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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #313794

Title: Sulfuric acid as a catalyst for ring-opening of biobased bis-epoxides

item Bantchev, Grigor
item Doll, Kenneth - Ken
item Biresaw, Girma
item Vermillion, Karl

Submitted to: Pacifichem Symposium
Publication Type: Abstract Only
Publication Acceptance Date: 5/15/2015
Publication Date: 12/15/2015
Citation: Bantchev, G.B., Doll, K.M., Biresaw, G., Vermillion, K. 2015. Sulfuric acid as a catalyst for ring-opening of biobased bis-epoxides. Pacifichem Symposium. ENRG 292.

Interpretive Summary:

Technical Abstract: Vegetable oils can be relatively and easily transformed into bio-based epoxides. Because of this, the acid-catalyzed epoxide ring-opening has been explored for the preparation of bio-based lubricants and polymers. Detailed model studies are carried out only with mono-epoxide made from methyl oleate, while most vegetable oils contain linoleic acid as the main component. As a result of the high linoleic content, the main component of epoxidized vegetable oil is a fatty acid chain with methylene-interrupted bis-epoxides. Based on the results from epoxidized methyl oleate, it is often assumed that the main product of acid-catalyzed ring-opening with alcohols is fatty acid chains with attached hydroxyl groups and side ether branches. In the current report, we show results of the reaction of epoxidized methyl soyate with 2-ethylhexanol in the presence of sulfuric acid. We observed that significant amounts of bis-epoxides did not yield the bis-hydroxy- or bis-ether-compounds as suggested in literature reports, but form cyclic compounds. Two of the formed compounds are furan fatty acids (mixture of methyl 8-(5-hexyl-2-furyl) octanoate and methyl 9-(5-pentyl-2-furyl)nonanoate). We report a preliminary study of the kinetics of their formation and suggest a possible mechanism of their formation.