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United States Department of Agriculture

Agricultural Research Service

Title: Convenient Preparation of Fatty Ester Cyclic Carbonates

Authors
item Kenar, James
item Tevis, Ian

Submitted to: European Journal of Lipid Science and Technology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: December 13, 2004
Publication Date: February 1, 2005
Citation: Kenar, J.A., Tevis, I.D. 2005. Convenient preparation of fatty ester cyclic carbonates. European Journal Lipid Science Technology. 107(2):135-137.

Interpretive Summary: In the interest of making bio-based compounds for use as additives in commercial products such as lubricants and fuel additives, several fatty compounds(materials derived from vegetable oils)were chemically modified in three steps to give good yields of a new type of compound which incorporates carbon dioxide. The isolation and characterization of these compounds, called fatty acid ester cyclic carbonates, is described. This work supplies fundamental information about these compounds not previously available to researchers in the fats and oils industry. This fundamental knowledge will be used by many other scientists to develop new applications for vegetable oils by incorporating more environmentally friendly processing steps. The development of new industrial products derived from vegetable oils, a renewable resource, not only benefits farmers in the United States, but also reduces our dependence on petroleum-based resources.

Technical Abstract: The 9,10-unsaturated site in methyl and 2-ethylhexyl oleate was converted into the corresponding 2-oxo-1,3-dioxolane (5-membered cyclic carbonate) functionality in good yields via a simple three step process. Epoxidation of oleate ester's double bond using H2O2 and formic acid followed by ring opening with HCl in acetone gave a regioisomeric mixture of the corresponding 9,10-chlorohydrins. In the key step, conversion of the chlorohydrins into the corresponding cyclic carbonate group was accomplished under mild conditions (CO2 atmosphere at 55 deg C) using tetramethylammonium hydrogen carbonate(TMAHC). The fatty acid ester carbonates were isolated in yields ranging from 84-91% after purification by distillation. The purified fatty ester carbonate compounds were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared (FTIR) spectroscopy, and gas-chromatography-mass spectrometry (GC/MS) using electron impact (EI) and positive chemical ionization (CI) ionization techniques. The excellent lubricating properties of the carbonate moiety make these interesting oleochemical carbonates of interest as potential lubricants, plasticizers, or additives for various industrial applications.

Last Modified: 7/24/2014
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