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United States Department of Agriculture

Agricultural Research Service

Title: The Improved Synthesis of Carbonated Soybean Oil Using Supercritical Carbon Dioxide at a Reduced Reaction Time

Authors
item Doll, Kenneth
item Erhan, Sevim

Submitted to: Green Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: October 10, 2005
Publication Date: October 24, 2005
Citation: Doll, K.M., Erhan, S.Z. 2005. The improved synthesis of carbonated soybean oil using supercritical carbon dioxide at a reduced reaction time. Green Chemistry. 7:849-854.

Interpretive Summary: We have made the useful cyclic carbonate of soybean oil from commercially available epoxidized soybean oil using a simple catalytic procedure. The key to our synthesis is that we use the supercritical carbon dioxide which has higher density and higher oil solubility making it more reactive than carbon dioxide gas by cutting the reaction time to 1/3 of that in a previous report. Our synthesis uses only a small amount of catalyst, which we can remove by previously unreported yet simple method. This research benefits the soybean oil industry by increasing the potential to commercialize new environmentally friendly polymer products.

Technical Abstract: We have demonstrated at improved synthesis of a cyclic carbonate of soybean oil (CSO) utilizing supercritical carbon dioxide (CO2) as the solvent. Because the mutual solubility of supercritical CO2 and oil is significantly higher than that of the gas, our method synthesizes the material in ~1/3 of the reaction time reported in the literature. We have also demonstrated a catalyst removal method for our system based on the simple Hofmann elimination reaction reducing the need for organic solvent extraction. CSO is a potential petroleum replacement, and may be useful in the synthesis of polymers based on bio-resources.

Last Modified: 12/22/2014