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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  5. Babot, E.D., Aranda, C., Kiebist, J., Scheibner, K., Ullrich, R., Hofrichter, M., Martínez, A.T., Gutiérrez, A. (2022). Enzymatic Epoxidation of Long-Chain Terminal Alkenes by Fungal peroxygenases. Antioxidants, 11, 522. DOI: 10.3390/antiox11030522
  6. Yoon, J.E., Lee, K.B., Yoo, C.J. Min, B.K., Lee, D.K., Won, D.H., Kim, S., Moon, J.H., Kim, C., Lee, U. (2024). Investigation of the sustainable production of ethylene oxide by electrochemical conversion: Techno-economic assessment and CO2 emissions. Journal of Cleaner Production, 475, 143539. DOI: 10.1016/j.jclepro.2024.143539
  7. Verkoyen, P., Frey, H. (2020). Long-Chain Alkyl Epoxides and Glycidyl Ethers: An Underrated Class of Monomers. Macromolecular Rapid Communications, 41, 2000225. DOI: 10.1002/marc.202000225
  8. Cogliano, T., Russo, V., Eränen, K., Tesser, R., Di Serio, M., Salmi, T. (2024). Epoxidation of vegetable oils in continuous device: kinetics, mass transfer and reactor modelling. Chemical Engineering Science, 294, 120079. DOI: 10.1016/j.ces.2024.120079
  9. Degaga, Y.A., Kassahun, S.K., Tiruneh, S.N. (2025). Green synthesis and characterization of bifunctional CaO-sulfated SnO2 catalyst for epoxidation of Brassica carinata seed oil: towards eco-friendly biolubricants. Biomass Conversion and Biorefinery, 15, 20281 – 20295. DOI: 10.1007/s13399-025-06647-w
  10. Moser, B.R., Cermak, S.C., Doll, K.M., Kenar, J.A., Sharma, B.K. (2022). A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications. Journal of the American Oil Chemists' Society, 99(10), 801-842. DOI: 10.1002/aocs.12623
  11. He, W., Zhu, G., Gao, Y., Wu, H., Fang, Z., Guo, K. (2020). Green plasticizers derived from poxidized soybean oil for poly (vinyl chloride): Continuous synthesis and evaluation in PVC films. Chemical Engineering Journal, 380, 122532. DOI: 10.1016/j.cej.2019.122532
  12. Ali, S.S., Elsamahy, T., Koutra, E., Kornaros, M., El-Sheekh, M., Abdelkarim, E.A., Zhu, D., Sun, S. (2021). Degradation of conventional plastic wastes in the environment: A review on current status of knowledge and future perspectives of disposal. Science of The Total Environment, 771, 144719. DOI: 10.1016/j.scitotenv.2020.144719
  13. Salmi, T., Perez-Sena, W.Y., Ciccarelli, F., Eränen, K., Medina, A., Cogliano, T., di Serio, M., Wärnå, J., Leveneur, S., Russo, V., (2024). Kinetics and reactor modelling of a complex three-phase system: Carbonation of epoxides on grafted catalysts. Chemical Engineering Science, 285, 119578. DOI: 10.1016/j.ces.2023.119578
  14. Gunawan, E.R., Suhendra, D., Arimanda, P., Asnawati, D., Murniati, (2023). Epoxidation of Terminalia catappa L. Seed oil: Optimization reaction. South African Journal of Chemical Engineering, 43, 128–134. DOI: 10.1016/j.sajce.2022.10.011
  15. Vanags, E., Kirpluks, M., Cabulis, U., Walterova, Z. (2018) Highly functional polyol synthesis from epoxidized tall oil fatty acids. Journal of Renewable Materials, 6(7), 764-771. DOI: 10.7569/JRM.2018.634111
  16. Cogliano, T., Russo, V., Eränen, K., Tesser, R., Serio, M.D., Salmi, T. (2025). Comparison of continuous technologies for vegetable oils epoxidation. Chemical Engineering Science, 301, 120726. DOI: 10.1016/j.ces.2024.120726
  17. Vanags, E., Abolins, A., Cabulis, U. (2023). Lipase Catalyzed Self-epoxidation of Tall Oil Fatty Acids in Batch and Continuous Flow Conditions. Journal of Polymers and the Environment, 31, 2166–2176. DOI: 10.1007/s10924-022-02739-0
  18. Podolean, I., Tudorache, M. (2024). Sustainable Biocatalytic System for the Enzymatic Epoxidation of Waste Cooking Oil. Materials, 17(18), 4518. DOI: 10.3390/ma17184518
