Catalysis for Fine Chemicals & Specialty Products - NCLinduscap.ncl.res.in/Resources/Presentations/Indus CaP_Catalysis... · Catalysis for Fine Chemicals & Specialty Products

The Center for Environmentally Beneficial Catalysis

Catalysis for Fine Chemicals &

Specialty Products Raghunath V. Chaudhari

Center for Environmentally Beneficial Catalysis

Department of Chemical and Petroleum Engineering

At Industrial catalysis & Catalytic Processes

Workshop at NCL, Pune

14 January, 2012


Impact of Catalysis in Life

• Catalysis contributed significantly to technological developments in various sectors of industry such as power, energy, materials, health & environment

• The 21st century has witnessed growth of Catalysis with a few serendipities, many patiently discovered facts and successful technological surprises

• Many future technological challenges will depend on breakthroughs in catalysis

Catalysis – A true multidisciplinary activity


Major Application Areas

Chemical Processes Hydrogenation, Dehydrogenation, Organic syntheses (Hydrogenolysis, Hydration, Reactive Partial Oxidation, Amination etc. ) Syn-gas Conversions and FT synthesis, Polymerizations and Oxidation

Petroleum Processes

Hydrodesulfurization, Hydrocracking, Hydrodenitrogenation, Hydrodemetalisation

Fine Chemicals and Pharmaceuticals

Hydrogenation, Carbonylation, Alkylation, Acylation, Oxidation, Amination, Hydroxylation, metathesis and C-C coupling reactions (Heck, Suzuki etc)

Biotechnology and Environmental Processes

Fermentation, Total oxidation, de-NOx, de-SOx, Auto- exhaust


Catalysts & Catalytic Processes: A Global Scenario

Products worth a Trillion Dollars are produced

annually using catalytic processes - More than GDP of

most of the countries. This excludes biocatalysts &

pollution control processes.

Value of Catalysts produced worldwide is more than US

$ 10 billion

Catalyst Usage

37 % Petroleum refining

34 % Chemical Processes

29 % Emission/Pollution control

80-90% of current Chemical Processes are based on

Catalysis


Catalysis & Green Chemistry

Growth of chemical industry has been associated

with generation of toxic and hazardous wastes

Our efforts in the last two decades in waste treatment, monitoring pollutants have improved pollution control, but, for pollution free processes Catalysis has a major role to play

Green approach in catalysis conceptualizes around use of green feedstock, high atom-efficiency & atom economy, recycling and diversification of downstream leftovers into value added products, green effluents


Green/Clean Technology Development

Major Challenges

• Replace hazardous and corrosive raw materials

/reagents

• Reduce waste products such as inorganic salts and/or

toxic co-products

• Substitute synthetic routes by catalytic ones

• Improve selectivity (atom efficiency) of desired

products

• Catalysis for processes under lower pressure and

temperatures

• Catalytic reaction engineering for optimization of

processes for higher productivity and safer operation


Examples of Catalysis in Clean Technologies

• Hydrogenation replacing stoichiometric reagents such as Fe-

HCl, NaBH4

• Oxidation using molecular oxygen or H2O2 to replace HNO3,

K2Cr2O7 type reagents

• Alkylation and acylation using solid acid catalysts to replace

Friedel-Craft synthesis with AlCl3

• Carbonylation reactions to produce carboxylic acid replacing

stoichiometric NaCN and HCN or HF/BF3

• Hydroformylation of olefins for synthesis of aldehydes and

alcohols

• Asymmetric catalysis for synthesis of enantiomerically pure

drugs, and agrochemicals, replacing the conventional optical

resolution methods


Application areas :

Fine & Specialty chemicals

Agricultural Chemicals Adhesives

Biocides Catalysts

Dyestuffs Electronic chemicals

Feed and food additives Flavors and fragrances

Industrial coatings Ind. & Inst. Cleaners

Lubricants & functional Fluids Paper additives

Pharmaceuticals Photographic chemicals

Pigments Plastics and polymers

Specialty surfactants Synthetic fibers & textiles

Sales > $ 140 billion


Fine Chemical Manufacturing Trends


Salient features of Fine chemicals

& pharmaceuticals Processes

Scale of production usually below 1000 TPA involving multiple organic synthesis

Batch processes are common

Varying market demands require product changeover

Stringent product specifications

Severe selectivity problems

Problems of corrosion, health hazards, safety, effluent disposal

Separation problems associated in the downstream processes


Key Business Aspects

Small manufacturing firms are starting up

Larger firms are expanding by

buying specialty companies

forming business alliances

establishing entrepreneurial divisions

Everyone is chasing chemistry professors

Product portfolios are expanding by “trees”


