The Effect of Solvent Hydrophilicity on the Enzymatic Ring-Opening Polymerization of L-Lactide by Candida rugosa Lipase

Catia Angli Curie; Muhammad Arif Darmawan; Dianursanti Dianursanti; Wiratni Budhijanto; Misri Gozan

doi:10.3390/polym14183856

The Effect of Solvent Hydrophilicity on the Enzymatic Ring-Opening Polymerization of L-Lactide by Candida rugosa Lipase

Polymers (Basel). 2022 Sep 15;14(18):3856. doi: 10.3390/polym14183856.

Authors

Catia Angli Curie^{1

2}, Muhammad Arif Darmawan³, Dianursanti Dianursanti⁴, Wiratni Budhijanto⁵, Misri Gozan¹

Affiliations

¹ Chemical Engineering Department, Faculty of Engineering, Universitas Indonesia, Depok 16424, Indonesia.
² Department of Chemical Engineering, Universitas Pertamina, Jakarta 12220, Indonesia.
³ Research Center for Process and Manufacturing Industry Technology, Research Organization for Energy and Manufacture, National Research and Innovation Agency, South Tangerang 15314, Indonesia.
⁴ Bioprocess Engineering Program, Department of Chemical Engineering, Faculty of Engineering, Universitas Indonesia, Depok 16424, Indonesia.
⁵ Chemical Engineering Department, Faculty of Engineering, Universitas Gadjah Mada, Yogyakarta 55281, Indonesia.

Abstract

Contradictions have been reported on the effect of organic solvents, especially toluene, on enzymatic ring-opening polymerization (eROP) of L-lactide. Studies have shown that log P, a common measure of hydrophilicity, affects enzyme activity. This study examines the effect of solvents with various log P values on the eROP of L-lactide, performed using Candida rugosa lipase (CRL). N,N-dimethylacetamide (DMA), 1,2-dimethoxybenzene, 1,4-dimethoxybenzene, diphenyl ether, and dodecane were used as the organic solvents. The eROP in ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF₆]) was also conducted to compare its performance with the organic solvents. The results show that [BMIM][PF₆]-mediated eROP gave better conversion and molecular weight than the organic solvent-mediated eROP. In this study, the effects of solvents hydrophilicity are discussed, including the possibility of hexafluorophosphate ion ([PF₆]^-) hydrolysis to occur.

Keywords: Candida rugosa lipase; L-lactide; [BMIM][PF6]; [PF6]− hydrolysis; enzymatic ring-opening polymerization (eROP); hydrophilicity; hydrophobicity; ionic liquid; organic solvents; polylactic acid.

Abstract

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