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IS 7647 (2003): Acetoacet-2-Toluidide [PCD 9: Organic
Chemicals Alcohols and Allied Products and Dye
Intermediates]
“!ान $ एक न’ भारत का +नम-ण”
Satyanarayan Gangaram Pitroda
““IInnvveenntt aa NNeeww IInnddiiaa UUssiinngg KKnnoowwlleeddggee””
“!ान एक ऐसा खजाना > जो कभी च0राया नहB जा सकता हहहहै””ै”
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“Knowledge is such a treasure which cannot be stolen”
0-
1S 7647:2003
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lndianStandard
ACETOACET-2-TOLUIDIDE—SPECIFICATION
(First Revision)
lCS 71.080.80
0 BIS 2003
BUREAU OF INDIAN STANDARDS
MANAK BHAVAN, 9 BAHADUR SHAH ZAFAR MARG
NEW DEI.H1 110002
Price Group 3
Dyes Intermediate Sectional Committee, PCD 11
FOREWORD
This Indian Standard (First Revision) was adopted by the Bureau of Indian Standards, after the draft finalized by
the Dyes Intermediate Sectional Committee had been approved by the Petroleum, Coal and Related Products
Division Council.
This standard was first published in 1975 and has been revised in the light of experience gained during the long
span of period. In the present revision, thin layer chromatography has been included as the method of test to keep
pace with the present trends in the industry.
Acetoacet-2-tolu idide (Cl, H,3NOZ)is an important dye intermediate, used in the manufacture of yellow organic
pigments. It is represented by the following structural formula:
CH3
/
NH- CO- CH.-CO-CHQ
L
Acetoacet-2-Toluidide
(Molecular Mass: 191.2)
CAS Registry No. (93-68-5)
“Ile composition of the Committee responsible for formulation of this standard is given in Annex C.
For the purpose of deciding whether a particular requirement of this standard is complied with the final value,
observed or calculated, expressing the result ofatest oranalysis, shall be rounded off inaccordance with IS 2: 1960
‘Rules for rounding off numerical values (revised)’. The number of significant places retained inthe rounded off’
value should be the same as that of the specified value in this standard.
IS 7647:2003
IndianStandard
ACETOACET-2-TOLUIDIDE—SPECIFICATION
(First Revision)
1SCOPE 4 PACKING AND MARKING
This standard prescribes the requirements and methods 4.1 Packing
of sampling and test for Acetoacet-2-toluidide.
The material shall be packed in steel drums (see
2 REFERENCES IS 2552) or as agreed to between the purchaser and
the supplier.
The following standards contain provisions which
through reference in this text constitute provisions of 4.2 Marking
this standard. At the time of publication, the editions
Each container shall be securely closed and shall bear
indicated were valid. All standards are subject to
legibly and indelibly the following information:
revision and parties to agreement based on this
standard are encouraged to investigate the possibility a) Name of the material;
of applying the most recent editions of the standards
b) Indication of the source of manufacture;
given below:
c) Net mass;
IS N(). Title d) Lot or Batch number;
1070:1992 Reagent grade water (third revision) e) Month and year of manufacture; and
f) The minimum cautionary note worded as
2552:1989 Steel drums (galvanized and
below:
ungalvanized) (third revision)
DANGER! HAZARDOUS SOLID AND
5299:2001 Methods for sampling and tests for VAPOURS RAPIDLY ABSORBED THROUGH
SKIN.
dye intermediates (&t revision)
4.2.1 BIS Certl~cation Marking
3 REQUIREMENTS
4.2.1.1 Each container may also be marked with the
3.I Description
Standard Mark.
The material shall be in the form of white crystalline
4.2.1.2 The use of the Standard Mark is governed by
powder and shall be free from visib le impurities.
the provisions of the Bureau of Indian Standards
3.2 The material shall also comply with the Act, 1986 and the Rules and Regulations made
requirements given in Table 1. thereunder. The details of conditions under which the
Table 1Requirements for Acetoacet-2-Toluidide
(Clauses 3.2,5 .3.1,5.3.2 and6.1)
SI Characteristic Requirement Method ofTest, Ref to
No. / — .
Annex ofthis Standard Clause of IS
(1) (2) (3) (4) (5)
O Melting point, ‘C, MirI 103 — 9of 1S5299
ii) Purity by coupling value, percent by mass, 98.0 A —
MItr
iii) Matter insoluble in sodium hydroxide 0.2 — 11of IS5299
(dilute) percent by mass, MUX
iv) Impurities:
o-’roluidine, percent by mass, Max 0.2 B —
1
IS 7647:2003
Iicence for the use ofthe Standard Mark maybe granted requirements of this standard if each of the individual
to manufacturers or producers may be obtained from test results satisfies the relevant requirements given in
the Bureau of Indian Standards. 3.1 and Table 1.
