DOI: https://doi.org/10.9767/bcrec.20836

Synthesis of Long-Chain Alkyl Epoxides via Chemoenzymatic Epoxidation of Fatty Acids of Terminalia catappa L. Oil

Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Mataram, Jl. Majapahit No. 62 Mataram, 83125, Indonesia

Received: 4 Sep 2026; Revised: 22 Sep 2026; Accepted: 23 Sep 2026; Available online: 26 Sep 2026; Published: 26 Dec 2026.
Editor(s): Istadi Istadi
Open Access Copyright (c) 2026 by Authors, Published by BCREC Publishing Group
Creative Commons License This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
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Abstract

Long-chain alkyl epoxides (LCAEs) derived from renewable vegetable oils are promising bio-based chemical intermediates and functional materials. This study aimed to synthesize LCAEs from unsaturated fatty acids derived from Terminalia catappa L. seed oil (FA-TCO) via chemoenzymatic epoxidation. TCO was first hydrolyzed using Lipozyme® TL IM, an immobilized lipase from Thermomyces lanuginosus, to obtain FA-TCO, which was subsequently subjected to epoxidation using H₂O₂ as the oxygen donor and lipase as the biocatalyst. The effects of reaction parameters were systematically investigated to determine the optimum epoxidation conditions. The optimum conditions were achieved at 50 °C, with an FA-TCO-to-enzyme mass ratio of 10:1 (w/w), an FA-TCO-to-H₂O₂ mass ratio of 5:4 (w/w), and an epoxidation time of 5 h. Under these conditions, the relative conversion to oxirane (RCO) reached 67.67 %, demonstrating effective conversion of C=C bonds into oxirane groups. FTIR analysis confirmed oxirane formation through characteristic bands at 884 and 1247 cm⁻¹. The formation of oxirane groups was further supported by 1H and 13C NMR spectroscopy, which showed resonances consistent with oxirane associated protons at 2.75–2.77 ppm and oxirane carbons at 62.2–62.5 ppm, respectively. Overall, the results demonstrate the feasibility of chemoenzymatic epoxidation for producing FA-TCO-based LCAEs from a renewable feedstock. Copyright © 2026 by Authors, Published by BCREC Publishing Group. This is an open access article under the CC BY-SA License (https://creativecommons.org/licenses/by-sa/4.0).

Keywords: Terminalia catappa L. seed oil; unsaturated fatty acid; epoxidation; chemoenzymatic; long chain alkyl epoxides
Funding: Ministry of Education, Culture, Research, and Technology of the Republic of Indonesia

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Section: Original Research Articles
Language : EN
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