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.
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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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Saturday, 29 April 2017
conversion of Nitrobenzene to phenylamine
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