Examples of Catalytic Reactions in

Pharmaceuticals

Ibuprofen, by a three step catalytic route involving acylation, hydrogenation and carbonylation (3500 TPA, Hoechst Celanese Corporation)

Hydroformylation of diacetoxybutenes to 2-Methyl-4- acetoxybutenal (an intermediate for Vitamin-A, > 600 TPA, Hoffmann-La Roche & BASF)

Heck Coupling of 3-Bromopyridine & But-1-ene-3,4-diol followed by asymmetric hydrogenation to pyridine diol (intermediate for drugs in treatment of allergic conditions of eyes, nose and skin, optimized on multi-kg scale by AstraZeneca)

Oxidation of p-cresol to p-hydroxybenzaldehyde (intermediate for antibiotics like Amoxicillin, Cephalosporin)

Hydrogenation of butynediol to cis-butenediol (intermediate for Vitamin B6) Rev. Chem. Eng, 8, 1 (1992)


Examples of Catalytic Reactions in

Pharmaceuticals ….contd. Hydrogenation of,

nitrobenzene to p-amino phenol (An intermediate for paracetamol

(Mallinkrodt Process)

4-Acetoxy-3-methoxy-a-acetamido cinnamic acid to L-Dopa (drug for

Parkinson’s disease, >200 TPA, Monsanto)

branched C13 allylic alcohol to Vitamin E intermediate (Multi kg scale

process, Takasago)

C22-C23 double bond of bacterial metabolite Avermectin B1 to

Ivermectin (antiparasitic agent, useful for the treatment of

onchocerciasis; Manufactured by Merck)

1-hydroxy-2-propanone to (S)-1,2-propanediol (Intermediate for (S)-

oxfloxazin, bactericide; Manufactured by Takasago – 50 TPA)

substituted b-keto esters to b-hydroxy esters, (chiral building blocks,

e.g. carbapenem intermediate; Manufactured by Takasago – 120 TPA)

CHEMTECH., 18, 184 (1988)


Catalysis to Replace Phosgene


Goal: Eliminate phosgene use in

production of key chemical intermediates

Polycarbonate (PC)

Dimethyl Carbonate (DMC)

Diphenyl Carbonate (DPC)

Monomers for polyurethanes

- Methylene Diphenyl Diisocyanate (MDI)

- Toluene Diisocyanate (TDI)

Carbaryl (insecticide)


Polycarbonate (PC) Production via

the Phosgene Process

Global production ~1.2M tonnes/yr

Approximate cost $3-7 per kg

Important applications:

• Electronics: CDs, DVDs, computer parts

• Medical: Compatible with USP VI standard

• Packaging, shields

• Automotive and aviation: Light casings, instrument panels, interiors

Phosgene BPA Polycarbonate

n


Oxidative Carbonylation:

A Non-Phosgene Route

Alternative to phosgene for synthesis of

carbamates, carbonates and urea derivatives

Clean catalytic and atom efficient route

Eliminates corrosion problems

Development of selective catalysts is a major

challenge


Oxidative Carbonylation of Phenol to

Diphenyl Carbonate

• Typical Catalyst :Pd (OAc)2/Co catalyst and promoter

• Temperature :80 - 100 0C

• Pressure : 50 -100 atm

• Conversion : 50%

• Selectivity : 90%

US Patent No. : 5,399,734 (1995)

• Early studies showed promise of an oxidative carbonylation route

as an alternative to phosgene

• Catalysts to date suffer from low turnovers and stability problems


Oxidative Carbonylation of Bisphenol A

to Polycarbonate (Example 1)

Novel catalyst developed :

Pd(acac)2/Co(SMDPT)/Terpyridine/TEAB

Temperature: 100oC, Pressure : 1000 psig

Oligomer yield based on BPA charged : 90%

TON ~ 100

Single step non-phosgene

route for polycarbonate

US Patent No. 6,222,002


Single-Step Oxidative Carbonylation

of BPA to Polycarbonate

Ultimate low cost simple process

But, still needs catalyst improvements and

increased product purity

Low molecular weight PC [~3000] obtained

Catalyst TON of 100 achieved at 95% BPA conversion; oligomer yield 90%

Control oligomer weight by reactive separation with proper choice of solvents

Initially envisage two-step process with further polymerization of low MW oligomers

