reqiurements
(xii) Domestic/Export Markets
Company has both domestic and export market. As per the requirments the producers are introduced in the market
(xiii) Employment Generation (Direct and Indirect) due to the project
The proposed project will generate employment during the construction and operation phase. Local skilled and semi-skilled workers will be hired during construction phase as well as operation phase. During the operation phase, technical staff, general staff for administrative work and other ancillary services i.e. O&M contractor and maintenance services will be required on a temporary basis. Details of manpower is given in Table 2-2.
Table 2-2: Manpower Details S.No. Particular Number of Workers
1 Permanent Employment-During Construction 30
2 Temporary Employment-During Construction 400
3 Permanent Employment-During Operation 150
4 Temporary Employment-During Operation 400
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Eco Chem Sales & Services, Surat Greenfield Technical Grade Pesticides and Intermediates Manufacturing Plant 9
3 PROJECT DESCRIPTION
(i) Type of project including interlinked and interdependent project, if any
The proposed project is not interlinked and interdependent project of the company
(ii) Location with co-ordinates
The project is proposed in Notified Industrial Estate at Plot No. D-3/5/3 GIDC Dahej Phase III, Tal Vagara, Dist. Bharuch, Gujarat. The area for Proposed plant is 100272.418 sqm (10.02 Ha). General & Specific location of project site is shown in Map 3-1 and Plant Boundary is shown in Map 3-2. Coordinates of project site are given in Table 3-1.
Map 3-1: General and Specific Location Map
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Eco Chem Sales & Services, Surat Greenfield Technical Grade Pesticides and Intermediates Manufacturing Plant 10
Map 3-2: Google Earth Image
Table 3-1: Co-ordinates of the project
Point Latitude Longitude 1 21.774334° 72.632066° 2 21.773791° 72.631352° 3 21.772032° 72.630724° 4 21.771479° 72.630521° 5 21.770919° 72.633800° 6 21.773952° 72.634568° 7 21.773840° 72.634080° 8 21.773758° 72.634025° 9 21.773744° 72.632819°
10 21.773941° 72.632799° 11 21.773974° 72.632085° 12 21.774234° 72.632121°
(iii) Details of Alternate Sites Considered
The site was selected based on following considerations:
1. Proximity to Centrally located Delhi-Mumbai (DMIC) Industrial Corridor that is easily approachable from all parts of India
2. Readily available world class infrastructure water, CETP, gas, power, raw material supplier
3. Proximity to Gujarat Chemical Port Terminal Company Limited (GCPTCL)
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Eco Chem Sales & Services, Surat Greenfield Technical Grade Pesticides and Intermediates Manufacturing Plant 11
4. Proximity to our R & D and pilot plant approx..150 km away from Dahej-III site. 5. Proximity to our formulation plant 140 km away from Dahej-III site
(iv) Size or Magnitude of the Operations The proponent proposes to manufacture 26700 MTPA of pesticides and 4400 MTPA of Intermediates. Details of Proposed Production Capacity are provided in Table 3-2.
Table 3-2: Details of Proposed Production Capacity S. No. Name Of Product Cas No. Ld50 Capacity
A Fungicides
11400 MTPA
1 Azoxystrobin Technical 131860-33-8 >5000 mg/kg 2 Boscalid Technical 188425-85-6 >5000 mg/kg 3 Carboxin Technical 5234-68-4 >3800 mg/kg 4 Chlorothalonil Technical 1897-45-6 >5000 mg/kg 5 Difenoconazole Technical 119446-68-3 >1450 mg/kg 6 Epoxiconazole Technical 106325-08-0 >5000 mg/kg 7 Hexaconazole Technical 79983-71-4 >2180 mg/kg 8 Kresoxim-Methyl Technical 143390-89-0 >5000 mg/kg 9 Penconazole Technical 66246-88-6 >2125 mg/kg 10 Picoxystrobin Technical 117428-22-5 >5000 mg/kg 11 Propiconazole Technical 60207-90-1 >1500 mg/kg 12 Prothioconazole Technical 178928-70-6 >6000 mg/kg 13 Pyraclostrobin Technical 175013-18-0 >5000 mg/kg 14 Tebuconazole Technical 107534-96-3 >3000 mg/kg 15 Thifluzamide Technical 130000-40-7 >5000 mg/kg 16 Trifloxystrobin Technical 141517-21-7 >5000 mg/kg B Insecticide
3300 MTPA
1 Chlorantraniliprole Technical 500008-45-7 >5000 mg/kg
2 Cyantraniliprole Technical 736994-63-1 >5000 mg/kg 3 Flubendiamide Technical 272451-65-7 >2000 mg/kg 4 Nitenpyram 150824-47-8 >1500 mg/kg 5 Pymetrozine Technical 123312-89-0 >5000 mg/kg 6 Spirodiclofen 148477-71-8 >2500 mg/kg 7 Spirotetramet 203313-25-1 >2000 mg/kg 8 Thiamethoxam Techncial 153719-23-4 >1563 mg/kg C Herbicides
12000 MTPA
1 Carfentrazone-Ethyl Technical 128639-02-1 >5100 mg/kg
2 Clethodim Technical 99129-21-2 >1600 mg/kg
3 Clodinafop-Propargyl Technical 105512-06-9 >1800 mg/kg
4 Clomazone Technical 81777-89-1 >2000 mg/kg 5 Chloransulam Technical 147150-35-4 >5000 mg/kg 6 Diclosulam Technical 145701-21-9 >5000 mg/kg
7 Fenoxaprop-P-Ethyl Technical 71283-80-2 >3500 mg/kg
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S. No. Name Of Product Cas No. Ld50 Capacity 8 Flufenacet Technical 142459-58-3 >1500 mg/kg 9 Fomesafen Technical 72178-02-0 >1250 mg/kg
10 Glufosinate-Ammonium Technical 77182-82-2 >2000 mg/kg
11 Glyphosate 1071-83-6 12 Mesotrione Techncial 104206-82-8 >5000 mg/kg 13 Penoxsulam Technical 219714-96-2 >5000 mg/kg 14 Pretilachlor Technical 51218-49-6 >6000 mg/kg 15 Propanil Technical 709-98-8 >2500 mg/kg 16 Propaquizafop Technical 111479-05-1 >5000 mg/kg 17 Sulfentrazone Technical 122836-35-5 >2500 mg/kg
Total 26700 MTPA D Intermediate
4400 MTPA 1 1,2,4-Triazole 288-88-0 >1350 mg/kg 2 Ccmt 105827-91-6 DNA 3 Mnio 153719-38-1 3914 mg/kg
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(v) Project Description with Process Details
FUNGICIDE
Azoxystrobin Step-I Phthalide is reacted with methyl formate in presence of Di methyl Carbonate and Sodium Hydride as well as Solvent -Toluene to form 3- Methoxy Methylidene -1- Benzofuran -2-(3-H) – One
OO
134.13Phthalide
+ CO
OCH3H
methyl formate
60.05
+ (CH3)2CO3
90.08
NaOH OO
COCH3
3-acetyl-1-benzofuran-2(3H)-one
+ Na2CO3
106+ CH3 OH
64.08
175.16
+ OH2
18.01
80 22
Step-II 3- Methoxy Methylidene -1- Benzofuran -2-(3-H) – One reacted with Sodium Methoxide in presence of Solvent – EDC to form Sodium -2- [1,3 Dimethoxy -3- Oxoprop -1- en -2- yl] Phenolate.
EDCOO
COCH3
3-acetyl-1-benzofuran-2(3H)-one
175.16
+ Na O CH3
sodium methanolate
ONa
COCH3
OCH3
O
sodium 2-(1-methoxy-1,3-dioxobutan-2-yl)phenolate229.18
Step-III Sodium -2- [1,3 Dimethoxy -3- Oxoprop -1- en -2- yl] Phenolate is reacted with 4,6 –Dichloro Pyrimidine in presence of Solvent – Toluene to give Methyl -2- [ 2- { ( 6- Chloro Pyrimidine -4 –yl)} Oxy Phenyl ] -3-methoxyprop -2- Ethanoate.
Toluene
ONa
COCH3
OCH3
O
sodium 2-(1-methoxy-1,3-dioxobutan-2-yl)phenolate
229.18
+NN
ClCl4,6-dichloropyrimidine
149
O
COCH3
OCH3
O
NN
Cl
methyl 2-{2-[(6-chloropyrimidin-4-yl)oxy]phenyl}-3-oxobutanoate
319.72
+ NaCl
58.44
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Step-IV Methyl -2- [ 2- { ( 6- Chloro Pyrimidine -4 –yl)} Oxy Phenyl ] -3- methoxyprop -2- Ethanoate O- Cyano Phenol in presence of Potassium Hydroxide and Solvent – Di Methyl Formamide to give the Final product as AZOXYSTORBIN
O
COCH3
OCH3
O
NN
Cl
methyl 2-{2-[(6-chloropyrimidin-4-yl)oxy]phenyl}-3-oxobutanoate
319.72
+
CN
OH
2-hydroxybenzonitrile119.12
DMFO
COCH3
OCH3
O
NN
O
CNKOH
+ + OH2
74.55 18.01
KCl
Azoxystrobin402.38
Process Flow Diagram
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Mass Balance
S. No.
Input(kg)/MT of Product
S. No.
Output/(kg) of Product
Raw Materials Quantity
Output Material Name
Product / By
Product Waste Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 Phthalate 320 1 Sodium carbonate- 258
2 Methyl Formate 142 2 Methanol 58
3 Di Methyl Carbonate 216 3 NaCl 140
4 Sodium Hydroxide 58 Toluene Loss 75
5 Toluene 2600 4 Toluene Recovery 2525
6 Sodium Methoxide 128 EDC loss 50
7 EDC 1200 5 EDC Recovery 1150
8 4,6 – Di Chloro
Pyrimidine 352 6 Azoxystrobin 1000
9 Ortho Cyano Phenol
283 7 KCl 180
10 Potassium Hydroxide 133 DMF Loss 40
11 DMF 1200 8 DMF Recovery 1160
12 Water 880 9 Aq. to ETP 857
10 Distillate residue 19
1636 857 0 4835 165 19
Total 7512 Total 7512
Boscalid Stage I: Preparation of 4-CPBA 1. Charge in a reactor THF and Mg, heat upto reflux, 2. Add slowly dichlorobenzene with toluene in 2 – 3 hours. 3. After complete addition cool mass to 15 ˚C 4. Add slowly trimethyl borate. 5. After complete addition reaction mass quenched in solution of HCl + water at low
temperature. 6. Layer separation 7. Recover solvent from organic layer and crude take to next step.
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Chemical reaction
Cl
Cl
+ Mg2+ THF, Toluene
MgCl
Cl
1,4-dichlorobenzene147
171.3
MgCl
Cl171.3
+ B OCH3
OCH3
OCH3
103.9Trimethoxy borate
B
Cl
OH
OH
156.37Intermediate - I
Stage II: Preparation of Intermediate-II
1. Charge in a reactor Intermediate-I and Toluene, add catalyst. 2. Add 1-chloro-2-nitrobenzene and heat the mass to reflux and maintain till reaction
complete. 3. Filter the mass and remove catalyst. 4. Recover solvent from organic mass. 5. Take crude to next step
Chemical reaction
B
Cl
OH
OH
156.37Intermediate - I
+
NO2
Cl
1-chloro-2-nitrobenzene157.55
catalystToluene
NO2Cl4'-chloro-2-nitrobiphenyl
233.65Intermediate - II
Stage III: Preparation of Intermediate-III 1. In pressure reactor charge Intermediate-II of stage-II. 2. Add methanol and catalyst and take pressure of hydrogen and heat up to 60 ˚C. 3. Maintain reaction till completion. 4. Filter to recover catalyst and recover methanol. 5. Take crude to next step
Chemical reaction
H2/Pd - CMethanol
NO2Cl4'-chloro-2-nitrobiphenyl
233.65Intermediate - II
NH2Cl4'-chlorobiphenyl-2-amine
203.66Intermediate - III
Stage IV: Preparation of 2-chloropyridine-3-carbonyl chloride (Intermediate-IV)
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1. Charge in a reactor Acetonitrile and CPCA 2. Add slowly PCl3 in 2 – 3 hours and maintain reaction up to completion. 3. After reaction completion add NaOH solution and stir for some time. 4. Separate layer. 5. Organic layer (Intermediate-III) to next step
Chemical reaction
Acetonitrile+ PCl3
N Cl
OH
O
2-chloropyridine-3-carboxylic acid157.55
N Cl
Cl
O
2-chloropyridine-3-carbonyl chloride176
Stage V: Preparation of Boscalid 1. Charge in a reactor Intermediate-III of stage –III and organic layer (intermediate-IV)
of stage-IV. 2. Add catalyst, and maintain reaction up to completion. 3. Filter the reaction mass and recover solvent. 4. In crude organic add XP-50, and reflux for 2 hours. 5. Cool to 10 ˚C, filter solid mass and dry Boscalid.
Chemical reaction
N Cl
Cl
O
2-chloropyridine-3-carbonyl chloride176
+ NH2Cl4'-chlorobiphenyl-2-amine
203.66
NHCl
Cl
N
O
2-chloro-N-(4'-chlorobiphenyl-2-yl)pyridine-3-carboxamide343.2
(BOSCALID)
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Process Flow Diagram
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Mass Balance
S. No.
Input/MT of Product Output/(MT) of Product
Raw Materials Quantity Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 1,4-dichlorobenzene 1000 Rec. Toluene 1950 2 Mg 170 Rec. THF 2950 3 Toluene 5000 Aq. layer 8430 4 THF 3000 Rec. catalyst 40 5 Trimethoxy borate 710 Rec. Toluene 3610
6 HCl 500 Rec.
Methanol 2450
7 water 5000 Methanol loss 50
8 1-chloro-2-nitrobenzene 1060 Process loss 200
9 Catalyst 70 Intermediate-III 1300
10 Methanol 2500 Organic layer (Intermediate-
IV) 2400
11 Pd-C 20 Rec. Solvent 1508 12 CPCA 1000 Rec. catalyst 50 13 Acetonitrile 3000 ML 2192 14 PCl3 350 Boscalid 2000
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S. No.
Input/MT of Product Output/(MT) of Product
Raw Materials Quantity Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
15 Sodium hydroxide 50 16 Intermediate-III 1300
17 Intermediate-IV 2400 18 XP-50 2000 16322 0 0 12558 250 0
Total 29130 Total 29130
Carboxin Step-I Process description:- Carboxin is manufactured by reacting acetoacetanilide (AA) with sulfuryl chloride (SO2Cl2) to
give 2‐chloro‐3‐oxo‐N‐phenylbutanamide intermediate (2‐CPB).
O
CH3
O
NH
3-oxo-N-phenylbutanamide
177.2
+ S
O
O
ClCl
sulfuryl dichloride134.97
O
CH3
O
NH
Cl
+ SO2
+ ClH
2-chloro-3-oxo-N-phenylbutanamide211.64
64.06
36.46
Step-II Process description:- This intermediate is further reacted with 2‐mercaptoethanol (2‐ME) in presence of triethyl amine (TEA) to give 2‐(2‐hydroxyethylthio)‐3‐oxo‐N‐phenylbutanamide (2‐HEPB).
O
CH3
O
NH
Cl
2-chloro-3-oxo-N-phenylbutanamide211.64
+ OHSH
2-sulfanylethanol
78.13
(2 - mercaproethanol)
TEA S
O
NH
CH3
O
OH
2-[(2-hydroxyethyl)sulfanyl]-3-oxo-N-phenylbutanamide
253.31
+ ClH36.46
Step-III Process description:- Finally it is cyclised using PTSA to give carboxin technical.
S
O
NH
CH3
O
OH
2-[(2-hydroxyethyl)sulfanyl]-3-oxo-N-phenylbutanamide
253.31
PTSA S
O
NH
CH3
O
2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
235.3
+ OH218.01
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Process Flow Diagram
Mass Balance
S. No.
Input/(kg) of Product S.
No.
Output/(kg) of Product
Raw Materials Quantity Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 Acetoacetanilide 994 1 SO2 gas 370
2 SO2Cl2 781 2 HCl gas 211
3 TEA 521 3 TEA HCl 708
4 2‐ME 403 4 Carboxin 660
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5 PTSA 231 5 PTSA 231
6 Benzene 5610 6 Water distilate 50
7 Acetone 2640 7 Benzene recovered 5346
8 Water 5280 8 Benzene loss 264
9 Acetone recovered 2520
10 Acetone loss 120
11 Water to ETP 5280
12 Organic impurity 700
1599 5330 581 7866 384 700
Total 16460 Total 16460
Chlorothalanil Process description Tetrachloroisophtalic acid on ammonylsis forms its ammonium salt, which on further reaction with phosphorous pentaoxide forms the product Chlorothalanil.
COOH
Cl
COOH
Cl
Cl
Cl
2,4,5,6-tetrachlorobenzene-1,3-dicarboxylic acid(Tetrachloro isophthalic acid)
303.91
2 NH3+34
CONH2
Cl
CONH2
Cl
Cl
Cl
2,4,5,6-tetrachlorobenzene-1,3-dicarboxamide301.94
+ 2 H2O36
P2O5
CN
Cl
CN
Cl
Cl
Cl
2,4,5,6-tetrachlorobenzene-1,3-dicarbonitrile(Chlorotalonil)
+
265.91
2 H2O36
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Process Flow Diagram
Mass Balance
S. No.
Input/MT of Product S.
No.
Output/(kg) of Product
Raw Materials Quantity
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 Tetrachloro Isophthalate 1055 1 Chlorthalonil 1020
2 Toluene 2000 2 Water Distillate 120
3 Ammonia Solution 125 3 Toluene
recovered 1950
4 Catalyst 20 4 Toluene loss 50
5 Water 850 5 Aq. layer to ETP 910
1020 1030 0 1950 50 0
Total 4050 Total 4050
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Difenconazole Step-I 1,3-Dichloro Benzene is reacted with Acetyl Chloride in presence of Aluminum Chloride and Solvent – Ethylene Di Chloride to get 2,4-Dichloro Acetophenone
Cl
Cl1,3-dichlorobenzene
147
+ CH3 C
O
Clacetyl chloride
78.49
AlCl3/EDCCl
Cl
CO CH3
+ ClH
1-(2,4-dichlorophenyl)ethanone189.03
36.46
Step-II 2,4-Dichloro Acetophenone further reacted with 4-Chloro Phenol in presence of Potassium Hydroxide and Solvent- DMF to get 2-Chloro-4-(4-Chlorophenoxy) Acetophenone.
DMFCl
Cl
CO CH3
+ ClH
1-(2,4-dichlorophenyl)ethanone189.03
36.46
+
OH
Cl4-chlorophenol
128.55
O
Cl
Cl
C
CH3
O
1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone281.13
Step-III 2-Chloro-4-(4-Chlorophenoxy) Acetophenone further reacted with Bromine in presence of Catalyst and Solvent - Ethylene Di Chloride to get 2-Chloro-4-(4-Chlorophenoxy) Phenacyl Bromide.
EDC/PTSA+ BrH
80.9
O
Cl
Cl
C
CH3
O
1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone281.13
+ Br Br
159.8
O
Cl
Cl
C
CH2
O
Br2-bromo-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone
360.03
Step-IV 2-Chloro-4-(4-Chlorophenoxy) Phenacyl Bromide reacted with Propylene Glycol in presence of Solvent -Toluene to get 3-Chloro-4-(2-Bromomethyl-4-methyl-1,3-Dioxolane-2-yl)-4’-Chloro Diphenyl Ether.
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Toluene+ OH2
18.01
O
Cl
Cl
C
CH2
O
Br
2-bromo-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone
360.03
+ CH2 CH CH3
OH OH
propane-1,2-diol76.09
O
Cl
Cl
C
CH2
O
Br
CH2
CHCH3
O
2-(bromomethyl)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolane
418.1
Step-V 3-Chloro-4-(2-Bromomethyl-4-methyl-1,3-Dioxolane-2-yl)-4’-Chloro Diphenyl Ether further reacted with 1,2,4-Triazole in presence of Potassium Hydroxide and Solvent DMF to get final product DIFENOCONAZOLE.
KOH/DMFO
Cl
Cl
C
CH2
O
Br
CH2
CHCH3
O
2-(bromomethyl)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolane
418.1
+NH
N
N
1H-1,2,4-triazole69.06
O
Cl
Cl
C
CH2
O
N
CH2
CHCH3
O
N
N
1-({2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole
406.26
+ BrH80.91
DIFENCONAZOLE
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Process Flow Diagram
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Mass Balance
Sr.No
Input/MT of Product Output/(kg) of Product Raw
Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 1,3 Di Chloro
Benzene 392 30% HCl 324
2 Acetyl Chloride 208 20% AlCl3 2448
3 Aluminium Chloride 490 EDC recovered 4720
4 EDC 4800 EDC loss 80 5 Water 3055 Potassium chloride 205
6 4- Chloro Phenol 340 DMF recovered 3840
7 Di Methyl Formamide 1900 DMF loss 60
8 KOH 473 20% HBr solution 775 9 Bromine 422 Catalyst recovered 10 10 Catalyst 10 Toluene recovered 1970
11 Propylene Glycol 198 Toluene loss 30
12 Toluene 2000 DIFENCONAZOLE 1000
13 1,2,4 – Triazole 180 Aq. layer to ETP 670
14 DMF 2000 Process loss 16 KBr 320
5072 670 16 10540 170 0
Total 16468 Total 16468
Epoxiconazole Step-I Fluorobenzene is reacted with Chloro Acetyl chloride in presence of Aluminum chloride and Solvent – Ethylene Di Chloride to get 4-Fluoro Phenacyl Chloride.
+ CH2 C
O
ClCl
AlCl3/EDC
F
CO CH2Cl
+ ClH36.46
chloroacetyl chloride112.94
F
fluorobenzene96.1
2-chloro-1-(4-fluorophenyl)ethanone172.58
Step-II 4-Fluoro Phenacyl Chloride reacted with 1,2,4-Triazole in presence of Potassium Hydroxide and Solvent DMF to give 2-(1H-1,2,4-Triazole-1-yl)-4-Fluoro Acetophenone.
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KOH/DMF
F
CO CH2Cl
+ ClH36.46
2-chloro-1-(4-fluorophenyl)ethanone172.58
+NH
N
N
1H-1,2,4-triazoleF
CO CH2 N
N
N
1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone205.18
69.06
Step-III 2-(1H-1,2,4-Triazole-1-yl)-4-Fluoro Acetophenone reacted with 2-Chloro benzyl chloride and Dimethyl Sulphide in presence of Potassium Hydroxide and Solvent DMF to give the final product EPOXICONAZOLE.
KOH/MIBK
F
CO CH2 N
N
N
1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone
205.18
+ CH3 S CH3
(methylsulfanyl)methane62.13
+
CH2
Cl
Cl
1-chloro-2-(chloromethyl)benzene161.02
F
CO CH2 NN
NCH
Cl
+ClH
1-{[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole
329.75
36.46
EPOXICONAZOLE
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Process Flow Diagram
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Mass Balance
Sr.No
Input/MT of Product Sr.
No.
Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product
Wates
Water
Air Emissio
n Recover
y Los
s Solid/Hazardou
s Waste (kg)
1 Fluoro Benzene 320 1 30% HCl 406
2 Chloro Acetyl
Chloride 375 2 20% AlCl3 2033
3 Aluminum Chloride 400 3 Rec. EDC 1270
4 EDC 1300 4 EDC loss 30 5 Water 2440 5 KCl 502
6 KOH 555 6 Epoxiconazole 1000
7 1,2,4 – Triazole 228 7 DMF
recovered 1765 8 DMF 1800 8 DMF loss 35
9 2- Chloro Benzyl
Chloride 530 9 Potassium
bisulphate 238
10 Di Methyl Sulphide 202 10 Aq. to ETP 853
11 Process loss 18
4179 853 18 3035 65 0 Total 8150 Total 8150
Hexaconazole Step-I 1,3-Dichloro benzene reacted with Pentanoyl chloride in presence of Aluminum chloride and Solvent – Ethylene Di Chloride to get 2,4-Dichloro Valerophenone.
+ CH2 CO
ClCH2CH2CH3
AlCl3/EDC
Cl
C
O
CH2
Cl
CH2 CH2 CH3
+ ClH36.46
Cl
Cl
1,3-dichlorobenzene147
231.11
pentanoyl chloride120.57 1-(2,4-dichlorophenyl)pentan-1-one
Step-II 2,4-Dichloro Valerophenone further reacted with Methylene-Triphenylphosphorane in presence of Solvent -THF to get 2-(2,4-Dichloro Phenyl)-n-hex-1-ene.
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THF
Cl
C
O
CH2
Cl
CH2 CH2 CH3
+
231.111-(2,4-dichlorophenyl)pentan-1-one
+ (H5C6)3 P CH2
Methylene-Triphenylphosphorane276.3 Cl
C
CH2
CH2
Cl
CH2 CH2 CH3
(H5C6)3 P O278
229.14
2,4-dichloro-1-(hex-1-en-2-yl)benzene
Step-III 2-(2,4-Dichloro Phenyl)-n-hex-1-ene reacted with Bromine and Hydrogen Peroxide in presence EDC to get 1-Bromo-2-(2,4-Dichlorophenyl)-hexane-2-ol.
+
Cl
C
CH2
CH2
Cl
CH2 CH2 CH3
229.14
2,4-dichloro-1-(hex-1-en-2-yl)benzene
+ Br2 + H2O2
159.8 34
EDC
Cl
C
CH2
CH2
Cl
CH2 CH2 CH3OH
Br
BrH + O21/280.91 16
326.05
1-bromo-2-(2,4-dichlorophenyl)hexan-2-ol
Step-IV 1-Bromo-2-(2,4-Dichlorophenyl)-hexane-2-ol further reacted with 1,2,4-Triazole in presence of Potassium hydroxide and Solvent DMF to get final product HEXACONAZOLE.
+KOH/DMF
Cl
C
CH2
CH2
Cl
CH2 CH2 CH3OH
Br
BrH80.91
326.051-bromo-2-(2,4-dichlorophenyl)hexan-2-ol
+NH
N
N
1H-1,2,4-triazole69.06 Cl
CCH2 CH2
Cl
CH2 CH2 CH3
OH
NN
N
2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol
314.2
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Process Flow Diagram
Mass Balance
Sr.No
Input/MT of Product Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 1,3 Di Chloro Benzene 510 30% HCl 421
2 Pentanoyl Chloride 417 20% AlCl3 3160
3 Aluminium Chloride 632 EDC
recovered 2790 4 EDC 2850 EDC loss 60
5 Water 3943 Tri Phenyl phosphanone 966
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Sr.No
Input/MT of Product Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
6 Methyl
Triphenyl Phosphorane
944 THF recovered
1150
7 THF 1200 THF loss 50 8 Bromine 540 28% HBr 1005
9 Hydrogen Peroxide 116 Oxygen 50
10 KOH 178 Hexaconazole 1000
11 1,2,4 – Triazole 220 DMF
recovered 1065 12 DMF 1100 DMF loss 35 KBr 410
Aq. to ETP 468
Process loss 20
6962 468 70 5005 145 0
Total 13580 Total 13580
Kresoxim Methyl Step-I Phthalide is reacted with O-cresol in presence of potassium Hydroxide and Solvent – Xylene to give 2-(2-Methyl Phenoxy methyl) Benzoic acid.
O
O
Phthalide134.13
OH
CH3
+ KOH/Xylene
CH3
O
COOH
2-methylphenol108.13
O-cresol
2-[(2-methylphenoxy)methyl]benzoic acid
242.27
Step-II 2-(2-Methyl Phenoxy methyl) Benzoic acid reacted with Thionyl Chloride in presence of Solvent - Xylene to give 2-(2-Methyl Phenoxy methyl) Benzoyl chloride.
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CH3
O
COOH + S OCl
Clthionyl dichloride
118.97
CH3
O
COCl+ SO2
ClH+64.06
36.46
HCl + KOH KCl OH2+36.46 56.1 74.55 18.01
NaOH + SO2 NaHSO340 64.06 104.05
2-[(2-methylphenoxy)methyl]benzoic acid
242.27 2-[(2-methylphenoxy)methyl]benzoyl chloride260.71
Step-III 2-(2-Methyl Phenoxy methyl) Benzoyl Chloride reacted with Sodium cyanide to give 2-(2-Methyl Phenoxy methyl) Benzoyl Cyanide.
CH3
O
COCl + NaCN
CH3
O
COCN + NaCl
58.4449
2-[(2-methylphenoxy)methyl]benzoyl chloride
260.72
{2-[(2-methylphenoxy)methyl]phenyl}(oxo)acetonitrile251.28
Step-IV 2-(2-Methyl Phenoxy methyl) Benzoyl Cyanide (Nitrile) further reacted with Methoxy amine in presence of Hydrochloric Acid and Solvent - Methanol to give final product KRESOXIM-METHYL
CH3
O
COCN ++ NH2 O CH3
O-methylhydroxylamine47.05 x 2 = 94.1
Methanol
30% HCl2
CH3
O
CN OCH3
C
OCH3
O
NH2 NH2
hydrazine32.04
{2-[(2-methylphenoxy)methyl]phenyl}(oxo)acetonitrile251.28 methyl
(2E)-(methoxyimino){2-[(2-methylphenoxy)methyl]phenyl}ethanoate
313.34
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Process Flow Diagram
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Mass Balance
Sr.No
Input/(kg) of Product
Sr.No
Output/(kg) of Product Raw
Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 Ortho Cresol 360 1 KCl 250
2 Phthalide 447 2 Sodium
bisulphite 413
3 Potassium Hydroxide 187 3
Water to ETP 402
4 Xylene 1800 4 NaCl 195
5 Thionyl Chloride 398 5
Xylene recovered 1760
6 Sodium Hydroxide 163 6
Xylene loss 40
7 NaCN 202 7 Kresoxim
Methyl 1000
8 30%
Hydrochloric Acid
131 8
Hydrazine 50
9 Methanol 1000 9 Mehanol
recovered 980
10 Methoxy Amine 156 10
Methanol loss 20
11 Water 3975 11 Aq. to ETP 3693
12 Distillation
residue 16
1908 4095 0 2740 60 16
Total 8819 Total 8819
Penconazole Step-I 2-(2,4-Dichlorophenyl) Pentyl Alcohol reacted with Methane Sulfonyl Chloride in presence of Sodium hydroxide and solvent- Toluene to give 2-(2,4-Dichloro Phenyl) Pentyl Methane Sulfonate.
Cl
Cl
CH CH2 CH2 CH3
CH2
OH
+NaOH/Toluene
+ ClH
36.46
2-(2,4-dichlorophenyl)pentan-1-ol233
CH3SO2Cl
Methanesulphonyl chloride114.55
Cl
Cl
CH CH2 CH2 CH3
CH2
O S
O
OCH3
2-(2,4-dichlorophenyl)pentyl methanesulfonate311.22
Step-II 2-(2,4-Dichloro Phenyl) Pentyl Methane Sulfonate further reacted with 1,2,4-Triazole in presence of Sodium Methoxide and Solvent DMF to give final product PENCONAZOLE.
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+CH3 OH
32.04
Cl
Cl
CH CH2 CH2 CH3
CH2
O S
O
OCH3
2-(2,4-dichlorophenyl)pentyl methanesulfonate
311.22
+NH
N
N
1H-1,2,4-triazole69.06
CH3ONa
DMF
Cl
Cl
CH CH2 CH2 CH3
CH2N
N
N
CH3SO3Na
+118.08
1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole284.18
Process Flow Diagram
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Mass Balance
Sr.No
Input/(kg) of Product Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 2-(2,4 –
dichlorophenyl) Pentyl Alcohol
905 30% HCl 478
2 Methane Sulphonyl Chloride
445 Rec. Toluene
1160
3 Sodium Hydroxide 155 Loss toluene 40
4 Toluene 1200 Penconazole 1000
5 1,2,4 – Triazole 264 Methanol 124
6 Sodium Methoxide 208
Methane Sulphonic
Acid Sodium Salt 466
7 DMF 1200 DMF loss 25 8 Water 858 DMF recov. 1175
Aq. layer to ETP 750
Process loss 17
2068 750 17 2335 65 0
Total 5235 Total 5235
Picxystrobin Step-I 3-Isochromanone is reacted with Methyl formate in presence of Di methyl carbonate and sodium hydride as well as Solvent - Toluene to give 4-(α-methyl Methylene)-3-Isochromanone.
O
O1,4-dihydro-3H-isochromen-3-one
148.15
+ CH3 O C
O
H
methyl formate60.05
(CH3)2CO3/NaOHToluene
O
O
H3CO
+ OH2
190.2
(4E)-4-(methoxymethylidene)-1,4-dihydro-3H-isochromen-3-one
18.01
Step-II 4-(α-methyl Methylene)-3-Isochromanone further reacted with Hydrochloric acid gas in presence of Solvent –EDC to give Methyl-2-(Chloromethyl)-α-methoxy Methylene-Benzene Acetate.
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O
O
CHH3CO
190.2
(4E)-4-(methoxymethylidene)-1,4-dihydro-3H-isochromen-3-one
+ ClHCl
O OCH3
OCH3
methyl (2E)-2-[2-(chloromethyl)phenyl]-3-methoxyprop-2-enoate
240.68
EDC
Step-III Methyl-2-(Chloromethyl)-α-Methoxy Methylene-Benzene acetate reacted with 2-Hydroxy-6-
Trifluoromethyl pyridine to give final product PICOXYSTORBIN.
XyleneCl
O OCH3
OCH3
methyl (2E)-2-[2-(chloromethyl)phenyl]-3-methoxyprop-2-enoate
240.68
+O
O OCH3
OCH3
NF3C
367.32
+ ClH36.46
NF3C OH
6-(trifluoromethyl)pyridin-2-ol163.09
methyl (2E)-3-methoxy-2-[2-({[6-(trifluoromethyl)pyridin-2-yl]oxy}methyl)phenyl]prop-2-enoate
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Process Flow Diagram
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.Mass Balance
Sr.No
Input/(kg) of Product Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 3 - Iso Chromanone 445 Toluene
recovered 1270
2 Methyl Formate 180 Toluene loss 30
3 Di Methyl Carbonate 270 Sodium
carbonate 650
4 Sodium Hydride 287 Methanol 96
5 Toluene 1300 EDC recovered 1365
6 HCl gas 110 EDC loss 35
7 EDC 1400 Picoxystrobin 1000
8 2-Chloro-6-
Trifluoro Methyl
Pyridine
483 KCl
223
9 Potassium Hydroxide 168 Aq. to ETP 627
10 Xylene 1000 Xylene recovered 980
11 Water 666 Xylene loss 20
Distillation
residue 13
1969 627 0 3615 85 13
Total 6309 Total 6309
Propiconazole Step-I 1,3-Dichloro benzene is reacted with Acetyl chloride in presence of Aluminum Chloride and Solvent – Ethylene Di Chloride to get 2,4-Dichloro Acetophenone.
+ CH3 CO
Cl
AlCl3/EDC
Cl
C
O
CH3
Cl
+ ClH36.46
Cl
Cl
1,3-dichlorobenzene147
acetyl chloride78.5
1-(2,4-dichlorophenyl)ethanone189.03
Step-II 2,4-Dichloro Acetophenone further reacted with bromine in presence of Solvent - Ethylene Di Chloride to get 2,4-Dichloro Phenacyl Bromide.
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PTSA/EDC
Cl
C
O
CH3
Cl
+ BrH80.91
1-(2,4-dichlorophenyl)ethanone189.03
+ Br2159.81
Cl
C
O
CH2
Cl
Br
2-bromo-1-(2,4-dichlorophenyl)ethanone267.93
Step-III 2,4-Dichloro Phenacyl bromide reacted with 1,2-Pentanediol in presence of Toluene to get 4-(2-Bromomethyl- 4-Propyl-1,3-Dioxolane-2-yl)-1,3-Dichlorobenzene.
Toluene+ OH2
18.01
Cl
C
O
CH2
Cl
Br
2-bromo-1-(2,4-dichlorophenyl)ethanone267.93
+ CH2 CH CH2 CH2 CH3
OH OHpentane-1,2-diol
104.14 Cl
CO
CH2
Cl
Br
CH2 CH CH2 CH2 CH3
O
2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolane
354.06 Step-IV 4-(2-Bromomethyl-4-Propyl-1,3-Dioxolane-2-yl)-1,3-Dichlorobenzene further reacted with 1,2,4-Triazole in presence of Potassium hydroxide and Solvent DMF to get final product PROPICONAZOLE.
KOH/DMF
+ BrH80.91
Cl
CO
CH2
Cl
Br
CH2 CH CH2 CH2 CH3
O
2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolane
354.06
+NH
N
N
1H-1,2,4-triazole69.06 Cl
CO
CH2
Cl
N
CH2 CH CH2 CH2 CH3
ON
N
1-{[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl}-1H-1,2,4-triazole
342.22
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Process Flow Diagram
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Mass Balance
Sr.no
Input/(kg) of Product Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Wates Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 1,3 Di Chloro
Benzene 452 30% HCl 375
2 Acetyl Chloride 238 20% AlCl3 2786
3 Aluminium Chloride 558 28% HBr
solution 890
4 EDC 1600 EDC recovered 1570
5 Water 3715 EDC loss 30
6 Bromine 553 Toluene recovered 980
7 Catalyst 10 Toluene loss 20
8 1,2 – Butanediol 320 Water
recovered 55
9 Toluene 1000 Propiconazole 1000
10 Potassium Hydroxide 166 DMF
recovered 975
11 1,2,4 – Triazole 210 DMF loss 25
12 DMF 1000 KBr 390
Aq. to ETP 712
Process loss 14
5441 712 14 3580 75 0
Total 9822 Total 9822
Prothioconazole
Step-I 1,2 Dichloro Benzene reacts with 1-Chloro Cyclo Propane & 2-Hydroxy Propanyl Chloride in presence of Solvent Xylene and Catalyst to give Intermediate (A) 1-Chlorocyclopropyl-3-(2-Chlorobenzyl)-2-Hydroxy Chloro Propane.
CH2 CH CH3
OH
Cl
1-chloropropan-2-ol
94.54
+Cl
chlorocyclopropane76.52
+
Cl
Cl
1,2-dichlorobenzene
147
catalystxylene
Cl
CH2 CH2C
OH
ClCl
+ ClH
1-chloro-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)propan-2-ol
279.59
36.46+ H2
2.01
Step-II Intermediate (A) when reacts with 1,2 Dihydro 3H – 1,2,4 Triazole 3-Thione in presence of Solvent & Catalyst to give the final product Prothioconazole.
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catalystCl
CH2 CH2C
OH
ClCl
+ ClH
1-chloro-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)propan-2-ol
279.59
36.46+
NH
N
NHS
1,2-dihydro-3H-1,2,4-triazole-3-thione101.13
Cl
CH2 CH2C
OH
Cl
N
N
NH
S2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione
344.26
Process Flow Diagram
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Mass Balance
Pyraclostrobin Step-I 1, 4 Dichloro Benzene reacts with 3-Chloro Pyrazole in presence of catalyst & solvent Xylene to form Intermediate (A) as 3-Chloro 4-Chloro Phenyl Pyrazole.
Cl
Cl1,4-dichlorobenzene
147
+N
NH
Cl
N
Cl
N
Cl
3-chloro-1H-pyrazole102.52
+ ClH
3-chloro-1-(4-chlorophenyl)-1H-pyrazole213.06
36.46
Step-II 2-Chloro Benzyl Alcohol reacts with N-Methoxy Carbamate to form second Intermediate (B) N-methoxy, N-(2-Oxymethyl Phenol) Carbamate.
Sr.No
Input/MT of Product Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardo
us Waste (kg)
1 1,2 Dichloro Benzene 455 30% HCl 750
2 Chloro Cyclopropane 236 Catalyst 20
3 2 – Hydroxy
Propanyl Chloride
295 Hydrogen 6
4 Xylene 2000 Prothioconazole 1015 5 Catalyst 20 Aq. to ETP 1059 6 Water 1543 Xylene recovered 1960
7 2,4 Dihydro
1,2,4 Triazole 5 –Thione
315 Xylene loss
40
Process loss 14
1765 1059 20 1960 40 20
Total 4864 Total 4864
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CH2
Cl
OH
2-chloro benzyl alcohol142.58
+ COCH3NH
O
H3CO
methyl methoxycarbamate105.09
CH2
N
OH CH3CO
O
OCH3 + ClH
methyl [2-(hydroxymethyl)phenyl]methoxycarbamate211.2
36.46
Step-III (A) & (B) then undergoes Condensation reaction in presence of Catalyst & Solvent Xylene gives the final product Pyraclostrobin.
CH2
N
OH CH3CO
O
OCH3
methyl [2-(hydroxymethyl)phenyl]methoxycarbamate
211.2
+N
N
Cl
Cl
N
N
Cl
OCH2
N
CH3CO
O
OCH3
+ ClH
Pyraclostrobin
387.82
36.46
3-chloro-1-(4-chlorophenyl)-1H-pyrazole213.06
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Process Flow Diagram
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Mass Balance
Sr.No
Input/MT of Product Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 1,4 Dichloro Benzene 422 Catalyst 10
2 3 – Chloropyrazole 275 30% HCl 840
3 Xylene 4000 Pyraclostrobin 1000
4 Catalyst 10 Aq. To ETP 955
5 2 –
Chlorobenzyl Alcohol
350 Xylene recovery 3950
6 N – Methoxy Carbamate 270 Xylene loss 50
7 Water 1500 Distillation residue 22
Total 1840 955 0 3950 50 32
Total 6827 Total 6827
Tebuconazole Step-I 1-(4-Chlorophenyl)-4,4-Dimethyl-3-Pentanone reacted with Sodium Methoxide & Dimethyl Sulfide in presence of Toluene to get 2- [ 2-( 4- Chlorophenyl)ethyl ]-2-(1,1 – Di methyl ethyl ) Oxirane.
CH2
Cl
CH2 C
O
C
CH3
CH3
CH3
1-(4-chlorophenyl)-4,4-dimethylpentan-3-one
224.72
+ CH3 O Na
sodium methanolate
54.02
+ CH3 S CH3
(methylsulfanyl)methane
62.13
Toluene
CH2
Cl
CH2 C
CH2
C
CH3
CH3
CH3O
2-tert-butyl-2-[2-(4-chlorophenyl)ethyl]oxirane
+
238.75
CH3OH32.04
+ CH3 S Na
70.09sodium methanethiolate
Step-II 2- [ 2-( 4- Chlorophenyl)ethyl ]-2-(1,1 – Di methyl ethyl ) Oxirane. is reacted with 1,2,4-Triazole in presence of DMF to give final product TEBUCONAZOLE
DMF
CH2
Cl
CH2 C
CH2
C
CH3
CH3
CH3O
2-tert-butyl-2-[2-(4-chlorophenyl)ethyl]oxirane
238.75
+NH
N
N
69.061H-1,2,4-triazole
CH2
Cl
CH2 C C
CH3
CH3
CH3OH
CH2
N
N
N
1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol
307.81
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Process Flow Diagram
Mass Balance
Sr.No
Input/(kg) of Product Sr.
No.
Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product
Wates
Water
Air Emissio
n Recover
y Los
s Solid/Hazardou
s Waste (kg)
1
1-(4 – Chloropheny
l) 4-4-Dimethyl -3- Pentanoate
675 1 Methanol 95
2 Sodium Methoxide 152 2 Rec. Toluene 1360
3 Di Methyl Sulphide 186 3 Loss toluene 40
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Sr.No
Input/(kg) of Product Sr.
No.
Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product
Wates
Water
Air Emissio
n Recover
y Los
s Solid/Hazardou
s Waste (kg)
4 Toluene 1400 4 20% Sodium
Methyl Sulphide
1048
5 Water 1706 5 Tebuconazole 1000
6 1,2,4 – Triazole 206 6 DMF loss 30
7 DMF 1100 7 DMF recov. 1070
8 Aq. layer to ETP 768
9 Process loss 14
2143 768 14 2430 70 0
Total 5425 Total 5425
Thifluzamide In the first step, Ethyl trifluoroacetate (ETFFA) is chlorinated at low temperature and the chlorinated compound is thioacetamide in presence of solvent and finally reacted NaOH and acidified to get thiazole acid. The acid is chlorinated by Thionyl chloride in toluene. Finally the thiazole acid chloride is reacted with 2,6‐dibromo‐4‐trifluoromethoxyaniline in presence of solvent. The product is isolated by filtration and washing and drying.
Step-I: Preparation of Ethyl - 4, 4, 4- Tri-fluoro -2 - Chloro Acetoacetate. Chemical reaction
O
F3C
O
OC2H5
Ethy l - 4, 4, 4 - trif luoro acetoacetate
184.11
+ Cl Clchlorine
70.9
O
F3C
O
OC2H5Cl
+ ClH
Ethy l 2 chloro - 4, 4, 4 - trif luoro acetoacetate218.55
36.45
ClH + Na OH +Na Cl OH2
36.46 39.99 58.44 18.01
Step-II: Preparation of 2 - Methyl -4 - trifluoromethyl -5 - thiazole carboxylic acid ethyl ester. Chemical reaction
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O
F3C
O
OC2H5Cl
Ethy l 2 Chloro - 4, 4, 4 - trif luoro acetoacetate
218.55
+
ClH + Na OH +Na Cl OH2
36.46 39.99 58.44 18.01
S
NH2CH3
ethanethioamide
75.13
ET3N / AcCS
N
CH3
CF3
O
OC2H5 + ClH
239.21
36.45
+ OH2
18.012- Methyl - 4 - trifluoromethyl - 5 -thiazole carboxylic acid ester
Step-III: Preparation of 2- Methyl- 4- trifluoromethyl -5 - thiazole carboxylic acid. Chemical reaction
NaOH/HClS
N
CH3
CF3
O
OC2H5
2 - Methy l - 4 - trif luoromethy l - 5 -thiazole carboxy lic acid ester
239.21
S
N
CH3
CF3
O
OH+
2 - Methy l - 4 - trif luoromethy l - 5 -thiazole carboxy lic acid
H5C2 OHethanol
211.1646.06
Step-IV: Preparation of 2- Methyl- 4- trifluoromethyl- 5- thiazole carboxylic acid chloride. Chemical reaction
S
N
CH3
CF3
O
OH
2 - Methy l - 4 - trif luoromethy l - 5 -thiazole carboxy lic acid
211.16
TolueneS
O
ClClthionyl dichloride
+
118.97
S
N
CH3
CF3
O
Cl+ ClH
SO2
36.45
64.06+
2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carbonyl chloride229.6
SO2 + 2 NaOH Na2SO4 + H2
64.06 80 142.04 2
Step-V: Preparation of N - (2, 6- dibromo -4 - (trifluoromethoxy) phenyl)-2-methyl-4- trifluoromethyl -5 - thiazolecarboxamide. Chemical reaction
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Acetonitri leS
N
CH3
CF3
O
Cl
2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carbonyl chloride
229.6
+
NH2
Br Br
OCF3
2,6-dibromo-4-(trifluoromethoxy)aniline
334.92
S
N
CH3
CF3
O
NH
Br
Br
OCF3
N-[2,6-dibromo-4-(trifluoromethoxy)phenyl]-2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide
528.06
+ ClH36.45
Process Flow Diagram
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Mass Balance
Sr.No
Input/MT of Product Output/(kg) of Product
Raw Material Name
Qty (kg)
Output Material Name
Product / By
Product Wates Water
Air Emission Recovery Loss Solid/Hazardous
Waste (kg)
1 Ethyl trifluoroacetate 598 NaCl 293
2 Chlorine gas 198 Water to ETP 1308
3 Sodium Hydroxide 131 AcC
recovered 950
4 Water 3241 AcC loss 50 5 Ethanethiomide 196 Process loss 59
6 Triethyl amine (ET3N) 15 Ethanol
recovred 115
7 Acetonitrile 1000 Aq. layer 1282 8 NaOH 475 30% HCl 565
9 HCl 30% 315 Toluene recovered 1920
10 Thionyl chloride 276 Toluene loss 80 11 Toluene 2000 Na2SO4 328 12 DBTFMA 705 H2 gas 4
Water to ME 1196
Thifluzamide 1000
2186 3786 63 2985 130 0
Total 9150 Total 9150
Trifloxystrobin Step-I 2-Methyl Aniline is reacted with Sodium Nitrite and Hydrochloric acid to give 2-Methyl benzene Diazonium salt by diazotization.
