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Title: Functionalization of Oleyl Carbonate by Epoxidation

item Kenar, James - Jim

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/14/2007
Publication Date: 5/1/2007
Citation: Kenar, J.A. 2007. Functionalization of oleyl carbonate by epoxidation. Journal of the American Oil Chemists' Society. 84(5):457-461.

Interpretive Summary: In the interest of expanding the use of bio-based compounds such as lubricants and fuel additives prepared from renewable resources, the preparation, characterization and chemistry of lipid-based compounds was investigated. This work provides fundamental information about the reactivity of these compounds which is not currently available. The basic knowledge gained from this research has clear importance for the potential utilization of the compounds studied. The development of new industrial products derived from renewable resource, not only benefits farmers in the United States, but also reduces our dependence on petroleum-based resources.

Technical Abstract: Increasing interest in commercial applications due to their physical properties and relatively straightforward synthesis. Herein, oleyl carbonate (1), an olechemical-based compound derived from oleyl alcohol, was epoxidized utilizing performic acid generated in situ from formic acid and 50% H2O2. The reaction proceeded smoothly and furnished the corresponding oleyl carbonate bisepoxide, (2, bis[8-(3-octyloxiran-2-yl)octyl] carbonate), in good yields (83-85% isolated yields after purification by silica gel chromatography). The carbonate moiety was found stable to the reaction conditions utilized for epoxidation and the isolated oleyl carbonate bisepoxide was subsequently characterized using Fourier transform infrared spectroscopy (FTIR), 1H and 13C nuclear magnetic resonance spectroscopy (NMR), and liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS). As epoxidized materials are important industrial materials, oleyl carbonate bisepoxide compound may be of potential interest as a plasticizer, monomer, or further chemical elaboration.