Azo dyes

Preparation & properties

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This is to certify that Purushottam
Gupta,
Of class 12 A
Of Delhi Public School, Noida
Has prepared the following project on
Preparation & properties of azo dyes
For the practicals of class 12
conduced by Central Board Of
Secondary Education
For the session 2009-2010
With complete sincerity under my
supervision

Sign:
(Mrs. Sandesh
Arora)
Senior chemistry
faculty 2
I would like to take this opportunity
To thank my chemistry teacher
Mrs. Sandesh Arora & Lab asst Mr.
Joshi Whose able guidance &
encouragement
Has enabled me to finish this project.

Introduction

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Dyes play an indispensable role in human history
since ancient time. Dyeing
processes are often considered as an important
characteristic of a particular civilisation or
culture. Dyes are used in almost every
commercial product such as food, clothing,
pigments and paints, etc.

There are many different classes of dyes in

which azo dyes are certainly one of the
most important classes. About half of the dyes
used in industry are azo dyes. Azo
dyes have the basic structure, Ar−N=N−Ar’,
where Ar and Ar’ are two aromatic
groups.

What are they?

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The unit containing the nitrogen-nitrogen double
bond is called an azo group. The nature of the
aromatic substituents on both sides of the azo
group controls the colours of the azo
compounds as well as the water-solubility of
the dyes and how well they bind to a particular
fabric.
Aromatic azo compounds are used as acid-base
indicators, biological stains, and commercial
colorants for clothing, plastics, cosmetics, and
food beverages. Many azo-dyes, such as
methyl red, methyl orange, and Congo red, can
be used as acid-base indicators due to their
ability to function as weak acids or bases.

Color changes are caused by changes in extent of

delocalization of electrons: more
delocalization shifts the absorption max to
longer wavelengths and makes the light
absorbed redder, while less delocalization
shifts the absorption max to shorter
wavelengths. Color changes can also be due to
geometrical isomerism of the azo group. UV
radiation can cause a trans azo group to
become cis

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Advantages

Azo dyes form 60-70% of all synthetic dyes used

as commercial colorants. Azo dyes have several
advantages over other commercial dyes
including their
1.Wide color range,
2.Good color fastness and
3.Ability to absorb light.
4.They can also be synthesized cheaply
because the starting materials are
5.Readily available,
6.Inexpensive compounds; most of the
chemistry is completed at or below room
temperature;
7.The environmental impact is low due to the
use of water as a solvent in all of the
reactions.

Cost advantages tend to compensate for the

lower resistance to bleaching and lower
brilliance of azo dyes compared to
anthraquinones, the second most used dye class.

The color differences are caused by different

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 substituents on the aromatic rings which lead to
differences in the extent of conjugation of the π
system in the azo dye. In general, the less
extensive the conjugated π system of a molecule,
the shorter the wavelength of visible light it will
absorb.

Colorless (shortest π system) → yellow →

orange → red → green →blue (longest π
system)

.
The synthesis of an azo dye requires two organic compounds
- a diazonium salt and a coupling component. The general
synthesis of azo dyes is shown above.

Mechanism
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Combinatorial chemistry is heavily used in drug
discovery research. Combinatorial methods
allow for the simultaneous synthesis of many
potentially valuable compounds. These are
screened for desirable biological activity. In a
“parallel synthesis”, a variety of reactants
(several nucleophiles which are assigned to the
rows) is allowed to react with a variety of
substrates (several electrophiles which are
assigned to the columns). In this way, an array of
chemicals can be synthesized.

Attachment

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Dye molecules bind to the fiber molecules in
cloth in one of the following ways:
via electrostatic attraction, by van der Waals
forces, through hydrogen bonding or even
by covalent bonds. In general, the greater the
number of polar groups that are present in
the fiber molecule, the easier the fabric is to dye.

Experiment
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Apparatus
300mL beaker, balance, measuring glass, ice
bath,
Chemicals= paranitro aniline 2g,sodium nitrite,
HCl 8mL,β napthol 0.2g,NaOH

Procedure
1.solutions were prepared as follows:
A 2g paranitro aniline, 20ml water, 8ml HCl
B 2g sodium nitrite, 20ml water
C β napthol 0.2g dissolved in 10%NaOH and
diluted with 10ml water

All three solutions are cooled in an ice bath for

30 min. solution B was added slowly above it
with stirring, then filtered & dried.

2.Para Red was obtained

Observation-the filtrate after drying was deep

red in colour.It gave needle shaped crystals on
drying.

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Precautions
1.The experiment should be performed in a
well-ventilated
laboratory or fume hood. Handle all chemicals
with great
care. Avoid direct contact of chemicals with
skin.

2.Sodium hydroxide solution and concentrated

hydrochloric
acid are highly corrosive. Avoid contact with
skin and put
on appropriate protective gloves whenever
available.
Concentrated hydrochloric acid gives the
choking gaseous hydrogen chloride, which
is corrosive to the respiratory organs.

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 BIBLIOGRAHY

Laboratory Manual in Chemistry for class 12

www.Wikipedia.com

Text book of chemistry class12 ncert.

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