NH2
CH3
2-methylaniline107.15
N+
CH3
N
+ OH2NaNO2 ClH
72.9269
Cl-
OH2
Na Cl58.44
+ +
154.6
22
36.02+
Step-II 2-Methyl Benzene Diazonium salt further reacted with Glyoxylic Acid methyl ester Oxime to give 2-Methyl phenyl glyoxalin acid methyl ester Oxime.
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N+
CH3
N Cl-
OH2
154.6
+H
OCH3 N
O
OH
methyl (2E)-(hydroxyimino)ethanoate
103.07
C
CH3
C
NOH
O
OCH3
methyl (2Z)-(hydroxyimino)(2-methylphenyl)ethanoate
193.2
N2 HCl+ +28 36.46
Step-III 2-Methyl Phenyl Glyoxylic Acid methyl ester Oxime reacted with Dimethyl sulfate in presence of Sodium Hydroxide to give 2-Methyl Phenyl Glyoxylate-o-methyl Oxime.
C
CH3
C
NOH
O
OCH3
methyl (2Z)-(hydroxyimino)(2-methylphenyl)ethanoate
193.2
+(CH3)2SO4
SO
O O
OCH3CH3
126.13
Methy lation/NaOHC
CH3
C
NO
O
OCH3
CH3
SO
O O
OCH3H
Methy l bisuphate2-Methyl Phenyl Glyoxylate-o-methyl Oxime
207.22
+
112.1
Step-IV 2-Methyl Phenyl Glyoxylate-o-methyl Oxime further on chlorination with chlorine gas in presence of Solvent –EDC gives 2-Methyl chloride phenyl Glyoxylate-o-methyl Oxime.
Chlorination/EDCC
CH3
C
NO
O
OCH3
CH3
2-Methyl Phenyl Glyoxylate-o-methyl Oxime
207.22
++ Cl Cl
70.91
C
CH2
C
NO
O
OCH3
CH3
Cl
ClH
methyl (2Z)-[2-(chloromethyl)phenyl](methoxyimino)ethanoate241.67
36.46
Step-V 2-Methyl chloride Phenyl Glyoxylate-o-methyl Oxime reacted with Sodium [-1- [3- ( Trifluoromethyl) Phenyl ] Ethylidene ] Amine ] Oxidanide in presence of Solvent – DMF to give final product TRIFLOXYSTORBIN.
DMF
+
C
CH2
C
NO
O
OCH3
CH3
Cl
NaCl
methyl (2Z)-[2-(chloromethyl)phenyl](methoxyimino)ethanoate
241.67
58.44
+F3C
CH3
N ONa
sodium ({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxidanide
225.14
C
CH2
C
NO
O
OCH 3
CH3
OC CF3
CH3
N
methyl (2Z)-(methoxyimino)(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanoate
408.37
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Process Flow Diagram
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Mass Balance
Sr.No
Input/MT of Product Output/(kg) of Product Input
Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Wates Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 2 – Methyl
Aniline 275 NaCl 580
2 Sodium Nitrite 177 N2 71
3
30% Hydrochloric
Acid 338 Water to ETP
303
4
Glyoxylic Acid Methyl Ester Oxime
259 Methyl bisulphate 151
5 Sodium
Hydroxide 306 30% HCl 310
6 Di Methyl Sulphate 160 EDC
recovered 1160
7 Chlorine
Gas 190 EDC loss 40
8 EDC 1200 Trifloxystrobin 1000
9
Sodium [1-{(3-Trifluoro
Methyl) Phenyl}
Ethylidene Amino]
Oxidanide
518 DMF recovered
1360
10 DMF 1400 DMF loss 40
11 Water 3792 Aq. to ETP 3582
Distillation
residue 18
2041 3885 71 2520 80 18
Total 8615 Total 8615
HERBICIDE Carfentrazone
Stage I: Intermediate – I Sodium sulfite solution was charged to a mixture of 2-fluoroaniline, sodium nitrite solution & hydrochloric acid at 40 – 45°C. The subsequent mass was basified with caustic lye solution & the resultant product of this step (Intermediate – I) was obtained by filtration.
NH2
F2-fluoroaniline
111.11
+ ClH + NaNO2Na2SO3NaOH
NH
F
NH2
126.13Intermediate
-I
(2-fluorophenyl)hydrazine
Stage II: Intermediate – II A mixture of Intermediate - II, acetaldehyde, sodium cyanate and acetic acid in solvent methanol was chlorinated using chlorine gas at 50 – 55 °C for 6 – 8 hours. Product of this step (Intermediate II) was filtered after recovery of methanol under reduced pressure.
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F
NH NH2
126.13Intermediate
-I
+ CH3CHO + NaOCN + CH3COOHCH3OH/Cl2
(2-fluorophenyl)hydrazine
F
NN
NH
O
CH3
2-(2-fluorophenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
193.17Intermediate
-II
Stage III: Intermediate – III A mixture of intermediate - II in solvent dimethyl formamide and potassium carbonate was heated to 175 – 180°C. Freon 22 gas was purged for 3 – 4 hours. The mass was cooled to 50 – 60°C and resultant solid was filtered. Chlorine gas was purged to the filtrate for 2 – 3 hours at 65 – 75°C. Dimethyl formamide was distilled off, residue quenched in water and the product of this step (Intermediate III) was obtained by filtration.
F
NN
NH
O
CH3
2-(2-fluorophenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
193.17Intermediate
-II
+ CHF2Cl
Freon gas
K2CO3+ DMF/Cl2
F
NN
N
O
CH3
Cl
CHF2
2-(4-chloro-2-fluorophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
277.63
Intermediate-III
86.46
Stage IV: Intermediate – IV Nitric acid was charged to a mixture containing Intermediate – III in solvent dichloroethane and oleum at room temperature. The reaction mass was quenched in water and the resultant product (Intermediate – IV) was obtained by filtration. Solvent dichloroethane recovered during the process was recycled.
F
NN
N
O
CH3
Cl
CHF2
2-(4-chloro-2-fluorophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
277.63
Intermediate-III
H2SO4/HNO3
F
NN
N
O
CH3
Cl
CHO2N F
F
2-(4-chloro-2-fluoro-5-nitrophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
322.62Intermediate
-IV
Stage V: Intermediate – V A solution containing intermediate – IV in solvent isopropyl alcohol (IPA) and Pd/C catalyst was pressurized using hydrogen at 70 – 80°C for a period of 11 – 12 hours. The mass was
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cooled to 50 – 60°C & Pd/C Catalyst was filtered off & recycled. Solvent IPA was distilled, residue was quenched in water and the product (Intermediate-IV) was obtained by filtration.
F
NN
N
O
CH3
Cl
CHO2N F
F
2-(4-chloro-2-fluoro-5-nitrophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
322.62Intermediate
-IV
5% Pd/C
IPA, H2
F
NN
N
O
CH3
Cl
CHNH2
F
F
2-(5-amino-4-chloro-2-fluorophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
292.64
Intermediate-V
Stage VI: Carfentrazone A mixture of Intermediate – V, ethyl acrylate and acetonitrile was charged to the reactor. Mixture was heated to 50 – 60°C and chlorine gas was purged. Acetonitrile was distilled off and the residue was quenched in water & the product was isolated by filtration. Recovered acetonitrile was recycled in subsequent batches.
F
NN
N
O
CH3
Cl
CHNH2
F
F
2-(5-amino-4-chloro-2-fluorophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
292.64
Intermediate-V
O
CH2
O
CH3
+
ethyl prop-2-enoate
100.11
F
NN
N
O
CH3
Cl
CHF
F
Cl
O
OCH3
ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate
412.19Carfentrazone
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Raw Materials Quantity Output Material Name
Product/ By-Product (kg)
Waste Water
Air Emission (kg)
Recovery (kg)
Solvent
Loss (kg)
Solid/Hazardous Waste
(kg)
1 2-fluoroaniline 730 Aqueous effluent
45546.25
2 Sodium nitrite 460 Sodium sulphite 1352
3 Hydrochloric acid 4210 Water Vapour 5408
4 Sodium sulphite 2710 Methanol recovered 3843
5 Water 42906 Methanol loss 321
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Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Raw Materials Quantity Output Material Name
Product/ By-Product (kg)
Waste Water
Air Emission (kg)
Recovery (kg)
Solvent
Loss (kg)
Solid/Hazardous Waste
(kg)
6 20% NaOH solution 4275
Scrubbed sodium
hydroxide solution
(containing sodium hypochlori
te)
2592
7 Caustic lye solution 2644 Drying
loss 734.25
8 Acetaldehyde 382 Dimethyl formamid
e 6141
9 Chlorine 1085 Dimethyl formamid
e loss 147.5
10 Acetic acid 500 Dichloroet
hane recovered 3074
11 Methanol 4000 Dichloroethane loss 176
12 10% sodium
hydroxide Solution
1500 Spent acid
14793.4
13 Potassium carbonate 924
Isopropyl alcohol
recovered 5700
14 Dimethyl formamide 7500
Isopropyl alcohol
loss 625
15 Dichlorodifluoromethane 665
Catalyst Pd/C
recovered 59.5
16 Freon gas 895 Carfentrazone 1000
17 Oleum 5565.2 Acetonitril
e recovered 4825
18 Nitric acid 502.2 Acetonitrile loss 475
19 Dichloroethane 3250 20 Isopropyl alcohol 6325 21 Catalyst Pd / C 59.5 22 Ethyl acrylate 425 23 Acetonitrile 5300
2352 62931.65 6142.25 23642.5 1744.
5 0
Total 96812.9 Total 96812.9 Clethodim Step-I 5 – (Propyl 2 thio Ethyl) Cyclohexane 1:3 Dione is reacted with propionyl chloride to form the intermediate as – I
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CHS CH3CH2CH3
CH2
OO
5-[2-(ethylsulfanyl)propyl]cyclohexane-1,3-dione214.32
+ CH2 CO
ClCH3
propanoyl chloride92.52
CHS CH3CH2CH3
CH2
OO CH2C
O
CH3
5-[2-(ethylsulfanyl)propyl]-3-oxocyclohex-1-en-1-yl propanoate270.38
Intermediate - 1Step-II Intermediate - I on isomerisation in presence of Aluminium Chloride gives the intermediate - II
CHS CH3CH2CH3
CH2
OO CH2C
O
CH3
5-[2-(ethylsulfanyl)propyl]-3-oxocyclohex-1-en-1-yl propanoate
270.38
Intermediate - 1
+ AlCl3133.34
CH2 C
O
CH3
CHS CH3CH2CH3
CH2
O OH
270.38Intermediate - 2
5-[2-(ethylsulfanyl)propyl]-3-hydroxy-2-propanoylcyclohex-2-en-1-one
Step-III Intermediate -II on reaction with 1 Chloro 3 - allyl Oxy amine in presence of Solvent gives the final product Clethodim
+
CH2 C
O
CH3
CHS CH3CH2CH3
CH2
O OH
270.38Intermediate - 2
NH2 O CH2 CH CH Cl
O-(3-chloroprop-2-en-1-yl)hydroxylamine107.53
Toluene
CH2C
NHCH3
CH
S
CH3
CH2
CH3
CH2
O
OCH2
CHCCl
H
O
2-[1-({[(2E)-3-chloroprop-2-en-1-yl]oxy}amino)propylidene]-5-[2-(ethylsulfanyl)propyl]cyclohexane-1,3-dione
359.91Clethodim
5-[2-(ethylsulfanyl)propyl]-3-hydroxy-2-propanoylcyclohex-2-en-1-one
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product / By-
Product (kg)
Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1
5-Propyl 2-Thio Ethyl
Cyclohexane 1,3 dione
625 Clethodim 1020
2 Propionyl Chloride 285 Recovered
Toluene 2450 3 AlCl3 450 Toluene loss 50
4 1-Chloro 3-Allyl Oxy Amine
330 20% NH3 solution 2250
5 Toluene 2500 Aq. layer to ETP 1220 6 water 2800
3270 1220 0 2450 50 0
Total 6990 Total 6990
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Clodinafop Propargyl Step-I 2,3 – Di Fluoro -5 - Chloro Pyridine is reacted with 2 - ( 4- Hydroxy Phenoxy) Propionic Acid in presence of Solvent - Di Methyl Formamide ( DMF) and Sodium Hydroxide to form 2- [ -4 – {( 5 Chloro -3- Fluoro -2-Pyridinyl ) Oxy} Phenoxy ] Propionic Acid.
FH + NaOH NaF + OH220 18.0140 41.99
N F
FCl
+
OH
O CH
CH3
C
OH
O
DMF
N O
FCl
O CH CH3
COHO
182.172-(4-hydroxyphenoxy)propanoic acid
+ FH205-chloro-2,3-difluoropyridine
149.52
2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoic acid
311.69
Step-II 2- [ -4 – {( 5 Chloro -3- Fluoro -2- Pyridinyl ) Oxy} Phenoxy ] Propionic Acid is reacted with Propargyl chloride in Presence of Sodium Hydroxide as well as Solvent -Toluene to form final product as CLODINAFOP PROPARGYL
DMF
N O
FCl
O CH CH3
COHO
+ ClH36.46
+ CH2 C CHCl
Propargyl chloride74.5
N O
FCl
O CH CH3
COO CH2 C CH
NaOH + ClH NaCl + OH240 36.46 18.0158.44
2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoic acid
311.69
prop-2-yn-1-yl 2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoate349.74
The starting material, the sodium salt of 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)-phenoxy]-propionate is obtained as follows:
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(a) 3-amino-2,3-dichloropyridine
To a solution of 129.2 g (0.69 mol) of 2,5-dichloro-3-nitropyridine in 1300 ml of dioxane is added 26.0 g of Raney-nickel, that has previously been washed with ethanol. This mixture is then hydrogenated with hydrogen under normal pressure at 20°-35° C. After uptake of 20% of the theoretical amount of hydrogen, another 30 g of washed Raney-nickel catalyst are added. After hydrogenating for 22 hours, the catalyst is filtered off, the solvent is evaporated and the residue is crystallized from hexane/ethyl acetate. Thus, 84.9 g of 3-amino-2,5-dichloropyridine (78% of the theory) are obtained, which melts at 129°-132° C.
N Cl
Cl N+
O
O-
2,5-dichloro-3-nitropyridine192.98
+ H2
6
Raney-Nickel
DioxaneN Cl
Cl NH2
2,5-dichloropyridin-3-amine163
+ OH22336.02
(b) 2,5-dichloro-3-fluoropyridine
To 450 ml (22.5 mol) of hydrogen fluoride in a stainless steel reaction vessel are added at a temperature of -5° to -1°, 163 g (1.0 mol) of 3-amino-2,5-dichloropyridine. Then there are added while stirring at the same temperature 82.8 g (1.2 mol) of sodium nitrite into the solution. The reaction mixture is stirred for 1.5 hours at -5° to -1°, then the temperature is slowly raised to +60° C. After the evolution of gas has ceased, the hydrogen fluoride is distilled off and the residue is taken up in methylene chloride. Ice/water is then added thereto and the cold mixture is neutralized with concentrated ammonium hydroxide solution. The organic phase separated and the water phase is extracted three times with methylene chloride. The organic phases are washed with water, dried over magnesium sulfate, filtered through silicagel and evaporated. Thus, 141.5 g (85% of the theory) of 2,5-dichloro-3-fluoropyridine are obtained.
N Cl
Cl NH2
2,5-dichloropyridin-3-amine163
+ FHhydrogen fluoride
20
Sodium nitrite solution
N Cl
Cl F
2,5-dichloro-3-fluoropyridine165.98
+ NH3
ammonia17.03
(c) 5-chloro-2,3-difluoropyridine
A suspension of 64.6 g (1.1 mol) of potassium fluoride and 11.25 g (0.075 mol) of cesium-fluoride in 240 ml of sulfolane (1,1-dioxo-tetrahydrothiophene) is heated to 140° C. By
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reducing the pressure 50 ml of sulfolane are distilled off. To the suspension a solution of 61.4 g (0.37 mol) of 2,5-dichloro-3-fluoropyridine in 20 ml of sulfolane is added. The reaction-mixture is then stirred for 35 hours at a temperature of 140°, cooled and poured into ice/water. The organic material is extracted with ether. The ethereal layer is washed with water dried over magnesium sulfate, filtered and evaporated to yield 48.7 g of a colourless oil (88% of the theory) which boils at 65°-66° at 133 mbar.
N Cl
Cl F
2,5-dichloro-3-fluoropyridine165.98
SO O
tetrahydrothiophene 1,1-dioxide120.17
+ KF58.09
+ CsF151.9
+N F
Cl F
5-chloro-2,3-difluoropyridine149.52
(d) 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)-phenoxy]-propionic acid methyl ester
To a stirred mixture of 21.6 g (0.11 mol) of 2-(4-hydroxyphenoxy)-propionic acid methyl ester, 15.2 g (0.11 mol) of potassium carbonate, 1.45 g (0.0055 mol) of 18-Crown-6 ether and 100 ml of acetonitrile is added dropwise a solution of 14.95 g (0.10 mol) of 5-chloro-2,3-difluoropyridine in 30 ml of acetonitrile and the mixture is heated at a temperature of 50° to 60° C. during 40 hours. The mixture is then poured into ice/water. The organic material is extracted with ethyl acetate, washed with a saturated salt solution, dried over magnesium sulfate, filtered and evaporated. The oily residue is purified by chromatography over a silica gel column with a hexane/ethyl acetate 3:1 solvent. After evaporation of the solvent one obtain 20.4 g of the above ester (63% of the theory) is obtained in crystalline form. The melting point is 63°-64° C.
N F
Cl F
5-chloro-2,3-difluoropyridine
149.52
OH
O
CH3
O
OCH3
methyl (2R)-2-(4-hydroxyphenoxy)propanoate196.2
+K2CO3
Acetonitrile O
O
CH3
O
OCH3
N
Cl
F
methyl (2R)-2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoate
325.72
(e) 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)-phenoxy]-propionic acid sodium salt
To a solution of 13.0 g (0.04 mol) 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)]-propionic acid methyl ester in 65 ml of dioxane is added 42 ml of 1N sodium hydroxide. Then it is stirred for
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21/2 hours at a temperature of 35° C. The mixture is then concentrated to dryness at room temperature in a rotatory evaporator. The remaining salt 13.2 g is used without further purification.
O
O
CH3
O
OCH3
N
Cl
F
methyl (2R)-2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoate
325.72
1N NaOH
DioxaneO
O
CH3
O
ONa
N
Cl
F
sodium (2R)-2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoate333.67
O
O
CH3
O
ONa
N
Cl
FHCl
DioxaneO
O
CH3
O
OH
N
Cl
F
sodium (2R)-2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoate
333.67
(2R)-2-{4-[(5-chloro-3-fluoropyridin-2-yl)oxy]phenoxy}propanoic acid311.69
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1
2, 3–Di Fluoro–5–
Chloro Pyridine
448 NaF 127
2
2–(4–Hydroxy
Phenoxy) Propionic
548 Rec.DMF
1170
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Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
Acid
3 NaOH 240 DMSO loss 30 4 DMF 1200 Water rec. 55
5 Propargyl Chloride 180 Clodinafop
Propargyl 1000 6 Toluene 1000 Toluene loss 980 7 Water 450 Toluene rec. 20
Residue 5
NaCl 175
Water to ETP 504
1302 504 0 2205 50 5
Total 4066 Total 4066
Clomazone Step-I Synthesis of 3-chloro-N-hydroxy-2, 2-dimethylpropanamide (CNHP)
CH2 C CO
ClCH3
CH3
Cl
3-chloro-2,2-dimethylpropanoyl chloride
Mol Wt. 155.02
+ N+
OH
HH
HClH
NaOHCH2 C C
O
NHCH3
CH3
ClOH
3-chloro-N-hydroxy-2,2-dimethylpropanamide Mol Wt. 151.59
+Mol Wt. 72.9
Cl-
hydroxylamine hydrochloride
Mol Wt. 69.46
2
ClH + NaOH NaCl + OH22 2 2 272.9 80 116.9 36.02
Step-II Synthesis of 4, 4-dimethyl-3-isoxazolidinone (DIO)
CH2 C CO
NHCH3
CH3
ClOH
3-chloro-N-hydroxy-2,2-dimethylpropanamide
Mol Wt. 151.59
NH
O
OCH3
CH3
4,4-dimethyl-1,2-oxazolidin-3-one
Mol Wt. 115.13
NaOH
+ ClHMol Wt. 36.46
Step-III Synthesis of Clomazone
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.
NH
O
OCH3
CH3
4,4-dimethyl-1,2-oxazolidin-3-one
Mol Wt. 115.13
+
Cl
CH2 ClNa2CO3
Cl
CH2 NC
O CH2
C
OCH3
CH3
2-(2-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one
(Clomazone)
Mol Wt. 239.7
+ ClH
Mol Wt. 36.46
1-chloro-2-(chloromethyl)benzene
Mol Wt. 161.02
Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1
3-chloro-2, 2-dimethylpropanoyl
chloride 713 NaCl 1850
2 hydroxylamine hydrochloride 318 Water to ETP 3869
3 50% NaOH
solution 1048 Clomazone 815
4 Water 3400 Dichloromethane recovered 2360
5
Sodium Carbonate or
NaOH 383 Dichloromethane
loss 40
6 2-chlorobenzyl
chloride 672 Hexane recovered 1950
7 Dichloromethane 2400 Hexane loss 50
8 Hexane 2000
2665 3869 0 4310 90 0 Total 10934 Total 10934
Cloransulam Step-I Hydrazine reaction 2-Ethoxy-4,6-difluoropyrimidine react with hydrazine in presence of Methanol to produce 2-Ethoxy-4-hydrazino-6-fluoropyrimidine
NN
OC2H5
FF2-ethoxy-4,6-difluoropyrimidine
160.12
+ NH2 NH2
hydrazine32.04
Methanol NN
OC2H5
NHF NH2
+ FH
2-ethoxy-4-fluoro-6-hydrazinylpyrimidine172.16
hydrogen fluoride20
Step-II Cyclization and isomerization reaction 2-Ethoxy-4-hydrazino-6-fluoropyrimidine react with CS2 in the presence of ET3N to get 5-ethoxy-7-fluoro-[1,2,4]triazolo[4,3-c]pyrimidine-3(2H)-thione approx.
