GB779239A - Improvements in or relating to the production of organic hydroxylamine compounds - Google Patents

Abstract

N-Organohydroxylamine is prepared by the oxidation of a primary amine, the amino group of which is linked to a primary or secondary carbon atom, characterized in that the oxidation is carried out using hydrogen peroxide in the presence of a catalyst consisting of a water-soluble salt of molybdic, tungstic or uranic acid and water-soluble salts of aminotriacetic or ethylene diamine-tetra-acetic acid at a temperature at which the primary amine and hydrogen peroxide react together in the molar proportion of 1:1. The reaction temperature is generally less than 12 DEG C., preferably does not exceed 0 DEG C., particularly at the beginning of the reaction. Thus the temperature may be kept sufficiently low so that an amine-hydroperoxide is first produced from the amine, hydrogen peroxide and the water-soluble salt of ethylenediamine-tetra-acetic or aminotriacetic acid, and the hydrperoxide is then contacted with the catalyst. The process may be carried out in a continuous manner. In the examples: (1) N-methylhydroxylamine is prepared by the reaction of sodium aminotriacetate, tungstic acid, sodium sulphate, methylamine and hydrogen peroxide in water, and is converted into the hydrochloride salt thereof; (2) n-butylamine, the sodium salt of ethylenediamine-tetra-acetic acid, sodium sulphate and hydrogen peroxide are reacted in water to form n-butylaminehydroperoxide which is then decomposed with a mixture of n-butylamine and tungstic acid in water to form N-n-butylhydroxylamine and is converted into the hydrochloride salt thereof; (3) N-n-propylhydroxylamine is prepared by the reaction of the sodium salt of ethylenediamine - tetra - acetic acid, tungstic acid, sodium sulphate, n-propylamine and hydrogen peroxide in water; (4) N-benzylhydroxylamine is prepared by first reacting benzylamine, the sodium salt of ethylenediamine-tetra-acetic acid, sodium sulphate and hydrogen peroxide in water, and the resulting oil, presumably benzylaminehydroperoxide, is treated with tungstic acid and benzylamine in water; (5) cyclohexylaminehydroperoxide is prepared as in (1), and is treated with cyclohexylamine, tungstic acid and sodium sulphate in water to form N-cyclohexylhydroxylamine. Specification 779,238 is referred to.