GB384314A - Process for the manufacture of derivatives of soap forming carboxylic acids - Google Patents

Abstract

Amines; ketones.--Amines are prepared by converting saturated soap-forming carboxylic acids, or mixtures thereof with other saturated carboxylic acids, into ketones and then treating the latter in the liquid phase with catalytically-activated hydrogen in the presence of ammonia or a primary amine. The soap-forming carboxylic acids are those containing at least 8 carbon atoms derived from oils, fats and waxes, e.g. coco-nut oil acids, naphthenic acids occurring in petroleum, or the acids obtained by the oxidation of paraffin. Acetic acid, benzoic acid, and phenylacetic acid are mentioned as other saturated carboxylic acids, and methylamine, benzylamine or aniline as primary amines. For the production of the ketones, catalytic processes are preferably employed, but chemical processes are also applicable. The products are useful for the manufacture of washing agents. According to the examples, (1) a mixture of coco-nut oil acids the acetic acid is passed over a thoria or manganese catalyst and the separated higher ketones hydrogenated under pressure in ammoniacal methyl alcohol in the presence of nickel; the acetic acid may be omitted in the preparation of the ketone starting material; (2) a ketone mixture obtained by the catalytic treatment of naphthenic acid or stearine with acetic acid is converted into an amine product by the process of (1) above; (3) pentadecylphenylmethylketone, obtained from palmitic acid and phenylacetic acid, yields 1-phenyl-2-aminoheptadecane when treated with hydrogen under pressure in the presence of ammonia and nickel; (4) stearic acid and acetic acid are converted into heptadecylmethylketone and this hydrogenated under pressure with n-butylamine in the presence of nickel to give 2-n-butylamino-nonadecane; the same ketone mixture yields 2-phenylaminononadecane when the n-butylamine is replaced by aniline; (5) 18-aminopentatriacontane is prepared from stearone, obtained by the thermal decomposition of stearic acid, using hydrogen under pressure, ammonia and nickel, at ordinary temperature; (6) methylstearylketone, obtained from stearic acid and acetic acid, is converted into the corresponding amine by means of hydrogen and ammonia in the presence of platinum black, room temperature and atmospheric pressure being employed. French Specification 529,159 is referred to. The Provisional Specification refers also to arachis oil acids and resin acids as soap-forming carboxylic acids.