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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of Cyclic Carbonates from Fatty Materials Using Supercritical Carbon Dioxide

item Doll, Kenneth
item Erhan, Sevim

Submitted to: Green Chemistry
Publication Type: Abstract Only
Publication Acceptance Date: March 31, 2006
Publication Date: June 27, 2006
Citation: Doll, K.M., Erhan, S.Z. 2006. Synthesis of cyclic carbonates from fatty materials using supercritical carbon dioxide [abstract]. 10th Annual Green Chemistry and Engineering Conference, Designing for a Sustainable Future. p. 24.

Technical Abstract: We have demonstrated the synthesis of the cyclic carbonates from the oleochemical based, methyl oleate, methyl linoleate, and methyl linolenate using a simple two step synthesis. First, we perform an environmentally friendly epoxidation reaction using hydrogen peroxide and formic acid. Next, the epoxidized materials; epoxidized methyl oleate (EMO), epoxidized methyl linoleate (EMLO), and epoxidized methyl linolenate (EMLEN), are reacted with supercritical carbon dioxide directly using a small amount of ring opening catalyst. We have also demonstrated similar carbonate syntheses starting from commercially available epoxidized soybean oil (ESO) and epoxidized 2-ethyl-hexyl soyate (VF). The use of supercritical carbon dioxide allows the synthesis to be performed at significantly reduced reaction time, compared to literature syntheses of the carbonated soybean oil. Our synthesis also avoids the use of environmentally unfriendly phosgene, and because the carbon dioxide is used directly, our reaction is highly atom efficient. The compounds that we have synthesized may be useful as lubrication fluids, and are valuable building blocks in the synthesis of isocyanate free polyurethanes.

Last Modified: 4/22/2015
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