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Sustainable epoxidation of expired palm oil–derived oleic acid via in situ peracid mechanism with applied ion resin Amberlite IR-120H: from waste to wealth

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Abstract

Over the last decade, there has been growing interest/global concern in synthesizing products from renewable energy sources. Epoxides are intermediate products that can be used to produce other materials such as polyols through the epoxidation of vegetable oils. In this study, expired palm oil was used to synthesize epoxides via in situ peracid mechanism utilizing an ion exchange resin catalyst. Based on the results, the relative conversion to oxirane (RCO) is 63%. The following optimum process parameters were used for the epoxidation process: (1) stirring speed: 600 rpm, (2) reaction temperature: 90 °C, and (3) formic acid/unsaturated fatty acid molar ratio: 1:1. Besides that, a mathematical model was developed by using the numerical integration Runge Kutta 4th Order method using MATLAB software. Based on the results of the kinetic study, the summation of error is smaller, and therefore, the kinetic model is validated.

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Data Availability

The data that support the findings of this study are available from the corresponding author upon reasonable request.

References

  1. Jalil MJ, Azmi IS, Hadi A (2021) Highly production of dihydroxystrearic acid from catalytic epoxidation process by in situ peracid mechanism. Environ Prog Sustain Energy :1–7. https://doi.org/10.1002/ep.13764

  2. Janković MR, Govedarica OM, Sinadinović-Fišer SV (2019) The epoxidation of linseed oil with in situ formed peracetic acid: a model with included influence of the oil fatty acid composition. Ind Crops Prod 143(June):2020. https://doi.org/10.1016/j.indcrop.2019.111881

    Article  Google Scholar 

  3. Azeman NH, Yusof NA, Othman AI (2015) Detection of free fatty acid in crude palm oil. Asian J Chem 27(5):1569–1573. https://doi.org/10.14233/ajchem.2015.17810

    Article  Google Scholar 

  4. Sardon H, Mecerreyes D, Basterretxea A, Avérous L, Jehanno C (2021) From lab to market: current strategies for the production of biobased polyols. ACS Sustain Chem Eng. https://doi.org/10.1021/acssuschemeng.1c02361

    Article  Google Scholar 

  5. Tesser R, Russo V, Turco R, Vitiello R, Di M (2020) Bio-lubricants synthesis from the epoxidized oil promoted by clays : kinetic modelling. Chem Eng Sci 214:115445. https://doi.org/10.1016/j.ces.2019.115445

  6. Freites Aguilera A, Hämäläinen R, Eränen K, Tolvanen P, Salmi T (2021) Salmi, Prilezhaev epoxidation of oleic acid in the presence and absence of ultrasound irradiation. J. Chem. Technol. Biotechnol. 96(7):1874–1881. https://doi.org/10.1002/jctb.6706

    Article  Google Scholar 

  7. Jalil MJ, Farhan A, Yamin M, Saufi M (2019) Synthesis of epoxidized oleic acid- based palm oil by peracid mechanism. https://doi.org/10.1088/1757-899X/551/1/012120

  8. de Haro JC, Izarra I, Rodríguez JF, Pérez Á, Carmona M (2016) Modelling the epoxidation reaction of grape seed oil by peracetic acid. J Clean Prod 138:70–76. https://doi.org/10.1016/j.jclepro.2016.05.015

    Article  Google Scholar 

  9. Beltrán Osuna AA, Boyacá Mendivelso LA (2010) Two-phase kinetic model for epoxidation of soybean oil. Ing Investig 30(2):188–196

  10. Farhan A, Yamin M, Jalil MJ, Adnan I, Vsiduru VG (2018) Numerical modeling of epoxidation palm kernel oil based oleic acid 7:123–126

    Google Scholar 

  11. Badri KH, Ngah MS (2015) A mini scale batch reactor for the production of palm-based polyol. Sains Malaysiana 44(6):861–867. https://doi.org/10.17576/jsm-2015-4406-12

    Article  Google Scholar 

  12. Fernandes FC, Kirwan K, Lehane D, Coles SR (2017) Epoxy resin blends and composites from waste vegetable oil. Eur Polym J 89(February):449–460. https://doi.org/10.1016/j.eurpolymj.2017.02.005

    Article  Google Scholar 

  13. Xie WQ, Chai XS (2017) Determination of epoxy groups in epoxy resins by reaction-based headspace gas chromatography. Polym Test 59:113–117. https://doi.org/10.1016/j.polymertesting.2017.01.020

    Article  Google Scholar 

  14. Azmi IS, Bakar MHA, Raofuddin DNA, Habri HH, Azmi MHM, Jalil MJ (2022) Synthesis and kinetic model of oleic acid-based epoxides by in situ peracid mechanism 71:209–214

    Google Scholar 

  15. Zych A et al (2021) Biobased, biodegradable, self-healing boronic ester vitrimers from epoxidized soybean oil acrylate. ACS Appl Polym Mater 3(2):1135–1144. https://doi.org/10.1021/acsapm.0c01335

    Article  Google Scholar 

  16. Montoya C et al (2014) Genetic architecture of palm oil fatty acid composition in cultivated oil palm ( Elaeis guineensis Jacq .) compared ´ s to its wild relative E . oleifera ( H . B . K ) Cortes. Plos One 9(5). https://doi.org/10.1371/journal.pone.0095412

