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Title:   Author  item
                                            Bantchev, Grigoritem
                                            Doll, Kenneth

                                                         - *Ken*item
                                            Biresaw, Girmaitem
                                            Vermillion, Karl
  Submitted to: Society of Tribologists and Lubrication Engineers
                                    Publication Type: Abstract Only
                                    Publication Acceptance Date: 12/1/2014
                                    Publication  Date: 5/17/2015
                                    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]. Society of Tribologists and Lubrication Engineers Annual Meeting & Exhibition. p. 38.Interpretive Summary:
                                Technical Abstract: Epoxidation of vegetable oils and consecutive epoxide ring-opening reaction is a widely investigated path for producing biobased lubricants and polymers. The reaction mechanism and products are considered well-studied and known. In the current study, the reactions of epoxidized alkyl soyate with four different alcohols 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, a mixture of alkyl 8-(5-hexyl-2-furyl) octanoate and alkyl 9-(5-pentyl-2-furyl) nonanoate). Evidence suggests that the FFE are formed by an acid-catalyzed rearrangement of the epoxidized linoleates. The FFE were formed in the 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.


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