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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Functional Foods Research » Research » Publications at this Location » Publication #327282
Research Project: Improved Utilization of Low-Value Oilseed Press Cakes and Pulses for Health-Promoting Food Ingredients and Biobased Products

Location: Functional Foods Research

Title: Synthesis and characterization of estolides containing epoxy and cyclic carbonate groups

Author
item Kenar, James - Jim
item Cermak, Steven - Steve
item Doll, Kenneth - Ken
item Isbell, Terry

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 5/1/2016
Publication Date: 5/4/2016
Citation: Kenar, J.A., Cermak, S.C., Doll, K.M., Isbell, T. 2016. Synthesis and characterization of estolides containing epoxy and cyclic carbonate groups [abstract]. American Oil Chemists' Society.

Interpretive Summary:

Technical Abstract: The unsaturated sites in 2-ethylhexyl estolides were converted into 5-membered cyclic carbonate groups utilizing a two-step process. First, epoxidation of the alkene bonds was accomplished using formic acid and hydrogen peroxide. The epoxidized estolide material was then reacted with supercritical carbon dioxide in the presence of tetrabutylammonium bromide catalyst to produce the cyclic carbonate moiety. The epoxidized intermediate and the carbonated estolides were characterized by FTIR and both 1H and 13C NMR spectroscopies. The signals at 1807 cm-1 and d 82 ppm in the FTIR and 13C NMR spectra, respectively, confirmed the desired cyclic carbonate was produced. The carbonated estolide exhibited a dynamic viscosity at 25 oC of 172 mPa•s as compared to 155 mPa•s for the estolide starting material.