Highly Selective Synthesis of Monolaurin via Enzymatic Transesterification under Batch and Continuous Flow Conditions

J Oleo Sci. 2019 Nov 7;68(11):1125-1132. doi: 10.5650/jos.ess19165. Epub 2019 Oct 15.

Abstract

This study aimed to investigate the highly selective production of monolaurin via enzymatic transesterification of methyl laurate and glycerol. It was determined that a binary solvent system (tert-butanol/iso-propanol, 20:80, wt./wt.) was suitable for the enzymatic production of monolaurin, especially in the continuous process. The highest mass fraction of monolaurin in the product mixture (80.8 wt.%) was achieved in a batch mode under the following conditions: a methyl laurate-to-glycerol molar ratio of 1:6, a substrate concentration (methyl laurate in the binary solvent) of 15 wt.%, an enzyme dosage of 6 wt.% of the amount of methyl laurate, and a reaction time of 1.5 h at 50°C. Compared with the results under the batch conditions, a slightly higher yield of monolaurin (82.5 ± 2.5 wt.%) was obtained in a continuous flow system at a flow rate of 0.1 mL/min, while the mass fraction of dilaurin in the product mixture was only 0.7 ± 0.6 wt.%. In addition, the yield of monolaurin remained almost unchanged during the 18 tested days of the continuous experiment.

Keywords: Lipozyme 435; binary solvent system; continuous process; enzymatic transesterification; monolaurin.

MeSH terms

  • 1-Propanol
  • Emulsifying Agents / chemical synthesis*
  • Esterification
  • Glycerol / chemistry
  • Laurates / chemical synthesis*
  • Laurates / chemistry
  • Monoglycerides / chemical synthesis*
  • Solvents
  • Temperature
  • Time Factors
  • tert-Butyl Alcohol

Substances

  • Emulsifying Agents
  • Laurates
  • Monoglycerides
  • Solvents
  • monolaurin
  • lauric acid methyl ester
  • 1-Propanol
  • tert-Butyl Alcohol
  • Glycerol