ET3NNN
OC2H5
NHF NH2
2-ethoxy-4-fluoro-6-hydrazinylpyrimidine172.16
+ CS2
76.14
NN
OC2H5
F
N
N
SH
5-ethoxy-7-fluoro[1,2,4]triazolo[4,3-c]pyrimidine-3(2H)-thione
214.22
+ SH2
34.08
Isomerisation From 5-ethoxy-7-fluoro-[1,2,4] triazolo[4,3-c]pyrimidine-3(2H)-thione to form 5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine-3-thiol
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NN
OC2H5
F
N
N
SH
5-ethoxy-7-fluoro[1,2,4]triazolo[4,3-c]pyrimidine-3(2H)-thione
214.22
NN
OC2H5
F
N
NSH
5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-thiol214.22
Step-III chlorosulfonylation 5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine-3-thiol to 5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride
.
NN
OC2H5
F
N
NSH
5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-thiol
214.22
NaClO4
ClH
NN
OC2H5
F
N
NSO2Cl
5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride
280.66
Step-IV Amidation 5-ethoxy-7-fluoro-[1,2,4] triazolo[1,5-c]pyrimidine-2-sulfonyl chloride in Dichloromethane react with 2-AMINO-3-CHLORO-BENZOIC ACID METHYL ESTER to get Cloransulam.
NN
OC2H5
F
N
NSO2Cl
5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonyl chloride
280.66
+ NH2
Cl
C OCH3
O
methyl 2-amino-3-chlorobenzoate185.6
NN
OC2H5
F
N
NS
O
O
NH
Cl
C OCH3
O
methyl 3-chloro-2-{[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulfonyl]amino}benzoate
429.81
+ ClH
36.46
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Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission (kg)
Recovery (kg)
Solvent Loss (kg)
Solid/Hazardous Waste
(kg)
1
2-Ethoxy-4,6-difluoropyrimidi
ne 627 Methanol
recovered 2630
2 hydrazine 80 % 255 Methanol loss 120
3 Methanol 2750 30% HF 262
4 Water 184 Drying loss 327
5 Triethyl amine 560 H2S 130
6 Carbon
disulphide 314 Filtrate to ETP 6461
7 Hydrogen
peroxide 30% 628 Cloransulam 1000 8 30% HCl 25 30% HCl 330
9
30% Sodium methylate- methanol solution
745 Dichloromethane recovered
550
10 Conc. HCl 422 Dichloromethane loss 40
11
Dichloromethane Hydrochloric
acid 980
12 Sodium
perchlorate 490 13 Water 278
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Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission (kg)
Recovery (kg)
Solvent Loss (kg)
Solid/Hazardous Waste
(kg) 0
14 Dichloromethan
e 590
15
2-Amino-3-Chlorobenzoic
acid methyl ester
500
1592 6461 457 3180 160 0
Diclosulam Process Description It is prepared from 5-ethoxy-)-7-fluoro-[1,2,4]-triazolo[1,5-c]pyrimidine-2-sulfonyl Chloride and 2,6-Dichloroaniline through a condensation reaction in an organic solvent in the presence of 3,5-Dimetylpyridine as catalyst. Reaction mass stir at 48 ° C for 24 hrs. After completion of the reaction, filter the reaction mass and dry the wet cake of product.
Process Flow Diagram
N NN S
Cl
NF
O O
O+
Cl
NH2
Cl
N NN S
NHN
F
O OO
Cl
Cl
5-Ethoxy-7-Fluoro[1,2,4]Triazolo[1,5-]Pyrimidine-2-Sulfonyl Chloride
2,6-Dichloro Aniline -(2,6-Dichlorophenyl)-5-Ethoxy-7-Fluoro[1,2,4]Triazolo[1,5- ]Pyrimidine-2-Sulfonamide
N
Mol. Wt.: 406.22Mol. Wt.: 162.02Mol. Wt.: 280.66
C C
N
CH3H3C
N
CH3H3C
+ + HCl
3,5-Dimethyl Pyridine
Mol. Wt.: 107.15
Hydrochloric Acid3,5-Dimethyl Pyridine
Mol. Wt.: 107.15 Mol. Wt.: 36.5
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1
5-ethoxy-)-7-fluoro-[1,2,4]-triazolo[1,5-
c]pyrimidine-2-sulfonyl Chloride
749 Product (Diclosulam) 1000
2 2,6-Dichloroaniline 642 3,5-
Dimetylpyridine 823
3 3,5-Dimetylpyridine 866 Hydrochloric
Acid 97 4 Acetonitrile 22942 Solvent 21801
5 Dimethyl Sulfoxide (DMSO)
8 Process Loss
1486
23721 0 0 0 1486 0
Total 25207 Total 25207
Fenoxaprop P Ethyl Step-I 2,6 - Dichloro Benzoxazole is reacted with 2- ( 4- Hydroxy Phenoxy ) Propionic Acid in presence of Sodium Hydroxide as well as Solvent – Di Methyl Sulfoxide ( DMSO) to form 2 – [ 4 - ( 6 –
Chloro -2- Benzoxazole ) Phenoxy ] Propionic Acid .
Chemical reaction
O
NCl
Cl
2,6-dichloro-1,3-benzoxazole188.01
+
O CH
CH3
CO
OH
OH
2-(4-hydroxyphenoxy)propanoic acid182.17
DMF/NaOHO
NO
Cl
O CH
CH3
CO
OH
2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoic acid
333.72
+ NaCl58.44
Step-II 2 – [ 4 - ( 6 – Chloro -2- Benzoxazole ) Phenoxy ] Propionic Acid undergoes chlorination by Thionyl Chloride in presence of Solvent – Toluene to form 2-[ 4 - ( 6 – Chloro -2- Benzoxazole ) Phenoxy ] Propionic Acid Chloride .
Chemical reaction
O
NO
Cl
O CH
CH3
CO
OH
2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoic acid
333.72
+ SCl
ClO
thionyl dichloride118.97
TolueneO
NO
Cl
O CH
CH3
CO
Cl2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoyl chloride
352.16
+ ClH + SO264.0636.46
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SO2
64.06 + NaOH Na2SO42
40 x 2 = 80 142.04+ H2
2 Step-III 2 – [ 4 - ( 6 – Chloro -2- Benzoxazole ) Phenoxy ] Propionic Acid Chloride is finally reacted with Sodium Ethoxide in presence of Solvent – Toluene to form the Final Product as FENOXYPROP P ETHYL.
Chemical reaction O
NO
Cl
O CH
CH3
CO
Cl+ CH2
CH3ONa
Toluene
2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoyl chloride
352.16
sodium ethanolate
68.05
O
NO
Cl
O CH
CH3
CO
O CH2 CH3
ethyl 2-{4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy}propanoate
361.77 + NaCl
58.44 Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 3, 6 – Di Chloro
Benzoxazole 610 NaCl 586
2
2 – (4 – Hydroxy
Phenoxy) Propionic
Acid
590 DMF recovered
1360
3 NaOH 121 Xylene loss 40 4 DMF 1400 30% HCl 398
5 Thionyl Chloride 384 Toluene
recovered 2420 6 Toluene 2500 Toluene loss 80
7 20% NaOH solution 1125 Na2SO4 400
8 Sodium Ethoxide 222 Water to ETP 905
9 water 1200 Fenoxaprop P Ethyl 1000
Aq. layer 963
2384 1868 0 3780 120 0
Total 8152 Total 8152
Flufenacet Process description 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole, catalyst & EDC are added in to the reactor under stirring to get uniform slurry. The solution of N-(4-fluorophenyl)-2-hydroxy-N-isopropylacetamide in Ethylene dichloride is added in the reaction mass to maintaining the desired temperature. 25% aqueous Sodium hydroxide solution is also added. Reaction mass is stirred at desired temperature, until the reaction is over. There after Layers are separated, Aqueous layer is further extracted and Acidified. Excess solvent is recovered for recycling. The mass is filtered to get crude product and washed by Methanol to get desired quality of final product. Solvents are recovered & recycled.
Chemical Reaction
CH3N
CH3O
F
OH
N-(4-fluorophenyl)-2-hydroxy-N-(propan-2-yl)acetamide
211.23
+N N
SS
O
O
CH3F
FF
2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole
232.2
25% NaOH
EDC N N
SF
FF
CH3N
CH3O
F
O
N-(4-fluorophenyl)-N-(propan-2-yl)-2-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}acetamide
363.33(FLUFENACET)
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 N-(4-fluorophenyl)-2-
hydroxy-Nisopropylacetamide
520 Flufenacet 1000
2 2-(Methylsulfonyl)-5-
(trifluoromethyl)-1,3,4-thiadiazole
635 EDC recovered
2328
3 PTSA 6 EDC loss 122
4 25% Sodium hydroxide 708 Methanol
recovered 1330
5 5% Hydrochloric acid 575 Methanol
loss 70
6 Methanol 1400 Aq. to ETP 1289
7 Ethylene dichloride 2450 Drying loss 155
1000 1289 155 3658 192 0
Total 6294 Total 6294
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Fomesafen Step-I 3 - Hydroxy -6- Nitro Benzoic Acid is reacted with 3,4 – Chloro Benzotrifluoride in presence of Solvent –Di Methyl Sulfoxide ( DMSO) and Sodium Hydroxide to form 2- Nitro -5- ( 2- Chloro -4- Trifluoro methyl Phenoxy) Benzoic Acid.
Cl
Cl
F
F
F+ NO2OH
COOH
O
Cl
F
F
F
NO2
COOH
1,2-dichloro-4-(trifluoromethyl)benzene215
DMSO NaOH
+ NaCl58.44
+ OH218.01
5-hydroxy-2-nitrobenzoic acid183.11
5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid
361.65(Intermediate - I)
Step-II 2- Nitro -5- ( 2- Chloro -4- Trifluoromethyl Phenoxy) Benzoic Acid (Intermediate – I) undergoes Chlorination by Thionyl Chloride in Presence of Solvent – Toluene to form Acid Chloride which on further reaction with Ammonium Hydroxide to form 2- Nitro -5- ( 2- Chloro -4- Trifluoromethyl Phenoxy) Benzamide.
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O
Cl
F
F
F
NO2
COOH
5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid
361.65(Intermediate - I)
+ S Cl
Cl
Othionyl dichloride
118.97
Toluene
NH4OH
O
Cl
F
F
F
NO2
COCl
35.04
NH4Cl53.49
64.06
2
2 + ClH
+ SO2
36.46
5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride380.1
O
Cl
F
F
F
NO2
CONH2
5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide360.67
+ + OH218.01
NaOH40
+ SO264.06
Na2SO3 + OH2126.04
218.01
Step-III 2- Nitro -5- (2- Chloro -4- Trifluoromethyl Phenoxy) Benzamide is further reacted with Methane Sulfonyl Chloride (MSC) in presence of Solvent – Toluene to form the final product Fomesafen.
O
Cl
F
F
F
NO2
CONH2
5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide360.67
+ CH3 SO2 Cl
114.55Methane sulphonyl chloride
Toluene
O
Cl
F
F
F
NO2
NHO
S O
CH3
O
5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide
438.76(Fomesafen)
+ClH36.46
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Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 3-Hydroxy-6-Nitro Benzoic
Acid 485 Rec. DMSO
2060
2 3,4-Di Chloro Benzotrifluoride 567 DMSO loss 40
3 DMSO 2100 Salt NaCl 154
4 NaOH 277 Rec. Toluene 1180
5 20% NH4OH solution 458 Toluene
loss 20
6 Toluene 2400 Salt NH4Cl 142 7 Water 910 30% HCl 342
8 Methane Sulfonyl Chloride
300 Sodium sulphite 270
Aq. layer 775
Rec. Toluene 1180
Toluene loss 24
30% HCl 300
Fomesafen 1000
Residue 10
2208 775 0 4420 84 10
Total 7497 Total 7497
Glufosinate Ammonium Process description
Charge water, HCl and n-Butyl (3-cyano-3-hydroxypropyl) methyl propionate in the reactor.
The mass is subjected to acidolysis at 45 – 50°C.
After the acidolysis reaction cool the mass to 20°C and purge ammonia gas at 20 – 25°C,
centrifuge and dry the cake to get Glufosinate Ammonium Technical. Send aqueous ML to
ETP.
Step-I
P
O
OHCH3 CH2 CH2 CH CN
NH2
(3-amino-3-cyanopropyl)methylphosphinic acid
162.12
+ ClH + OH2236.46 36.02
P
O
OHCH3 CH2 CH2 CH COOH
NH2
2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid(Glufosinate)
181.12
+ NH4Cl53.49
Step-II
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P
O
OHCH3 CH2 CH2 CH COOH
NH2
2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid(Glufosinate)
181.12
+ NH3 + OH217.03 18.01
P
O
OHCH3 CH2 CH2 CH C
NH2
ONH4
O
[3-amino-4-(aminooxy)-4-oxobutyl]methylphosphinic acid
(Glufosinate Ammonium)196.14
+ OH218.01
Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 WATER 3718 Glyphosate tech 1000
2 SODIUM TUNGSTATE 5 CO2 247
3 PMIDA 1621 Aq. later to ETP 4722.8
4 SODIUM METABISULFITE 21
5 VANADIUM SULPHATE 0.4
6 H2O2 604
1000 4722.8 247 0 0 0
Total 5969.4 Total 5969.8
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Glyphosate Process description
Phosphono Methyl Imino Diacetic Acid (PMIDA) is charged in water in a reactor under stirring. Catalyst Sodium Tungstate is charged and the temperature is raised to 65 – 70°C while stirring.
Hydrogen peroxide is then added to the mass at the same temperature. A clear solution is formed. Cool to 30°C and add catalyst Vanadium sulphate to form Glyphosate.
Product slurry is cooled to 20°C, centrifuged and dried to get Glyphosate technical.
Step-I
N
O O
OH
P
OH
OH
OH O
2,2'-[(phosphonomethyl)imino]diacetic acid227.1
+ OH OHhydrogen peroxide
34.01
NH
O
OH
P
OH
OH O+ CH2 O
[(phosphonomethyl)amino]acetic acid169.07
formaldehyde30.02
+44 18.01
+ OH2CO2
Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 WATER 2385 Glyphosate tech 1000
2 SODIUM TUNGSTATE 5 CO2 247
3 PMIDA 1621 Aq. later to ETP 4722.8
4 SODIUM METABISULFITE 21
5 VANADIUM SULPHATE 0.4
1 H2O2 604
2 Water for washing 1333
1000 4722.8 247 0 0 0
Total 5969.4 Total 5969.8
Mesotrione Step-I The desired quantities of 1,3-cyclohexadione, EDC, acetone cyanohydrin, Triethyl amine and 2-nitro-4-methylsulfonyl benzoyl chloride under a nitrogen blanket are added in to the reactor. Heated the mass up to desired temperature until reaction is completed.
After the completion of the reaction, cool the reaction mass and water is added. pH is adjusted by sulfuric acid then layers are separated. Organic layer is washed by sodium hydroxide solution and layers are separated. Solvent is recovered from organic layer and recycled. Aqueous layer pH is adjusted by sulfuric acid, Cooled & filtered to get product. Wet cake is then dried as a finished product.
NO2
Cl
O
SO
OCH3
methyl 4-(chlorocarbonyl)-3-nitrobenzenesulfinate
263.65
+O O
cyclohexane-1,3-dione112.12
1,2 Dichloroethane
ET3N. Acetonecynohydrine
NO2 O
SO
OCH3
O
O
methyl 4-[(2,6-dioxocyclohexyl)carbonyl]-3-nitrobenzenesulfinate
339.32
+ ClH36.46
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg)
Waste
Water
Air Emission (kg)
Recovery (kg)
Solvent Loss (kg)
Solid/Hazardous Waste (kg)
1 1,3-
cyclohexadione
387 30% HCl 430
2 Ethylene Dichloride 9000 Mesotrion
e 1000
3 Acetone Cyanohydrin 107 EDC
recovered 8940 4 Triethylamine 100 EDC loss 60
5
2-nitro-4-methylsulfonyl
benzoyl chloride
914 Aq. layer
4935
6 Water 3300 Drying loss 182
7 Sulfuric acid sol. 835 Organic
residue 96
8 10% Sodium hudroxide sol. 1000
1430 4935 182 8940 60 96
Total 15643 Total 15643
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Penoxsulam Process description
To the mixture of trizolopyrimidine amine, DMSO and pyridine was added substituted benzene sulphonyl chloride and reaction mixture was stirred for 8h. After completion of reaction DMSO is distilled out completely. To the crude mixture water was added, stirred and filtered. Filtrate was dried completely to afford desired product as penoxsulam.
NN
N
N
OCH3
OCH3
NH2
5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine195.18
+
S
OF
F
F
FFO
O
Cl
+N
2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride324.65
pyridine70.1
DMSO
NN
N
N
OCH3
OCH3
NH S
O
F
F
FFF
O
O
2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide
483.37
+N
ClH
pyridine hydrochloride
115.56
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 Trizolopyrimidine amine 404 Penoxsulam 1000
2 Sulphonyl chloride 672 Water to
ETP 1160
3 Pyridine 164 DMSO recovery 1930
4 DMSO 2020 DMSO loss 90 5 Water 1000 Drying loss 80
1000 1160 80 1930 90 0 Total 4260 Total 4260
Pretilachlor Step-I In the first step, 2,6‐Diethylanilie ( DEA ) is taken excess in a reactor and is reacted with
Propoxychloroethane at reflux temperature for 20 hours. After completion of the reaction, the mass is neutralized by caustic and the aqueous is separated. The organic is taken for the recovery of the excess DEA and the product N‐Propoxyethyl‐2,6‐diethylaniline (PEDA) is vacuum distilled.
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CH3CH3
NH2
2,6-diethylaniline
149.23
+CH3
OBr
1-(2-bromoethoxy)propane167.04
Na2CO3/water CH3CH3
NH CH3
O
+ BrH
2,6-diethyl-N-(2-propoxyethyl)aniline235.36
80.91
BrH80.91 x 2 = 161.82
+ Na2CO3106
NaBr + CO2 H2O22
102.89 x 2 = 205.78 44+
18.01
Step-II In the second step, the step 1 product PEDA is reacted with chloroacetylchloride in presence of solvent N-hexane at room temperature. After the reaction, the acid HCl is neutralized and the product is washed with water and the solvent is distilled and the product is packed as technical Pretilachlor.
CH3CH3
NH CH3
O
2,6-diethyl-N-(2-propoxyethyl)aniline235.36
+ ClCl
O
chloroacetyl chloride112.94
TolueneCH3CH3
N CH3
OCl
O
+ ClH
2-chloro-N-(2,6-diethylphenyl)-N-(2-propoxyethyl)acetamide
(PRETILACHLOR)311.84
36.45
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Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 2,6-
diethyl aniline
1699 NaBr 222
2
1-Bromo-2-
Propoxy Ethane
466 CO2
60
3 Sodium carbonate 403 Water
distillate 25
4 Water 5300 2,6-diethyl
aniline recov
1130
5 CAC 387 2,6-diethyl aniline loss 5
6 Triethyl amine 363 Aq. to ETP 5720
7 Toluene 1500 Pretilachlor 1000
Toluene recovery 1425
Toluene loss 75
30% HCl 416
Organic residue 40
1638 5745 60 2555 80 40 Total 10118 Total 10118
Propanil Process description
Propanil tech manufacture is a single step process. It involves reaction of 3, 4‐Dichloroaniline (DCA) with propionic acid at 140‐150°C. Water is formed during the course of reaction.
Excess propionic acid and azeotropic water are removed. The residual mass thus obtained in molten state is Propanil technical. Chemical
NH2
Cl
Cl
3,4-dichloroaniline162
+O
CCH2
CH3OH
propanoic acid74.07
NH
Cl
Cl C
O
CH2 CH3
+ OH2
N-(3,4-dichlorophenyl)propanamide(PROPANIL)
218.07
18.01
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product (kg)
Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 3,4‐DCA 747 Propanil 1000
2 Propionic acid 404 Water distillate 80
Process loss 71
1000 80 71 0 0 0
Total 1151 Total 1151
Propaquizafop
Process description Thionyl chloride was added to the stirred solution of (R)-2-(4-((6-chloroquinoxalin-2-yl)oxy) phenoxy)propanoic acid in toluene and stirred for few hours. After completion of reaction toluene was distilled out. Into this DMF and propan-2-one O-(2-hydroxyethyl) oxime was charged, pyridine was added slowly into this reaction and stirred for 6h. After completion of reaction DMF was distilled completely and crude mixture was treated with water. White solid was filtered and dried to get desired product.
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N
N O
OCH3
OOH
CH3
344
+
OH
O
CH3
N
CH3
2-[(propan-2-ylideneamino)oxy]ethanol117.14
(R)
N
N
OCH3
OO N
OCH3
Cl
O CH3
(R)+ SO2 + C5H5N.HCl
443
64 115
Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product (kg)
Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 Carboxylic acid 777 Propaquizafop 1000
2 Alcohol 265 Toluene recovered 2960
3 Thionyl chloride 269 Toluene loss 148
4 Pyridine 178 DMF recovery 3690 5 DMF 3885 DMF loss 195 6 Toluene 3108 Water to ETP 2300 7 Water 2000 Drying loss 189
1000 2300 189 6650 343 0 Total 10482 Total 10482
Sulfentrazone
STEP I: Intermediate – I A mixture of phenyl hydrazine, acetaldehyde, sodium cyanate and acetic acid in solvent methanol was chlorinated using chlorine gas over a period of 6 – 8 hours at 50 – 55 °C. Product of this step (Intermediate I) was filtered after recovery of methanol under reduced pressure.
NH NH2
+ CH3CHO +
phenylhydrazine108.14
NaOCN + CH3COOHMethanol/Cl2
N
NNH
O
CH35-methyl-2-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one
175.18Intermediate-I
STEP II : Intermediate – II A mixture of intermediate - I in solvent dimethyl formamide and potassium carbonate was heated to 175 – 180°C. Freon 22 gas was purged for 3 – 4 hours. The mass was cooled to 50 – 60°C and the resultant solid was filtered. Chlorine gas was purged to the filtrate over a period of 4 – 5 hours maintaining the temperature of the mass at 65 – 75°C. Solvent dimethyl formamide was distilled off under reduced pressure, residue quenched in water and filtered to give Intermediate – II.
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DMF/Cl2N
NNH
O
CH3
5-methyl-2-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one
175.18Intermediate-I
+ CHF2ClFreon gas
K2CO3+ N
NN
O
CH3
ClCl
CHF2
294.08Intermediate-II
2-(2,4-dichlorophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
STEP III : Intermediate – III Nitric acid was charged to a mixture containing Intermediate – II in solvent dichloroethane and oleum at ambient temperature. The mass was quenched in water & the resultant product (Intermediate – III) was obtained by filtration. Solvent dichloroethane recovered during the process was recycled.
