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है”ह”ह

IS 8552 (1977): 1 - (4' - Sulphophenyl) - 3 - Carboxy - 5 -Pyrazolone [PCD 9: Organic Chemicals Alcohols and AlliedProducts and Dye Intermediates]

IS : 8552 - 1977

Indian Standard SPECIFICATION FOR

l-( 4’-SULPHOPHENYL )-3-CARBOXY- 5-PYRAZOLONE

Dye Intermediates Sectional Committee, CDC 46

Chairman

~HRI RAJENDRA SRANKER

Members

Representing

Indian Dyestuff Industries Ltd, Bombay

SHRI M. S. TAWAKLAY ( Alternate to Shri Rajendra Shanker )

DR S. C. AMIN Universal Dyesluff Industries Ltd, Vadodara DR V. M. VAISHNAV ( Alternate )

SHRI V. K. ATRE Hickson & Dadajee Ltd, Bombay SHRI N. S. MURTHY ( Alternate )

SHRI S. D. BHARDWAJ Ajanta Chemical Industries, New Delhi SHRI KAPIL DEV ( Alternate )

SERI P. B. BHATTACRARJEE Luxmi Narayan Dyestuff & Chemical Works Pvt Ltd, Calcutta

$HRI B. M. BRAHME Atic Industries Ltd, Bulsar DR M. M. DESHPANDE Suhrid Geigy Ltd, Vadodara

SHRI N. G. AMIN ( Alternate ) SHRI P. K. KAMATH

SHRI N. C. BAESHI ( Alternate ) I. C. I. ( India ) Pvt Ltd, Calcutta

SHRI G. A. KULKARNI Amar Dye-Chem Ltd, Bombay SHRI S. V. DESAI (Alternate )

SHRI S. M. MEHTA Atul Products Ltd, Bulsar SHRI M. V. DESAI ( Alternate )

DR R. J. RATHI Sudarshan ChemicaI Industries Pvt Ltd, Pune SHRI K. L. RATHI ( Alternate )

SRRI T. SADASIVAN Ciba-Geigy of India Ltd, Bombay SHRI M. N. KHOPKAR ( Alternate )

SHRI SANTOKB. SINQH National Chemical Industries Pvt Ltd, New Delhi SHRI KULWANT SIN~R ( Alternate )

SHRI S. N. SAXENA Directorate General of Technical Development, New Delhi

SHRI S. K. LUTIIRA ( Alternate ) DR H. A. SHAH Development Commissioner, Small Scale Industries

Ltd, New Delhi SHRI G. G. SUTAONE ( Alternate )

( Continued on page 2 )

@ Copyright 1977 INDIAN STANDARDS INSTITUTION

This publication is protected under the Indian Copyright Act ( XIV of 1957 ) and reproduction in whole or in part by any means except with written permission of the publisher shall be deemed to be an infringement of copyright under the said Act.

IS-: 8552 - 1977

( Continued from Page 1 )

Members Rejwesenting

SHRI S. J. SHAH Indian Chemical Manufacturers’ Association, Calcutta

Sum M. B. MWHTA ( Alternate ) DR D. R. SRIDHAR Indian Drugs & Pharmaceuticals Ltd, New Delhi

DR R. N. DHAR ( Alternate ) DR P. V. SUBRAMANIA~~ Colour-Chem Ltd, Bombay SBRI MUKUND TURAKI~IA The Dyestuffs Manufacturers Association of India,

Bombay SHRI ANIL MEHTA ( Alternate )

SRRI V. G. UPADHYE Synthofine Chemicals of India Pvt Ltd, Bombay SHRI H. K. VENKATARAMAIAH Hindustan O:gonic Chemicals Ltd, Rasayani

DR G. M. S~XE:N.~, Director ( Chem )

( Maharashtra ) Director General, IS1 ( Ex-o&o Member )

