Three-Step Chemo Enzymatic Continuous-Flow Cascade Synthesis of 1-Monoacylglycerol

Abstract

Abstract In this work, a three-step chemo enzymatic cascade reaction is reported for 1-monoacylglycerols from glycerol derived from biodiesel industry under continuous-flow conditions. Glycerol protection was performed using H2SO4/SiO2 (2.5% w/v) solid catalyst and acetone, generating 87% of solketal under 55 °C at 0.1 mL/min with glycerol–acetone ratio of 1.5:1. Coupled esterification between the formed solketal and stearic acid catalyzed by Rhizomucor miehei enzyme (RM IM) was able to maintain 90% of conversion until 1.5 M of substrate concentration at 0.1 mL/min flow rate and could be recycled up to 18 times. Final ketal cleavage was performed with the same H2SO4/SiO2 solid catalyst and the amount of water generated in the esterification reaction, whereas a flow rate of 0.2 mL/min was the best condition where the formation of 1-monoacylglycerol was maximized and byproducts were not detected.