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-α,β-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
2SO
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.
View full abstract