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Hydroxylamine
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Hydroxylamine
Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula NH2OH. The compound exists as hygroscopic colorless crystals. Hydroxylamine is almost always provided and used as an aqueous solution or more often as one of its salts such as hydroxylammonium sulfate, a water-soluble solid.
Hydroxylamine and its salts are consumed almost exclusively to produce Nylon-6. The oxidation of NH3 to hydroxylamine is a step in biological nitrification.
Hydroxylamine was first prepared as hydroxylammonium chloride in 1865 by the German chemist Wilhelm Clemens Lossen (1838-1906); he reacted tin and hydrochloric acid in the presence of ethyl nitrate. It was first prepared in pure form in 1891 by the Dutch chemist Lobry de Bruyn and by the French chemist Léon Maurice Crismer (1858-1944). The coordination complex ZnCl2(NH2OH)2 (zinc dichloride di(hydroxylamine)), known as Crismer's salt, releases hydroxylamine upon heating.
Hydroxylamine and its N-substituted derivatives are pyramidal at nitrogen, with bond angles very similar to those of amines. The conformation of hydroxylamine places the NOH anti to the lone pair on nitrogen, seeming to minimize lone pair-lone pair interactions.
Hydroxylamine or its salts (salts containing hydroxylammonium cations [NH3OH]+) can be produced via several routes but only two are commercially viable. It is also produced naturally as discussed in a section on biochemistry.
NH2OH is mainly produced as its sulfuric acid salt, hydroxylammonium sulfate ([NH3OH][SO4]), by the hydrogenation of nitric oxide over platinum catalysts in the presence of sulfuric acid.
Another route to NH2OH is the Raschig process: aqueous ammonium nitrite is reduced by HSO−3 and SO2 at 0 °C to yield a hydroxylamido-N,N-disulfonate anion:
This ammonium hydroxylamine disulfonate anion is then hydrolyzed to give hydroxylammonium sulfate:
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Hydroxylamine
Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula NH2OH. The compound exists as hygroscopic colorless crystals. Hydroxylamine is almost always provided and used as an aqueous solution or more often as one of its salts such as hydroxylammonium sulfate, a water-soluble solid.
Hydroxylamine and its salts are consumed almost exclusively to produce Nylon-6. The oxidation of NH3 to hydroxylamine is a step in biological nitrification.
Hydroxylamine was first prepared as hydroxylammonium chloride in 1865 by the German chemist Wilhelm Clemens Lossen (1838-1906); he reacted tin and hydrochloric acid in the presence of ethyl nitrate. It was first prepared in pure form in 1891 by the Dutch chemist Lobry de Bruyn and by the French chemist Léon Maurice Crismer (1858-1944). The coordination complex ZnCl2(NH2OH)2 (zinc dichloride di(hydroxylamine)), known as Crismer's salt, releases hydroxylamine upon heating.
Hydroxylamine and its N-substituted derivatives are pyramidal at nitrogen, with bond angles very similar to those of amines. The conformation of hydroxylamine places the NOH anti to the lone pair on nitrogen, seeming to minimize lone pair-lone pair interactions.
Hydroxylamine or its salts (salts containing hydroxylammonium cations [NH3OH]+) can be produced via several routes but only two are commercially viable. It is also produced naturally as discussed in a section on biochemistry.
NH2OH is mainly produced as its sulfuric acid salt, hydroxylammonium sulfate ([NH3OH][SO4]), by the hydrogenation of nitric oxide over platinum catalysts in the presence of sulfuric acid.
Another route to NH2OH is the Raschig process: aqueous ammonium nitrite is reduced by HSO−3 and SO2 at 0 °C to yield a hydroxylamido-N,N-disulfonate anion:
This ammonium hydroxylamine disulfonate anion is then hydrolyzed to give hydroxylammonium sulfate:
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