Secretary

SHRI N. K. S~~nnr.4 Deputy Director ( Chem ), IS1

Panel for Pyrazolonrs, CDC 46 : P9

Conocner

DR P. V. SUBRAMANIAM

Members

SHRI V. K. ATRE

Colour-Chem Ltd, Bombay

SHRI N. S. MARTY ( Alternate) Hickson & Dadajee Ltd, Bombay

SHRI M. V. DESAI Atul Products Ltd, Bulsar DR S. R.~G. SARXA ( Alternate )

DR N. F. DESAI DR S. B. P~TEL ( Akrnate )

Sandoz ( India ) Ltd, Bombay

Dn M. M. DESHP~NDE Suhrid Geigy Ltd, Vadodara Dn S. S. GUPTE SHRI G. A. KULKARNI

Indian Dyestuff Industries Ltd, Bombay

SHRI V. K. MENON ( Alternate ) Amar Dye-Chem Ltd, Bombay

SHRI SANTOKH SINQR National Chemicals Industries Pvt Ltd, New Delhi SHRI KULBIR SINGE (Alternate)

SHRI R. K. TULSIBAGWALE Synthofine Chemicals of India Pvt Ltd, Bombay

2

IS:8552 -1977

Indian Standard SPECIFICATION FOR

1-( 4’-SULPHOPHENYL )-3-CARBOXY- 5-PYRAZOLONE

0. FOREWORD

0.1 This Indian Standard was adopted by the Indian Stand~ards Institution on 27 July 1977, after the draft finalized by the Dye Intermediates Sectional Committee had been approved by the Petroleum, Coal and Related Products Division Council.

0.2 l-( 4’-sulphophenyl )-3-carboxy-5-pyrazolone ( CloHsNzO& ) is an important dye intermediate used in the manufacture of azo dyes. It has the following structural formula:

o= r-1 \ ,, SOjH

H2C N -cl-

\//

COOH

l-( 4’-Sulphophenyl)-3-Carboxy-5-Pyrazolone ( Molecular Mass 284 )

0.3 For the purpose of deciding whether a particular requirement of this standard is complied with, the final value, observed or calculated, expressing the result of a test or analysis, shall be rounded off in accordance with IS : 2-1960*. The number of significant places retained in the rounded off value should be the same .as that of the specified value in this standard.

*Rules for rounding off numerical values ( revised ).

3

IS : 8552 - 1977

1. SCOPE

1.1 This standard prescribes the requirements and the methods of sampling and test for 1-( 4’-sulphophenyl )-3-carboxy-5-pyrazolone.

2. REQUIREMENTS

2.1 Description - The material shall be in the form of crystalline yellowish powder and shall be free from visible impurities.

2.2 The material shall also comply with the requirements given in Table 1.

TABLE 1 REQUHIEMENTS FOR I-( 4’:SULPHOPHENYL )-3- CARBOXY-5-PYRAZOLONE

SL CHARACTERISTIC REQCIREWXT METHOD OF TEST, No. RFF TO CL No. TN

APPENDIX A

(1) (2) (3) (4)

i) Assay ( on dry basis ), 75 A-2 percent by mass, Min

ii) Solubility in sodium To pass test A-3 hydroxide solution

3. PACKING AND MARKING

9.1 Packing - The material shall be packed in steel drums ( see 1s : 2552-1970* ) lined with suitable polyethylene film or as agreed to between the purchaser and the supplier. Each container shall be securely closed.

3.2 Marking - Each container shall bear legibly and indelibly the following information:

a) Name of the material;

b) Name of the manufacturer and his recognized trade-mark, if any;

c) Batch number; and

d) Tare, net and gross mass.

*Specification for steel drums ( galvanized and ungalvanized ) (first p.&&,n ).

4

IS:8552-1977

3.2.1 The containers may also be marked with the IS1 Certification Mark.

NOTE --The use of the ISI Certification Mark is governed by the provisions of the Indian Standards Institution ( Certification Marks ) Act and the Rules and Regulations made thereunder. The ISI Mark on products covered by an Indian Standard conveys the assurance that they have been produced to comply with the requirements of that standard under a well-defined system of inspection, testing and quality control which is devised and supervised by IS1 and operated by the producer. IS1 marked products are also continuously checked by IS1 for conformity to that standard as a further safeguard. Details of conditions under which a licence for the use of the ISI Certification Mark may be granted to manufacturers or processors, may be obtained from the Indian Standards Institution.