  19. Kutyła, M., Majdan, M., Szajnecki, L., Świca, A., Stankevič, M., Typek, R., van Berkel, W.J.H., Trytek, M. (2024). Chemoenzymatic Epoxidation of Terpenes by Lyophilized Mycelium of Psychrophilic Cladosporium cladosporioides 01. Industrial & Engineering Chemistry Research, 63, 17790-17802. DOI: 10.1021/acs.iecr.4c02228
  20. Kumar, A., Dhar, K., Kanwar, S.S., Arora, P.K .(2016). Lipase catalysis in organic solvents: advantages and applications. Biological Procedures Online, 18,1–11. DOI: 10.1186/s12575-016-0033-2
  21. Abolins, A., Kirpluks, M., Vanags, E., Fridrihsone, A., Cabulis, U. (2020). Tall Oil Fatty Acid Epoxidation Using Homogenous and Heterogeneous Phase Catalysts. Journal of Polymers and the Environment, 28, 1822–1831. DOI: 10.1007/s10924-020-01724-9
  22. Zhang, F., Bian, F., Dong, Y., Lin, S., Gui, X., Hu, J. (2023). Epoxidation reaction of soybean oil: process optimization and kinetic studies. Chemical Papers, 77, 7849–7863. DOI: 10.1007/s11696-023-03029-2
  23. Jalil, M.J., Rahman, S.J.A., Masri, A.N., Yusof, F.A.M., Azman, M.A.S.C.M., Jites, P.P.A., Azmi,I.S. (2024). Epoxidation of oleic acid derived palm oil and subsequent ring opening by in situ hydrolysis. Polymer Bulletin, 81, 14371–14383. DOI: 10.1007/s00289-024-05358-y
  24. Mahadi, M.B., Azmi, I.S., Ahmad, M.A., Rahim, N.H., Jalil, M.J. (2025). Catalytic epoxidation of sunflower oil derived by linoleic acid via in situ peracid mechanism. Biomass Conversion and Biorefinery, 15, 9505–9512. DOI: 10.1007/s13399-024-05658-3
  25. Salvi, H.M. Yadav, G.D. (2020). Chemoenzymatic Epoxidation of Limonene Using a Novel Surface-Functionalized Silica Catalyst Derived from Agricultural Waste. ACS Omega, 5, 22940−22950. DOI: 10.1021/acsomega.0c02462
  26. Fontes, A.L., Pimentel, L.L., Soares, A.M.S., Domingues, M.R., Rodríguez-Alcalá, L.M., Gomes, A.M. (2023). Study of the viability of using lipase-hydrolyzed commercial vegetable oils to produce microbially conjugated linolenic acid-enriched milk. Food Chemistry, 413, 135665. DOI: 10.1016/j.foodchem.2023.135665
  27. Wikström, W., Aguilera, A.F., Tolvanen, P., Lassfolk, R., Medina, A., Eränen, K., Salmi, T. (2023). Fatty Acid Epoxidation on Enzymes: Experimental Study and Modeling of Batch and Semibatch Operation. Industrial & Engineering Chemistry Research, 62, 9169−9187. DOI: 10.1021/acs.iecr.3c00890
  28. ASTM D5554-95 (2011) – Standard Test Method for Determination of the Iodine Value of Fats and Oils
  29. Amrutha, N.R., Murthy, P.S.K., Reddy, J.P.(2025). Epoxidized safflower oil: Synthesis and evaluation of its performance as bioplasticizer for polylactic acid films. Industrial Crops and Products, 224, 120360. DOI: 10.1016/j.indcrop.2024.120360
  30. Azmi, I.S., Jalil, M.J., Hadi, A. (2024). Epoxidation of unsaturated fatty acid–based palm oil via peracid mechanism as an intermediate product. Biomass Conversion and Biorefinery, 14, 7847–7855. DOI: 10.1007/s13399-022-02862-x
  31. Rasib, I.M., Mubarak, N.M., Azmi, I.S., Jalil, M.J. (2025). Epoxidation of neem oil via in situ peracids mechanism with applied ion exchange resin catalyst. Biomass Conversion and Biorefinery, 15, 13707–13717. DOI: 10.1007/s13399-024-06137-5
  32. Kadir, M.Z.A. Azmi, I.S., Kasmin, N.D., Rahman, S.J.A., Jalil, M.J. (2024). Green catalytic epoxidation of hybrid oleic acid derived from waste palm cooking oil + palm oil. Polymer Bulletin, 81, 6979–6994. DOI: 10.1007/s00289-023-05029-4
