PRESENTATION CONVENT SENIOR

SECONDARY SCHOOL

Chemistry project:

Preparation of Yellow Dye

BY: Prakriti
XII B
28
 CERTIFICATE

This is to certify that ………………………………..

of class XII section ............... bearing roll
number ……… has performed the project
entitled …………………………………………………
satisfactorily under the expert supervision
of Mr. Amarjeet Singh for the year 2018-
2019.

Principal’s Signature Teacher’s Signature

 Index

S.NO TOPIC

1 Introduction

2 Aniline Dyes

3 Formula of Aniline Dye

4 Uses of Aniline Dye

5 Preparation of Azo Aye From Aniline

6 Azo Dyes

7 Early History

8 Modern History

9 Experiment of Yellow Dye

INTRODUCTION
 INTRODUCTION
Human's love of color reaches back almost to prehistoric times, yet
it is not actually until the modern era that the full range of the
rainbow has been accessible to the majority of people in their
clothes and other textiles. Ancient or medieval times have often
been described as being quite splendid with their "Tyrian Purple"
and medieval scarlet, but closer examination shows that some of
these colours were quite dull by today’s standards. We know that all
organic compounds can be classified as aliphatic and aromatic
compounds. Aliphatic compounds are open chain or branched
compounds with single or multiple covalent bonds between carbon
atoms. Alkanes, alkenes and alkynes are most common aliphatic
compounds. Aromatic compounds are well known for their aroma
and extra stability due to delocalization of electrons. Benzene is the
simplest aromatic compound. Aromatic compounds play important
role in organic chemistry and act as precursor for several other
organic compounds.
ANILINE DYES
 ANILINE DYES
Aniline dye can be defined as the coloring substance that is
mainly prepares from aniline. It is mainly used to color fabric,
leather, and wood. Aniline dyes are synthetic organic
compounds which are available in a variety of colors. They are
well known for their clarity. First aniline dye was discovered by
William Henry Perk during the preparation of a synthetic version
of the anti-malaria drug quinine and named it as Mauvine. Later
this dye was used in textile industries. Aniline dyes are mainly
used in the leather and woodworking industries. Aniline wood
dyes provide clarity and saturation over wood surface as these
dyes do not leave pigmentation on the surface due to more
absorption into porous. The aniline dyes which are used to dye
leather are considered to be of a higher quality dyes as these
dyes provide a unique texture to leather surface. Today we have
a large number of aniline dyes which are commercially available
in the form of powders. These dyes can be dissolved in different
solvents like water, alcohol or oil. Aniline Yellow is one of the
most common aniline dyes. It is a yellow azo dye which is mainly
prepared by aromatic amine (aniline). It is an orange color
powdered derivate of azobenzene.
 FORMULA
Aniline dyes are azo compounds with amino group on
aromatic ring. Azo compounds can be easily recognized with
highly delocalized electron system with benzene rings and the
N=N (azo group) in the molecule. The delocalization of
electrons makes the molecule stable. In the presence of
white light, it absorbs some wavelengths and causes color
due to non-absorbed wavelengths. The group which is
responsible for color in the compound is called as a
chromophore. A little modification in the molecule can
change the wavelength of light absorbed as well as color of
compound. The structure of aniline yellow and aniline black
are given below. Aniline yellow is formed by reaction of
aniline with diazonium compound at low temperature.
PREPARATION OF AZO AYE FROM
ANILINE