Future challenge: design a highly active/stable catalyst with minimal components

Current status


Synthesis and Use of Dimethyl Carbonate (DMC)

Trans-esterification of DMC with phenol to yield DPC

Oxidative carbonylation of Methanol

Conditions

CuCl/ KCl catalyst, T=130 oC, 2.4 Mpa, 35-250 g/l/h productivity

DPC used as a raw material for polycarbonates


Polycarbonate Synthesis by

Transesterification

Reaction uses trans-esterification catalysts and either phenol or

Bis-Phenol A as the reactant to obtain either DPC or PC


Exciting New Process: Asahi

Kasei’s CO2-based Non-Phosgene

Polycarbonate

• First process to use carbon dioxide as a starting material.

• 50,000 tonnes/yr plant operating in Taiwan since 2002.


Commercial Isocyanate Products

Monomeric MDI

Oligoisocyanate MDI

Monomeric TDI

4,4’-MDI 2,4’-MDI 2,2’-MDI

2,4-TDI 2,6-TDI

• MDI & TDI represent 90 % of the isocyanate market and are the key

monomers for polyurethanes (4M TPA in US)

• Diisocyanates are reacted with polyols to produce polyurethanes. The range

of polyurethane types, from flexible or rigid light weight foams to tough, stiff

elastomers, are used in a wide diversity of consumer and industrial

applications.


Applications of Polyurethanes

MDI-Polyurethanes

TDI-Polyurethanes

MDI-Polyurethane

Domestic

insulation

Multipurpose

adhesives

Automotive

interiors

Composite

wood products

Synthetic

leather

TDI-Polyurethane


Growth in MDI Demand


Conventional Process for MDI uses

Phosgene

Condensation

Neutralization

Phosgenation

Disadvantages

Handling of toxic and corrosive phosgene, used in high excess

Produces large quantity of HCl and NaCl

Poor selectivity to pure monomeric MDI

Difficulty in removal of hydrolysable chlorine compounds

Polyamine

Poly-MDI


Alternative: Oxidative Carbonylation

Route to MDI

-H2O

OR

NHCOOEt + 2CO2 2NO + 3CO + EtOH

(EPC)

3. Decomposition

+ 2 EtOH

( 4,4' - , and 2,4' - MDI)

NCO CH2OCNNHCOOEt CH2EtOCONH

Second Step : Intermolecular transfer reaction

+ EPC

( 4,4' -, and 2,4' - MDU)

EtOCONH 2CH NHCOOEt EPC+N CH2 NHCOOEt

COOEt

( N-benzyl compound)

2

First Step : Condensation

2. Condensation

(MDU)

COOEt

NHCOOEt N CH2NHCOOEt + HCHO

1. Carbonylation

(EPC)

NHCOOEt + H2OO22

1+ CO + EtOH + NH2

A clean catalytic

process without

using toxic and

corrosive phosgene

Requires cheaper

raw materials like

CO and O2, aniline

being common in all

the routes

Eliminates inorganic

salts and HCl

formation providing

environmentally

benign process

Novel Features of non-Phosgene Route


Heterogeneous Catalysts Work Well in

Oxidative Carbonylation

• Separable Catalysts

• Efficient catalysts with

high activity, selectivity

and recyclability

Conversion: 98.5%

Selectivity: 96.4%

TOF: 157 h-1

0

20

40

60

0 1 2 3 4

Recycle No.

Con

v/ Y

ield

, %

0

20

40

60

80

100

DP

U S

elec

tivit

y, %

ConversionYieldSelectivity


Reactions Conditions:

Catalyst: Supported Pd/NaI,

Temperature: 190oC

Total Pressure: 1000 psig, Yield of

Polycarbamate: 94%

Oxidative Carbonylation of Poly-DADPM

Single step non-phosgene process

Novel catalyst with high selectivity to Poly-MDU

Chaudhari et al, WO-01/47871 A2


• A non-phosgene route for the synthesis of methyl N-phenyl carbamate from dimethyl carbonate and N,N-diphenyl urea under mild conditions.