N
NN
O
CH3
ClCl
CHF2
294.08Intermediate-II
+ H2SO4 + HNO3 N
NN
O
CH3
ClCl
O2NCHF2
339.08Intermediate-III
2-(2,4-dichlorophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
2-(2,4-dichloro-5-nitrophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
STEP IV: Intermediate – IV A solution containing intermediate – III in solvent isopropyl alcohol (IPA) and Pd/C catalyst was pressurized using hydrogen at 70 – 80°C for a period of 10 – 11 hours. The mass was cooled to 50 – 60°C & Pd/C Catalyst was filtered off and recycled. Solvent IPA was distilled, residue was quenched in water and the product (Intermediate-IV) was obtained by filtration.
N
NN
O
CH3
ClCl
O2NCHF2
339.08Intermediate-III
5% Pd/CIPA, H2 N
NN
O
CH3
ClCl
NH2 CHF2
309.1Intermediate-IV
2-(2,4-dichloro-5-nitrophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
2-(5-amino-2,4-dichlorophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
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STEP V: Sulfentrazone A mixture of Intermediate – IV, toluene and pyridine was charged to the reactor. Mixture was heated to 50 - 60°C and methane sulfonyl chloride was charged. Reaction was subjected to a series of extractions. Pyridine was recovered by extraction with dichloromethane. Toluene was distilled and the residue was quenched in water and filtered to yield Sulfentrazone technical. Recovered toluene was recycled in subsequent batches.
N
NN
O
CH3
ClCl
NH2 CHF2
Intermediate-IV
CH3SO2Cl+Pyridine
Toluene N
NN
O
CH3
ClCl
NH
SO2CH3
CHF2
309.1 SULFENTRAZONE387.19
2-(5-amino-2,4-dichlorophenyl)-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
N-{2,4-dichloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]phenyl}methanesulfonamide
Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-
Product (kg)
Waste Water
Air Emission (kg)
Recovery (kg)
Solvent
Loss (kg)
Solid/Hazardous Waste
(kg)
1 Phenyl hydrazine 765 Methanol recovered 3788
2 Acetaldehyde 376 Methanol loss 344.5
3 Sodium cyanate 530 Aqueous effluent
38815.2
4 Chlorine 530
Scrubbed NaOH
solution (containing
sodium hypochlorite
)
2472
5 Acetic acid 500 Drying loss 805.3
6 20% NaOH solution 500 DMF recovered 6578.5
7 Methanol 4000 DMF loss 132.5
8 Water 36685 Dichloroeth
ane recovered
4352.85
9 Potassium carbonate 900 Dichloroeth
ane loss 580.7 10 Dimethyl formamide 7550 Spent acid 10291.6
11 Dichlorodifluoromethane 650 IPA
recovered 2566.75 12 Chlorine gas 1778 IPA loss 606.1
13 10% sodium hydroxide 1000 Catalyst Pd
/ C 63.2
14 Oleum 4450 Sulfentrazone 1000
15 Nitric acid 385.5 Toluene recovered 4599.9
16 Dichloroethane 2620 Toluene loss 498.4
17 Isopropyl alcohol 6415 Pyridine recovered 441.5
18 Catalyst Pd / C 63.2 Pyridine loss 49.1
19 Methane sulfonyl chloride 689
20 Pyridine 490.6
21 Toluene 4983.8
22 Dichloromethane 2125
11291.6 41287.2 805.3 22327.5 2211.
3 63.2
Total 77986.1 Total 77986.1
INSECTICIDE Chlorantraniliprole
Process description The desired quantities of 2-amino-5-chloro-N,3-dimethylbenzamide, Toluene, 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride and Triethyl amine are charged in to the reactor and stirred at desired temperature until reaction is over.
Once the reaction is completed, water is added in to the reaction mass, Heat the mass up to desired temperature then layers are separated, Organic layer is cooled and the product is isolated by filtration and Solvent is recovered from ML for recycle.
Chemical Reaction
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NH2
CH3Cl
ONHCH3
2-amino-5-chloro-N,3-dimethylbenzamide
198.65
+N
NN
Cl
Br
Cl
O
3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride
320.95
NH
CH3Cl
ONHCH3
N
NN
Cl
Br
O
3-bromo-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide
483.14
+ ClH
36.46
Process Flow Diagram
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Mass Balance
S. No.
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1
2-amino-5-chloro-N,3-
dimethyl benzamide
440 Chlorantraniliprole 1000
2
3-bromo-1-(3-
chloropyridin-2-yl)-1H-
pyrazole-5-carbonyl chloride
706 Aq. layer to ETP 2255
3 Triethyl amine 225 Toluene
recovered 2990
4 Toluene 3150 Toluene loss 160
5 Water 2300 30% HCl 270
Drying loss 146
1270 2255 146 2990 160 0
Total 6821 Total 6821
Cyantraniliprole Process description
The desired quantities of Xylene, 2-amino-5-cyano-N,3-dimethylbenzamide, 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride and Triethyl amine are charged in to the reactor. The reaction mass is stirred at the desired temperature until reaction is over. Once the reaction is completed, water is added in to the reaction mass and heated up to desired temp., then layers are separated, Organic layer is cooled to isolate the product by filtration and dried the product. solvent is recovered from Organic ML and reused.
Chemical Reaction
CH3
ONHCH3
NH2
N
+N
NN
Cl
Br
Cl
O
3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride
320.95
+ ClH
36.46
2-amino-5-cyano-N,3-dimethylbenzamide
189.21
CH3
ONHCH3
NH
N
N
NN
Cl
Br
O
3-bromo-1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-1H-pyrazole-5-carboxamide
473.71
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1
2-amino-5-cyano-N, 3-
dimethyl benzamide
430 Cyantraniliprole 1000
2
3-bromo-1-(3-
chloropyridin-2-yl)-1H-
pyrazole-5-carbonyl chloride
725 Aq. layer to ETP 2455
3 Triethyl amine 230 Xylene
recovered 3150
4 Xylene 3320 Toluene loss 170
5 Water 2500 30% HCl 275
Drying loss 155
1275 2455 155 3150 170 0
Total 7205 Total 7205
Flubendiamide
Step-1: Preparation of N-(1, 1-Dimethyl-3-Methylthioethyl)-3-Iodo-Phthalamic Acid
It is prepare from 3- Iodophthalic Anhydride and 1, 1-Dimethyl-2-Methylthioethylamine using Dimethylacetamide (DMA) as solvent in presence of Triethylamine. The reaction mixture is stir for 1.0 hr at room temperature. After completion of reaction, the solvent is remove under reduced pressure.
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Step-2: Preparation of 3-(1, 1-Dimethyl-2-Methylthioethylimino)-4-Iodo-3H-Isobenzofuran-1-one It is prepare from N-(1, 1-Dimethyl-3-Methylthioethyl)-3-Iodo-Phthalamic Acid and Trifluoroacetic Anhydride using Toluene as solvent. The reaction mixture is stir for 30 min at room temperature. The solvent is remove under reduced pressure to obtain the product.
Step-3: Preparation of N2-[1, 1-Dimethyl-2-(Methylthio) ethyl]-3-Iodo-N1-[2- Methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl) ethyl] Phenyl]-1,2-Benzenedicarboxamide It is prepare by reacting of 3-(1, 1-Dimethyl-2-Methylthioethylimino)-4-Iodo-3H-Isobenzofuran- 1-one and 4- Heptafluoroisopropyl-2-Methylaniline using Acetonitrile as solvent in presence of Trifluoroacetic Acid as a catalyst. The reaction mixture is stir for 3.0 hrs. The precipitate is collect by filtration and dry the product.
OR
O
O
O
I
H2NS
OR
Et3N
I
NH S
O
COOH
OR
Mol. Wt.: 393.24
+
Mol. Wt.: 274.01
4-Iodo-2-Benzofuran-1,3-Dione 3-Iodo-2-{[2-Methyl-1-(Methylsulfanyl)Propan-2-yl]Carbamoyl}Benzoic Acid
Mol. Wt.: 119.23
2-Methyl-1-(Methylsulfanyl)Propan-2-Amine
1,1-Dimethyl-2-Methylthioethylamine3-Iodopthalic Anhydride N-(1,1-Dimethyl-3-Methylthiomethyl)-3-Iodo-pthalamic Acid
I
NH S
O
COOH
(CF3CO)2O
Mol. Wt.: 393.24
OR OR
Mol. Wt.: 375.23
O
N
O
I
S2CF3COOH
3-Iodo-2-{[2-Methyl-1-(Methylsulfanyl)Propan-2-yl]Carbamoyl}Benzoic Acid
+
(3Z)-4-Iodo-3-{[2-Methyl-1-(Methylsulfanyl)Propan-2-yl]Imino}-2-Benzofuran-1(3H)-One
Mol. Wt.: 210.03
Trifluoroacetic Anhydride
N-(1,1-Dimethyl-3-Methylthiomethyl)-3-Iodo-pthalamic Acid
3-(1,1-DImethyl-2-Methylthioethylamino-4-Iodo-3H-Isobenzofuran-1-One
+
Mol. Wt.: 228.04
Trifluoroacetic Acid
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Step-4: Preparation of N2-[1, 1-Dimethyl-2-(methylsulfonyl) ethyl]-3-iodo-N1-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl) ethyl]phenyl]-1,2-benzenedicarboxamide (Flubendiamide) It is prepared by oxidation of N2-[1, 1-Dimethyl-2-(Methylthio) ethyl]-3-Iodo-N1-[2- Methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl) ethyl] Phenyl]-1,2-Benzenedicarboxamide with M-Chloroperbenzoic Acid (MCPBA) using Dichloromethane (DCM) as solvent. The reaction mixture is then stir for 3.0 hrs at room temperature. The solvent is remove under reduced pressure.
O
N
O
IS H3C
H2N
CF3
CF3
FCF3COOH
OR
Mol. Wt.: 375.23
OR
I
S
CF3
F3CF
HN
NH
O
O
Mol. Wt.: 650.39
CF3COOH
N2-[1,1-Dimethyl-2-(Methylthio)Ethyl]-3-Iodo-N1-[2-Methyl-4-[1,2,2,2-Tetrafluoro-1-(Trifluoromethyl)Ethyl]Phenyl]-1,2-Benzenedicarboxamide
(3Z)-4-Iodo-3-{[2-Methyl-1-(Methylsulfanyl)Propan-2-yl]Imino}-2-Benzofuran-1(3H)-One
4-[1,1,1,2,3,3,3-Heptafluoropropane-2-yl]-2-Methylaniline
Mol. Wt.: 275.17 Mol. Wt.: 114.02
+ +
(Catalyst)
4-Heptafluoropropyl]-2-Methylaniline3-(1,1-DImethyl-2-Methylthioethylamino-4-Iodo-3H-Isobenzofuran-1-One
Trifluoroacetic Acid
Mol. Wt.: 114.02
+
Trifluoroacetic Acid
I
S
CF3
F3CF
HN
NH
O
O
COOOH
Cl
Mol. Wt.: 650.39 Mol. Wt.: 345.14 Mol. Wt.: 682.39
O
O
CF3
OI
HN
NH
S
F3CF
O COOH
Cl
Mol. Wt.: 313.14
+
N2-[1,1-Dimethyl-2-(Methylthio)Ethyl]-3-Iodo-N1-[2-Methyl-4-[1,2,2,2-Tetrafluoro-1-(Trifluoromethyl)Ethyl]Phenyl]-1,2-Benzenedicarboxamide
N2-[1,1-Dimethyl-2-(Methylsulfonyl)Ethyl]-3-Iodo-N1-[2-Methyl-4-[1,2,2,2-Tetrafluoro-1-(Trifluoromethyl)Ethyl]Phenyl]-1,2-Benzenedicarboxamide
Flubendiamide
2.
M-Chloroperbenzoic Acid
2.
M-Chlorobenzoic Acid
+
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Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name Qty (kg)
Output Material Name
Product (kg)
Waste
Water
Air Emissio
n (kg) Recover
y (kg) Solvent Loss
(kg)
Solid/Hazardous
Waste (kg)
1
N2-[1, 1-Dimethyl-2-(Methylthio) ethyl]-3-Iodo-N1-[2- Methyl-4-[1,2,2,2- tetrafluoro-1-(trifluoromethyl) ethyl]
Phenyl]-1,2-Benzenedicarboxamid
e
1415
3-(1, 1-Dimethyl-2-Methylthioethylimino)-
4-Iodo-3H-Isobenzofuran-1-one
1357
2 1,1-Dimethyl-2-Methylthioethylamine 768 Flubendiamide 1000
3 3- Iodophthalic Anhydride 1768 M-Chlorobenzoic Acid
(MCBA) 510
4
3-(1, 1-Dimethyl-2-Methylthioethylimino)-
4-Iodo-3H-Isobenzofuran-1-one
1357 N-(1, 1-Dimethyl-3-Methylthioethyl)-3-
Iodo-Phthalamic Acid 2032
5 4-
Heptafluoroisopropyl-2-Methylaniline
503
N2-[1, 1-Dimethyl-2-(Methylthio) ethyl]-3-Iodo-N1-[2- Methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl) ethyl]
Phenyl]-1,2-Benzenedicarboxamid
e
1415
6 Acetonitrile 4605 Process Losses 2687 7 Dichloromethane
(DCM) 8581 Recovered Acetonitrile 4500
8 Dimethylacetamide (DMA) 6647 Recovered DCM
(Dichloromethane) 8405
9 M-Chloroperbenzoic Acid (MCPBA) 548 Recovered DMA
(Dimethylacetamide) 6315
10 N-(1, 1-Dimethyl-3-Methylthioethyl)-3-
Iodo-Phthalamic Acid 2032 Recovered
Triethylamine 123
11 Toluene 5587 Removed Toluene 5510 12 Triethylamine 129 Trifluoroacetic Acid 1178 13 Trifluoroacetic Acid 7 14 Trifluoroacetic
Anhydride 1085 15 13002 0 0 19343 2687 0
Total 35032 35032
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Nitenpyram Step-I Synthesis of Vinylidene Chloride
Elimination reaction to 1,1,2-trichloroethane as a starting material, hydrogen sodium hydroxide solution the reaction was carried out at -15 ° C~100 ° C elimination reaction, to give vinylidene chloride, the reaction equation:
CH CH2 ClCl
ClNaOH
1,1,2-trichloroethane133.4
C CH2Cl
Cl
1,1-dichloroethene96.94
+ OH2 Na Cl+58.4418.01
Step-2 Synthesis of 1,1,1- trichloro-2-nitroethane the nitration reaction, the vinylidene chloride in the presence of a catalyst Al, nitrification reaction with nitric acid and hydrochloric acid, to give 1,1,1- trichloro-2-nitroethane was isolated and purified after the reaction, reaction equation:
C CH2Cl
Cl
1,1-dichloroethene96.94
HNO3
C CH2Cl
Cl
Cl
NO2
1,1,1-trichloro-2-nitroethane178.4
+ OH2
18.01HCl
63.01
36.46
Step-3 Synthesis of Intermediate N-ethyl-2-chloro-5-pyridyl methyl amine N- alkylation reaction with 2-chloro-5-chloromethyl pyridine starting materials, water as solvent, at -10~50 ° C, and triethylamine phase transfer catalyst under reaction A2, the reaction product was desolventized, alkali washing, distillation of the intermediate N - ethyl-2-chloro-5-pyridyl methyl amine, reaction equation:
NCl
CH2Cl
2-chloro-5-(chloromethyl)pyridine162.01
+ CH3 CH2 NH2
ethanamine45.08
NCl
CH2 NH CH3CH2
N-[(6-chloropyridin-3-yl)methyl]ethanamine
170.64
+ ClH36.46
Step-4 Synthesis of Intermediate I- chloro -N- {(6 - pyridin-3-chloro) methyl} -N- ethyl-2-nitroethylene-amine condensation reaction of the ethyl-2-chloro-5-pyridin-N- methylamine with said I, I, I- trichloro-2-nitroethane in a methylene chloride solvent, acid binding agent is added, in the A3 phase transfer catalyst, at -10~50 ° C, the reaction to give a condensate I- chloro -N- {(6 - pyridin-3-chloro) methyl} -N- ethyl-2-nitroethylene-amine, reaction equation:
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NCl
CH2 NH CH3CH2
N-[(6-chloropyridin-3-yl)methyl]ethanamine
170.64
+ C CH2Cl NO2
Cl
Cl
1,1,1-trichloro-2-nitroethane
178.4
NCl
CH2 N CHC
C2H5
Cl
NO2
1-chloro-N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-2-nitroethenamine
276.11
+ 2 HCl72.92
Step-5 Synthesis of Nitenpyram
methylamino reaction, the a group of reaction with said condensation reaction is carried out in the same reaction pot, after completion of the condensation reaction to give a condensate I- chloro -N - {(6- chloro-Jie ratio given -3- Jie) methyl } -N_ ethyl-2-nitro-vinylamine, then at -10~50 ° C, aqueous methylamine was added dropwise, the reaction product was extracted, desolventized, recrystallized nitenpyram, reaction equation :
NCl
CH2 N CHC
C2H5
Cl
NO2
1-chloro-N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-2-nitroethenamine
276.11
NCl
CH2 N CHC
C2H5
NH
NO2
CH3CH3 NH2+methanamine
31.05
+ ClH36.46
N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-N'-methyl-2-nitroethene-1,1-diamine
270.7
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Process Flow Diagram
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Mass Balance
Sr.No
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name Qty(kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 1,1,2- trichloroethane 940 NaCl
recovered 421
2 NaOH 282 Water to ETP 5532
3 water 5340 30% HCl 2879
4 HCl 30% 764 Methylene chloride
recovered 1160
5 HNO3 396 Methylene chloride
loss 40
6 2-chloro-5-
chloromethyl pyridine
950 nitenpyram 1000
7 Ethyl amine 265 Process loss 63
8 20% NaOH 800
9 Methylene chloride 1200
10 methane amine 158 3879 5532 63 1581 40 0
Total 11095 Total 11095
Pymetrozine Process description
Charge 3-Pyridine carboxaldehyde, 1,2,4-Triazine-3(4H)-1,4-Amino-5,6-dihydro-6-methyl
and toluene in a reactor under stirring. Raise the temperature to 65°C and maintain for 6 hrs.
Once the reaction completes, distil half of the toluene and cool to crystallize the mass.
Centrifuge and dry the crude mass to get technical grade Pymetrozine. Recover the toluene
from the ML by distillation.
N
H
O
pyridine-3-carbaldehyde107.11
+N
NH
N
NH2
O
CH3
4-amino-6-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one
128.13
Toluene N
NH
N
N
O
CH3N
H
+ OH2
6-methyl-4-[(pyridin-3-ylmethylidene)amino]-4,5-dihydro-1,2,4-triazin-3(2H)-one
217.22
18.01
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product (kg)
Waste
Water
Air Emissio
n (kg) Recover
y (kg) Solvent Loss (kg)
Solid/Hazardous Waste (kg)
1 3 Pyridine
Carboxaldehyde
519 Pymetrozone 519
2
1,2,4 Triazine-3 (4H) 1,4 -
Aamino-5,6 -(Dihydro-6-
Methyl)
639 Water recovered 639
3 Toluene 2000
Toluene recovered 2000
4 Water for washing
1500 Toluene loss 1500
519 0 0 2639 1500 0
Total 4658 Total 4658
Spirodiclofen
Step I: 1-cyano-cyclohexanol
Preparation of 1-cyano-cyclohexanol Under mechanical stirring, was added 748 kg of cyclohexanone in 500ml three-necked flask, 296 holding temperature of sodium cyanide, in 1000 lit of water, ice bath at 5-10 ° C, was slowly added dropwise 40% sulfuric acid solution, addition time holding tank, after the completion of the dropwise addition stirring was continued for 30min, the product was extracted with ethyl acetate, the combined ethyl acetate layer was washed with water, dried over anhydrous over sodium sulfate, and concentrated to give 820 kg of liquid product, 86.0% yield, was used without purification in the next reaction.
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O
98.14
NaCNOH CN
125.16cyclohexanone 1-hydroxycyclohexanecarbonitrile
Step II: Intermediate – II ( 2,4- dichloro phenylacetyl chloride) added to the reaction flask 1926 kg 2,4- dichloro-phenylacetic acid and thionyl chloride 2300 kg heated 75-100 C The reaction was stirred at reflux for 4h, thionyl chloride was distilled off under reduced pressure to give a yellow liquid 2074 kg, 98. 8% yield.
Cl
Cl
COOH
(2,4-dichlorophenyl)acetic acid205.03
S
O
ClCl
thionyl dichloride
118.97
Cl
Cl
O
Cl
(2,4-dichlorophenyl)acetyl chloride223.48
+ ClH + SO2
36.46 64.06
Step III: Intermediate – III (2,4-dichloro-1-cyano-acid cyclohexyl ester) A reaction flask was added dropwise 2074 kg 2,4 dichlorophenylacetyl chloride (Intermediate-II) and 4148 kg dichloromethane under 820 kg crude cyclohexanol cyano (Intermediate-I), pyridin-1442 kg of, 6222 kg dichloromethane, ambient conditions mixture was left Ih addition was complete, the reaction and stirring was continued for 12h, 10370 3% hydrochloric acid solution was added and extracted 3 times with ethyl acetate, the ethyl acetate layer was washed with 5% sodium carbonate solution twice, and finally washed with water, then dried over anhydrous sodium sulfate, and concentrated to give a brown paste 2406 kg, it was used directly without purification in the next step.
OH CN
1-hydroxycyclohexanecarbonitrile
125.16
+O
Cl
Cl
Cl
(2,4-dichlorophenyl)acetyl chloride223.48
O
O
Cl
Cl CN
1-cyanocyclohexyl (2,4-dichlorophenyl)acetate
312.19
+ ClH
36.46
Step IV: Intermediate – IV
Add 2,4-dichloro acid 1-cyano-cyclohexyl ester 2406 reaction flask crude sulfuric acid and methanol 16043 kg (1003 kg sulfuric acid, methanol 15040 kg ), was heated to reflux and stirred for 60-80 ° C, the reaction 2¾ so, after most of the methanol was distilled off, wait a cooled 40 ° C was added 50ml of water, the product was extracted three times with ethyl acetate, ethyl acetate layers were combined, washed with 5% sodium bicarbonate solution
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three times and then washed with water, dried over anhydrous sodium sulfate, and concentrated to give crude product 1772 kg, it can be used in the next reaction without purification.
O
O
Cl
Cl CN
1-cyanocyclohexyl (2,4-dichlorophenyl)acetate
312.19
+ CH3 OH
methanol32.04
O
O
Cl
Cl CH3COOH
INTERMEDIATE-IV
346.52
1-[2 [(2,4-dichloro-phenyl)-2-acetoxy]-1-cyclohexane carboxylic acid methyl ester
Step V: Intermediate – V 3- (2,4-dichlorophenyl) -2-oxo-1-oxa-spiro W. 5] - Preparation of decyl alcohol _3_ alkenyl _4_ , [0019] 1772 kg- reaction flask was added [2_ (2,4-dichloro - phenyl) - acetoxy] - cyclohexanecarboxylic acid methyl ester group and 399 kg of magnesium ethoxide in 4000 kg ethanol, -5 to 10 ° C reaction 14h. 45. 3%。 After most of the solvent was distilled off, 11075 kg of 5% hydrochloric acid was added, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated to give solid crude product 1220 kg, 95% after recrystallization from ethanol to give product 1174 The above 3 steps 45.3% overall yield.
