Contents

Introduction 2

Etymology 2

Azo dyes and pigments 3

Aryl azo compounds 3

Alkyl azo compounds 4

References 4

1
Introduction:
Azo compounds are chemical compounds with the general formula R-N=N-R',
where R and R' can be either aryl (aromatic) or alkyl (aliphatic) functional
groups. The N=N group is called an azo group, although the parent
compound, HNNH, is called diimide. The more stable azo compounds contain
two aryl groups. Azo compounds with alkyl functional groups are particularly
unstable and should be handled with care, to prevent them from exploding.
Aryl azo compounds have vivid colors, especially reds, oranges, and yellows.
They are therefore used as dyes and are classified as azo dyes. Examples
include methyl red and Disperse Orange 1. The ability to manufacture azo
dyes was an important step in the development of the chemical industry.

Etymology:
The name azo comes from azote, the French name for nitrogen, which is
derived from the Greek a (not) + zoe (to live).

2
Azo dyes and pigments:
As noted above, aryl azo compounds are brightly colored and are useful as
dyes and pigments. In chemical terms, their colors are attributed to
delocalization of п (pi) electrons.

Some azo compounds, such as methyl orange and methyl red, are used as
acid-base indicators because their acid and salt forms have different colors.
Methyl red is red at pH below 4.4, yellow at pH over 6.2, and orange in
between.

Azo pigments are colorless particles (typically earths or clays) that have been
colored using azo compounds. Azo pigments are important in a variety of
paints, including artist's paints. They have excellent coloring properties, again
mainly in the yellow to red range, as well as lightfastness (that is, colorfast
when exposed to light). The lightfastness depends not only on the properties
of the organic azo compound, but also on the way they have been adsorbed
on the pigment carrier. Azo pigments are advantageous because they are
non-toxic.

Aryl azo compounds:

Aryl azo compounds are usually stable, crystalline species. Azobenzene is the
prototypical aromatic azo compound. It exists mainly as the trans isomer, but
upon photolysis, converts to the cis isomer. Aromatic azo compounds can be
synthesized by using an azo coupling reaction, which entails an electrophilic
substitution reaction where a aryl diazonium cation attacks another aryl ring,
especially those substituted with electron-releasing groups.[1] Since
diazonium salts are often unstable near room temperature, the azo coupling
reactions are typically conducted near ice temperatures.
The oxidation of hydrazines (R-NH-NH-R') also gives azo compounds.

3
Alkyl azo compounds:
Aliphatic azo compounds (R and/or R' = aliphatic) are less commonly
encountered than the aryl azo compounds. One example is diethyldiazene,
EtN=NEt.[3] At elevated temperatures or upon irradiation, the carbon-nitrogen
(C-N) bonds in certain alkyl azo compounds cleave with the loss of nitrogen
gas to generate radicals. Owing to this process, some aliphatic azo
compounds are utilized as radical initiators. Representative is
azobisisobutylonitrile (AIBN) which is widely used as an initiator in
polymerization. Because of their instability, especially for aliphatic ones, care
should be taken with the handling of azo compounds or an explosion may
occur.

References:
 Research gate
 slide share
 google scholar