Loading AI tools
Chemical reaction converting nitro compounds From Wikipedia, the free encyclopedia
The Béchamp reduction (or Béchamp process) is a chemical reaction that converts aromatic nitro compounds to their corresponding anilines using iron as the reductant:[1]
Bechamp reduction | |
---|---|
Named after | Antoine Béchamp |
Reaction type | Organic redox reaction |
Identifiers | |
RSC ontology ID | RXNO:0000498 |
This reaction was once a major route to aniline, but catalytic hydrogenation is the preferred method.[2]
The reaction was first used by Antoine Béchamp to reduce nitronaphthalene and nitrobenzene to naphthylamine and aniline, respectively.[3] The Béchamp reduction is broadly applicable to aromatic nitro compounds.[4][5] Aliphatic nitro compounds are however more difficult to reduce, often remaining as the hydroxylamine. Tertiary aliphatic nitro compounds, however, are converted in good yield to the amine using the Béchamp reduction.[6]
The reduction proceeds in a multistep manner. First, the nitro group is reduced to nitroso, which undergoes hydrogenation to a hydroxylamino group prior to further reduction to the amine.[7]
The traditional Béchamp reduction cogenerates gray-black iron oxides. The Laux process is based on the finding that the oxide coproduct is strongly affected by various additives, such as ferrous chloride, aluminium chloride, and even simply sulfuric acid, which are added before heating the iron-nitrobenzene mixture. The innovations from Laux have shifted the emphasis of the Béchamp reduction for the manufacture of anilines to the production of valuable iron oxide pigments.[8] The method is still effective for reduction of nitroaromatics.[9]
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.