GB471130A - Manufacture of new aliphatic and cycloaliphatic halides - Google Patents

Abstract

An amide or urethane of the formula RCONHR<1> or ROCONHR<1>, where R and R<1> are aliphatic or cycloaliphatic hydrocarbon radicles, is treated with a hydrogen halide and formaldehyde or a polymer thereof such as paraformaldehyde, whereby products believed to be N-halogenmethyl derivatives of the amides or urethanes are obtained. The products are hydrolyzed by water and react with amines; they yield quaternary ammonium salts by addition of tertiary amines, particularly cycloaliphatic or heterocyclic tertiary amines such as pyridine or quinoline. Both the N-halogenmethyl compounds and the quaternary salts obtainable therefrom are useful in textile-treating processes. In the examples, (1) stearomethylamide (from stearic acid or stearyl chloride and methylamine) yields N-chloromethyl-N-methylstearamide by reaction with paraformaldehyde and hydrogen chloride; (2) methyl heptadecylcarbamate similarly yields N - heptadecyl - N - chloromethylcarbamic acid methyl ester; (3) methyl undecylcarbamate similarly yields N - undecyl - N - chloromethylcarbamic acid methyl ester; (4) methyl butylcarbamate similarly yields N - butyl - N - chloromethylcarbamic acid methyl ester; (5) acetoundecylamide (from acetyl chloride and undecylamine) similarly yields N-chloromethyl-N-undecylacetamide; (6) stearomethylamide, paraformaldehyde and hydrogen bromide yield N - bromomethyl - N - methylstearamide; (7) laurocyclohexylamide (from lauryl chloride and cyclohexylamine) yields N - chloromethyl - N - cyclohexyllauramide by reaction with paraformaldehyde and hydrogen chloride; the pyridinium salt obtainable from the product yields foaming aqueous solutions. The reaction may be effected in the cold or at a moderately raised temperature, preferably in an inert diluent such as benzene and in the absence of water; the water formed in the reaction may be removed by azeotropic distillation or by addition of dehydrated magnesium sulphate.