ARS | Publication request: SYNTHESIS OF CARBONATED METHYL OLEATE FROM METHYL OLEATE EPOXIDE (EMO) IN SUPERCRITICAL CARBON DIOXIDE

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: March 1, 2006
Publication Date: April 1, 2006
Citation: Doll, K.M., Erhan, S.Z. 2006. Synthesis of carbonated methyl oleate from methyl oleate epoxide (EMO) in supercritical carbon dioxide [abstract]. 97th American Oil Chemists' Society Annual Meeting and Expo. p. 89.

Technical Abstract: Various linear carbonates have been synthesized from oleochemicals, with possible applications in the cosmetic, personal care, and detergent industries. The synthesis of cyclic carbonates from ethylene oxide has been practiced on an industrial scale. However, with the exception of glycerol carbonate, there has been less work in the synthesis of cyclic carbonates from oleochemicals. Epoxidized methyl oleate (EMO) was synthesized from methyl oleate using hydrogen peroxide and a formic acid catalyst. The epoxide was then converted to the carbonate using a base catalysis (tetrabutylammonium bromide) in supercritical carbon dioxide. The carbon dioxide serves not only as a reaction solvent, but also as a reactant. Conversion was shown to be complete by 1H NMR in 20 hrs at 100 deg C (1500 PSI of CO2). The final product was also characterized by IR spectroscopy. Because of its functional groups, carbonated methyl oleate has potential to be a good building block for both monomeric and polymeric products and the bio-based product may also find application in the lubricant, textile, and detergent industries.