ARS | Publication request: Improved Synthesis of Carbonated Soybean Oil in Supercritical Carbon Dioxide

Submitted to: American Chemical Society National Meeting
Publication Type: Abstract
Publication Acceptance Date: March 23, 2005
Publication Date: March 25, 2005
Citation: Doll, K.M., Erhan, S.Z. 2005. Improved synthesis of carbonated soybean oil in supercritical carbon dioxide. American Chemical Society National Meeting. p. 191.

Technical Abstract: Carbonates from oleochemical origin have shown recent promise for use in the cosmetics, filter, and detergent industries. Carbonates may also form building blocks for polymeric materials. Especially of interest are cyclic carbonates, which upon addition to an amine, form a non-isocyanate urethane. Many traditional preparations of carbonates are expensive and involve environmentally unfriendly phosgene, or metal catalysis. However, it is possible to use a simple base catalyst to directly add carbon dioxide to an epoxide. We have synthesized and characterized carbonated soybean oil from commercially available epoxidized soybean oil using a tetrabutylammonium bromide catalyst. Our synthesis takes advantage of the higher density of super critical carbon, as compared to CO2 under conventional temperature and pressure, to considerably reduce the time required for the reaction. Fully epoxidized product could be produced in 40 hours at 100 deg C (1500 PSI of CO2), as opposed to the 70 hours reported in the literature.