A novel synthesis of succinic acid type Gemini surfactant by the functional group interconversion of Corynomicolic acid

2,3-Bis(undecyl)succinic acid, succinic acid type Gemini surfactant, was successfully synthesized from Corynomicolic acid by the functional interconversion of OH of Corynomicolic acid to COOH via (1) mesylation of OH of syn-isomer, (2) elimination of methanesulfonate group using base to E-alpha,beta-unsaturated ester, (3) Michael addition of CN(-) with 18-crown-6 and (4) hydrolysis. In most hydrolysis conditions, a mixture of syn- and anti-2,3-bis(undecyl)succinic acid was obtained, but hydrolysis in 75% H(2)SO(4) gave only anti-2,3-bis(undecyl)succinic anhydride. After converting a mixture of syn- and anti-2,3-bis(undecyl)succinic acids to corresponding acid anhydrides, syn- and anti-anhydride isomers were separated by column chromatography, and by following hydrolysis syn- and anti-2,3-bis(undecyl)succinic acid was selectively prepared. Based on the surface tension measurement, the effect of stereochemistry on surface tension isotherms was discussed in terms of the hydrophobic interaction between two alkyl groups and the electrostatic repulsion between two hydrophilic COO(-) groups.