• A homogenous catalyst, sodium methoxide exhibited excellent activity in the synthesis of methyl N-phenyl carbamate under atmospheric pressure.

Green Chem., 2007

Synthesis of Methyl N-phenyl Carbamate

from CO2


2-Arylpropionic acids (NSAIDs):

Carbonylation Route


Profens: 2-Arylpropionic acids (non-steroidal anti-inflammatory drugs)

Ibuprofen

(Boots, Hoechst Celanese)

Naproxen

(Syntex) Ketoprofen

(Wyeth-Ayerst)

Indoprofen

(Farmitalia)

Fenoprofen

(Lilly)

Carprofen

(Hoffmann-LaRoche) Flurbiprofen

(Upjohn)


Ibuprofen – Classical Routes

Toxic NaCN required

Generation of large quantity of inorganic salts

Hazardous downstream effluent handling

6-step synthesis

Stoichiometric AlCl3 required

Enormous byproduct salts generated

Overall Atom Economy ~ 40%

OTHER STOICHIOMETRIC ROUTE

BOOTS PROCESS


Alternative: Catalytic Carbonylation Route for

Ibuprofen

Total world production of Ibuprofen is > 15,000 tpa*

Ibuprofen by Hoechst Celanese (Currently BASF) via the carbonylation route : ~ 3500 tpa

High regioselectivity (>95%) to the branched isomer (Ibuprofen) is attained but at high CO pressures (>160 bar)

Clean and eco-friendly process with ~77-99 % overall atom economy‡

* Myers R. L. The 100 Most Important Chemical Compounds: A Reference Guide, 150, 2007

‡ http://www.rsc.org/education/teachers/Resources/green/ibuprofen/home.htm

http://www.rsc.org/education/teachers/Resources/green/ibuprofen/home.htm


Catalyst Performance Improved with

Novel Low-Pressure Catalyst

Stud. Surf. Sci. Catal. 1998, Catal. Lett. 1999, Org. Lett., 2000

Catalyst

Biphasic

PdCl2(PPh3)2

/10% Aq. HCl

Homogeneous

PdCl2(PPh3)2/

HCl

Homogeneous

PdCl2(PPh3)2 /

TsOH-LiCl

Homogeneous

Pd(pyca)(PPh3)(O

Ts) /TsOH-LiCl

Temp, °C 130 115 115 115

CO Pressure,

bar

160 54 54 54

TOF, h-1 42 90 829 840

iso sel., % >95 93 96 99.5

CO, H2OCOOH

RR

COOH+

LiCl, TsOHR

OH

Major (iso) Minor (n)

Novel Pd(pyca)(PPh3)(OTs) complex showed distinct improvement

lower reaction temperature

CO pressure reduced from 160 to 54 bar

20-fold enhancement of TOF

Improvement of Catalyst Performance


Another Option: Aqueous Biphasic Catalyst Water-soluble [Pd(Pyca)(TPPTS)]+TsO- complex prepared

by exchanging PPh3 with TPPTS

Chem. Comm., 2000

Gas

phase

Organic

phase

Aqueous

phase

Substrate Product Conv

, %

TOF

, h-1

Regiosel,

%

Iso n

81 147 98 1.5

45 10 93 6.5

Temp = 388K, PCO = 5.4 MPa

CO

CO

CO

Li+

Cl- Higher activity than the BHC biphasic process

High iso-selectivity was observed

Catalyst active on recycles under CO atm only


Yet Another Option: Supported Pd Catalysts

LiCl-TsOH, PPh3 promoters used

Catalyst Conv

%

Regiosel

%

TOF

h-1

1% Pd-C 96 99.2 3375

1% Pd/ -alumina 92 99.5 2475

1% Pd/H ZSM 5 90 99.0 2285

1% Pt-C 90 99.2 550

Pd metal 97 99.3 90

Comments

High activity and selectivity observed

Pd-C catalyst recycled efficiently for at least 6 times

Active Pd-complex leaches out during reaction and re-adsorbed to support after reaction

Chem. Comm., 1999


Metal complex: Pd(pyca)(PPh3)(OTs)

Support: MCM-41, MCM- 48, SBA-15

Distinctions

High activity (TOF 450 h-1)

High selectivity ( 99% to iso)

Easily separable & recyclable

Highly stable (Pd leaching 10-4 %)

