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3 Biotech

, 9:34 | Cite as

Influence of ionic liquid on Novozym 435-catalyzed the transesterification of castor oil and ethyl caffeate

  • Shangde SunEmail author
  • Yaping Lv
  • Sha Zhu
Original Article
  • 39 Downloads

Abstract

Caffeic acid (CA), one kind of phenolic acids widely occurring in the plant kingdom, can be used as potential UV protective ingredient and antioxidant. However, the application of CA was limited because of its unsatisfactory solubility in hydrophilic and lipophilic media. In this work, BMIMPF6, one kind of ionic liquids (ILs), was developed as an environmental friendly reaction media for the enzymatic preparation of CA derivatives by the transesterification of castor oil (CO) and ethyl caffeate (EC). Different series of ILs with \({\text{BF}}_{4}^{ - },\) \({\text{TF}}_{2}^{ - }\), and \({\text{PF}}_{6}^{ - }\) were screened and compared, and the effects of transesterification variables [temperature (60–100 °C) enzyme concentration (10–90 mg/mL), substrate molar ratio (CO/EC, 1:1–5:1), water load (0–8%), and reaction pressure] were also investigated. Results showed that, in the IL system, hydrophilic and lipophilic products were formed by two competitive reactions [(i) hydrolysis + transesterification and (ii) transesterification]. The maximum hydrophilic caffeoyl lipids yield (26.10 ± 0.28%) and reaction selectivity for hydrophilic caffeoyl lipids (0.4) was achieved in BMIMPF6 system. The increases of substrate ratio (molar ratio of CO to EC, from 1:1 to 5:1), water load (from 0 to 8%), and enzyme concentration (from 10 to 90 mg/mL) were in favor of hydrophilic caffeoyl lipid formation. However, the vacuum system and high temperature (from 70 to 100 °C) are favorable for lipophilic caffeoyl lipids formation. Under the optimal reaction conditions (90 °C, 75 mg/mL enzyme concentration, substrate ratio 3:1, 60 h, and 10 mmHg vacuum pressures), the maximum EC conversion was 72.48 ± 2.67%. The activation energies of the transesterification, and the selective formations of lipophilic and hydrophilic products were calculated as 44.55, 47.65, and 54.96 kJ/mol, respectively.

Keywords

BMIMPF6 Ionic liquids Caffeoyl lipids Immobilized lipase Activation energy Reaction selectivity 

Abbreviations

CA

Caffeic acid

CG

Caffeoyl glycerol

CO

Castor oil

CDAG

Caffeoyl di-acylglycerol

CMAG

Caffeoyl mono-acylglycerol

DCG

Dicaffeoyl glycerol

Ea

Activation energies

EC

Ethyl caffeate

HPLC–ESI-MS

High-performance liquid chromatography–electrospray ionization-mass spectroscopy

ILs

Ionic liquids

Notes

Acknowledgements

Financial support came from the National Natural Science Foundation of China (31771937) and the funding scheme for Young Teachers Cultivating Program in Henan University of Technology.

Compliance with ethical standards

Conflict of interest

No conflict of interest was declared.

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Copyright information

© King Abdulaziz City for Science and Technology 2019

Authors and Affiliations

  1. 1.Lipid Technology and Engineering, School of Food Science and EngineeringHenan University of TechnologyZhengzhouPeople’s Republic of China

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