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Synergistic epoxidation of palm oleic acid using a hybrid oxygen carrier solution

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Abstract

The gradual depletion of fossil fuel reserves and the sharp rise in the cost of fossil fuels have generated a frenzy of activities in the quest to search for renewable source-based alternatives. Epoxides are an intermediate product that can be converted into value-added polymers. In the industry, epoxidation of vegetable oils is most frequently carried out with performic and peracetic acids. The aim of this study is to investigate the influence of the type of oxygen carrier (formic acid, acetic acid, and hybrid solution of formic and acetic acid) on the epoxidation of palm oleic acid. The peracids were formed in situ in this study. Based on the results, the highest relative conversion to oxirane (RCO) is achieved using formic acid, with a value of 82% at a reaction time of 25 min. Interestingly, a high RCO (82%) can also be achieved by using a hybrid solution of formic and acetic acid at a molar ratio of 1:1. The use of a hybrid oxygen carrier solution can help minimize the use of formic acid, which would create a strong acidic environment. In addition, the kinetic model is capable of predicting the reaction kinetics of the epoxidation process since the simulation results show good agreement with the experimental data, particularly for a formic acid/acetic acid molar ratio of 0.5:1.0.

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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. 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 9(32):10664–10677. https://doi.org/10.1021/acssuschemeng.1c02361

    Article  Google Scholar 

  2. Azmi IS, Jalil MJ, Hadi A (2022) Epoxidation of unsaturated fatty acid–based palm oil via peracid mechanism as an intermediate product. Biomass Convers Biorefin 1–9. https://doi.org/10.1007/s13399-022-02862-x

  3. Saurabh T, Patnaik M, Bhagt SL, Renge VC (2011) Epoxidation of vegetable oils: a review. Int J Adv Eng Technol 2(4):491–501

  4. Arniza MZ et al (2015) Synthesis of transesterified palm olein-based polyol and rigid polyurethanes from this polyol, JAOCS. J Am Oil Chem Soc 92(2):243–255. https://doi.org/10.1007/s11746-015-2592-9

    Article  Google Scholar 

  5. González-Benjumea A et al (2021) High epoxidation yields of vegetable oil hydrolyzates and methyl esters by selected fungal peroxygenases. Front Bioeng Biotechnol 8:1–12. https://doi.org/10.3389/fbioe.2020.605854

    Article  Google Scholar 

  6. Performik A, Hong LK, Yusop RM, Salih N, Salimon J (2015) Optimization of the in situ epoxidation of linoleic acid of Jatropha curcas oil with performic acid. Malaysian J Anal Sci 19(1):144–154

    Google Scholar 

  7. Bashiri S, Ghobadian B, DehghaniSoufi M, Gorjian S (2021) Chemical modification of sunflower waste cooking oil for biolubricant production through epoxidation reaction. Mater Sci Energy Technol 4:119–127. https://doi.org/10.1016/j.mset.2021.03.001

    Article  Google Scholar 

  8. Nugrahani RA, Redjeki AS, Mentari Y, Jannah M, Wibowo TY (2017) Study effect of temperature and reaction kinetics model selection epoxidation against rice bran oil methyl ester with catalyst Amberlite Ir-120. ARPN J Eng Appl Sci 12(13):3947–3952

    Google Scholar 

  9. Budiyati E, Rochmadi R, Budiman A, Budhijanto B (2020) Studies on epoxidation of tung oil with hydrogen peroxide catalyzed by sulfuric acid. Bull Chem React Eng Catal 15(3):674–686. https://doi.org/10.9767/BCREC.15.3.8243.674-686

    Article  Google Scholar 

  10. Allauddin S, Somisetti V, Ravinder T, Rao BVSK, Narayan R, Raju KVSN (2016) One-pot synthesis and physicochemical properties of high functionality soy polyols and their polyurethane-urea coatings. Ind Crops Prod 85:361–371. https://doi.org/10.1016/j.indcrop.2015.12.087

    Article  Google Scholar 

  11. Xia W, Budge SM, Lumsden MD (2016) 1H-NMR characterization of epoxides derived from polyunsaturated fatty acids, JAOCS. J Am Oil Chem Soc 93(4):467–478. https://doi.org/10.1007/s11746-016-2800-2

    Article  Google Scholar 

  12. Nwosu-Obieogu K, Aguele F, Chiemenem L (2020) Optimization on rubber seed oil epoxidation process parameters using response surface methodology. Iran J Chem Chem Eng 40(5):1575–1583

    Google Scholar 

  13. Kurańska M, Niemiec M (2020) Cleaner production of epoxidized cooking oil using a heterogeneous catalyst. Catalysts 10(11):1–13. https://doi.org/10.3390/catal10111261

    Article  Google Scholar 

  14. Ranganathan S, Tebbe J, Wiemann LO, Sieber V (2016) Optimization of the lipase mediated epoxidation of monoterpenes using the design of experiments—Taguchi method. Process Biochem 51(10):1479–1485. https://doi.org/10.1016/j.procbio.2016.07.005

