Hydroxylamine

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 intermediate in biological nitrification.

History

Hydroxylamine was first prepared as hydroxylamine hydrochloride in 1865 by the German chemist Wilhelm Clemens Lossen (1838–1906); he reacted tin with hydrochloric acid and nitric acid.

Production

Hydroxylamine is produced industrially by the raschig process, which involves the reaction of ammonia with chlorine in aqueous solution to give ammonium chloride and nitrogen. The net reaction is:

NH3 + Cl2 + H2O → NH2OH + 2 HCl

Applications

Hydroxylamine and its salts are commonly used in organic synthesis for the conversion of ketones and aldehydes to oximes, which are key intermediates in many industrial processes. It is also used in the production of pharmaceuticals, rubber, textiles, and plastics.

Safety

Hydroxylamine is a potential explosive that can detonate. It forms explosive mixtures with air and can react with oxidizing materials. It is also harmful if swallowed, inhaled or absorbed through the skin.

See also

• Ammonia
• Oxime
• Raschig process