Bechamp Reduction
Encyclopedia
The Bechamp reduction is used to reduce aromatic nitro
compounds to their corresponding aniline
s, using iron
and hydrochloric acid
.
This reaction was originally used to produce large amounts of aniline for industry, but catalytic hydrogenation is the preferred method. The Bechamp reaction is presently of interest as a route to iron oxide pigments.
The reaction was first used by Antoine Béchamp
to reduce nitronaphthalene and nitrobenzene
in 1854.
.
Nitro
-Chemistry:*Nitroglycerin, an explosive chemical compound*Nitromethane, the simplest organic nitro compound; also used to fuel high-performance internal-combustion engines*Nitrous oxide, "laughing gas", used in some dental procedures as an anaesthetic...
compounds to their corresponding aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
s, using iron
Iron
Iron is a chemical element with the symbol Fe and atomic number 26. It is a metal in the first transition series. It is the most common element forming the planet Earth as a whole, forming much of Earth's outer and inner core. It is the fourth most common element in the Earth's crust...
and hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
.
This reaction was originally used to produce large amounts of aniline for industry, but catalytic hydrogenation is the preferred method. The Bechamp reaction is presently of interest as a route to iron oxide pigments.
The reaction was first used by Antoine Béchamp
Antoine Béchamp
Pierre Jacques Antoine Béchamp was a French biologist. He studied silkworm parasites, and was the first to synthesise Atoxyl.-Biography:...
to reduce nitronaphthalene and nitrobenzene
Nitrobenzene
Nitrobenzene is an organic compound with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale as a precursor to aniline. Although occasionally used as a flavoring or perfume...
in 1854.
Reaction scope
The Bechamp reaction is broadly applicable to aromatic nitro compounds. Aliphatic nitro compounds are more difficult to reduce, often remaining as the hydroxylamineHydroxylamine
Hydroxylamine is an inorganic compound with the formula NH2OH. The pure material is a white, unstable crystalline, hygroscopic compound. However, hydroxylamine is almost always provided and used as an aqueous solution. It is used to prepare oximes, an important functional group. It is also an...
.