Patent GB-428153-A (GB)
Title: Manufacture of sulphuric acid derivatives of organic acid amides
Filed: 1934-03-17
Abstract: Products stated to be soap substitutes having wetting and foaming properties are obtained by sulphonating acid amides having the formula RO(S, NR1)XNR2R3 in which R denotes an aliphatic, aromatic or cycloaliphatic residue, R1 and R2 hydrogen or any organic residue, R3 an aliphatic or hydroaromatic residue having at least six carbon atoms and X an aliphatic carboxylic or sulphonic acid residue.  The acid amides, which must contain a double bond or benzene ring may be prepared (a) by reacting halogen carboxylic or sulphonic acid amides having an aliphatic or cycloaliphatic residue with at least six carbon atoms attached to the nitrogen, with alcohols, phenols, mercaptans or primary or secondary amines.  Thus, a (b  : g -dioxypropyloxy) lauric-N-cyclohexylamide, b -phenoxyethanesulphonic - N - methyldodecylamide, tolylmercaptoethanesulphonic-N-hexadecylamide and anilinoacetic-N-undecylamide may be made from the corresponding halogenated acid amide and the monosodium compound of glycerol, sodium phenolate, sodium tolylmercaptan and aniline respectively or (b) by reacting oxy, mercapto or amino aliphatic carboxylic or sulphonic acids substituted at the oxygen, sulphur or nitrogen, or esters, anhydrides, halides or lactones thereof with the higher aliphatic or cycloaliphatic primary or secondary amines.  Thus, phenylaminoacetic N-cyclohexylamide may be prepared from cyclohexylamine and phenylaminoaceticmethylester, which may be obtained by reacting aniline with chloraceticmethylester. Oxyethoxyacetic-N-undecylamide is similarly obtained from undecylamine and the lactone of oxyethoxyacetic acid.  In examples: (1) a mixture of acid amides is prepared from oxyethoxyacetic lactone (obtained from monosodiumglycol and sodium chloracetate) and the mixture of amines derived from coco-nut fatty acid amides by Hofmann's reaction; sulphonation is effected by means of chlorsulphonic acid in the presence of ether; (2) phenoxyacetic-N-cyclohexylamide is sulphonated; (3) the mixture of acid amides obtained from phenoxyacetic acid and the amines derived from coco-nut fatty acid amides is sulphonated with sulphuric acid. The octodecenyl residue and the residues of alcohols obtained by reducing resinic and naphthenic acids are mentioned as examples of higher aliphatic and cycloaliphatic residues.  Reference is made to the use of the products in the cosmetic and pharmaceutical industries.  Samples have been furnished under Sect. 2 (5) of products obtained by sulphonating butylmercaptoacetic - N - dodecyl - N - b  - oxyethylamide, anilinoacetic - N - dodecylamide, b  - phenoxyethanesulphonic - N - methyl - N - dodecylamide, b  - benzylmercaptoethanesulphonic - N - hexadecylamide and N - di(b  - oxyethyl) glycine - N - dodecylamide.  a  - Bromlauric - N - cyclohexylamide may be prepared by reacting cyclohexylamine with a -bromlauric acid bromide.  b  - Chlorethanesulphonic - N - methyldodecylamide may be prepared by reacting methyldodecylamine with chlorethanesulphonic acid chloride. Bromethanesulphonic-N-hexadecylamide may be prepared from hexadecylamine and bromethane sulphonic acid chloride. Bromacetic-N-undecylamide may be prepared from undecylamine and bromacetic acid bromide.