We know that aniline is an aromatic amine in which one

NH2 groups is directly bonded to benzene ring. Azo dyes are
also aromatic compounds with N=N bond in the molecule
which is called as azo linkage. Azo dyes are also used as pH
indicators. Some common examples of azo dyes are methyl
yellow, methyl orange, methyl red, congo red and alizarine
yellow. The preparation method azo dye consists of two
steps.
Preparation of an aromatic diazonium ion from an aniline or
aniline derivative.
Coupling of the diazonium salt with an aromatic compound
to get desired azo dye.
AZO DYES
 EARLY HISTORY
The history of dyeing can be divided into two great periods, the "pre-
aniline," extending to 1856 and the "post-aniline" period. The former
was characterized by a rather limited range of colors
that were based on dye-producing animals and plants. The main
vegetable dyes available were extracted from madder root (Asia and
Europe), producing a brilliant red and leaves of the indigo
plant (India), yielding the blue dye still used today in jeans. Among
the most important animal based dyes is the famous and expensive
"Tyrian Purple" which was obtained from the small shellfish nurez.
We have the ancients' word that this dye was unbelievably beautiful,
but evidence taken from ancient samples prove that it ranges through
a rather uninspiring series of reds and purples. After seeing it, we
wish that Homer had written about some of today’s inexpensive coal-
tar purples and reds. A far more beautiful natural color was
introduced to Europe from Mexico in 1518, the brilliant scarlet dye
cochineal, which had been produced from tiny lice which infest
certain types of cactus.
 MODERN HISTORY
Aniline (C6H5-NH2) became available from coal tar in the 19th
century and in 1856, William Henry Perkin at the age of 17 used
it in the synthesis of Mauveine (a mixture of 4 compounds, one
of which is shown below). The era of synthetic dyes was born.
Soon thereafter, the main component of the dye in the madder
root, Alizarin, was isolated by Carl Graebe and Carl Liebermann,
prepared in the lab and the process commercialized. Starting in
1865, recognizing the potential of synthetic dyes, Adolph von
Baeyer researched the synthesis of indigo and determined its
structure and first synthesis in 1870.
In 1897 the large scale industrial synthesis of indigo started and
rapidly reached 10,000 tons a year, completely replacing the
agricultural production.
 SYNTHESIS
Azo dyes are compounds that contain two aromatic fragments
connected by a N=N double bond. You may have encountered
these in chemistry experiments as they are typical pH indicators.
Methyl yellow, methyl orange, methyl red, congo red and
alizarine yellow are some of the examples. They are
straightforward to make and of industrial importance. Azo dyes
are prepared in a two step reaction, the first being the
synthesis of an aromatic diazonium ion from an aniline
derivative. The next step is coupling of the diazonium salt with
an aromatic compound. The colours of azo dyes include
different shades of yellow, red, orange, brown, and
blue. The stoichiometry (a 1:1 mole ratio) must be kept the
same and due to changing molecular weights of the starting
materials, different amounts of starting materials are used so
there are separate procedures for each combination.
 METHYL YELLOW
Methyl yellow, or C.I. 11020, is an organic compound with the formula
C6H5N2C6H4N(CH3)2. It is an azo dye derived from dimethylaniline. It is
a yellow solid. According to X-ray crystallography, the C14N3 core of the
molecule is planar.
It is used as a dye for plastics may be used as a pH indicator.
In aqueous solution at low pH, methyl yellow appears red. Between pH
2.9 and 4.0, methyl yellow undergoes a transition, to become yellow
above pH 4.0
4-Dimethylaminoazobenzene is used as a dye for coloring polishes, wax
products, and soap. Acute (short-term) dermal exposure to 4-
dimethylaminoazobenzene may result in contact dermatitis in humans.
No information is available on the chronic (long-term), reproductive,
developmental, or carcinogenic effects of 4-
dimethylaminoazobenzenein humans. Animal studies have reported
birth defects in the offspring of mice exposed to 4-
dimethylaminoazobenzene and tumors of the lung, liver, and bladder
from oral exposure to 4-dimethylaminoazobenzene. EPA has not
classified 4-dimethylaminoazobenzene for carcinogenicity. The
International Agency for Research on Cancer (IARC) has classified 4-
dimethylaminoazobenzene as a Group 2B, possibly carcinogenic to
humans.
4-Dimethylaminoazobenzene (or butter yellow) has been used as a
laboratory hepatocarcinogen to study the mode of action of this
class of compounds, including structure activity relationships.
Because of its characteristic color change as a function of pH, it
was the first carcinogen that demonstrated binding to cellular
macromolecules. Because of the flavin-dependent azo dye
reductase, it was also one of the first carcinogens with a clear-cut
nutritional modulation of its activity. Substitution with polar
groups such as sulfonic acid in simple azo dyes usually abolishes
carcinogenicity and mutagenicity. Thus, molecules such as FD and
C Red No. 2 (amaranth) are not mutagenic or carcinogenic. On the
other hand, tetra-azo dyes such as direct black 38 or direct blue 6,
which are not mutagenic and are quite polar, can release the
mutagenic carcinogenic benzidine upon reduction of the azo link
by bacteria. Such dyes are highly carcinogenic.
Novel yellow azo dyes are synthesized by diazotization of
aromatic amines followed by coupling with 2-morpholin-4-yl-1,3-
thiazol-4(5H)-one and fully characterized. The geometries of the
synthesized dyes for azo and hydrazone tautomeric forms were
optimized using B3LYP, CAM-B3LYP and M06 functional and 6-
31G(d) and 6-311++G (d,p) basis sets, also their electronic
excitation properties were evaluated using density functional
theory. The optimized geometries reveal that the hydrazone for is
more stable than the azo form. Photophysical properties of the
synthesized dyes were evaluated by UV–Visible spectroscopy and
compared with computed vertical excitation obtained from
TDDFT. The results clearly illustrate existence of dye 8a, 8b and 8c
in hydrazone tautomeric form, while 8d exist in both azo as well
as hydrazone form. Thermal stabilities were estimated by using
thermo gravimetric analysis, and results revels that the
synthesized dyes have good thermal stability.