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.
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.