Synthesis of carbonated fatty methyl esters using supercritical carbon dioxide

The two-step syntheses of the cyclic carbonates carbonated methyl oleate (CMO) and carbonated methyl linoleate (CIVIL) are reported. First, synthesis of epoxides through well-precedented chemical reactions of unsaturated fatty methyl esters with hydrogen peroxide and formic acid was accomplished. Next, a carbonation reaction with a simple tetrabutylammonium bromide catalyst was performed, allowing the direct incorporation of carbon dioxide into the oleochernical. These syntheses avoid the use of the environmentally unfriendly phosgene. The carbonated products are characterized by IR, H-1 NMR, and C-13 NMR spectroscopy and studied by thermogravimetric analysis (TGA). Also reported is the synthesis of a similar cyclic carbonate from the commercially available 2-ethylhexyl epoxy soyate. These carbonates show properties that may make them useful as petrochemical replacements or as biobased industrial product precursors.