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Practical 5.15 Prep of An Azo Dye

This document provides instructions for preparing an azo dye through a coupling reaction. It involves first generating a benzenediazonium ion by reacting an aromatic amine like phenylamine with nitrous acid at low temperatures. This ion is then coupled with a phenol like phenol or 2-naphthol to form the azo dye. Safety precautions must be taken since the chemicals involved like phenylamine and phenol are toxic. The reaction is carried out by carefully adding a sodium nitrite solution to the amine solution cooled in an ice bath, and then adding the resulting diazonium chloride solution dropwise to a phenol solution to form the colored azo dye product.

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652 views2 pages

Practical 5.15 Prep of An Azo Dye

This document provides instructions for preparing an azo dye through a coupling reaction. It involves first generating a benzenediazonium ion by reacting an aromatic amine like phenylamine with nitrous acid at low temperatures. This ion is then coupled with a phenol like phenol or 2-naphthol to form the azo dye. Safety precautions must be taken since the chemicals involved like phenylamine and phenol are toxic. The reaction is carried out by carefully adding a sodium nitrite solution to the amine solution cooled in an ice bath, and then adding the resulting diazonium chloride solution dropwise to a phenol solution to form the colored azo dye product.

Uploaded by

deeyamulla
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Student 1 of 2

Practical 5.15 Preparation of an azo dye

Purpose

Safety

To describe and carry out the reaction, where


appropriate, of aromatic amines with nitrous
acid to form benzenediazonium ions followed by
a coupling reaction with phenol to form a dye
[5.4.1d]

Wear eye protection. Phenylamine is toxic


and volatile. Phenol is corrosive and toxic
wear gloves when handling phenol. Sodium
nitrate(III) is oxidising and toxic. 1M sodium
hydroxide is corrosive. 2-naphthol is harmful.

Background
Azo dyes are brightly coloured synthetic dyes. They are produced in a reaction called
coupling. The first stage is the preparation of the unstable benzenediazonium ion using
phenylamine and nitrous acid. This is followed by the addition of phenol. The reaction
scheme is:
NH2

NaNO2/HCl

NN Cl

5 C

OH

yellow
an azo-dye

OH
4-hydroxyazobenzene

Phenylamine is toxic and volatile. A better alternative is its salt phenylammonium chloride,
which, although toxic, is much less volatile and therefore avoids the use of a fume cupboard.
If phenylamine is used, then it should be stored and used in a fume cupboard.

Each group of students will need:


Eye protection
Gloves (nitrile)
Weighing boats
Boiling tubes and bungs
Dropping pipettes
Thermometer, 0110C
Phenylammonium chloride toxic
or Phenylamine toxic
Concentrated hydrochloric acid corrosive

Sodium nitrate(III) oxidising, toxic


1M sodium hydroxide corrosive
Phenol corrosive, toxic
2-naphthol, if required harmful
Deionised water
Ice
Access to:
Balance
Fume cupboard if phenylamine is used

Edexcel practical materials adapted from Nuffield Advanced Chemistry materials

163

2 of 2 Student

Practical 5.15 (cont.) Preparation of an azo dye

Method
1 Put 3cm3 of phenylamine and 10cm3 of distilled water in a boiling tube, and add 8cm3
of concentrated hydrochloric acid.
2 Fit the bung to the tube and carefully shake to dissolve the amine (care must be taken as
the reaction is exothermic).
3 Cool the boiling tube immediately in an ice bath.
4 Keep checking the temperature until the solution has cooled down to about 5C.
5 In the meantime, dissolve 3g of sodium nitrite in 8cm3 of water in another boiling tube
and add this to the ice bath. Keep checking the temperature until it reaches 5C.
6 When both boiling tubes have reached 5C, carefully add the sodium nitrite solution
dropwise to the phenylamine solution, so that the temperature does not rise above 10C.
You have now made the benzenediazonium chloride solution in the first step of the
coupling reaction.
7 Into another boiling tube, put 23 crystals of phenol with 2cm3 of 1M sodium
hydroxide.
8 Cool this solution on ice and then add the benzenediazonium chloride solution drop by
drop.

Questions
1 In the preparation of the diazonium ion, why is it necessary to keep the temperature
below 10C?

2 Describe what happens in step 8.

3 Write the balanced formula equation for the formation of benzenediazonium chloride
from phenylamine and nitrous acid.

4 2-naphthol can be used in place of phenol in this coupling reaction. Draw the structure of
the azo dye that would be formed.
OH

Edexcel practical materials adapted from Nuffield Advanced Chemistry materials

164

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