Saturday 29 April 2017

conversion of Nitrobenzene to phenylamine



Nitrobenzene to phenylamine
The conversion is done in two main stages:
Stage 1: conversion of nitrobenzene into phenylammonium ions
Nitrobenzene is reduced to phenylammonium ions using a mixture of tin and concentrated hydrochloric acid. The mixture is heated under reflux in a boiling water bath for about half an hour.
Under the acidic conditions, rather than getting phenylamine directly, you instead get phenylammonium ions formed. The lone pair on the nitrogen in the phenylamine picks up a hydrogen ion from the acid.
The electron-half-equation for this reaction is:
The nitrobenzene has been reduced by gaining electrons in the presence of the acid.
The electrons come from the tin, which forms both tin(II) and tin(IV) ions.


Stage 2: conversion of the phenylammonium ions into phenylamine
All you need to do is to remove the hydrogen ion from the -NH3+ group.
Sodium hydroxide solution is added to the product of the first stage of the reaction.
The phenylamine is formed together with a complicated mixture of tin compounds from reactions between the sodium hydroxide solution and the complex tin ions formed during the first stage.
The phenylamine is finally separated from this mixture. The separation is long, tedious and potentially dangerous - involving steam distillation, solvent extraction and a final distillation.

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