Epoxidation of Methyl Oleate and Subsequent Ring-Opening Catalyzed by Lipase from Candida sp. 99–125

A green method for chemo-enzymatic epoxidation of methyl oleate is developed, resulted in epoxidized methyl oleate. Subsequently, excessive hydrogen peroxide and extended reaction time led to polyols through ring-opening reaction catalyzed by immobilized lipase from Candida sp. 99–125. The corresponding reaction conditions are systematically investigated. High epoxy number is obtained at 70 °C for 5 h when 1.5 wt% immobilized lipase and 1.5 equivalent of hydrogen peroxide are used. Interestingly, no hydrolysis reaction of epoxidized methyl oleate is observed. Moreover, epoxidized methyl oleate generated shows good plasticizing effect on PVC resin. On the basis of epoxidation reaction, more hydrogen peroxide and extended reaction time are employed in the ring-opening reaction, resulting in more polyols. Polyurethane rigid foams with good thermal conductivity, dimensional stability, and compress strength can be successfully prepared through the use of polyols acquired by ring-opening reaction of epoxidized soybean oil. In addition, the enzyme shows good reusability toward epoxidation and ring-opening reaction. Practical Applications: The epoxides can be widely used as stabilizers for plasticizers, ingredients of lubricants, and the intermediates for surfactants. The bio-based polyols are the potential alternative petrochemicals in polyurethane industry. Furthermore, successful achievement of this study can provide a powerful technical support for the application of enzyme catalysis in organic synthesis. An NMR-based metabolomic approach,using “one-to-one” OPLS-DA models, allows to identify biomarkers of different production zones in “Bosana” Sardinian EVOO.