4. SAMPLING

4.1 Representative samples of the material shall be drawn as prescribed in 3 of IS : 5299-1969”.

4.2 Number of Tests - Tests for assay and solubility in sodium hydroxide solution shall be- conducted on each of the individual samples.

4.3 Criteria for Conformity - The lot shall be declared as con- forming to the requirements of this standard if each of the test results as obtained in 4.2 satisfy the corresponding requirements given in Table 1.

5. TEST METHODS

5.1 Tests shall be carried out according to the methods prescribed in Appendix A, as indicated in co1 4 of Table 1.

5.2 Quality of Reagents - Unless specified otherwise, pure chemicals and distilled water ( see IS : 1070-19777 ) shall be employed in tests.

NOTE - i Pure chemicals ’ shall mean chemicals that do not contain impurities which affect the results of analysis.

*Methods of sampling and tests for dye intermediates. tSpecification for water for general laboratory use ( second revision ).

5

IS :8552-1977

APPENDIX A

( Table 1, and Clause 5.1)

METHODS OF TEST FOR 1-( 4’-SULPHOPHENYL )-3-CARBOXY-5-PYRAZOLONE

A-1. PREPARED SAMPLE

A-1.l Dry the material at 90° + 5°C to constant mass. Grind and mixwell. Transfer the material to a wide-mouthed bottle and stomer it.Do not expose the sample to an atmosphere containing acidic or ~lkalinefumes. Use this prepared sample for tests.

A-2. ASSAY

A-2.O Outline of the Method — An accurately weighed quantity of theprepared sample ( see A-1.1 ) is dissolved in alkaline solution and titratedagainst a standard solution of diazotized 4-chloroaniline.

A-2.1 Reagents

A-2.1.1 Hydrochloric Acid — 30 percent (m/v).

A-2.1.2 Sodium JVitrite Solution — 10 percent (m Iv).

A-2.1.3 4-Chloroaniline — pure.

A-2.1.4 Sodium Hydroxide Solution — 40 percent (m/V).

A-2.1.5 Dilute Acetic Acid — 20 percent (m/v).

A-2.1.6 Sodium Acetate Solution – 40 percent (m/v).

A-2.1.7 H Acid Indicator Solution — Dissolve 0“5 g of H acid in 100 ml ofwater containing 1 g of sodium carbonate.

A-2.1.8 Starch Iodide Test Papers

A-2.2 Procedure

A-2.2.1 Preparation of Standard 4Chloroaniline Diazonium Salt Solution —weigh accurately about 7 g of 4-chloroaniline and dissolve in 25 ml ofhydrochloric acid and 100 ml of water. COOI to OQc in an ice. bath.

~iazotize with mechanical stirring -by the addition of sodium nitritesolution from a burette dropwise untd a siight excess of nitrite is shownon the starch iodide paper. The nitrite reaction should be faintlypositive even after about 20 minutes. Transfer the clear diazoniumsolution to a 500-ml volumetric flask and make up the volume withice-cold water. Store this standard solution in an ice-bath in the dark.

A-2.2.2 Determination of 1-( 4Weigh accurately about 20 g of tin 15 ml of sodium hydroxidevolumetric flask. Pipette out 50dilute to about 300 ml with wateacetic acid until the pH is 7 assuspension 200 ml of sodium acettally, add the diazonium salt sowith a jacket through which ice-should be of amber-coloured’ glasdiazonium salt by light. Titratethe end point of tiration, pyrz. . . . .excess ot the diazonium salt spyrazolone, place a drop of the tibring it into contact with the drosolution. A yellow colour deveksolution indicates the presencidiazonium salt use the H acidcolour developing at the zonediazonium salt.

A-2.2.3 It is advantageous to cdiazonium standard solution inmate range in which the end pftitration by adding the diazonibeginning, and then in 0“2 mlNote the volume of the diazotitration.

