Lipase-catalyzed transesterification of epoxidized soybean oil to prepare epoxy methyl esters

Abstract

SUMMARY:Epoxidized soybean oil methyl esters could be efficiently prepared with the transesterification of epoxidized soybean oil (ESBO) with a lower dosage of methanol using lipase Novozym 435 as catalyst. The optimum parameters were as follows: the molar ratio of 5:1 (methanol to ESBO), 5% Novozym 435 as catalyst, at 45 °C for 14 h, with a stirring speed of 600rpm, under which the epoxidized soybean oil methyl esters (ESBOME) could be obtained at a 95.7% yield. During the enzymatic transesterification process, the oxirane oxygen values were kept unchangeable, which indicated that excellent functional group tolerance could be achieved under such mild reaction conditions. In addition, the recyclability of the immobilized enzyme Novozym 435 in this transesterification process was examined and the results showed that the biocatalyst could be reused ten times without losing any reaction activity or selectivity. And the final products of ESBOME were also identified by IR and NMR analysis. The kinetic data obtained followed the Ping-Pong Bi mechanism model (V max = 6.132 mol·L RESUMEN:Transesterificación catalizada por lipasa en aceite de soja epoxidado para preparar epoxi metil ésteres. Los ésteres metílicos de aceites de soja epoxidados pueden prepararse eficientemente mediante la transesterificación del aceite de soja epoxidado (ESBO) con una menor dosificación de metanol utilizando la lipasa Novozym 435 como catalizador. Los parámetros óptimos fueron los siguientes: relación molar 5:1 de metanol:ESBO, 5% de Novozym 435 como catalizador, 45 °C durante 14 h, velocidad de agitación de 600 rpm, bajo la cual los ésteres metílicos de aceites de soja epoxidados (ESBOME) pueden obtenerse con un rendimiento del 95,7%. Durante el proceso de transesterificación enzimática, los valores de oxígeno de oxirano se mantuvieron inalterables, lo que indicó que se logra una excelente estabilidad del grupo funcional en tales condiciones de reacción suaves. Además, se examinó la reciclabilidad de la enzima inmovilizada Novozym 435 en este proceso de transesterificación y los resultados mostraron que el biocatalizador podría reutilizarse durante diez veces sin perder ninguna actividad de reacción o selectividad. Los productos finales de ESBOME se identificaron por IR y análisis de RMN. Los datos cinéticos obtenidos siguieron el modelo de mecanismo Ping-Pong Bi (V max = 6,132 mol·L

Intensification of Enzymatic Sorbityl Laurate Production in Dissolved and Neat Systems under Conventional and Microwave Heating

“…Liu and Duan reported that Novozym 435 can be recycled using filtration, which was also demonstrated up to three cycles in this work. The catalytic activity of the enzyme in 2M2B remained high with a rising number of cycles.…”

Novozym 435: the “perfect” lipase immobilized biocatalyst?

“…300 The transesterification of epoxidized soybean oil catalyzed by N435 permitted the production of epoxidized soybean oil methyl esters with a 95.7% yield. 301 The biocatalyst was reutilized in 10 cycles maintaining the activity. Vinyl acetate and 2-phenethyl alcohol have been used to produce 2-phenylethyl acetate in hexane employing N435 as a catalyst.…”

Lipase-Catalyzed Production of Sorbitol Laurate in a “2-in-1” Deep Eutectic System: Factors Affecting the Synthesis and Scalability

“…At least on the tube scale, it is likely that, in the case of Novozym 435 ® , the costs associated with the immobilization might be fully compensated [ 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 ]. Indeed, the formulation can be recycled, using filtration, for sometimes up to 10 cycles, as a report from Liu et al demonstrates [ 49 ]. It is also important to remember that in such a bead-adsorbed enzyme formulation, the non-catalytic ballast of the carrier represents a tremendous portion of the biocatalyst’s mass (90 to >99 wt.%) [ 37 , 50 ].…”