Still Another Option: Anchored Pd-complex

Catalysts in Mesoporous Supports

J. Am. Chem. Soc.,2002


Ossification of Pd-complexes

Aq. TPPTS

Aq. Ba(NO3)2

Catalytically active

Coordination sphere

Insoluble appendage

Facile synthesis steps

Making Aq. Soluble Pd-

complexes having –SO3-

groups

Simple admixing with Ba2+

ions

Stable intrinsically insoluble

metal complex formed

Wide applicability to all

similar aqueous soluble

catalysts to obtain solid

catalysts


Asymmetric Catalysis


A major advancement in synthesis of enantiopure chiral drugs, agrochemicals and flavoring agents by asymmetric hydrogenation, isomerization , oxidation and hydroformylation reactions.

Majority of the pharmaceutical products prescribed presently involve molecules with at least one chiral center and a stringent enantiopurity is required in 80% of products.

Asymmetric Catalysis

Drugs

Agrochemicals

Flavouring agents


Why Asymmetric Catalysis ?

The demand for single enantiomeric

products is increasing at > 9 %

annually with sales of $ 147 bn

Large differences in the activities of

individual enantiomers. In many cases,

one of the stereo isomer is either

inactive or toxic

Racemic switch : Product line

extension for existing racemates for

expired patents

Asymmetric catalysis provides a clean,

atom efficient route for synthesis of

single enantiomers involving minimum

synthesis steps and minimized waste

generation


Selectivity is Important

Chemo-Selectivity

The selective conversion of one functional group in the

presence of other dissimilar but reactive groups

Regio-Selectivity

The selective conversion of a functional group to a

desired regio-isomer

Stereo-Selectivity

The selective conversion to one stereo-isomer in

preference to another, represented as Enantiomeric

excess (ee) defined as : (R – S) /(R + S)


Asymmetric Hydrogenation of C=C Bonds

• Aroma compound (Both R & S isomers are useful fragrance compds)

• This reaction is H2-pressure dependent - low pressures trigger

isomerization to nirol

• Chirality of BINAP (R or S) and product configuration (R or S) are

reverse

• Commercialized by Takasago on 300t/a scale

ee 97 %; TOF-500 h-1

Noyori et al , JACS, 109, (1987) 1596


L-Dopa Synthesis by Asymmetric Hydrogenation

1 2

Hydrogenation is carried out in a slurry of substrate (S/C ratio = >20000:1)

Reaction involves simultaneous dissolution of H2 and sparingly soluble substrate followed by reaction to produce precipitating solid product

The precipitate, essentially optically pure is collected by filtration while the catalyst and the racemic product remain in solution

95% ee for L-Dopa derivative is obtained

Commercialized by Monsanto - > 2 tons/a

‘Asymmetric Catalysis on Industrial scale’ Ed. H.

U. Blaser, E. Schmidt WILEY-VCH 2004

drug for Parkinson’s disease


Metolachlor synthesis

• Metolachlor is the active ingredient of Dual® – One of the most

important grass herbicides

• Out of the four isomers, two isomers with (1’S) configuration account

for ~ 95 % of the herbicide activity of Metolachlor

• An example of Chiral Switch - It is marketed as a racemic mixture of

all 4 from 1976, but recently changed to (1’S) Metolachlor

• Racemic Metolachlor Synthesis: Pt catalyzed reductive alkylation of

2-methyl-5-ethyl aniline (MEA)

• (1’S) Metolachlor: Asymmetric hydrogenation of MEA imine


Asymmetric Hydrogenation of C=N Bond: Metolachlor Synthesis

• Rh-diphosphine: Low ee: 69%; Low TOF: 15h-1

• Ir-diphosphine: Good ee: 84%; Low TOF: 250 h-1

• Ferrocenyl diphosphines: New class of ligands was synthesised and found to be highly active e.g. Xyliphos

• Optimization of reaction conditions: - Acetic acid as solvent was found to be effective - Quaternary ammonium iodide (NBu4I) increased the rate by 5 times and

leads to 100 % conversion in 1/20th time

- ee values decreased from 83% at –10º C to 76% at 60º C - Optimum conditions: 50º C and 80 bar H2 pressure


Metolachlor Process

Syngenta’s Metolachlor plant - C & EN 82 (2004)

Important Issues: Synthesis of MEA imine in required purity Development of Xyliphos synthesis from g to kg scale in reproducible form and quality Catalyst instability: Liquid formulation developed for intermittent catalyst addition

Choice of reactor technology: A loop reactor was used for optimum mass and heat transfer

Process Features: ee: 84 %; TON: 1000000; TOF: 200000 h-1

Plant capacity: 10000 ton/a of (S)-NAA Largest scale catalytic enantio-selective hydrogenation plant in the world ‘Asymmetric Catalysis on Industrial scale’ Ed. H.