5.3.2 For Composite Samples
5 SAMPLING
For declaring the conformity of the tot to the
5.1 The method of drawing representative samples of
requirements of matter insoluble and description whiIe
the material shall be as prescribed in 4 of 1S5299.
tested on the composite sample, the test result shal I
5.2 Number of Tests satisfy the relevant requirements given in Table 1.
Tests for melting point, purity by nitrite value and 6 TEST METHODS
impurities shall be conducted on each ofthe individual
6.1 Tests shall beconducted according to the methods
sample.
prescribed and as indicated in COI4 of Table 1.
Test for determination of volubility description shall
be done on composite sample. 6.2 Quality of Reagents
Unless specified otherwise, pure chemicals and
5.3 Criteria for Conformity
distilled water (see IS 1070) shall be employed intests.
5.3.1 For [ndividual Samples
NOTE—‘Pure chemicals’ shall mean chemicals that do not
The lot shall be declared as conforming to the contain impurities which affect the results ofanalysk.
ANNEX A
[Table 1,,S1No. (ii)]
METHODS OF TEST FOR ACETOACET-2-TOLUID1DE
A-1 PURITY BY NITRITE VALU E A-1.1.7 H-Acid Indicator Solution — Dissolve 0.5 gof
H-acid in 100ml of water containing 1g of soda ash.
A-1.0 Outline of the Method
A-1.1.8 Acetoacet-2-Toluidide — Reference sample of
A diazonium solution is prepared by reacting
known purity.
4-nitroaniline with sodium nitrite solution. It is
standardized by titrating against acetoacet-2-tolu idide A-1. 1.9 Tetrazodianisidine Solution — Take 2 g of
of known purity. The sample of acetoacet-2-tol uidide dianisidine base in a beaker and dissolve in 7 mI of
to be tested is then titrated against this standard hydrochloric acid (heat, ifnecessary upto 50”C). Cool
diazonium solution. with ice at about O°C and add immediately 12 mIot’
sodium nitrite solution and make up the volume to
A-1.1 Reagents 100 ml with ice cold water. Shake mildly. Test for
excess nitrite with starch-iodide test paper. Store this
A-1. 1.1 Hydrochloric Acid — 30 percent (m/v).
solution in an amber-coloured bottle in a cool place.
A-1. 1.2 Sodium Nitrite Solution — 10percent (m/v).
A-1.1.10 Starch-Iodide Test Papers
A-1. 1.3 4-Nitroaniline — 99 percent pure.
A-1. 1.4 .$’odiurn Hydroxide Solution — 40 percent A-1.2 Procedure
(m/v).
A-1 .2.1 Preparation of Diazonium Solution c,~
A-l. ].5 Dilute Acetic Acid— 25 percent (m/v). 4-Nitroaniline
A-1. 1.6 Sodium Acetate Solution — 20 percent (m/v). Take about 2 g of 4-nitroaniline in a 250-ml glass
~
IS 7647:2003
beaker containing 5 ml of hydrochloric acid and of diazonium salt. If a pink colour develops at the
100ml ofwater, heat upto 60°C todissolve completely. junction, excess of diazonium solution is indicated.
Cool externally to Oto 5°C with ice. Then add 10ml
Initially add diazonium solution in 1to 2 ml portions,
of sodium nitrite solution with stirring. Test for excess
testing titration mixture after each addition for excess
ofsodium nitrite by spotting on starch-iodide test paper.
of acetoacet-2-toluidide and diazonium salt. As the
Allow to stand for 30 min and then repeat the above
end-point approaches, diazonium standard solution
test. Filter to remove insoluble matter and then make
should be added in portions of 0.2 ml. The end-point
up the filtrate to 200 ml in a volumetric flask. Store
isreached when no reddish brown colour isgiven with
the solution in an ice-bath in the dark.
tetrazodianisidine solution and no pink colour or very
A-1.2.2 Standardization of the Diazonium Solution faint colour is given with H-acid indicator. Note the
volume of diazonium solution required for titration.
Weigh accurately 0.700 g of acetoacet-2-toluidide of
knbwn purity and dissolve with 1 ml of sodium A-1.2.3 Repeat the titration as prescribed in A-1.2.2
hydroxide solution in 25 ml of water. Dilute the using the test sample of acetoacet-2-toluidide.
solution to about 300 ml with water. With stirring add
A-1.3 Calculation
drop-wise dilute acetic acid till pH is 7 which maybe
judged by using pH paper. Add to the suspension A-1.3.1 Normality of
~= PXO.7
100 ml of sodium acetate solution. While stirring diazonium solution
VX19.12
mechanically add the diazonium solution (see A-1.2.1)
where
from a burette equipped with ajacket through which
water iscirculating at about 10“C. The burette should P = purity (percent by mass) of the known
be of amber glass to minimize any decomposition of sample; and
the diazonium salt by light.
k’ = volume, in ml, of diazonium solution
required for the known sample.
