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Introduction

Azo compounds are organic compounds containing the functional group R-N=N-R’ in
which the hydrocarbons can be either an aryl or akyl. They are characterized by two arenes
linked by nitrogen atoms in a double bond They are derivatives of diazene (diimide), HN=NH,
where both hydrogens are substituted by hydrocarbon groups.

They are highly conjugated structure caused by the extended conjugated 𝜋 electron
system which allows the absorption of light in the visible region of the electromagnetic
spectrum. Because of this property, they are highly colored thus they are usually used as dyes.
An example of an azo compound is 1-phenylazo-2-naphthol (Sudan 1) which is a red dye
previously used for textiles and food coloring. However, it hasbeen classified as a potential
human carcinogen, dueto its tendency to cause tumours in the liver andurinary bladder of rats,
mice and rabbits (Stiborovaet. al., 2002).

Figure 1. Structure of 1-phenylazo-2-naphthol (Photo taken from


https://www.sigmaaldrich.com/catalog/product/sial/103624?lang=en&region=PH)

In order to synthesize an azo compound, diazodium-coupling reaction is performed. It is an


electrophilic aromatic subsitution reaction between an arenediazonium ion and a highly
reactive compound (McMurry, 2008). First, aniline is reacted with nitroud acid in a process
called diazotization followed by the coupling reaction of a diazonium salt and beta-naphthol to
form the azo dye. The quality of the dyes formed from the diazocoupling reaction are judged by
two qualities: itsfastness and its levelness. Levelness is the uniformityof the dye upon its
application on the surface of thefabric, while fastness is the ability of the dye to stickto maintain
its colou

Amine is any member of a family of nitrogen-containing organic compounds with two lone pairs
that is derived either in principle or in practice from ammonia (NH 3) (Smith and Block, 2018);
where one or more hydrogen atom/s is are replaced by substituent such as alkyl or aryl group.
The presence of lone pair makes amines both basic and nucleophilicImportant amines include
amino acids, biogenic amines, and aniline.
Nitrous acid (HNO2 or HONO) reaction with aliphatic amines is useful test to distinguish
primary (RNH2) , secondary (R2NH) and tertiary amines (R3N). Primary amines can react with
nitrous acid or nitrile salts in acidic medium to yield diazonium salts in a process called
diazotization reaction. These salts are the most versatile intermediates in organic synthesis
since they can undergo replacement and coupling reaction.

This process can occur in amines with alkyl or aromatic group. However, alkylamines
diazonium products can not be isolated since they are very reactive which is why the method is
used for primary arylamines. The general reaction is shown below: