GB1386875A - Sulpho-succinic acid esters - Google Patents

Abstract

1386875 Sulphosuccinic acid semi-esters DEUTSCHE GOLDUND SILBER-SCHEIDEANSTALT 12 May 1972 [12 May 1971] 22402/72 Heading C2C [Also in Divisions A5 and C5] Novel compounds of the formula in which R<SP>1</SP> is C 1-18 alkyl, R<SP>2</SP> is H, C 1-4 alkyl or benzyl, R<SP>3</SP> is H, C 1-4 alkyl, -CH 2 CH 2 OH or M is Na or K, m is 1 or 2 and n is 1-4, are prepared by reacting or a C 1-4 alkyl ester thereof with at least an equimolar quantity of R<SP>4</SP>NHCH 2 CH 2 OH (in which R<SP>4</SP> is H, C 1-4 alkyl or -CH 2 CH 2 OH) at elevated temperature (at least 100‹ C. in the case of the acid), to form the corresponding amide, reacting this with one or two moles of maleic anhydride to form the maleic semi-ester, and reacting the latter at elevated temperature with an aqueous solution of a stoichiometric quantity of Na 2 SO 3 or K 2 SO 3 . Starting materials.-1-Methylamino-, 1-butylamino- and 1-benzylamino-2-hydroxydodecane are prepared from 1,2-epoxydodecane and the corresponding amine. N-Methyl-2-hydroxydodecylaminoacetic acid ethyl ester is prepared from 1-methylamino-2-hydroxydodecane and ethyl chloroacetate. N-Methyl-N-(2-hydroxydodecyl)-#-alanine butyl ester is prepared from 1-methylamino-2-hydroxydodecane and butyl acrylate. The reaction of 1,2-epoxydodecane with sarcosine yields N-(2-hydroxydodecyl)- sarcosine. The reaction of 1,2-epoxydodecane with aminopropionitrile followed by hydrolysis with NaOH gives the sodium salt of N-(2- hydrozydodecyl)-#-alanine, acidification then giving the free acid. γ-Hydroxytridecylaminopropionic acid butyl ester is prepared from γ- hydroxytridecylamine and butyl acrylate. The compounds of the invention are antimicrobial and surface active and may be used in washing, cleaning or cosmetic compositions.