GB355970A - Manufacture of para-nitroso-amino compounds or para-quinone-oxime-imino compounds ofthe aromatic series - Google Patents

Abstract

p-Nitrosamines or p-quinoneoxime - imines.-Amines of the general formula <FORM:0355970/IV/1> where X is either an alkyl group, in which case one of the substituents Y and Z is alkyl and the other hydrogen, or X and Y together represent an attached benzene or hydrogenated benzene ring, Z being, in that case, hydrogen, are converted into p-nitroso-amines or p-quinoneoxime-imines by treatment in concentrated sulphuric acid solution with nitrous acid in the cold. The products, obtained as sulphuric acid salts, are decomposed with alkaline agents and may be converted into p-diamines by treatment with reducing agents, and into quinoneoxines by saponification. According to examples, (1) p-xylidine (1:2:5) is treated in concentrated sulphuric acid with sodium nitrite, and the product treated with sodium carbonate to give the p-nitroso compound; (2) o-xylidine (1:2:3) is treated similarly, and the p-nitroso product obtained is saponified with caustic soda to give the quinone-oxine; (3) 1-amino-5:6:7:8 tetrahydronaphthalene sulphate, treated as in example 1 gives the corresponding p-nitroso-compound, which on reduction gives the diamine; (4) x-naphthylamine treated as in example 1 gives the corresponding p-nitroso compound, from which is obtained the 1:4 naphtho-quinone-oxime-imine by treatment with sodium acetate, followed by heating the hydrochloride or sulphate with water to get the 1:4 naphthoquinone oxime.