Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Reduction of nitrobenzene via Al + HCl ?
Ionic Chemist
Harmless
*




Posts: 39
Registered: 22-3-2011
Member Is Offline

Mood: Polymerizing

[*] posted on 21-9-2013 at 01:17
Reduction of nitrobenzene via Al + HCl ?


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......




"Discoveries are not made by idly sitting around and hoping something interesting might happen; they are made by getting out there and doing something to push the results and odds in your favour." "Chemistry always works... just not always in the way you want."
View user's profile Visit user's homepage View All Posts By User
Scr0t
Hazard to Others
***




Posts: 118
Registered: 14-1-2012
Location: Europe
Member Is Offline

Mood: Desiccated

[*] posted on 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.

View user's profile View All Posts By User

  Go To Top