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Functionalization of Oleyl Carbonate by Epoxidation

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  • Published:
Journal of the American Oil Chemists' Society

Abstract

Carbonates (esters of carbonic acid H2CO3) are a class of compounds that are of increasing interest in commercial applications due to their physical properties and relatively straightforward synthesis. Herein, oleyl carbonate, an oleochemical-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, (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, 1H and 13C nuclear magnetic resonance spectroscopy (NMR), and liquid chromatography electrospray ionization mass spectrometry. Oleyl carbonate bisepoxide compound may be of potential interest as a plasticizer, monomer, or a substance for further chemical elaboration.

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Acknowledgments

The author thanks Ian D. Tevis for help in preparing these compounds, Dr. Karl E. Vermillion for collection of the NMR data, and Sandra M. Duval for collection of LC-ESI-MS data.

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Authors and Affiliations

  1. Cereal Products and Food Science Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, US Department of Agriculture, 1815 N. University St, Peoria, IL, 61604, USA

    James A. Kenar

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  1. James A. Kenar
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Correspondence to James A. Kenar.

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Disclaimer: “Product names are necessary to report factually on available data; however, mention of trade names or commercial products in this article is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the US Department of Agriculture.”

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Kenar, J.A. Functionalization of Oleyl Carbonate by Epoxidation. J Amer Oil Chem Soc 84, 457–461 (2007). https://doi.org/10.1007/s11746-007-1058-0

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  • DOI: https://doi.org/10.1007/s11746-007-1058-0

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