Functionalization of Oleyl Carbonate by Epoxidation

• Published in: Journal of the American Oil Chemists' Society
• Main Author: Kenar, James A.
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2007
• Subjects: Carbonic acid
• Online Access: http://dx.doi.org/10.1007/s11746-007-1058-0; https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-007-1058-0

Abstract Carbonates (esters of carbonic acid H 2 CO 3 ) 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% H 2 O 2 . 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, 1 H and 13 C 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.