  33. González-Benjumea, A., Marques, G., Herold-Majumdar, O.M., Kiebist, J., Scheibner, K., del Río, J.C., Martínez, A.T., Gutiérrez, A. (2021). High Epoxidation Yields of Vegetable Oil Hydrolyzates and Methyl Esters by Selected Fungal Peroxygenases. Frontiers in Bioengineering and Biotechnology, 8, 605854. DOI: 10.3389/fbioe.2020.605854
  34. Montenegro, J.A.S., Ries, A., Silva, I.D.S., Luna, C.B.B., Souza, A.L., Wellen, R.M.R. (2023). Enzymatic and Synthetic Routes of Castor Oil Epoxidation. Polymers, 15, 2477. DOI: 10.3390/polym15112477
  35. Yu, L., Zou, C., Li, Q., Liu, Z., Liu, Y., Tang, A. (2023). Improving efficiency and reducing enzyme inactivation during lipase-mediated epoxidation of α-pinene in a double-phase reaction system. Bioprocess and Biosystems Engineering, 46, 1331–1340. DOI: 10.1007/s00449-023-02902-4
  36. Bajwa, A.S., Sathaye, S., Kulkarni, V.M., Patwardhan, A.V. (2016). Chemoenzymatic epoxidation of Karanja oil: an alternative to chemical epoxidation?. Asia-Pacific Journal of Chemical Engineering, 11(2), 314-322. DOI: 10.1002/apj.1979
  37. Kabir, M.F., Ju, L. (2023). On optimization of enzymatic processes: Temperature effects on activity and long-term deactivation kinetics. Process Biochemistry, 130, 734-746. DOI: 10.1016/j.procbio.2023.05.031
  38. Den, G. (2024). The Effect of Temperature on Enzyme Activity: Mechanisms and Practical Implications. Biochemistry and Molecular Biology Journal, 10(02), 017. DOI: 10.36648/2471-8084-10.02.17
  39. Kirpluks, M., Pomilovskis, R., Vanags, E., Abolins, A., Mierin, I., Fridrihsone, A. (2022). Influence of different synthesis conditions on the chemo-enzymatic epoxidation of tall oil fatty acids. Process Biochemistry, 122(1), 38-49. DOI: 10.1016/j.procbio.2022.08.024
  40. Habri, H.H., Shahrizan, A.S.A., Azmi, I.S., Hambali, N., Shamjuddin, A., Salaeh, S., Jalil, M.J. (2024). Degradation autocatalytic epoxidation of oleic acid derived from palm oil via in situ performic acid mechanism. Environmental Progress & Sustainable Energy, 43(6), e14498. DOI: 10.1002/ep.14498
  41. Kurańska, M., Niemiec, M. (2020), Cleaner production of epoxidized cooking oil using a heterogeneous catalyst. Catalysts, 10(11), 1261. DOI: 10.3390/catal10111261
  42. Sun, S., Li, P., Bi, Y., Xiao, F. (2014). Enzymatic epoxidation of soybean oil using ionic liquid as reaction media. Journal of Oleo Science, 63(4), 383-390. DOI: 10.5650/jos.ess13197
  43. Budiyati, E., Rochmadi, R., Arief, B., Budhijanto, B. (2020). Studies on epoxidation of tung oil with hydrogen peroxide catalyzed by sulfuric acid. Bulletin of Chemical Engineering & Catalysis, 15(3), 674-686. DOI: 10.9767/bcrec.15.3.8243.674-686
  44. Putrawan, I.D.G.A., Azharuddin, A., Jumrawati, J. (2023). Preparing epoxidized vegetable oil from waste generated by the kapok fiber industry and assessing its thermal stabilization effect as a co-stabilizer for polyvinyl chloride. Heliyon, 9, e19624. DOI: 10.1016/j.heliyon.2023.e19624
  45. Ashine, F., Balakrishnan, S., Kiflie, Z., Tizazu, B.Z. (2023). Epoxidation of Argemone mexicana oil with peroxyacetic acid formed in-situ using sulfated tin (IV) oxide catalyst: Characterization, kinetic and thermodynamic analysis. Heliyon, 9, e12817. DOI: 10.1016/j.heliyon.2023.e12817
  46. Jalil, M.J., Rani, N.H.A., Yamin, A.F.M., Anuar, N.R.A, Azmi, I.S., Hadi, A. (2019). Epoxidation reaction parameter of palm olein for synthesis of dihydrostearic acid (DHSA) via hydrolysis reaction. IOP Conf. Series: Materials Science and Engineering. 551, 012001. DOI: 10.1088/1757-899X/551/1/012001
  47. Derawi, D., Salimon, J., Ahmed, W.A., 2014. Preparation of epoxidized palm olein as renewable material by using peroxy acids. The Malaysian Journal of Analytical Science, 18 (3), 584–591

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