Enzymatic Synthesis and Crosslinking of Novel High Molecular Weight Polyepoxyricinoleate

Abstract: Methyl epoxyricinoleate was prepared in high yield by the lipase-catalyzed epoxidation of methyl ricinoleate with H₂O₂. A high molecular weight polyepoxyricinoleate (PER) with a maximum weight average molecular weight (M_w) of 272,000 was enzymatically prepared by the polycondensation of methyl epoxyricinoleate using immobilized lipase from Burkholderia cepacia (lipase PS-IM) in bulk at 80 °C for 5 d. PER showed good low temperature fluidability. PER was readily cured by maleic anhydride (MA) at 80 °C to produce a chloroform-insoluble PER-MA film. Both the glass transition temperature and Young’s modulus increased with increasing MA content and PER M_w. In contrast, the elongation at break decreased with increasing MA content and PER M_w. Methyl epoxyricinoleate, PER and PER-MA showed biodegradability by activated sludge, and that of the PER-MA film decreased with increasing MA content.