U. Blaser, E. Schmidt WILEY-VCH 2004


Challenges in Asymmetric Catalysis

Processes

While enantioselectivity is of prime importance, it is the overall rate of reaction that will decide industrial feasibility

The enantioselectivity is more sensitive to higher temperature than chemo selectivity or regioselectivity

Synthesis of chiral catalysts at lower cost on commercial scale

Catalyst-product separation is complex due to non-volatile and thermally sensitive products. Opportunity for development of Heterogenized chiral catalysts

Detailed kinetic analysis is required as, most reactions involve gas-liquid or gas-liquid -solid systems with complex chemistry

the reactivity of the intermediates of respective enantiomers differs radically in many cases

the Non-Linear Effect between ee of chiral auxiliaries and products

In some cases the individual enantiomers differ in their solubility properties e.g. L-Dopa


Catalyst Invention

Research Concept

Catalyst Synthesis

Catalyst Characterization

Rapid Catalyst Screening

Basic Rxn. Kinetics

Preliminary Process Economics

Market Input

Catalyst Modification

Catalyst Life Studies

More Detailed Kinetics

Detailed Process Economics

Lab Reactor Evaluations

Commercial Application

Pilot-Plant Evaluation

Catalyst Scale-Up

Discovery “Good Science”

Development Commercialization “Good Engineering”

- from Discovery to Commercialization -

P. L. Mills, J. F. Nicole and M. P. Harold, Stud. Surf. Sci. Catal. , Vol 133, 2001


New Trends in Green Technology

Development

• Novel synthetic routes & New Chemistry

One pot reactions

Tandem synthesis

Multifunctional catalysts

Immobilized catalysts

• Novel Reactor concepts

Batch to continuous operations

Microchannel reactors

• Green solvents or Solventless Processes


Center for Environmentally

Beneficial Catalysis

• Established in 2003 by NSF

• >$30 million invested

• World-class faculty;

• Modern laboratories

• Industry-guided research

• Revenue-generating projects

The Center for Environmentally Beneficial Catalysis 54

Core Projects: Some Recent Advances

4 L Spray Oxidation Reactor:

1st extended continuous runs

Inexpensive

soluble polymer

ligands for

hydroformylation

Nanofiltered:

soluble polymer-

bound methyltri-

oxorhenium for

oxidation

Cu-Pd/Graphene Nanocatalysts

for biomass conversions

Multi-

functional

mesoporous

catalysts


• ADM

• Chevron Phillips

• ConocoPhillips

• Dupont

• Evonik

• ExxonMobil

• P&G

• UOP

• Zeachem

• BASF Catalysts

• BP

• CritiTech, Inc

• Eastman

• Gevo

• KTEC

• Novozymes

• Pharma Roundtable

• SI Group

15 Industrial Partners Total


Current Industry Advisors

56

Former Partners BASF Catalysts

BP

CritiTech, Inc

Eastman

Gevo

KTEC

Novozymes

Pharma Roundtable

SI Group

Conclusions Advances in Catalysis are providing improved process

economics, environmental compatibilities, and product quality

replacing stoichiometric processes.

Wide ranging opportunities exist in the design of innovative

high-performance multicomponent catalyst systems and process

routes.

Asymmetric catalysis provides a cost effective, environmentally

acceptable alternative for synthesis of enantiopure products,

however, the success would largely depend on development of

lower cost chiral ligands and catalyst-product separation

technology

Enantioselectivity coupled with high productivity (TOF) and

stability is essential in catalyst development to expand the

applicability of Asymmetric Catalysis

The challenges can be met through integrated efforts in catalysis

science and engineering.

Documents

Catalysis for Fine Chemicals & Specialty Products - NCLinduscap.ncl.res.in/Resources/Presentations/Indus CaP_Catalysis... · Catalysis for Fine Chemicals & Specialty Products