Aromatic Chemistry

Phenylamine and Use of Aromatic Compounds

Phenylamine and Use of Aromatic Compounds

Phenylamine

Nitrobenzene is mainly used to produce phenylamine which is an important aromatic amine.

Nitrobenzene is used to reduce phenylamine when heated under reflux and through a treatment with tin and concentrated HCl.

  • Sn and HCl produce SnCl2which is a good reducing agent
  • LiAlH4 and NaBH4should not be used as they create different products.

It is possible to use hydrogen gas with a suitable catalyst present:

C6H5NO2 + 6[H] ? C6H5NH2 + 2H2O

Basic properties of phenylamine

As its lone pair which is located on the nitrogen atom is absorbed into the delocalised system meaning that it is not available for bonding with a proton, phenylamine makes a much weaker base than apliphatic amines.

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Uses of Aromatic Compounds

Explosives

The explosive trinitrotoluene (more commonly known as TNT) is formed through the nitration of methylbenzene.

Dyestuffs

Through a reaction with nitrous acid, phenylamine can be converted into benzenediazonium chloride. This can be used to form a variety of dyes.

Polystyrene

In the presence of AlCl3 and HCl, ethylbenzene can be created on an industrial basis from benzene and ethene.

  • At a high temperature and in the presence of iron oxide, ethylbenzene can be dehydrogenated to create phenylethene or ‘styrene’.
  • Phenylethene can then be polymerised to create polystyrene or polyphenylethene.