GB701789A - Process for the production of compounds containing an -nh group from carboxylic acids and organic carbonyl compounds - Google Patents

Abstract

A compound containing an -NH-group is obtained from a carboxylic acid or an organic carbonyl compound by introducing an alkali metal azide into concentrated sulphuric acid and then adding the carboxylic acid or carbonyl compound thereto, the reaction temperature being controlled by the rate of addition and by cooling. The invention also comprises a continuous process for the production of a compound containing an -NH-group from a carboxylic acid or organic carbonyl compound by dissolving alkali metal azide in concentrated sulphuric acid, dissolving the carboxylic acid or carbonyl compound in a solvent therefor, and feeding the azide-sulphuric acid mixture and the carboxylic acid or carbonyl solution into a reaction vessel or into a plurality of reaction vessels, the overflow from one reaction vessel flowing into another reaction vessel or vessels. The sulphuric acid to which the alkali metal azide is added may be covered with a layer of an organic solvent for hydrazoic acid, e.g. chloroform, benzene, trichlorethylene, or methylene chloride. The carboxylic acid used may be a dicarboxylic acid and the latter may be converted to an amino-monocarboxylic acid by employing one mol. of hydrazoic acid for each mol. of the dicarboxylic acid. In examples: (1) sodium azide is introduced at a temperature not exceeding 10 DEG C. into concentrated sulphuric acid covered with a layer of methylene chloride and adipic acid added to the mixture with cooling and the mixture worked up to yield d -amino-m -valeric acid, some tetramethylene diamine being also formed; (2) sodium azide is dissolved in concentrated sulphuric acid covered with a layer of methylene chloride and sebacic acid then introduced at 25-30 DEG C., the mixture being then diluted with water and worked up to yield octamethylene diamine; (3) heptadecyl amine is obtained by forming a solution of sodium azide in concentrated sulphuric acid and then covering the solution with a layer of stearic acid in methylene chloride and cooling to 20-25 DEG C., the mixture being worked up to precipitate the amine as sulphate; (4) anthraquinone is added to a cooled mixture of sodium azide in concentrated sulphuric acid and the mixture worked up to yield the lactam of 2-(2-aminobenzoyl)-benzoic acid.