O
O
Cl
Cl CH3COOH
INTERMEDIATE-IV
346.52
1-[2 [(2,4-dichloro-phenyl)-2-acetoxy]-1-cyclohexane carboxylic acid methyl ester
O
OHCl
ClO
3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one
313.17
base
Step VI: Spirodiclofen A reaction flask at room temperature was added 927 kg 3- (2,4_ dichlorophenyl) _2_ oxo-oxa-spiro [4.5] - dec-3-ene-4- ol), 1000 kg triethylamine, 2000 kg dichloromethane, 663 kg 2,2- dimethylbutyryl chloride was added dropwise, with stirring at room temperature the reaction cell. The reaction solution was washed 3 times with hydrochloric acid, then twice with saturated sodium bicarbonate solution, and finally washed twice with water, dried over anhydrous sodium sulfate, and concentrated to give a solid product 5. Sg, after recrystallization from 95% ethanol to give 1000 kg product, yield 94.0%, content of 98. 4%
O
OHCl
ClO
3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one
313.17
+ CH3
Cl
O
2,2-dimethylbutanoyl chloride134.6
O
OCl
ClO
411.36
Spirodiclofen
+ ClH
36.46
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Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg)
Waste
Water
Air Emissio
n (kg) Recover
y (kg)
Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 2,2-
dimethylbutyryl chloride
400 Aq to ETP
15052
2 2,4- dichloro-phenylacetic
acid 565 Dichloroethane
loss 60
3 3%
hydrochloric acid solution
1500 Dichloroethane recovered
3020
4 5%
hydrochloric acid
1000 dichloromethane loss
50
5 5% sodium bicarbonate 1000 Dichlorometha
ne recovered 1950
6 5% sodium carbonate solution
1800 Ethanol loss
150
7 Cyclohexanone 340 ethanol
recovered 3350
8 Dichloromethane 5080 Ethyl acetate 1440
9 Ethanol 3500 Ethyl acetate loss 150
10 Ethyl acetate 5240 Ethyl acetate recovered 2910
11 hydrochloric acid 1000 HCl gas 308
12 magnesium ethoxide 232 Methanol
recovered 2400 13 Methanol 2500 Process loss 9 14 Pyridine 762 SO2 176
15 sodium
bicarbonate solution
2000 Spirodiclofen 1000
16 sodium cyanide 170
Thionyl chloride recovery
340
17 Sulphuric acid 450
18 Thionyl chloride 676
19 Triethylamine 1000 20 Water 3150
2440 1505
2 484 13970 419 0
Total 32365 Total 32365
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Spirotetramet
Step I: 1-Intermediate-I
1,4-dioxaspiro[4,5]decan-8-one reacts with Potassium cyanide and ammonium carbonate in presence of Methanol and water at 60 C and then neutralize with HCl at 0 C to get Intermediate-I
O O
O1,4-dioxaspiro[4.5]decan-8-one
156.18
+ Na C NSodium cyanide
49
+ (NH4)2CO3
Ammonium carbonate96
MeOH/water
HCl
O O
NHO
NH O
9,12-dioxa-1,3-diazadispiro[4.2.4.2]tetradecane-2,4-dione226.23
+ NaCl + NH4Cl58.44 53.49
Step II: Intermediate – II Intermediate-I under hydrolysis with 3N NaOH gives Intermediate-II
3 N NaOH to pH 6
O O
NHO
NH O
9,12-dioxa-1,3-diazadispiro[4.2.4.2]tetradecane-2,4-dione
226.23
reflux
O O
NH2
O
OH
8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylic acid201.2
Step III: Intermediate – III Intermediate-II react with methanol in acidic condition to geies Intermediate-III
Dry HCl
reflux
O O
NH2
O
OH
8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylic acid
201.2
O O
NH2
O
OCH3
+ CH3 OH
methanol32.04
methyl 8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylate215.24
+ OH2
18
Step IV: Intermediate – IV
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Intermediate-III react with (2,5-dimehtlphenyl)acetyl chloride using solvent Acetonitrile to give Intermediate-IV
Acetonitrile
K2CO3
O O
NH2
O
OCH3
methyl 8-amino-1,4-dioxaspiro[4.5]decane-8-carboxylate
215.24
+ CH3 CH3
O
Cl
(2,5-dimethylphenyl)acetyl chloride182.64
CH3
CH3
NHO
O
O OCH3O
Intermediate IV361.43
138.2
+ ClH36.46
k2CO3 + 2 HCl 2 KCl + CO2 + OH2
138.2 72.92 149.1 44 18.01
Step V: Intermediate – V Intermediate-IV undergo rearrangement in the presence of DMF and Potassium t-Butoxide to produce Intermediate-V
DMF
CH3
CH3
NHO
O
O OCH3O
Intermediate IV361.43
CH3
CH3
NH
O
O
O
OH
329.39
CH3 OH
32.04
t-BuOK+
11-(2,5-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one
methanol
Step VI: Intermediate-VI Intermediate-V under go refulux in presence of 4N HCl, to produce Intermediate-VI
Reflux
CH3
CH3
NH
O
O
O
OH
329.39
4N HCl
11-(2,5-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one
CH3
CH3
NH
O
O
OH +
O
oxirane
44.05
3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione
285.33Step VII: Spirotetramet
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Intermediate-V under go refulux in presence of 4N HCl, to produce Intermediate-VI
CH3
CH3
NH
O
O
OH
285.33
CH3
O
Cl
78.5
CH3
CH3
NH
O
O
O
OCH3
ClH
327.37
(SPIROTETRAMET)
36.46
HCl NaOH NaCl OH2
36.46 40 58.44 18.01
3-(2,5-dimethylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione
+
acetyl chloride
+
3-(2,5-dimethylphenyl)-2,8-dioxo-1-azaspiro[4.5]dec-3-en-4-yl acetate
DCM, TEA
4-DMAP
+ +
Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name Qty (kg)
Output Material Name
Product (kg)
Waste Water
Air Emission
(kg) Recover
y (kg)
Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 (2,5-
dimehtlphenyl)acetyl chloride
676 Acetonitrile recovered
2200
2 1,4-
dioxaspiro[4,5]decan-8-one
628 Ammonium chloride 204
3 20% NaOH in scrubber 680 Aq to ETP 2415
4 3N NaOH 1500 CO2 128
5 4-dimethylaminopyridine 20 DCM
recovered 3000 6 4N HCl 1500 DMF loss 50
7 Acetonitrile 2200 DMF recovered 2450
8 Acetyl chloride 272 Filtrate to ETP 3432
9 Ammonium carbonate 284 KCl 524
10 Dichloromethane 3000 Methanol loss 110
11 DMF 2500 Methanol recovered 3910
12 Dry HCl 140 ML to ETP 664 13 HCl gas 488 NaCl 664
14 K2CO3 510 Oxirane recovered 140
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Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name Qty (kg)
Output Material Name
Product (kg)
Waste Water
Air Emission
(kg) Recover
y (kg)
Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
15 Methanol 3900 Process loss 137
16 NaOH solution in scrubber 160 Spirotetramet 1000
17 Potassium t-Butoxide 100 Water recovered 66
18 Sodium Cyanide 196 19 TEA 200 20 Water 2140 2392 6511 128 11766 297 0
Total 21094 Total 21094
Thiamethoxam The desired quantities of DMC (solvent), 2-chloro-5-chloromethyltriazole, 3-Methyl 1-1-Nitroimino-perahydrooxadiazine and Catalyst are charged along with K2CO3 into the reactor. The stirred mixture is heated to reaction temp till the whole reactants reached to desired level.
Once the reaction is over, the reaction mass pH is adjusted with HCl & Water. The excess solvent from organic layer is recovered for re-cycling & the product is cooled, filtered & dried.
Chemical reaction
S
NCl
Cl
2-chloro-5-(chloromethyl)-1,3-thiazole
168.04
+N
O
NHCH3
NNO2
(4Z)-3-methyl-N-nitro-1,3,5-oxadiazinan-4-imine160.13
S
NCl
N N
O
CH3
NNO2
(4E)-3-[(2-chloro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine
291.71
+ ClH36.46
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Process Flow Diagram
Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name Qty (kg)
Output Material Name
Product (kg)
Waste
Water
Air Emission (kg)
Recovery (kg)
Solvent
Loss (kg)
Solid/Hazardous Waste
(kg)
1 N,N Dimethyl Carbonate 4774
Thiamethoxam 1000
2 2-chloro-5- chloromethyltriazole 764 Aq. layer 5297
3 3-Methyl 1-1-
Nitroiminoperahydrooxadiazine
836 DMC recovered 4536
4 Methyl ammonium hydroxide penta hydrate 18 Residue 135
5 K2CO3 1100 Drying loss 431
6 Water 2725
7 HCl 1182
1000 5297 431 4536 0 135
Total 11399 Total 11399
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INTERMEDIATE 1,2,4 – Triazole:
Step -I: Formic Acid is reacted with dry Ammonia to form Formamide which on reaction with Hydrazine hydrate gives the final Product 1,2,4 Triazole. During the reaction ammonia & water molecules are formed in stichiometric quantities.
Chemical Reaction:
CHO
OHformic acid
46.02
+ NH3
17.03
CHO
NH2
+ OH2
formamide45.04
18.01
CHO
NH2
formamide45.04 x 2 = 90.08
+ NH2 NH2 OH2
hydrazine hydrate50.06
NH
N
N
1H-1,2,4-triazole69.06
+ OH2 + NH3
18.01 x 3 = 54.03 17.032 3
Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product (kg)
Waste Water
Air Emission
(kg) Recovery
(kg) Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 Formic Acid 85% 2000 1,2,4
Triazole 1032
2 Ammonia Gas 900 Distilled
water 983
3 Hydrazine Hydrate
80% 1000
Recovered Formic Acid
366
4 water 2315 Recovered Hydrazine Hydrate
75
Recovered Liquid
Ammonia 3759
1032 983 0 4200 0 0
Total 6215 Total 6215
2-Chloro-5-Chloromethylthiazole
Step-1: Preparation of 1, 2, 3-Trichloroprapane
It is prepare by Chlorine gas bubbled continuously into Allyl Chloride at a rate of about 5-
10 gm/hrs. under constant stir at 450C – 500C for 3-4 hrs.
Chemical Reaction:
ClCl2
Cl
Cl
Cl
Allyl Chloride 1,2,3-trichloropropane
Mol. Wt.: 76.52 Mol. Wt.: 147.43
+
Chlorine
Mol. Wt.: 2 x 35.5
45-50 0C
3-4 hrs
Step-2: Preparation of 2, 3-Dichloroprop-1-ene
2, 3-Dichloroprop-1-ene is prepared from 1, 2, 3-trichloropropane by adding slowly 25%
aqueous NaOH solution at room temperature in presence of phase transfer catalyst. The
pH is kept at about 14 and stirring is continue to overnight. The reaction progress is
monitored by GC. After completion of reaction, adding water to separate the layer and
the organic layer as well as crude is distilled the product at 69-72°C under 30 mmHg
vacuum.
Chemical reaction:
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Cl
Cl
Cl
NaOH
H2O
TEBA
Cl
Cl
NaCl H2O
2,3-dichloroprop-1-ene
Mol. Wt.: 110.97
+
1,2,3-trichloropropane
Mol. Wt.: 147.43
+
Mol. Wt.: 40
Sodium Hydroxide
+
Mol. Wt.: 58.44
Sodium Chloride
Step-3: Preparation of 2-Dichloro-3-Isothiocyanato prop-1-ene
It is prepare by reacting of 2, 3-dichloropropene with sodium thiocyanate in presence of
TEBA (Triethyl benzyl ammonium chloride as phase transfer catalyst using toluene as
solvent. The mixture is heat under reflux (about 100 ℃ to 105 ℃) for 1.5 to 2.0 hours
and then cooled to room temperature. Add water under stirring and stir for 15 min. The
reaction mixture is allow to stand for layer separation. Toluene from the organic layer is
distil under vacuum and also the residue was distilled under high vacuum. The distillate
of 2-Dichloro-3-Isothiocyanato prop-1-ene (Product) is recover as a yellow oil liquid.
Chemical reaction:
Cl
Cl
NaSCN
H2O
N C SCl
NaCl
2-chloro-3-isothiocyanato prop-1-ene
Mol. Wt.: 133.60
2,3-dichloroprop-1-ene
Mol. Wt.: 110.97
+ +
Mol. Wt.: 81.07
TEBA
100-105 0C & 1.5 to 2 hrs
[58.44]
Step-4: Preparation of 2-Chloro-5-Chloromethylthiazole (CCMT)
It is prepared by reacting of 2-Dichloro-3-Isothiocyanato prop-1-ene with Sulfuryl Chloride and toluene. The reaction mixture is warm to 45 °C and add dropwise sulfuryl chloride in 2.0 hrs at 45 ° C. and thereafter 1.0 hr the mixture was further stir at 80 °C. The toluene is distil under reduced pressure and finally product is also distil under high vacuum.
N C SCl
SO2Cl2
S
N
Cl
Cl SO2 HCl
2-chloro-5-chloromethylthiazole
Mol. Wt.: 168.04
2-chloro-3-isothiocyanato prop-1-ene
Mol. Wt.: 133.60
+
Sulfuryl Chloride
Mol. Wt.: 134.97
+ +Toluene
[64.06] [36.46]
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Process Flow Diagram
Prefeasibility Report SHREEJI PESTICIDES PVT. LTD.
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emissio
n (kg) Recover
y (kg) Solvent Loss
(kg)
Solid/ Hazardous Waste (kg)
1 Allyl Chloride 760.78 Process Loss 871.1
2 Chlorine gas 684.69 Sodium
Chloride 1018.98
3 Sodium
Hydroxide, (Flakes)
358.13 Water 2037.6
1
4 TEBA (Catalyst) 20.33 Recovered
Toluene 2034.02
5 Total Water
2126.87 Toluene Loss 239.1
6 Sodium
Thiocyanate
700.39 2-Chloro-5-
Chloromethylthiazole
1000
7 Toluene 3478.27
Sulphur Dioxide 493.86
8 Sulfuryl Chloride
1052.01
Hydrochloric Acid 281.65
Recovered
Toluene 1205.15
Total 2018.98 2319.26 1364.96 3239.17 239.1 0
Total 9181.47 Total 9181.47
3-Methyl-N-Nitroimino-Perhydro-l, 3, 5-Oxadiazine
Step-1: Preparation of N-Methyl-N’-Nitroguanidine
It is prepare by reacting of N-Nitroguanidine with aqueous Methyl Amine in aqueous
medium at 60 0C and evolved of Ammonia gas during the reaction.
NHNH2
NH
N+
O
O-
CH3NH2
Mol. Wt.: 104.07
NH NH
NH
N+
O
O-
N-Nitroguanidine
+
Methyl Amine
Mol. Wt.: 31.06
N-Methyl-N'-Nitroguanidine
Mol. Wt.: 118.09
+ NH3
Ammonia Gas
Mol. Wt.: 17
Step-2: Preparation of 3-Methyl-N-Nitroimino-Perhydro-l, 3, 5-Oxadiazine (MNIO)
3-Methyl-N-Nitroimino-Perhydro-l, 3, 5-Oxadiazine (MNIO) from N-Methyl-N’-
Nitroguanidine and Paraformaldehyde at room temperature using Formic acid (98-100%)
The reaction is carried out by refluxing the reaction mixture at 105°C -107°C for 5-6 hrs
and separate out Water with Formic acid azeotropically. Distilled out formic acid under
vacuum, add DM water and agitate for 15.0 minute at room temperature. Filter and dry
the cake at 80-90°C. Formic acid can be recycled.
Chemical reaction:
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HCHO
O N
NH
NN+
O
O-
Mol. Wt.: 160.13
OOH
N-Methyl-N'-Nitroguanidine
Mol. Wt.: 118.09
+ +
Mol. Wt.: 30.03
Formaldehyde Formic Acid
Mol. Wt.: 46.03
3-Methyl-4-Nitroimino-Perhydro 1, 3, 5-Oxadiazine
HCHO+
Mol. Wt.: 30.03
Formaldehyde
+ H2O
Mol. Wt.: 18
Water
NH NH
NH
N+
O
O-
Process Flow Diagram
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Mass Balance
Sr.no
Input(kg)/MT of Product Output/(kg) of Product
Input Material Name
Qty (kg)
Output Material Name
Product/By-Product
(kg) Waste Water
Air Emission (kg)
Recovery (kg)
Solvent
Loss (kg)
Solid/Hazardous Waste (kg)
1 N-Nitroguanidine 939.65 Water
2740.45
2 25% Aq .Methyl Amine
1358.05
Ammonia Gas 153.5
3 Water 1634.97
Process Loss 507.02
4 Paraformaldehyde 468.2
3-Methyl-N-
Nitroimino-
Perhydro-l, 3, 5-
Oxadiazine
1000
5 Formic Acid 4680.1 Recovered Formic
Acid 4586.5
Formic Acid Loss 93.5
1000 2740.45 660.52 4586.5 93.5 0
Total 9080.97 Total 9080.97
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(vi) Raw Materials & Final Products
Proposed productwise raw material details are provided in Table 3-3.
