ARS | Publication request: Synthesis of New Multifunctional Polyols from An Oleic Acid Derivative

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: February 15, 2006
Publication Date: April 30, 2006
Citation: Zerkowski, J.A., Solaiman, D. 2006. Synthesis of new multifunctional polyols from an oleic acid derivative [abstract]. Annual Meeting and Expo of the American Oil Chemists' Society. p. 75.

Technical Abstract: Sophorolipids (SL) can be obtained in abundant yield from fermentation of inexpensive agricultural coproducts. Acid alcoholysis of SL removes the sugar portion to give 17- and 18-hydroxy fatty acid esters, usually stearate and oleate, essentially quantitatively. Linoleic products result when safflower oil is used as feedstock. Using some well-known reactions of organic chemistry --- Sharpless asymmetric dihydroxylation, allylic hydroxylation, dehydrohalogenation --- as well as newer procedures such as borohydride reduction of active esters, we have converted hydroxy fatty acids into diols, triols, tetrols, and pentols. When protecting groups are introduced regioselectively, polyols with both masked and free hydroxy groups are obtained. Alternatively, protection allows other derivatives, such as epoxides, to be prepared. The new functionality can be introduced at different sites along the C18 chain to create a range of isomers, each of which should have unique properties for applications such as lubricants or incorporation into polymers.