  17. Biermann U et al (2000) {N}ew {s}yntheses with {o}ils and {f}ats as {r}enewable {r}aw {m}aterials for the {c}hemical {i}ndustry. Angew Chemie Int Ed 39(13):2206–2224. https://doi.org/10.1002/1521-3773(20000703)39:13%3c2206::AID-ANIE2206%3e3.0.CO;2-P

    Article  Google Scholar 

  18. Ismail KN et al (2021) High yield dihydroxystearic acid (DHSA) based on kinetic model from epoxidized palm oil. Kem u Ind 70(1–2):23–28. https://doi.org/10.15255/kui.2020.016

    Article  Google Scholar 

  19. Coman AE et al (2021) Synthesis and characterization of renewable polyurethane foams using different biobased polyols from olive oil. Eur Polym J 149(February):110363. https://doi.org/10.1016/j.eurpolymj.2021.110363

  20. Azmi IS, Jalil MJ, Hadi A (2022) Epoxidation of unsaturated fatty acid–based palm oil via peracid mechanism as an intermediate product. Biomass Convers Biorefinery 1. https://doi.org/10.1007/s13399-022-02862-x

  21. Kurańska M et al (2019) Evaluation of application potential of used cooking oils in the synthesis of polyol compounds. J Environ Chem Eng 7(6). https://doi.org/10.1016/j.jece.2019.103506

  22. Yeoh FH, Lee CS, Kang YB, Wong SF, Cheng SF (2018) One-pot synthesis of palm oil-based polyester polyol for production of biodegradable and biocompatible polyurethane. J Appl Polym Sci 135(44):1–16. https://doi.org/10.1002/app.46861

    Article  Google Scholar 

  23. Alsofiany AA, Faiz Mukhtar Gunam Resul M (2021) Epoxidation of waste cooking palm oil with peracetic acid catalyzed by sulfuric acid. Int Congr Adv Technol Eng 2021:4–8. https://doi.org/10.1109/ICOTEN52080.2021.9493511

  24. Hadi A, Jumain M, Aliff J, Mohd F, Intan Y, Azmi S (2022) Single step synthesis of dihydroxystearic acid ( DHSA ) from Epoxidized Palm Oil

  25. Zaimahwati, Agusnar H, Rihayat T, Reflianto D, Gea S (2015) The manufacture of palm oil-based polyurethane nanocomposite with organic montmorillonite nanoparticle as paint coatings. Int J Chem Tech Res 7(5):2537–2544

  26. Tee YB, Talib RA, Abdan K, Chin NL, Basha RK, Md Yunos KF (2016) Comparative study of chemical, mechanical, thermal, and barrier properties of poly(lactic acid) plasticized with epoxidized soybean oil and epoxidized palm oil. BioResources 11(1):1518–1540. https://doi.org/10.15376/biores.11.1.1518-1540

  27. Sun X, Zhao X, Du W, Liu D (2011) Kinetics of formic acid-autocatalyzed preparation of performic acid in aqueous phase. Chinese J Chem Eng 19(6):964–971. https://doi.org/10.1016/S1004-9541(11)60078-5

    Article  Google Scholar 

  28. Ifa L, Syarif T, Sabara Z, Nurjannah N, Munira M, Aryani F (2018) Study on the kinetics of epoxidation reaction of RBD palm olein. IOP Conf Ser Earth Environ Sci 175(1). https://doi.org/10.1088/1755-1315/175/1/012035

  29. Rangarajan B, Havey A, Grulke EA, Culnan PD (1995) Kinetic parameters of a two-phase model for in situ epoxidation of soybean oil 72(10):1161–1169

    Google Scholar 

  30. Campanella A, Baltan MA (2006) Degradation of the oxirane ring of epoxidized vegetable oils in liquid – liquid heterogeneous reaction systems.  Chem Eng J 118:141–152. https://doi.org/10.1016/j.cej.2006.01.010

  31. Jalil MJ et al (2022) Optimization of epoxidation palm-based oleic acid to produce polyols. Chem Chem Technol 16(1):66–73. https://doi.org/10.23939/chcht16.01.066

    Article  Google Scholar 

  32. Jumain M, Intan J, Azmi S, Hadi A, Farhan A, Yamin M (2022) In situ hydrolysis of epoxidized oleic acid by catalytic epoxidation ‑ peracids mechanism. J Polym Res :1–12. https://doi.org/10.1007/s10965-022-02944-4

  33. Santacesaria E, Turco R, Russo V, Di Serio M, Tesser R (2020) Kinetics of soybean oil epoxidation in a semibatch reactor. Ind Eng Chem Res 59(50):21700–21711. https://doi.org/10.1021/acs.iecr.0c04530

    Article  Google Scholar 

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Funding

Universiti Teknologi MARA and Comgreat Solution Sdn. Bhd, provided support with RMI file no: 100-RMC 5/3/SRP PRI (022/2022).

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Authors

Contributions

Mahazmi Burhanuddin Mahadi: writing and experiment work.

Intan Suhada Azmi: data curation.

Mohd Zulkipli Ab Kadir: methodology.

Mariam A. Rahman: experiment work.

Noorfazlida Mohamed: editing.

Mohd Jumain Jalil: conceptualization and methodology.

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Correspondence to Mohd Jumain Jalil.

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Mahadi, M.B., Azmi, I.S., Kadir, M.Z.A. et al. Sustainable epoxidation of expired palm oil–derived oleic acid via in situ peracid mechanism with applied ion resin Amberlite IR-120H: from waste to wealth. Biomass Conv. Bioref. (2023). https://doi.org/10.1007/s13399-023-04019-w

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  • DOI: https://doi.org/10.1007/s13399-023-04019-w

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