Preparing Aromatic Amines
Aromatic amines are made by reducing aromatic nitro compounds. The key example is making phenylamine from nitrobenzene.
Step 1: reduction. Nitrobenzene is heated under reflux with tin and concentrated hydrochloric acid. The tin and acid act as the reducing agent. Because the mixture is strongly acidic, the amine formed is protonated, so the product at this stage is the salt phenylammonium chloride, C6H5NH3+Cl−.
Step 2: release the amine. Sodium hydroxide solution is added to remove the proton and release free phenylamine, which can then be separated (for example by steam distillation).
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