    Article  Google Scholar 

  15. Campanella A, Baltanás MA, Capel-Sánchez MC, Campos-Martín JM, Fierro JLG (2004) Soybean oil epoxidation with hydrogen peroxide using an amorphous Ti/SiO2 catalyst. Green Chem 6(7):330–334. https://doi.org/10.1039/b404975f

    Article  Google Scholar 

  16. Singh I, Samal SK, Mohanty S, Nayak SK (2020) Recent advancement in plant oil derived polyol-based polyurethane foam for future perspective: a review. Eur J Lipid Sci Technol 122(3):1–23. https://doi.org/10.1002/ejlt.201900225

    Article  Google Scholar 

  17. Jalil MJ, Hadi A, Azmi IS (2021) Catalytic epoxidation of palm oleic acid using in situ generated performic acid — optimization and kinetic studies. Mater Chem Phys 270:124754. https://doi.org/10.1016/j.matchemphys.2021.124754

    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. Jalil MJ (2019) Optimization of palm oleic acid epoxidation via in situ generated performic acid using Taguchi orthogonal array design and the study of reaction kinetics. Smart Sci 7(4):252–259. https://doi.org/10.1080/23080477.2019.1663392

    Article  Google Scholar 

  20. 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 29(3):1–12. https://doi.org/10.1007/s10965-022-02944-4

    Article  Google Scholar 

  21. Kushairi A et al (2019) Oil palm economic performance in Malaysia and R&D progress in 2018. J Oil Palm Res 31(2):165–194. https://doi.org/10.21894/jopr.2019.0026

    Article  Google Scholar 

  22. Benaniba MT, Belhaneche-bensemra N, Gelbard G (2007) Kinetics of tungsten-catalyzed sunflower oil epoxidation studied by 1H NMR. Eur J Lipid Sci Technol 109(12):1186–1193. https://doi.org/10.1002/ejlt.200700114

    Article  Google Scholar 

  23. 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. Kemija u industriji: Časopis kemičara i kemijskih inženjera Hrvatske 71(3–4):209–214

    Google Scholar 

  24. Chou T, Chang J (2007) Acetic acid as an oxygen carrier between two phases for epoxidation of oleic acid. Chem Eng Commun 41(1):253–266. https://doi.org/10.1080/00986448608911722

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

    Google Scholar 

  26. 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):012035. https://doi.org/10.1088/1755-1315/175/1/012035

    Article  Google Scholar 

  27. Campanella A, Baltanás MA (2005) Degradation of the oxirane ring of epoxidized vegetable oils in liquid-liquid systems: I Hydrolysis and attack by H2O2. Latin Am Appl Res 35(3):205–210

    Google Scholar 

  28. Gan LH, Goh SH, Ooi KS (1992) Kinetic studies of epoxidation and oxirane cleavage of palm olein methyl esters. J Am Oil Chem Soc 69(4):347–351

    Article  Google Scholar 

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Funding

The author would like to thank Universiti Teknologi MARA for the financial support with RMI file no: 600-RMC/GIP 5/3 (097/2022).

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Authors and Affiliations

  1. School of Chemical Engineering, Universiti Teknologi MARA, Cawangan Johor, Kampus Pasir Gudang, Masai, Johor, 81750, Malaysia

    Intan Suhada Azmi

  2. Centre for Chemical Engineering Studies, Universiti Teknologi MARA, Cawangan Pulau Pinang, Kampus Permatang Pauh, 13500, Permatang Pauh, Pulau Pinang, Malaysia

    Tunku Arif Zafri Tunku Ozir, Ismail Md. Rasib & Mohd Jumain Jalil

  3. Department of Chemical Engineering, Faculty of Engineering, Universitas Pembangunan Nasional “Veteran” Jawa Timur, Rungkut Madya No. 1, Gunung Anyar, Surabaya, 60294, East Java, Indonesia

    Silvana Dwi Nurherdiana

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  1. Intan Suhada Azmi
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  2. Tunku Arif Zafri Tunku Ozir
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  3. Ismail Md. Rasib
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Contributions

Intan Suhada Azmi: data curation and writing — original draft.

Tunku Arif Zafri Tunku Ozir: data curation and writing.

Ismail Md. Rasib: data curation.

Silvana Dwi Nurherdiana: writing and methodology.

Mohd Jumain Jalil: conceptualization, investigation, and methodology.

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Correspondence to Mohd Jumain Jalil.

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Azmi, I.S., Ozir, T.A.Z.T., Rasib, I.M. et al. Synergistic epoxidation of palm oleic acid using a hybrid oxygen carrier solution. Biomass Conv. Bioref. (2022). https://doi.org/10.1007/s13399-022-03325-z

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  • DOI: https://doi.org/10.1007/s13399-022-03325-z

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