Table 3-3: Raw Material details
S.No. Product Raw Materials Consumption for (Per MT) Indigenous/Imported Transportation
Fungicide
1 Azoxystrobin
Phthalide 320 Indigenous/Imported Road/Sea Methyl Formate 142 Indigenous/Imported Road/Sea
Di Methyl Carbonate 216 Indigenous/Imported Road/Sea Sodium Hydride 58 Indigenous Road
Toluene 1400 Indigenous Road Sodium Methoxide 128 Indigenous/Imported Road/Sea
EDC 1200 Indigenous Road 4,6 – Di Chloro
Pyrimidine 352 Indigenous/Imported Road/Sea
Ortho Cyano Phenol 283 Indigenous/Imported Road/Sea Potassium Hydroxide 133 Indigenous Road
DMF 1200 Indigenous Road Water 880 Indigenous Road
2 BOSCALID
1,4-dichlorobenzene 1000 Indigenous/Imported Road/Sea Mg 170 Indigenous Road
Toluene 5000 Indigenous Road THF 3000 Indigenous Road
Trimethyl borate 710 Indigenous/Imported Road/Sea HCl 500 Indigenous Road
Water 5000 Indigenous Road 1-chloro-2-nirobenzene 1060 Indigenous/Imported Road/Sea
Catalyst 20 Indigenous/Imported Road/Sea Methanol 2500 Indigenous Road
Pd/C 20 Indigenous/Imported Road/Sea Acetonitrile 3000 Indigenous Road
PCl3 350 Indigenous Road NaOH 50 Indigenous Road
Catalyst 50 Indigenous/Imported Road/Sea XP-50 2000 Imported Road/Sea
3 Carboxin
Acetoacetanilide 1506 Indigenous/Imported Road/Sea SO2Cl2 1183 Indigenous Road
TEA 789 Indigenous Road 2‐ME 611 Imported Road/Sea PTSA 350 Indigenous Road
Benzene 8500 Indigenous Road Acetone 4000 Indigenous Road Water 8000 Indigenous Road
4 Chlorothalanil
Tetrachloro Isophthalic acid 1055 Imported Sea/Road
Toluene 2000 Indigenous Road Ammonia Solution 125 Indigenous Road
Catalyst (phosphorous pentaoxide) 20 Indigenous/Imported Sea/Road
Water 850 Indigenous Road
5 Difenconazole
1,3 Di Chloro Benzene 392 Imported/Indigenous Sea/Road Acetyl Chloride 208 Imported/Indigenous Sea/Road
Aluminium Chloride 490 Imported/Indigenous Sea/Road EDC 4800 Indigenous Road KOH 473 Indigenous Road
4- Chloro Phenol 340 Imported/Indigenous Sea/Road Di Methyl Formamide 3900 Indigenous Road
Bromine 422 Imported/Indigenous Sea/Road Catalyst 10 Imported/Indigenous Sea/Road
Propylene Glycol 198 Imported/Indigenous Sea/Road 1,2,4 – Triazole 180 Imported/Indigenous Sea/Road
Toluene 2000 Indigenous Road
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S.No. Product Raw Materials Consumption for (Per MT) Indigenous/Imported Transportation
Water 3055 Indigenous Road
6 Epoxiconazole
Fluoro Benzene 320 Imported/Indigenous Sea/Road Chloro Acetyl Chloride 375 Imported/Indigenous Sea/Road
Aluminium Chloride 400 Imported/Indigenous Sea/Road EDC 1300 Indigenous Road KOH 555 Indigenous Road
1,2,4 – Triazole 228 Imported/Indigenous Sea/Road DMF 1800 Indigenous Road
2- Chloro Benzyl Chloride 530 Imported/Indigenous Sea/Road
Di Methyl Sulphide 202 Imported/Indigenous Sea/Road Water 2440 Indigenous Road
7 Hexaconazole
1,3 Di Chloro Benzene 510 Imported/Indigenous Sea/Road Pentanoyl Chloride 417 Imported/Indigenous Sea/Road Aluminium Chloride 632 Imported/Indigenous Sea/Road
EDC 2850 Indigenous Indigenous Methylene Triphenyl
Phosphorane 944 Imported/Indigenous Sea/Road
Bromine 540 Indigenous Indigenous THF 1200 Indigenous Indigenous
Hydrogen Peroxide 116 Indigenous Indigenous KOH 178 Indigenous Indigenous
1,2,4 – Triazole 220 Imported/Indigenous Sea/Road DMF 1100 Indigenous Indigenous Water 3943 Indigenous Indigenous
8 Kresoxim Methyl
Ortho Cresol 360 Imported/Indigenous Sea/Road Phthalide 447 Imported/Indigenous Sea/Road
Potassium Hydroxide 187 Indigenous Road Xylene 1800 Indigenous Road
Thionyl Chloride 398 Indigenous Road Sodium Hydroxide 163 Indigenous Road Sodium Cyanide 172 Indigenous Road
30% Hydrochloric Acid 131 Indigenous Road Methanol 1000 Indigenous Road
Methoxy Amine 156 Imported/Indigenous Sea/Road Water 3975 Indigenous Road
9 Penconazole
2-(2,4 – dichlorophenyl) Pentyl Alcohol 905 Imported Sea/Road
Methane Sulphonyl Chloride 445 Imported Sea/Road
Sodium Hydroxide 155 Indigenous Road Toluene 1200 Indigenous Road
1,2,4 – Triazole 264 Imported/Indigenous Sea/Road Sodium Methoxide 208 Indigenous Road
DMF 1200 Indigenous Road Water 858 Indigenous Road
10 Picoxystrobin
3 - Iso Chromanone 445 Imported Sea/Road Methyl Formate 180 Imported/Indigenous Sea/Road
Di Methyl Carbonate 270 Imported/Indigenous Sea/Road Sodium Hydride 287 Imported/Indigenous Sea/Road
Toluene 1300 Indigenous Road HCl gas 110 Indigenous Road
EDC 1400 Indigenous Road 2-Chloro-6-Trifluoro
Methyl Pyridine 483 Imported Sea/Road
Potassium Hydroxide 168 Indigenous Road Xylene 1000 Indigenous Road Water 666 Indigenous Road
11 Propiconazole
1,3 Di Chloro Benzene 452 Imported Sea/Road Acetyl Chloride 238 Imported/Indigenous Sea/Road
Aluminium Chloride 558 Imported/Indigenous Sea/Road EDC 1600 Indigenous Road
Bromine 553 Indigenous Road Catalyst 10 Imported/Indigenous Sea/Road
1,2 – Butanediol 320 Imported/Indigenous Sea/Road Toluene 1000 Indigenous Road
Potassium Hydroxide 166 Indigenous Road 1,2,4 – Triazole 210 Imported/Indigenous Sea/Road
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S.No. Product Raw Materials Consumption for (Per MT) Indigenous/Imported Transportation
DMF 1000 Indigenous Road Water 3715 Indigenous Road
12 Prothioconazole
1,2,4 triazole 353 Imported/Indigenous Sea/Road paraformaldehyde 154 Imported/Indigenous Sea/Road
chloroform 2500 Indigenous Road Thionyl chloride 1200 Indigenous Road
Sulphur 169 Indigenous Road DMF 4500 Indigenous Road
Ethyl acetate 2600 Indigenous Road saturated sodium
bicarbonate 1000 Indigenous Road
magnesium turnings 125 Indigenous Road tetrahydrofuran 2500 Imported/Indigenous Sea/Road
I- (1- chloro-cyclopropyl) -2- (2-chlorophenyl)
ethanone 888 Imported Sea/Road
10% aqueous acetic acid 1000 Indigenous Road dichloromethane 1500 Indigenous Road
13 Pyraclostrobin
1,4 Dichloro Benzene 422 Imported/Indigenous Sea/Road 3 – Chloropyrazole 275 Imported Sea/Road
Xylene 4000 Indigenous Road Catalyst 10 Imported/Indigenous Sea/Road
2 – Chlorobenzyl Alcohol 350 Imported Sea/Road N – Methoxy Carbamate 270 Imported Sea/Road
Water 1500 Indigenous Road
14 Tebuconazole
1-(4 – Chlorophenyl) 4-4-Dimethyl -3-
Pentanoate 675 Imported Sea/Road
Sodium Methoxide 152 Imported/Indigenous Sea/Road Di Methyl Sulphide 186 Imported/Indigenous Sea/Road
Toluene 1400 Indigenous Road 1,2,4 – Triazole 206 Imported/Indigenous Sea/Road
DMF 1100 Indigenous Road Water 1706 Indigenous Road
15 Thifluzamide
Ethyl trifluoroacetate 598 Imported Sea/Road Chlorine gas 198 Indigenous Road
Ethanethiomide 196 Imported/Indigenous Sea/Road Triethyl amine (ET3N) 15 Indigenous Road
Acetonitrile 1000 Indigenous Road NaOH 606 Indigenous Road
HCl 30% 315 Indigenous Road Thionyl chloride 276 Indigenous Road
Toluene 2000 Indigenous Road Water 3241 Indigenous Road
2,6-dibromo-4-(trifluoromethoxy)aniline
(DBTFMA) 705 Imported Sea/Road
16 Trifloxystrobin
2 – Methyl Aniline 275 Imported/Indigenous Sea/Road Sodium Nitrite 177 Indigenous Road
30% Hydrochloric Acid 338 Indigenous Road Glyoxylic Acid Methyl
Ester Oxime 259 Imported Sea/Road
Sodium Hydroxide 306 Indigenous Road Di Methyl Sulphate 160 Imported/Indigenous Sea/Road
Chlorine Gas 190 Indigenous Road EDC 1200 Indigenous Road
Sodium [1-{(3-Trifluoro Methyl) Phenyl}
Ethylidene Amino] Oxidanide
517 Imported Sea/Road
DMF 1400 Indigenous Road Water 3792 Indigenous Road
Herbicide
1 Carfentrazone
2-fluoroaniline 730 Imported Sea/Road Sodium Nitrite 460 Indigenous Road
Hydrochloric Acid 4210 Indigenous Road Sodium Sulfite 2710 Indigenous Road
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S.No. Product Raw Materials Consumption for (Per MT) Indigenous/Imported Transportation
Caustic lye Solution 2644 Indigenous Road 20% Sodium Hydroxide 4275 Indigenous Road 10% Sodium Hydroxide 1500 Indigenous Road
Acetaldehyde 382 Indigenous Road Chlorine 1085 Indigenous Road
Acetic Acid 500 Indigenous Road Methanol 4000 Indigenous Road
Potassium Carbonate 924 Indigenous Road Dimethylformaide 7500 Indigenous Road
Dichlorofluoromethane 665 Indigenous/Imported Sea/Road Oleum 5565.2 Indigenous Road
Nitric Acid 502.2 Indigenous Road Dichloroethane 3250 Indigenous Road Catalyst Pd/C 59.5 Indigenous Road Ethyl Acrylate 425 Indigenous Road
Acetonitrile 5300 Indigenous Road IPA 6325 Indigenous Road
Water 42906 Indigenous Road Freon gas 895 Indigenous/Imported Road
2 Clethodim
5-Propyl 2-Thio Ethyl Cyclohexane 1,3 dione 625 Imported Sea/Road
Propionyl Chloride 285 Imported/Indigenous Sea/Road Aluminum Chloride 450 Imported/Indigenous Sea/Road 1-Chloro 3-Allyl Oxy
Amine 330 Imported/Indigenous Sea/Road
Toluene 2500 Indigenous Road Water 2800 Indigenous Road
3 Clodinafop Propargyl
2, 3 – Di Fluoro–5–Chloro Pyridine 448 Imported Sea/Road
2–(4–Hydroxy Phenoxy) Propionic Acid 548 Imported Sea/Road
Sodium Hydroxide 240 Indigenous Road Di Methyl Formamide
(DMF) 1200 Indigenous Road
Propargyl Chloride 180 Imported/Indigenous Sea/Road Toluene 1000 Indigenous Road Water 450 Indigenous Road
4 Clomazone
3-chloro-2, 2-dimethylpropanoyl
chloride 875 Imported Sea/Road
hydroxylamine hydrochloride 390 Indigenous/Imported Sea/Road
50% NaOH solution 1286 Indigenous Road Water 4172 Indigenous Road
Sodium Carbonate or NaOH 470 Indigenous Road
2-chlorobenzyl chloride 825 Indigenous/Imported Sea/Road Dichloromethane 2945 Indigenous Road
Hexane 2454 Indigenous Road
5 Cloransulam
2-Ethoxy-4,6-difluoropyrimidine 627 Imported Sea/Road
hydrazine 80 % 255 Imported/Indigenous Sea/Road Carbon disulphide 314 Indigenous Road
methanol 2750 Indigenous Road Triethylamine 560 Indigenous Road
Hydrogen peroxide 30% 628 Indigenous Road Hydrochloric acid 30% 447 Indigenous Road
30% Sodium methylate- methanol solution 745 Indigenous Road
Dichloromethane Hydrochloric acid 980 Indigenous Road
Sodium perchlorate 490 Indigenous Road Dichloromethane 590 Indigenous Road
2-AMINO-3-CHLORO-BENZOIC ACID METHYL ESTER
500 Imported/Indigenous Sea/Road
water 2964 Indigenous Road 6 Diclosulam 5-ethoxy-)-7-fluoro- 749 Imported Sea/Road
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S.No. Product Raw Materials Consumption for (Per MT) Indigenous/Imported Transportation
[1,2,4]-triazolo[1,5-c]pyrimidine-2-sulfonyl
Chloride 2,6-Dichloroaniline 642 Imported/Indigenous Sea/Road 3,5-Dimetylpyridine 866 Imported/Indigenous Sea/Road
Acetonitrile 22942 Indigenous Road Dimethyl Sulfoxide
(DMSO) 8 Indigenous Road
7 Fenoxaprop P Ethyl
3, 6 – Di Chloro Benzoxazole 610 Imported Sea/Road
2 – (4 – Hydroxy Phenoxy) Propionic Acid 590 Imported Sea/Road
Sodium Hydroxide 121 Indigenous Road DMF 1400 Indigenous Road
Thionyl Chloride 384 Indigenous Road Toluene 2500 Indigenous Road
20% NaOH solution 1125 Indigenous Road Sodium Ethoxide 222 Imported Sea/Road
Water 1200 Indigenous Road
8 FLUFENACET
N-(4-fluorophenyl)-2-hydroxy-
Nisopropylacetamide 520 Imported Sea/Road
2-(Methylsulfonyl)-5-(trifluoromethyl)-1,3,4-
thiadiazole 635 Imported Sea/Road
PTSA 6 Indigenous Road 25% Sodium hydroxide 708 Indigenous Road 5% Hydrochloric acid 575 Indigenous Road
Methanol 1400 Indigenous Road Ethylene dichloride 2450 Indigenous Road
9 Fomesafen
5-Hydroxy-2-Nitro Benzoic Acid 485 Imported Sea/Road
3,4-Di Chloro Benzotrifluoride 567 Imported Sea/Road
Sodium Hydroxide 277 Indigenous Road Dimethyl sulphoxide 2100 Imported/Indigenous Sea/Road
20 % Ammonium Hydroxide Solution 458 Indigenous Road
Toluene 2400 Indigenous Road Methane Sulfonyl
Chloride 300 Imported/Indigenous Sea/Road
Water 910 Indigenous Road
10 Glufosinate Ammonium
n-Butyl (3-cyano-3-hydroxypropyl) methyl
propionate 850 Imported Sea/Road
HCl 35% 549 Indigenous Road AMMONIA 100 Indigenous Road
WATER 1800 Indigenous Road
11 Glyphosate
SODIUM TUNGSTATE 5 Imported/Indigenous Sea/Road PMIDA 1621 Imported/Indigenous Sea/Road
SODIUM METABISULFITE 21 Indigenous Road
VANADIUM SULPHATE 0.4 Imported/Indigenous Sea/Road H2O2 604 Indigenous Road Water 3718 Indigenous Road
12 Mesotrione
1,3-cyclohexadione 387 Imported Sea/Road Ethylene dichloride 9000 Indigenous Road
Acetone cyanohydrins 107 Imported Sea/Road Triethylamine 100 Indigenous Road
2-nitro-4-methylsulfonyl benzoyl chloride 914 Imported Sea/Road
Sulfuric acid solution 835 Indigenous Road 10 %Sodium hydroxide 1000 Indigenous Road
water 3300 Indigenous Road
13 Penoxsulam
Trizolopyrimidine amine 404 Imported Sea/Road Sulphonyl chloride 672 Indigenous Road
Pyridine 164 Indigenous Road DMSO 2020 Indigenous Road
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S.No. Product Raw Materials Consumption for (Per MT) Indigenous/Imported Transportation
Water 1000 Indigenous Road
14 Pretilachlor
2,6-diethyl aniline 1699 Imported Sea/Road 1-Bromo-2-Propoxy
Ethane 466 Imported Sea/Road
Sodium carbonate 403 Indigenous Road CAC 387 Imported Sea/Road
Triethyl amine 363 Indigenous Road Toluene 1500 Indigenous Road Water 5300 Indigenous Road
15 PROPANIL 3,4‐DCA 747 Imported Sea/Road Propionic acid 404 Imported/Indigenous Sea/Road
16 PROPAQUIZAFOP
Carboxylic acid 777 Imported/Indigenous Sea/Road Alcohol 265 Indigenous Road
Thionyl chloride 269 Indigenous Road Pyridine 178 Indigenous Road
DMF 3885 Indigenous Road Toluene 3108 Indigenous Road Water 2000 Indigenous Road
17 Sulfentrazone
Phenyl Hydrazine 765 Imported/Indigenous Sea/Road Acetaldehyde 376 Imported/Indigenous Sea/Road
Sodium Cyanate 530 Imported/Indigenous Sea/Road Acetic acid 500 Indigenous Road Chlorine 2308 Indigenous Road Methanol 4000 Indigenous Road
20% Sodium Hydroxide 500 Indigenous Road Potassium Carbonate 900 Indigenous Road
Dimethylformaide 7550 Indigenous Road Dichlorofluoromethane 650 Imported/Indigenous Sea/Road
Oleum 4450 Indigenous Road Nitric Acid 385.5 Indigenous Road
Dichloroethane 2620 Imported/Indigenous Sea/Road Catalyst Pd/C 63.2 Imported/Indigenous Sea/Road
Methane Sulfonylchloride 689 Imported/Indigenous Sea/Road
Pyridine 490.6 Indigenous Road Toluene 4983.8 Indigenous Road
Dichloromethane 2125 Indigenous Road IPA 6415 Indigenous Road
Water 36685 Indigenous Road 10% Sodium Hydroxide 1000 Indigenous Road
Insecticide
1 Chlorantraniliprole
2-amino-5-chloro-N,3-dimethylbenzamide 440 Imported/Indigenous Sea/Road
3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl
chloride
706 Imported/Indigenous Sea/Road
Triethyl amine 225 Indigenous Road Toluene 3150 Indigenous Road Water 2300 Indigenous Road
2 CYANTRANILIPROLE
2-amino-5-cyano-N, 3-dimethyl benzamide 430 Imported Sea/Road
3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl
chloride
725 Imported Sea/Road
Triethyl amine 230 Indigenous Road Xylene 3320 Indigenous Road Water 2500 Indigenous Road
3 Flubendiamide
3- Iodophthalic Anhydride 1768 Imported Sea/Road
1,1-Dimethyl-2-Methylthioethylamine 768 Imported Sea/Road
Triethylamine 129 Indigenous Road Trifluoroacetic Anhydride 1085 Indigenous Road 4- Heptafluoroisopropyl-
2-Methylaniline 503 Imported/Indigenous Sea/Road
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S.No. Product Raw Materials Consumption for (Per MT) Indigenous/Imported Transportation
Trifluoroacetic Acid 7 Indigenous Road M-Chloroperbenzoic
Acid (MCPBA) 548 Imported/Indigenous Sea/Road
Dimethylacetamide (DMA) 6647 Imported/Indigenous Sea/Road
Toluene 5587 Indigenous Road Acetonitrile 4605 Indigenous Road
Dichloromethane (DCM) 8581 Indigenous Road
4 Nitenpyram
1,1,2- trichloroethane 940 Imported Sea/Road NaOH 282 Indigenous Road
30 % HCl 764 Indigenous Road HNO3 396 Indigenous Road
Ethyl amine 265 Indigenous Road 20% NaOH 800 Indigenous Road
Methylene chloride 1200 Indigenous Road Methane amine 158 Imported/Indigenous Sea/Road
Water 5340 Indigenous Road 1,1,1- trichloro-2-
nitroethane 1009 Imported Sea/Road
5 Pymetrozine
3 Pyridine Carboxaldehyde 519 Imported Sea/Road
1,2,4 Triazine-3 (4H) 1,4 -Aamino-5,6 -(Dihydro-6-
Methyl) 639 Imported Sea/Road
Toluene 2000 Indigenous Road Water 1500 Indigenous Road
6 Spirodiclofen
Cyclohexanone 340 Indigenous Road sodium cyanide 170 Imported/Indigenous Sea/Road
Ethyl acetate 5240 Indigenous Road Water 3150 Indigenous Road
2,4- dichloro-phenylacetic acid 565 Imported Sea/Road
Thionyl chloride 676 Imported/Indigenous Sea/Road Dichloromethane 5080 Indigenous Road
Pyridine 762 Indigenous Road 3% hydrochloric acid
solution 1500 Indigenous Road
5% sodium carbonate solution 1800 Indigenous Road
Sulphuric acid 450 Indigenous Road Methanol 2500 Indigenous Road
5% sodium bicarbonate 1000 Indigenous Road magnesium ethoxide 232 Imported/Indigenous Sea/Road
Ethanol 3500 Indigenous Road HCl for 5% hydrochloric
acid 1000 Indigenous Road
Triethylamine 1000 Indigenous Road 2,2- dimethylbutyryl
chloride 400 Imported Sea/Road
hydrochloric acid 1000 Indigenous Road sodium bicarbonate
solution 2000 Indigenous Road
7 Thiamethoxam
N,N Dimethyl Carbonate 4774 Imported Sea/Road 2-chloro-5-
chloromethyltriazole 764 Imported Sea/Road
3-methyl-4-nitroimino-perahydro 1,3,5-
oxadiazine (Solid) 836 Imported Sea/Road
Tetramethylammonium hydroxide pantahydrate 18 Indigenous Road
Potassium carbonate (K2CO3) 1100 Indigenous Road
Hydrochloric acid (HCl) 1182 Indigenous Road Water 2725 Indigenous Road
8 Spirotetramet 1,4-
dioxaspiro[4,5]decan-8-one
628 Imported Road
Sodium Cyanide 196 Imported/Indigenous Sea/Road
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S.No. Product Raw Materials Consumption for (Per MT) Indigenous/Imported Transportation
Ammonium carbonate 284 Indigenous Road HCl gas 488 Indigenous Road
Methanol 3900 Indigenous Road 3N NaOH 1500 Indigenous Road Dry HCl 140 Indigenous Road NaOH 160 Indigenous Road (2,5-
dimehtlphenyl)acetyl chloride
676 Imported/Indigenous Sea/Road
Acetonitrile 2200 Indigenous Road K2CO3 510 Indigenous Road
Potassium t-Butoxide 100 Imported/Indigenous Sea/Road DMF 2500 Indigenous Road
4N HCl 1500 Indigenous Road Acetyl chloride 272 Indigenous Road
Dichloromethane 3000 Indigenous Road TEA 200 Indigenous Road
4-dimethylaminopyridine 20 Imported/Indigenous Sea/Road 20% NaOH in scrubber 680 Indigenous Road
water 2140 Indigenous Road
Intermediate
1 1,2,4 – Triazole
Formic Acid 85% 2000 Imported/Indigenous Sea/Road Ammonia Gas 900 Indigenous Road
Hydrazine Hydrate 80% 1000 Imported/Indigenous Sea/Road Water 2315 Indigenous Road
2 CCMT
Allyl Chloride 761 Imported/Indigenous Sea/Road Chlorine gas 685 Indigenous Road
Sodium Hydroxide, (Flakes) 358 Indigenous Road
TEBA (Catalyst) 20 Imported/Indigenous Sea/Road Sodium Thiocyanate 700 Indigenous Road
Sulfuryl Chloride 1052 Imported/Indigenous Sea/Road Toluene 3478 Indigenous Road Water 2127 Indigenous Road
3 MNIO
N-Nitroguanidine 940 Imported/Indigenous Sea/Road 25% Aqueous Methyl
Amine 1358 Indigenous road
Paraformaldehyde 468 Imported/Indigenous Sea/Road Formic Acid 4680 Imported/Indigenous Sea/Road
Water 1636 Indigenous road
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(vii) Storage and Transportation Details of Raw Materials
Storage and transportation details of raw materials are provided in Table 3-4.
Table 3-4: Storage and Transportation Details of Raw Materials Sr. No.
Raw Material Max. Storage capacity (Qty. MT/)
Hazards Mode of Storage
No. of units
Physical state of Raw Material
Mode of Transportation
Safety measures to be provided
1 Conc. Sulphuric acid
10 Corrosive Storage tank, MS/PPFRP
1 Liquid By Tanker/ By road
Safety showers Dyke wall Caution note Level gauge Double drain valve Scrubber Required PPEs
2 Dimethyl Formamide
20 Flammable Storage tank, MS/CS
2 Liquid By Tanker/ By road
Double static earthing Dyke wall around solvent
storage area. Fire extinguisher and
hydrant point Tanker unloading
procedure Flame arrestor on vent line
of tank Jumper clips on flanges Fencing and No smoking
and prohibited area. Flame proof pumping
station
3 Acetonitrile 20 Flammable Storage tank, MS/CS
1 Liquid By Tanker/ By road
4 EDC 20 Flammable Storage tank, MS/CS
2 Liquid By Tanker/ By road
5 Toluene 20 Flammable Storage tank, MS/CS
2 Liquid By Tanker/ By road
6 Monochloro Benzene
10 Flammable Storage tank, MS/CS
1 Liquid By Tanker/ By road
7 Xylene 20 Flammable Storage tank, MS/CS
2 Liquid By Tanker/ By road
8 Methanol 15 Flammable Storage tank, 1 Liquid By Tanker/ By
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Sr. No.
Raw Material Max. Storage capacity (Qty. MT/)
Hazards Mode of Storage
No. of units
Physical state of Raw Material
Mode of Transportation
Safety measures to be provided
MS/CS road 9 Hexane 15 Flammable Storage tank,
MS/CS 1 Liquid By Tanker/ By
road 10 Chlorine 10 Toxic/
Corrosive MS cylinder (900 kg)
11 Pressurized gas
By Road Exhaust hood connected with caustic scrubber over chlorine handling area.
Facility for eye wash station and quick drenching proximal to work area.
Solution of Sodium Thiosulphate provided near Bromine handling area for neutralization.
11 Bromine 10 Toxic/ Corrosive
Storage tank MSGL
1 Liquid By Tanker/ By road
12 Thionyl Chloride 15 Toxic/ Corrosive
Storage tank MSGL
1 Liquid By Tanker/ By road
Exhaust hood connected with caustic scrubber over Thionyl chlorine handling area.
13 Hydrochloric acid 40 Corrosive PPFRP/Syntex tank
3 Liquid By Tanker/ By road
Safety showers Dyke wall Caution note Level gauge Double drain valve Scrubber Required PPEs
14 Nitric acid 40 Corrosive Storage tank, MS/PPFRP
3 Liquid By Tanker/ By road
15 Hydrogen gas 50 kg Flammable MS cylinder (0.5 kg)
100 Pressurized gas
By Road Fire extinguisher and hydrant point
16 Sodium cyanide 3 Toxic Drums (50 kg) 60 Solid By Road Adequate PPEs and safety
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Sr. No.
Raw Material Max. Storage capacity (Qty. MT/)
Hazards Mode of Storage
No. of units
Physical state of Raw Material
Mode of Transportation
Safety measures to be provided
gears for all workers. Adequate ventilation
system in working area. Adequate antidote provision
for sodium cyanide leakage available in facility.
Ware house shall be made as per statutory requirement with restricted area.
17 PCl3 1 Toxic/ Corrosive
Drums (200 kg)
5 Liquid By Road Adequate PPEs and safety gears for all workers.
Adequate ventilation system in working area.
Adequate antidote provision for sodium cyanide leakage available in facility.
Ware house shall be made as per statutory requirement with restricted area.
Facility for Eye wash station and quick drenching proximal to all workers.
18 Hydrazine hydrate 10 Toxic HDPE Drums (200 kg)
50 Liquid By Road
19 Triethyl amine 10 Toxic Storage tank, MS
1 Liquid By tanker/ By road
20 Caustic lye 48% 15 Corrosive Storage tank, MS
2 Liquid By tanker/ By road
Dyke wall around the storage tank
21 Dichloro Benzene 10 Flammable Storage tank, 1 Liquid By Tanker/ By Double static earthing
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Sr. No.
Raw Material Max. Storage capacity (Qty. MT/)
Hazards Mode of Storage
No. of units
Physical state of Raw Material
Mode of Transportation
Safety measures to be provided
MS/CS road Dyke wall around solvent storage area.
Fire extinguisher and hydrant point
Tanker unloading procedure
Flame arrestor on vent line of tank
Jumper clips on flanges Fencing and No smoking
and prohibited area. Flame proof pumping
station
22 Ethyl acetate 15 Flammable Storage tank, MS/CS
1 Liquid By Tanker/ By road
23 Isopropyl alcohol 15 Flammable Storage tank, MS/CS
1 Liquid By Tanker/ By road
24 Ethanol 10 Flammable Storage tank, MS/CS
1 Liquid By Tanker/ By road
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(viii) Resource optimization/recycling and reuse envisaged in the project
Leakages and spillages will be avoided to minimize the product loss.