A-2.3 Calculation

A-2.3.1 Normality of the diaz,

where

P = purity in percenl

Ml = mass in g of 4cI

A-2.3.2 Away, percent by mass

where

V = volume in ml of

N = normality of di~

M2 = mass in g of tesl

6

IS :8552 -1977

A-2.2.2 Determination of I-( 4’-Sulphophenyl )-3-Carboxyd-Pyrazolone - Weigh accurately about 20 g of the prepared sample ( see A-l.1 ), dissolve in 15 ml of sodium hydroxide solution and make up to 500 ml in a volumetric flask. Pipette out 50 ml of the solution into a beaker and d~ilute to about 300 ml with water. Under stirring, add dropwise dilute acetic acid until the PH is 7 as indicated by pH paper. Add to the suspension 200 ml of sodium acetate solution. While stirring mechani- cally, add the diazonium salt solution from a burette which is provided with a jacket through which ice-cold water is circulated. The burette should be of amber-coloured glass to minimize any decomposition of the diazonium salt by.light. Titrate as rapidly as the s-pot test permits. At the end point of tiration, pyrazolone should be absent and a trace excess of the diazonium salt should be present. To test for excess pyrazolone, place a drop of the titration mixture on a filter paper and bring it into contact w~ith the drop of the 4-chloroaniline diazonium salt solution. A yellow colour developing at the zone of contact of the two solution indicates the presence of pyrazolone. To test for excess diazonium salt use the H acid indicator solution similarly. A pink colour developing at the zone of contact indicates the presence of diazonium salt.

.

A-2.2.3 It is advantageous to carry out a pilot titration by adding the diazonium standard solution in 1 ml portions to ascertain the approxi- mate range in which the end point lies. Now carry out the accurate titration by adding the diazonium salt solution in 1 ml portions at the beginning, and then in 0.2 ml portions as the end point approaches. Note the volume of the diazonium salt solution required for the titration.

A-2.3 Calculation

A-2.3.X Normality of the diazonium salt solution = 12:.5: $50

where

P = purity in percent by mass of 4-chloroaniline, and

Mr = mass in g of 4-chloroaniline taken.

A-2.3.2 Assay, percent by mass = L’ x .jV x 284

M, --

where

V - volume in ml of diazonium salt solution,

N = normality of diazonium salt solution ( see A-2.3.1 ), and

MS = mass in g of test sample in 500 ml stock solution.

7

.

IS:8552 - 1977

A-3. TEST FOR SOLUBILITY IN SODIUM HYDROXIDE SOLUTION

A-3.1 Procedure - Weigh 1 g of the prepared sample ( see A-l.1 ) into _a test-tube. Add exactly 10 ml of sodium hydroxide solution to it and stir with a glass rod. The material shall dissolve completely at room temperature and shall give a clear yellow coloured solution in order to pass the test.

m 1 I AMEMIMENT ND. 1 NOVEMBER1986

TO

IS:85524977 SPECIFICATION FOR l-(4'~SIJLPHOPHENYL)- 3-CAREXIXY-S-PYRAZOLONE

(Rtge 8, ctcruse A-3.2, line 8) - Substitute secod sentence with theiollowirg:

%dd exactly 10 ml of 1 I'4 sodium hydroxide Solution to it ard stir with a glass rods.

(mc 11)

RerographyUnit, ISI, HewDeLlA, India

c

AMENDMENT NO. 2 MAY 2002TO

IS 4552:1977 SPECIFICATIONFORl-(4-SULPHOPHENYL)-3-CARBOXY-

5-PYRAZOLONE( Page 3, clause 0.2, Structural Forrrrula ) — Insert the following lEIOW the

structural formula:

‘ (CAS No. 118-47-8)’.

[ Page 4, Table 1, S1No. (ii)] — Substitute the following for the existing:

(1) (2) (3) (4)

ii) Matter insoluble in dilute sodium hydroxide 0.2 when tested as persolution, percent by mass, Mm IS 5299:2001

(PCD1l)Reprography Unit, 91S, New Delhi, India