Patent GB-538718-A (GB)
Title: Manufacture of acid salts of quaternary ammonium bases
Filed: 1939-12-05
Abstract: 538,718. Acid salts of quaternary ammonium bases. GEIGY AKT.-GES., J. R. Dec. 5, 1939, No. 31512. Convention date, Dec. 6, 1938. Samples furnished. [Class 2 (iii)] Acid quaternary ammonium salts are prepared by reacting (a) a quaternary mono or poly ammonium base containing at least one radicle of 8 or more carbons with an aliphatic or cycloaliphatic carboxylic acid having at least 8 carbon atoms and an acid having a molecular weight below 144 in either order ; (b) a tertiary mono or polyamine containing at least one radicle of 8 or more carbons with an aliphatic or cycloaliphatic carboxylic acid having at least 8 carbons and reacting the resulting salt with an alkylating agent which introduces an anionoid radicle having a molecular weight below 144 ; or (c) a tertiary amine containing at least one hydrogen attached to oxygen or other hetero atom with an aliphatic or cycloaliphatic acid having at least 8 carbons in sufficient proportion that after acylation at least one molecular proportion of acid is available for salt formation and treating the acylated product with an alkylating agent which introduces an anionoid radicle having a molecular weight below 144. In an example, 4-dimethylamine - 4<SP>1</SP> -methylhydroxyethylaminodiphenylmethane is melted with a mixture of stearic and palmitic acids and the esterification completed by heating and raising the pressure by introducing carbon dioxide. An acid quaternary salt is produced by treating with olein and dimethylsulphate. Products are mentioned which are prepared from the following bases : (1) methylhydroxyethylaniline ; (2) α:#-dihydroxypropylmethyltoluidine (from methyltoluidine and glycerolchlorhydrin) ; (3) 4:4<SP>1</SP>- di-(p-dimethylaminobenzyl) diphenylamine, prepared from: 1 mol. diphenylamine and 2 mols. p-dimethylaminobenzylsulphanilic acid ; (4) a tertiary base prepared from methylhydroxyethylaniline and N-(dimethylaminobenzyl) sulphanilic acid; (5) a tertiary base from ethylhydroxyethylaniline and N-(dimethylaminobenzyl) sulphanilic acid ; (6) a tertiary base from methyl-#-α-dihydroxypropylaniline and N-(dimethylaminobenzyl)-sulphanilic acid; (7) a tertiary base from 2-amino-5-dimethylaminotoluene and N-(dimethylaminobenzyl) sulphanilic acid ; (8) a tertiary base from 1 mol. 4-dimethylaminoaniline and 2 mols. N-(dimethylaminobenzyl)-sulphanilic acid ; (9) a tertiary base from 1 mol. 4:4<SP>1</SP>-diaminodiphenylmethane and 4 mols. of N-(dimethylaminobenzylsulphanilic acid. Samples have been furnished under Sect. 2(5) of products prepared (a) by esterifying 4-dimethylamino - 4<SP>1</SP> - methylhydroxyethylaminodiphenylmethane with stearic acid and converting the resulting ester into a bis quaternary salt with dimethylsulphate ; the free bis quaternary base is then formed by means of alcoholic potash and reacted with stearic and acetic acids; (b) by esterifying 2:4-(p-dimethylaminobenzyl) N-methylhydroxyethylaniline, prepared from N-methylhydroxyethylaniline hydrochloride and twice the molecular quantity of N-(p-dimethylaminobenzyl) sulphanilic acid, with stearic acid chloride and converting the resulting ester into a tris quaternary salt with dimethylsulphate; the free base is then treated with stearic and acetic acids.