(ix) Availability of water its source, Energy/power requirement and source
Availability of water its source, Energy/power, Fuel required and its source are described in following sections:
Water
Total water requirement will be 1445KLD. 1183.4 KLD fresh water will be sourced from GIDC, Dahej, 240 KLD boiler condensate will be recycled in boilers and 21.6 KLD for gardening water will be sourced from proposed Sewage Treatment Plant. Details of water consumption is provided in Table 3-5. Water Balance is provided in Figure 3-1.Table 3-5
Table 3-5: Details of Water Consumption Water Consumption Source
Sr No Usages Types Quantity KLD
1 Domestic 30 GIDC
2 Industrial
a) Processing 435 GIDC
b) Cooling 460 GIDC
c) Boiler 480 [240 KLD recycled + 240 KLD fresh]
d) Washing 15 GIDC
e) Gardening 25 [21.6 KLD treated STP + 3.4 KLD Fresh]
Total 1445
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Figure 3-1: Water Balance Diagram
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Energy/ Power
Details of Energy and Power requirement are tabulated in Table 3-6.
Table 3-6: Power Requirements and Its Source
Sr No Particulars Quantity Source/Remarks
1 Domestic Power 50 KWH DGVCL 2 Industrial Power 4500 KWH 1 D.G.Set 4 Back Up
Diesel Generator will be kept as power backup.
Fuel
Coal / Natural Gas / Furnace oil will be used as primary fuel. HSD will be used as fuel for D.G Set. Details of fuel used in provided in Table 3-7.
Table 3-7: Fuel details
Sr No Particulars Quantity Source/Remarks
1 FO, or 25000 Liters/day HPCL 2 NG, or 33000 SCM GAIL 3 Coal 62 TPD Indian/ Imported 4 HSD (D.G.Set) 25000 Liters/day Local
(x) Quantity of wastes (Liquid, gas & Solid) to be generated and scheme for their Management / disposal
Waste Water and its Management
ETP shall be design for 625 KLD. All required Equipment space and sizing shall also be
considered as per KLD. Details of wastewater generation is provided in Table 3-8.
Trade or process plant effluent This is expected from production plant and utilities typically from:
1. Process / Manufacturing operations
2. Utilities
a. Boiler Blow Down
b. Cooling Tower Blow Down
Domestic Effluent
a. Wastewater from washroom
b. Wastewater from canteen
Table 3-8: Waterwater generation details Waste water Generation Disposal
Sr No Usages Types Quantity KLD 1 Domestic 24 STP 2 Industrial
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Waste water Generation Disposal a) Processing 174 ETP b) ATFD 245.52 ETP c) Boiler 86 ETP d) Washing 15 ETP e) Sub-Total 520.52 ETP f) Total 545
Treatment to meet discharge effluent standards
1. Domestic Wastewater.i.e sewage will be treated in separate STP of 25 KLD. 2. Effluent from Boiler Blow Down, Cooling Tower Blow Down and High TDS stream
from process will be treated in Multi Effect Evaporator 3. Effluent from washing, Low TDS stream from process and MEE condensate will be
treated in proposed Effluent Treatment Plant.
Recovery of water
1. Domestic wastewater treated in sewage treatment plant will be treated and used in gardening.
2. Boiler condensate will be recycled and reused in process.
Design Details of ETP
Design details of all civil units of the proposed ETP are given in Table 3-9. Effluent
treatment scheme is provided in Figure 3-2 and Sewage treatment scheme is provided
in Figure 3-3.
Table 3-9:ETP details Description Capacity Qty MoC Total Vol. (M³)
Screen Chamber 2000*1000*600 1 RCC 1.2
Oil & Grease Trap 2000*3500*3600 2 RCC 25.2
Oil & Grease Trap 2000*2650*3600 1 RCC 19.08
Equalisation Tank 5000*4700*3600 1 RCC 84.6
Equalisation Tank 5000*3400*3600 1 RCC 61.2
Equalisation Tank 5000*2600*3600 1 RCC 46.8
Settling Tank 5000*2500*3200 5 RCC 40
Collection Tank 8000*2600*4000 4 RCC 83.2
Bioreactor Tank 38000*7500*4000 2 RCC 1140
Supernatant Tank 3500*5500*3000 1 RCC 57.75
Treated Water Tank 11500*3000*3000 1 RCC 103.5
Sludge Tank 3500*5500*3000 1 RCC 57.75
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Description Capacity Qty MoC Total Vol. (M³)
Lime Dosing Tank 2000*2500*2500 2 RCC 12.5
Alum Dosing Tank 2000*1600*2500 2 RCC 8
Poly Dosing Tank 710*700*1000 1 RCC 0.497
Urea Dosing Tank 780*700*1000 1 RCC 0.546
Dap Dosing Tank 710*700*1000 1 RCC 0.497
Floculation Tank 1000*2500*1200 3 RCC 3
Primary Treatment
Raw effluents will be collected in a tank at plant. Then it will be pumped to neutralization
tank, where alkali will be administered to achieve nearly 10 pH. Then effluent will be
pumped to a flash mixer & primary clarifier to undergo physico-chemical treatment.
Coagulant will be also added to aid settling / floatation of charged particulate matters if
any. The effluent leaving the flash mixer will gravitates to a primary settling tank wherein
polyelectrolyte will be added to aid in the settling of particulate matter by allowing them
to agglomerate into large easily settleable flocks.
Secondary Treatment
The clarified effluent from the primary clarifier will be taken to plain aeration tanks where
the pH will be adjusted to near neutral. This aerated effluent will be routed subsequently
to undergo two-stage aerobic biological treatment using the activated sludge process.
Herein the organic matter in the effluent undergoes biological oxidation in the Aeration
tank to produce carbon dioxide and water. There will be an increase in the population of
micro organisms within the Aeration tank which need to be removed by a secondary
clarifier. A major portion of the settled biomass will be re-circulated back to the Aeration
tank to maintain a viable population of micro-organisms to have an aerobic environment
due to which efficient oxidation of organic matter can occur. The remaining portion of the
biomass depending on the growth kinetics of the population of micro organisms within
the reactor will be generated / treated as sludge. This sludge will be separated by
decanter and then dried on beds and finally sent to BEIL for land disposal.
Multi Effect Evaporator (MEE)
We will be installing a forward feed four effect system to suit the requirement. The Feed
from the feed balance tank shall be pumped to a series of the shell & tube type heat
exchangers using the vapors of each effect as a heating media. Pre-heated feed from
feed preheaters is feed to Forced circulation calendria and then passed through the next
Forced circulation evaporator. The Vapors from the preceding effects are used as a
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heating medium on the shell side of next calendria. The part of the solution is recycled
back to the same effect to maintain the flow characteristics. Sufficient areas have been
provided on each effect to ensure effective heat transfer. Vapor liquid separators
mounted at the Top part of Forced circulation calendria, with tangential entry are
provided to ensure the efficient separation of liquid and vapors. These shall be of
adequate capacity with sight glass/light glass and manholes.
For circulation specially designed highly efficient Axial Flow pump has been provided.
Product is extracted by means of a product pump. An efficient thermo compressor is
mounted on the vapors separator 1 which compresses the vapors from the same effect
and discharge to shell side of calendria – 1 as heating media. The dry saturated steam
at 3.5 kgs/cm2 (g) is used as motive. Vacuum Pump/ Steam jet ejedtor connected to a
barometric condenser to maintain the desired vacuum level.
Figure 3-2: Effluent Treatment SchemeSewage Treatment Plant
Domestic effluent will be treated in Sewage treatment plant (STP Capacity 25 KLD). The
various unit operations of STP consist of primary sedimentation tank, grit chamber,
aeration tank, sedimentation tank, chlorination tank and sludge drying bed.
First the raw sewage will be collected in primary sedimentation tank where suspended
solids and BOD will be removed to some extent.
The remaining BOD levels are proposed to be reduced in aeration tank followed by
secondary sedimentation tank. The purpose of an aeration tank is mainly to increase the
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DO content of effluent and to convert biological dissolved solids to suspended solids.
The dissolved oxygen content can be increased by mechanical surface aerators. It also
provides vigorous agitation and mixing in the water to disperse the oxygen and keeps
the solids in suspension.
The effluent will be passed into the secondary sedimentation tank where the converted
suspended solids will settle and will be removed as sludge. In this system BOD levels
will be reduced to greater extent.
The treated effluent will be chlorinated and will be disposed on land for irrigation. The
sludge which will be collected from primary sedimentation tank and secondary
sedimentation tank will be disposed on drying beds which consist of well drained beds of
sand and gravel. The sludge cake, which will be formed on top of the sand beds, will be
used for manure.
The treated sewage will be further chlorinated and diluted and then used for green belt
development.
Figure 3-3 Schematic diagram of Sewage Treatment plant
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Air Emissions Details
Details of process gas emission is provided in Table 3-10 and flue gas emission is provided in
Stack no.
Stack attached to
Stack height in meter
Air pollution control system Parameter Permissible
limit Stack Dia (mm)
1 Process plant -1 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm HCl 20 mg/ Nm3 Cl2 9 mg/ Nm3 HBr 5 mg/ Nm3
2 Process plant -2 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm HCl 20 mg/ Nm3 Cl2 9 mg/ Nm3 HBr 5 mg/ Nm3
3 Process plant -3 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm HCl 20 mg/ Nm3 Cl 9 mg/ Nm3
HBr 5 mg/ Nm3
4 Process plant - 4 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm HCl 20 mg/ Nm3 Cl 9 mg/ Nm3
HBr 5 mg/ Nm3
5 Process plant -5 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm H2S 20 mg/ Nm3 NO2 9 mg/ Nm3 HCl 5 mg/ Nm3 Cl 100 mg/ Nm3
HBr 5 ppm
Table 3-11.
Table 3-10: Process gas emission details Stack
no. Stack attached
to Stack height
in meter Air pollution
control system Parameter Permissible limit Stack Dia (mm)
1 Process plant -1 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm HCl 20 mg/ Nm3 Cl2 9 mg/ Nm3 HBr 5 mg/ Nm3
2 Process plant -2 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm HCl 20 mg/ Nm3 Cl2 9 mg/ Nm3 HBr 5 mg/ Nm3
3 Process plant -3 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm HCl 20 mg/ Nm3 Cl 9 mg/ Nm3
HBr 5 mg/ Nm3
4 Process plant - 4 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000 H2S 5 ppm NO2 50 ppm HCl 20 mg/ Nm3 Cl 9 mg/ Nm3
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Stack no.
Stack attached to
Stack height in meter
Air pollution control system Parameter Permissible
limit Stack Dia (mm)
HBr 5 mg/ Nm3
5 Process plant -5 30 Water/Caustic Scrubber
PM 100 mg/ Nm3
1000
H2S 5 ppm NO2 50 ppm H2S 20 mg/ Nm3 NO2 9 mg/ Nm3 HCl 5 mg/ Nm3 Cl 100 mg/ Nm3
HBr 5 ppm
Table 3-11: Flue gas emission details
S. No.
Source of emission Stack
Type of Fuel
Quantity of Fuel Type of
emissions i.e. Air Pollutants
Air Pollution Control Measures
With Capacity Height (meter) MT/Day (APCM)
1 DG Set (750 KvA) (4 Nos.) 20 HSD 15
PM – 150 mg/ Nm3; SOx – 100 ppm; NO2 – 50
ppm
DG will be used as stand by
2 Boiler – 15 Tonnes 45 NG/ HSD 10
PM – 150 mg/ Nm3; SOx – 100 ppm; NO2 – 50
ppm
For NG as fuel, APCM is not considered
In case of other feuls, standard APCM norms are considered
3 Boiler - 15 Tonnes 45 NG/ HSD 10
PM – 150 mg/ Nm3; SOx – 100 ppm; NO2 – 50
ppm
For NG as fuel, APCM is not considered
In case of other feuls, standard APCM norms are considered
4 Boiler – 15 Tonnes 45 NG/ HSD 10
PM – 150 mg/ Nm3; SOx – 100 ppm; NO2 – 50
ppm
For NG as fuel, APCM is not considered
In case of other feuls, standard APCM norms are considered
5 TFH - 1 30 Thermic oil 10
PM – 150 mg/ Nm3; SOx – 100 ppm; NO2 – 50
ppm
For NG as fuel, APCM is not considered
In case of other feuls, standard APCM norms are considered
Solid and Hazardous Wastes and Management
Details of Solid and Hazardous generated along with its management is provided in Table 3-12.
Table 3-12: Details of Solid & Hazardous Waste and its Management
Sr No Type of Waste Waste
Quantity
Category (as per HWM Rules,
2016) Method of Disposal
1 Used Lube Oil 500 Lit./month 5.1 Given to CPCB Authorized reprocessors
2 Process /Distillation Residue
1102.68 MT/year 29.1 Incineration in Common
Incineration facility 3 ETP Sludge 150 kg/day 29.2 Disposal at BEIL
4 Date Expired /off
Specification Products
25 MT /year 29.3 Incineration in Common Incineration facility
5 Spent Solvent 150 MT/ month 29.4
Incineration in Common Incineration facility
6
Packing Materials
Empty Bags 2000 Bags/month 33.1
Given to GPCB
Barrel 1000 Barrel Authorized Vendor
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/month
7 Spent Carbon from ETP 250 kg/ month 36.2
Incineration / Common Incineration facility of BEIL
Ankleshwar
8 Sludge from wet scrubber
1000 kg/ month 37.1
Incineration / Common Incineration facility
9
Production and /or industrial use of glues, organic
cements, adhesive and resins
1.0 MT / year 23.1 Given back to the supplier
(manufacturer) against new resins.
10 MEE Salt 10 MT/day 35.3 Disposal to BEIL
Contaminated PPE's, Insulation waste Batteries , E-Waste, Lead & lead compounds, Non –recyclable plastic waste/Gaskets/Insulations/ PPE’s will be generated and will be handled based on prevailing legislation. The domestic waste generated will be recycled as manure and used for green belt development
(xi) Schematic representations of the feasibility drawing which give information of EIA purpose
Schematic representation of the feasibility drawing which give information of EIA purpose: A Schematic representation of the feasibility drawing is provided in Figure 3-4.
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Figure 3-4: EIA Purpose
Type of Industry
Pesticide & Pesticide Secific Intermediates
Type of category as per EIA notification (Catagery -5(b) -A)
Proposed Activity:
Pesticides Tecnical & intermediates manufacturing greenfield project
Submission of Form-1 and Pre-Feasibility
Report & Draft ToR
Resource requirments
Raw Material : Sourced from Manufacturer / Traders of the same.
Land: GIDC, Dahej
Water: Will be sourced from GIDC
Power: Power will be sourced through Madhya Gujarat Vij Co. Limited
Env. Mgt. Plan (EMP)
Air Pollution Control Measures: Adequate air pollution control system will be installed.
Water Pollution : STP and ETP provided. Treated effluent to be disposed in GIDC drain.
Greenbelt Area: Above 33% of the total area will be developed.
Health & Safety measures will be followed properly.
Domestic: Will be treated in STP.
Industrial:: High TDS will be treated in MEE and low TDS in ETP.
Gas emissions: Adequate APCM will be provided.
Hazardous waste: will be disposed off as per hazardous waste 2016
Fugitive emission: efficient control system
Presentation before the EAC for ToR/EC
Site location :
Plot No. D-3/5/3 GIDC Dahej Phase III, Tal
Vagara, Dist. Bharuch, Gujarat
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4 SITE ANALYSIS
(i) Connectivity
The project will be located in Dahej GIDC, which is very well connected to State Highway. Details of site connectivity is provided in Table 4-1.
Table 4-1: Site Connectivity
Particular Details Distance with direction
Nearest Road SH-6 Adjacent in West direction
Nearest railway station Dahej 8.3 km towards SW Bharuch 38.3 km towards ESE
Nearest Airport Surat 73 km towards S
Vadodara 86.61 km towards NE
(ii) Land Form, Land Use and Land ownership The land is in the form of industrial shed owned by Gujarat Industrial Development Corporation. The Plot has been allotted by GIDC and documents of the same is enclosed as Annexure 1.
(iii) Topography (along with map) Dahej GIDC is located on west of Bharuch district at Gulf of Khambhat. Topographically, the area is almost flat with gentle slope toward south and southwest i.e. toward Gulf. Geologically, entire area is covered with recent age deposits of fluvial and marine origin. Major part of it is covered with dark gray to brown Stiff clayey soil. Toposheet of the region is attached as Annexure 2.
(iv) Existing land use pattern
Proposed project is the barren and un-developed land/plot which is located in Gujarat Industrial Development Corporation (GIDC), Phase III Dahej. The existing land is an undeveloped land and does not include agricultural, forestry, CRZ and there are no national parks, wild life sanctuary, eco sensitive areas within the study area
(v) Existing Infrastructure
GIDC Notified Industrial Estate of Dahej has available infrastructure like water, electricity, roads, rail, transportation, availability of raw material and drainage system.
(vi) Soil Classification The project area falls under South Gujarat Agro-Climatic Zone-II and AEZ-21(Bharuch District).The Zone is characterized by 70-80 cm rain fall, 1-3 % soil slope .The soil depth is >100 cm and predominantly soils are clayey but near port soils are sandy in texture. Majority soils of this area have developed from the trap and mostly having montmorrilonite predominant clay mineral. The soil salinity is < 2.0 dS/m but due to ingress of sea water soils are highly saline especially in Lakhigam. At and around project are soils are barren
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and Prosopis julifera (Gandobaval) is seen. However, in the surrounding area sorghum, cotton, tur and fodder crops are grown.
(vii) Climatic Data from Secondary Sources
The general agro-climatic zone of the study area is Semi-arid.
Information presented in subsequent paragraphs is from the most recently published Long Term Climatological Tables for the nearest observatory, Bharuch by the Indian Meteorological Department (IMD).
Rainfall Data
The total rainfall in year is observed to be 924.8 mm. Distribution of rainfall by season is 2.3 mm in winter (December, January, February), 14.3 mm in summer (March, April, May), 869.3 mm in monsoons (June, July, August, September) and 38.9 mm in post-monsoon (October - November).
Temperature Data
Mean daily maximum temperature is recorded in the month of April at 40 °C.
From October to December, both day and night temperatures begin to decrease rapidly. January is generally the coldest month, with a minimum temperature of 11.9 °C.
During the post-monsoon months of October and November, day temperatures remain between 16.9-22.0 ºC. In winters, i.e. December, January and February, average day temperatures remain between 11.9-14.4 ºC.
Humidity
Most humid conditions are found in the monsoons, followed by post-monsoons, winter and summer in that order. Mornings are more humid than evenings and humidity ranges from a high of 80-90% in monsoon mornings to a low of 26-38% in summer evenings. During post-monsoon season, in morning humidity remains between 68-75% and in the evening it remains between 37-44%.
Cloud Cover
The area remains cloudy between June - September, which is the active period of the monsoon season. Cloud cover is 6-8 oktas during monsoon season, while it is 0-2 oktas in post monsoon, winter and summer season.
Seismic Zone: The general agro-climatic zone of the study area is Semi-arid.
(viii) Social Infrastructure
Key infrastructure such as hospitals, schools, bank, places of worship and social/ community facilities such as park, market, playground etc. education, health care, community development, income distribution, employment and social welfare are available in nearby area of Dahej Industrial Estate.
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5 PLANNING BRIEF
(i) Planning concept
There is a cluster of numerous large-scale, medium-scale and small-scale industries which includes Agro Based, Soda Water, Cotton textiles, Leather, Chemical, Engineering units, Mineral based specialilty chemicals, pesticides and others in the Gujarat Industrial Development Corporation (GIDC) notified Estate of Dahej.
(ii) Population Projection Not applicable
(iii) Landuse Planning
Proposed project is located within the Notified Industrial Estate by Government of Gujarat and due to the proposed project there will not be any change in the land use pattern of the region.The area statement of the project area is provided in Table 5-1.
Table 5-1: Area Statement Sr No Particulars Area Sq mts
1 Plant 7200 2 ETP and WTP 2360 3 Storage 3930 4 Admin, Security, Canteen 1777 5 Greenbelt Area (33% of Total Plot Area) 33379 6 Utility, R&D, Solvent Recovery 2501 7 Parking 11371 8 Open Area 37007
9 Pump Room for Fire Tank, Toilet and Hydrogenation Area 748
Total 100272
Site layout plan is provided in Figure 5-1.
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Figure 5-1: Plant layout
(iv) Assessment of Infrastructure Demand
There is no need for any infrastructure demand in terms of physical or social needs for the proposed expansion.
(v) Amenities/ Facilities
Basic Amenities like public transport, water supply, telecommunications, educational institutions, hospitals etc. are available in nearby area of Dahej Industrial Estate.
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6 PROPOSED INFRASTRUCTURE
(i) Industrial Area (Processing Area)
Proposed infrastructure will be developed as per standard engineering design considering
all the relevant parameters related to environment, health and safety.
(ii) Residential Area (Non Processing Area)
No residential area is involved in the proposed project.
(iii) Green Belt
Green belt will be provided and maintained at the tune of 33% of the total land area.
(iv) Social Infrastructure
Availability of drinking water facilities, toilets, parking area etc.
(v) Connectivity (Traffic and Transportation Road/ Rail/ Metro/ Water ways etc)
The project site is very well connected by road network.
(vi) Drinking Water Management
The water will be supplied by Gujarat Industrial development Corporation (GIDC).
(vii) Industrial Waste Management
Details of Industrial Waste management are already provided in section above.
(viii) Power Requirement & Supply/ Source
The power requirement is 4550 KW which will be procured from Dakshin Gujarat Vij Company Ltd. For emergency and as back-up D.G set (4 Nos.) of 750 KVA will be installed.
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7 REHABLITATION & RESETTLEMENT (R & R) PLAN
(i) Policy to be adapted (Central /State) in respect of the project affected persons including home outsee, Land outsee and Landless labourers
There will be no rehabilitation and resettlement undertaken as labors and workers from local & nearby areas for the proposed construction activity which will be minor as the proposed expansion activity is to be undertaken at the existing site.
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8 PROJECT SCHEDULE AND COST ESTIMATE
(i) Likely date of start of construction and likely data of completion
After obtaining Environmental clearance and Consent to Establish from GPCB, the company shall start the proposed construction and commissioning of the project and complete the project within 20 months.
(ii) Estimates project cost along with analysis in terms of economic viability of the project
Estimated project capital cost along recurring cost is given in Table 8-1 and Table 8-2 respectively.
Table 8-1: Capital Cost Projection
Sr No. Description Cost Rs. In Lakh
1 Land 2153
2 Land / Site development 547
3 Building 5667
4 Plant & Machinery 7770
5 Misc. Assets 113
6 STP Cost 10
7 ETP Cost 650
8 APCM Cost 70
9 Greenbelt Development 20
Total 17000
Table 8-2:Recurring/Operating Cost Per Annum
Component Proposed (Rs. in Lacs/annum)
Environment & Safety Management System 530
Air 12
Water 24
Solid waste Disposal 62
Greenbelt Maintenance 5
Total 633
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9 ANALYSIS OF THE PROPOSAL (FINAL RECOMMENDATIONS)
(i) Financial and social benefits with special emphasis on the befit to the local people including tribal population, if any, in the area Proposed project will provide benefits to the local people in terms of financial and social welfare. From the proposed project, there shall be increase to foreign exchange generated by
Exports. Reduce dependence on Imports hence reducing for risks. There shall be direct or indirectly increase in employment generation for the local
people and lead to ensure continued employment to existing workforce without affecting work conditions and hence supporting their families.
The company will allocate budget for CER activities, which can lead to improved social infrastructure, if planned properly.
The proposed expansion project shall not have any adverse environmental impacts because adequate protection measures will be provided to achieve permissible norms of GPCB.
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ANNEXURE
S
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Annexure 1: Plot allotment letter
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Annexure 2: Toposheet of the Region
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Annexure 3: PCPIR Document
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