Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: February 9, 2008
Publication Date: May 21, 2008
Citation: Doll, K.M., Erhan, S.Z. 2008. Oleochemical synthesis of an acid cleavable hydrophobe for surfactant use [abstract]. American Oil Chemists' Society. p. 147-148. Technical Abstract: The synthesis of a series of branched hydroxy stearates from commercially available methyl oleate and common organic acids is reported. A variety of different acids, with 3 to 8 carbon atoms, and also varying in their branching and functionality, were used. The kinetics of the ring opening reaction was studied, under both pseudo 1st order conditions, and 2nd order conditions. An Arrhenius activation energy of 66.7 kJ mol-1 (16.0 kcal mol-1) was found in a system using propanoic acid as the ring opener. The resultant compounds have calculated molar volumes of ~375 cm3 making them a candidate for use as surfactant hydrophobes. The added oxygen groups and branched structures may allow the synthesis of improved surfactants from these materials as well. The general ease of the method should also allow its use with a variety of commercially available substrates, in order to obtain desired molecular structure. Finally, commercially available epoxidized soybean oil may also be modified by this method if a product with higher molecular weight is desired.