ARS | Publication request: Oleochemical synthesis of an acid cleavable hydrophobe for surfactant use

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: January 10, 2007
Publication Date: May 13, 2007
Citation: Doll, K.M., Erhan, S.Z. 2007. Oleochemical synthesis of an acid cleavable hydrophobe for surfactant use [abstract]. Annual Meeting and Expo of the American Oil Chemists' Society. p. 97.

Technical Abstract: The reaction between epoxidized methyl oleate and the multifunctional carboxylic acid, levulinic acid, is shown to give two products of differing chemical reactivity. A branched alpha-hydroxy ester product which is acid stable, and a ketal product, which shows acid cleavability can be formed. The calculated molar volumes of the two compounds, in methyl ester form, are 377 and 400 cm3 respectively. However, upon addition of acid, the ketal product will show a reduction in molar volume to less than 325 cm3 where as the branched ester product will remain unchanged. This difference in behavior makes these compounds of interest in extraction applications such as oil recovery and protein recovery. The synthesis has been examined and it has been shown that either compound can be made in large excess through adjustment of the conditions. In short, higher temperatures and higher pH conditions favor branched ester formation, lower temperature and lower pH favor ketal formation.