One-Pot Tandem Catalytic Epoxidation—CO2 Insertion of Monounsaturated Methyl Oleate to the Corresponding Cyclic Organic Carbonate

Abstract

Conversion of unsaturated fatty acids, FAMEs or triglycerides into the corresponding cyclic organic carbonates involves two reaction steps—double-bond epoxidation and CO2 insertion into the epoxide—that are generally conducted separately. We describe an assisted-tandem catalytic protocol able to carry out carbonation of unsaturated methyl oleate in one-pot without isolating the epoxide intermediate. Methyl oleate carbonate was obtained in 99% yield and high retention of cis-configuration starting from methyl oleate using hydrogen peroxide and CO2 as green reagents, in a biphasic system and in the presence of an ammonium tungstate ionic liquid catalyst with KBr as co-catalyst.