Synthesis of 2-ethylhexyl oleate catalyzed by Candida antarctica lipase immobilized on a magnetic polymer support in continuous flow

Bioprocess Biosyst Eng. 2020 Apr;43(4):615-623. doi: 10.1007/s00449-019-02257-9. Epub 2019 Nov 25.

Abstract

This study investigated the synthesis of 2-ethylhexyl oleate catalyzed by Candida antarctica lipase immobilized on magnetic poly(styrene-co-divinylbenzene) particles in a continuous packed-bed bioreactor. Runs were carried out in a solvent-free system at 50 °C. The performance of the reactor was evaluated for substrates composed by oleic acid and 2-ethylhexanol at five molar ratios (1:4-4:1), determining its operation limits in terms of substrate flow rate. The system performance was quantified for three different flow rates corresponding to space-time between 3 and 12 h. For each condition, the influence of the space-time in the ester formation, esterification yield and productivity was determined. The molar ratio of acid-to-alcohol interfered, in a remarkable way, in the formation of 2-ethylhexyl oleate and the best performance was attained for substrate at equimolar ratio running at 12 h space-time. Under this condition, average 2-ethylhexyl oleate concentration was 471.65 ± 2.98 g L-1 which corresponded to ester productivity of 23.16 ± 0.49 mmol g-1 L-1 h-1. This strategy also gave high biocatalyst operational stability, revealing a half-life time of 2063 h. A model based on the ping-pong Bi-Bi mechanism was developed to describe the kinetics of the esterification reaction and validated using experimental data. The goodness of fit of the model was satisfactory (R2 = 0.9310-0.9952).

Keywords: Esterification; Immobilized lipase; Kinetic modeling; Magnetic polymer; Packed-bed reactor.

MeSH terms

  • Bioreactors*
  • Catalysis
  • Enzymes, Immobilized / chemistry*
  • Esterification
  • Fungal Proteins / chemistry*
  • Lipase / chemistry*
  • Magnetic Fields*
  • Oleic Acids* / chemical synthesis
  • Oleic Acids* / chemistry
  • Polystyrenes / chemistry*

Substances

  • Enzymes, Immobilized
  • Fungal Proteins
  • Oleic Acids
  • Polystyrenes
  • divinylbenzene-polystyrene copolymer
  • Lipase
  • lipase B, Candida antarctica