(275e) Enzymatic Process for Making Plasticizers from High Oleic Soybean Oil

Epoxidized soybean oil (ESBO) is a chemically modified soybean oil derivative that is used to make plastics pliable as well as for making bio-based polyurethanes for coatings, epoxide-based resins, and high temperature lubricants. While traditional conversion methods use peroxyacetic acid to catalyze the reaction, lipases can also catalyze epoxidation reactions. In this paper we show conversion of soybean oil and high-oleic content soybean oil using immobilized lipase derived from Candida antarctica without the need for additional solvents, such as toluene, or added free fatty acids. At 35°C, soybean oil can be epoxidized with >90% yield within 15 hours, while using peroxyacetic acid only obtains 70% yield at 50°C after 10 hours of reaction time as side reactions reduced the selectivity of the epoxidation. Reaction kinetics for individual unsaturated fatty acids will be presented, as well as characterization of the enzymatic ESBO compared to the peroxyacetic acid conversion with both soybean oil and high-oleic content soybean oil. Recyclability of the immobilized enzyme is discussed in the context of potential commercial applications as a continuous process.