Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 11/10/2014
Publication Date: 5/3/2015
Citation: Bantchev, G.B., Doll, K.M., Biresaw, G., Vermillion, K. 2015. Formation of furan fatty alkyl esters from their bis-epoxide fatty esters [abstract]. Annual Meeting and Expo of the American Oil Chemists' Society. Abstract No. 61580.
Technical Abstract: Reactions of epoxidized alkyl soyate with four different alcohols: ethanol, isopropyl alcohol, 2-ethylhexanol, and benzyl alcohol were investigated in the presence of Bronsted acid catalyst. Products not reported in prior studies of similar reactions were found. These were furan fatty acid alkyl esters (FFE, mixture of alkyl 8-(5-hexyl-2-furyl) octanoate and alkyl 9-(5-pentyl-2-furyl) nonanoate) which were unambiguously identified by means of GC-MS and two-dimensional NMR. Evidence suggests that the FFE are formed by an acid-catalyzed rearrangement of the epoxidized linoleates. The FFE were formed in presence of all four alcohols tested and in the presence of either sulfuric acid or Amberlyst 15 catalyst. Yields of up to 13%, as quantified by GC and NMR spectroscopies, were observed. A mechanism for the formation of the FFE is offered on the basis of kinetics studies.