Ionic Chemist - 21-9-2013 at 01:17
Hello everyone.... I would like to know if it is possible to reduce nitrobenzene by the use of aluminium
metal in an acidic medium, such as hydrochloric acid, to yield the aromatic amine, aniline. Typical methods for the reaction call for the use of iron
filings with hydrochloric acid, the bechamp reduction, or tin in hydrochloric acid. However, is it possible that the iron can be substituted with aluminium in the reaction and an
appreciable yield of aniline be collected post reaction?
This is of particular interest because aluminium, based on standard electrode potentials, appears to be a stronger reducing agent and thus it seems that it would have a better chance at reducing the nitro
group, compared to iron. This also coupled with the fact that aluminium, rather than iron, can be purchased easily in a reaction suitable form as
foil; and its hydroxide is amphoteric, thus when isolating the hopeful aniline product excess sodium hydroxide could be used to render the aluminium hydroxide precipitate
soluble as sodium aluminate, hence simplifying steam distillation of the mixture.
Thank You......
Scr0t - 21-9-2013 at 09:46
I have done this for 2-Nitrotoluene using H2SO4 as the acid according to US2446519 however the primary product would be 4-Aminophenol (~75% yield) with only small
amounts of Aniline being formed.
Maybe more Aniline could be formed if the amount of acid used was varied.