Titrate asrapidly asspot test permits. To test for excess
acetoacet-2-tolu idide place a few drops of titration A-1.3.2 Purity by coupling
~xNx19.12
mixture on a filter paper. About 1cm away from the value, percent by mass .—
0.7
edge of the liquidmark, placea few drops of
where
tentrazodianisidine solution. Where the two liquid
portions meet on the filter paper, a brown colour will V, = volume, in ml, of diazonium solution
develop if excess of acetoacet-2-toluidide is present. required for the test sample, and
Similady try with H-acid indicator to test the excess N = normality of diazonium solution.
ANNEX B
[Table 1,N No. (iv)]
THIN LAYER CHROMATOGRAPHIC ANALYSIS FOR
DETERMINATION OF IMPURITIES
A-1 GENERAL
Impurities are determined by thin layer chromatography. Reference may be made to IS 5299 for details of
TLC test method to be followed. However, necessary details of test conditions are given below for guidance
only:
a) Product name Acetoacet-2-TohLidide
b) Sample solution (on 100 percent basis) : 1percent in methanol
c) Application/sample volume for spotting : 5 pl (for sample)
2 PI and 4 VI(for impurities)
d) Standard Reference standard
e) Test substance for impurities o-Toluidine (0.05 percent in methanol)
3
IS 7647:2003
f) Plate type Silica gel G
g) Eluent Benzene
h) Elution time 25 min
j) Temperature 25 + 5°C
k) Detection spray ‘)Diazotize and couple with American base
solution
m) Evaluation Semi-quantitative
n) Approximate R~value—Main band Acetoacet-2-Toluidide : Rf0.5
—Impurities o-Toluidine : Rf0.7
I)Alne.icall base solution ; N.1 (NaPthYl) ~thYlenediamine–D i hydr~~hloride 1percentsolutionin(9:1)Methanol :Water.
4
IS 7647:2003
ANNEX C
(Foreword)
COMMITTEE COMPOSITION
Dyes Intermediate Sectional Committee, PCD 11
Orgarri:a/iorr Representative(s)
Atul Limited. Valsad, Gujartat DRH. KAIWAR (Cl?airman)
SHRJH. B. DHOVAD(Alternate I)
DRJ. G. DESAI(Alternate 11)
SHRJA. R. DESAI(Alternate 111)
Ajanla Cbcmical Iodustrics. New Delhi SHRIS. D. BHARDWAJ
SHRIKAPILDEV(Alternate)
Colour-Cbem ltd. Mumbai DRS. SIDDHAN
SHJUA. K. CHAITERJEE(Alfernate 1)
SHRJK. K. MEHTA(Alternate 11)
Clwiant India Ltd. Mumbai DRJ. N. SHAH
SHRJK. S. RJP4tIANJ(A/ter7rate)
Dcvclopmeot Commissioner Small Scale Industries, New Delhi SHRIS. R. SINGH
DRJ. S. REKHJ(Akwrate)
IIindustao C’iba-Geigy India Ltd, Mmnbai SHRIS. RAIAGOPALAN
SHRID. K. MURTHY(Alternate)
tlindustao tlrganic Chemicals Ltd, Rasayaoi SHRJR. B. BHANDARE
DRS. S. PATJL(Alfernate)
Indian Dyestutt’ ]nduslr’ies Ltd, Mumbai DRS. R. DESHMUKH
SHMS. D. PAWAR(Alternate)
Indian Chemical Manoticturers Association, Kolkata SHRJG. C. DESAI
National Chemical Laboratory, Pune DRK. V.SRNWVASAN
Sudirrshan (’hcnnical Industries Ltd, PLInc SHRIR.SATYANARAYAN
SHINP. K. PARAB(Alternate)
‘The Dyestutl Manrrfacturcr’s Association of India, Mumbai DRM. G. NARSIAN
DRS. C. AMIN(Aikernate)
‘1’heGujarat Small Scale Dyestuft’s M anufacturer’s Association, SHRIR. S. PATEL
Ahmedabzrd SHRJR. R. SHAH(Alternate)
111SDirectorate General SHRIANJANKAR,Director and Head (PCD)
[Representing Director General (Ex-ojicio)]
Member Secretary
DK(SHRJMATI)VIJAY MALIK
Director (PCD), BIS
5
