Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 10/16/2008
Publication Date: 11/1/2008
Citation: Bantchev, G.B., Kenar, J.A., Biresaw, G. New Sulfide Derivatives of Vegetable Oils [abstract]. In Society of Tribologists and Lubrication Engineers Annual Meeting, October 13-16, 2008, Cincinnati, OH. p. 15.
Technical Abstract: Vegetable oils containing sulfide group were synthesized using a UV initiated thiol-ene reaction. The reaction involved addition of butyl thiol to the double bonds of the vegetable oil without the presence of a solvent. The effects of temperature, reaction time, type of vegetable oil, thiol to vegetable oil ratio, and presence of initiator were investigated. It was found that low temperature and high thiol to vegetable oil ratio increased the addition of thiol to the vegetable oil double bonds and generation of the desired thiol product. On the other hand, higher temperature and lower thiol to vegetable oil ratio resulted in reduced addition of the butyl thiol into the vegetable oil double bond in favor of formation of telomers. Corn and canola oils were used in the synthesis. The higher proportion of oleic acid in canola oil led to slightly higher conversion rate of the double bonds. Reaction products were analyzed using NMR, IR, and GC-MS methods. Under optimized reaction conditions, up to 90% conversion of the double bonds of soybean oil to sulfide were achieved with an isolated yield of 60%.