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.