Enzymatic Synthesis and Crosslinking of Novel High Molecular Weight Polyepoxyricinoleate

Abstract

Abstract:Methyl epoxyricinoleate was prepared in high yield by the lipase-catalyzed epoxidation of methyl ricinoleate with H 2 O 2 . 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.

Improving thermal and mechanical properties of biomass-based polymers using structurally ordered polyesters from ricinoleic acid and 4-hydroxycinnamic acids

“…27,28 The poly(ricinoleic acid) (PRA) obtained from self-condensation of RA is a viscous liquid at room temperature. 29,30 Therefore, PRA has been generally considered suitable for lubricants; it has not been an attractive choice for the scaffold of bioplastics, with the exception of cross-linked PRA 30,31 and PRA composites with llers. 32 Numerous copolymers of RA with various comonomers, 29,[33][34][35][36] such as L-lactic acid, 37 have been developed with the aim of tuning thermal and mechanical properties.…”

Technological Aspects of Chemoenzymatic Epoxidation of Fatty Acids, Fatty Acid Esters and Vegetable Oils: A Review

“…Epoxidation reactions obtaining methyl epoxyricinoleate in the presence of lipase B have been studied by Kazariya and Matsumura for [78]. Lipase and hydrogen peroxide (30 wt %) were added to a solution of methyl ricinoleate in toluene, and the mixture was stirred at room temperature for 24 h. After separation, methyl epoxyricinoleate was polycondensed to polyepoxyricinoleate with an average molecular weight M w = 272,000.…”

Cost‐effective synthesis of polyricinoleate: Investigation of coating characteristics,in vitrodegradation, and antibacterial activity

“…32 In another study, high-molecular-weight polyepoxyricinoleate (M w = 272 000 gmol −1 ) was prepared by enzymatic polycondensation of methyl epoxyricinoleate using immobilized lipase from Burkholderia cepacia for 7 days, at 80 C. Polyepoxyricinoleate was later cured by maleic and succinic anhydride to obtain biodegradable films. 33 We suspect that scientific research on high-molecular-weight polyricinoleates is limited due to high price of pure methyl ricinoleate (monomer) and lipase catalysts. High purity monomer is required to obtain high-molecular weights because other mono functional fatty acids can untimely terminate growing polymer chain.…”