Skip to main content

Advertisement

SpringerLink
Log in

In situ hydrolysis of epoxidized oleic acid by catalytic epoxidation-peracids mechanism

  • Original Paper
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

The aim of this study to produce in situ hydrolysed dihydroxystrearic acid (DHSA) from epoxidized oleic acid (EOA). In this study, EOA was produced by using in situ formed performic acid. The physicochemical properties in situ hydrolysed DHSA were compared, the results indicates that the in situ hydrolysed DHSA has the potential to be commercialized because the synthesis route is simpler and high relative conversion to oxirane (85.7%). Then, a mathematical model was developed by using the numerical integration Runge Kutta 4th Order method. In this model, the method was integrated with genetic algorithm and particle swarm optimization to determine the process model that fit with the experimental data using MATLAB software. The results showed that there was good agreement between the simulation and experimental data, which validates the kinetic model. Overall, a high yield in situ hydrolysed DHSA was successfully produced from oleic acid by using optimum process parameters of epoxidation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

Data availability

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

References

  1. 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

    Article  CAS  Google Scholar 

  2. Gupta SS, Guchhait A, Sarkar S, Ghosh M (2016) Comparative Evaluation of the Physico-chemical Properties of Chemically and Enzymatically Epoxidised Soybean Oil 1

  3. 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 51:1479–1485. https://doi.org/10.1016/j.procbio.2016.07.005

    Article  CAS  Google Scholar 

  4. Jumain M, Mohamed N, Khatijah S, Som A, Rafizan A, Daud M, Alam S (2014) Epoxidation of Palm Kernel Oil-based Crude Oleic Acid 906:125–130. https://doi.org/10.4028/www.scientific.net/AMR.906.125

    Article  CAS  Google Scholar 

  5. 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 124754. https://doi.org/10.1016/j.matchemphys.2021.124754.

  6. Chen S, Cai W, Chen D, Ren Y, Li X, Zhu Y, Ruoff RS (2010) Synthesis of Epoxidized Oleic Acid- Based Palm Oil by Peracid Mechanism. IOP Conf Ser Mater Sci Eng 551. https://doi.org/10.1088/1757-899X/551/1/012120.

  7. Jalil MJ, Kamal KA, Yamin AFBM, Azmi IS, Hassan MH, Hidayu AR, Ismail KN (2021) High Yield Dihydroxystearic Acid (DHSA) Based on Kinetic Model from Epoxidized Palm Oil. Kem u Ind 70:23–28. https://doi.org/10.15255/kui.2020.016.

  8. Dinda S, Patwardhan AV, Goud VV, Pradhan NC (2008) Epoxidation of cottonseed oil by aqueous hydrogen peroxide catalysed by liquid inorganic acids 99:3737–3744. https://doi.org/10.1016/j.biortech.2007.07.015

    Article  CAS  Google Scholar 

  9. Saurabh T (2011) Epoxidation of Vegetable Oils: a Review Int J Adv Eng Technol

  10. Vanags E, Kirpluks M, Cabulis U, Walterova Z (2018) Highly functional polyol synthesis from epoxidized tall oil fatty acids. J Renew Mater 6(7):764-771

  11. Vlček T, Petrović ZS (2006) Optimization of the chemoenzymatic epoxidation of soybean oil. J Am Oil Chem Soc 83:247–252. https://doi.org/10.1007/s11746-006-1200-4

    Article  Google Scholar 

  12. Jalil MJ, Habr HH, Hadi A, Yamin AFM, Ismail KN, Rani NHA (2020) Formation of Dihydroxystearic Acid (DHSA) from Epoxidized Palm Oleic Acid by Peracid Mechanism and their Kinetic Study. J Mech Eng 17:85–94

    Google Scholar 

  13. Jalil MJ, Azmi IS, Rafizan A, Daud M, Engineering C, Mara UT, Pinang CP (2017) An Overview of Epoxidation of Vegetable Oils with Peracid- Reaction Mechanism. Recent Innov Chem Eng 10:1–8. https://doi.org/10.2174/2405520410666170614113317

  14. Jalil MJ, Zaini MSM, Yamin AFM, Chang SH, Mora N, Hadi A (2019) Kinetika epoksidirane oleinske kiseline dobivene iz palmina ulja in situ proizvedenom permravljom kiselinom Kinetics of epoxidized oleic acid derived from palm oil by in situ generated performic acid. Kem u Ind 68:181–187. https://doi.org/10.15255/kui.2018.039.

  15. Pielichowski K, Czub P, Pielichowski J (2011) Characterization of the Cure of Some Epoxides and Their Sulphur-Containing Analogues with Hexahydrophthalic Anhydride by DSC and TGA, 4628. https://www.researchgate.net/publication/239674567_Characterization_of_the_cure_of_some_epoxides_and_their_sulphur-containing_analogues_with_hexahydrophthalic_anhydride_by_DSC_and_TGA

  16. Weber N, Vosmann K, Fehling E, Mukherjee KD, Bergenthal D (1995) Analysis of hydroxylated fatty acids from plant oils. J Am Oil Chem Soc 72:361–368. https://doi.org/10.1007/BF02541097

    Article  CAS  Google Scholar 

  17. Cai X, Zheng JL, Aguilera AF, Vernières‐Hassimi L, Tolvanen P, Salmi T, Leveneur S (2018) Influence of ring-opening reactions on the kinetics of cottonseed oil epoxidation. 1–16. https://doi.org/10.1002/kin.21208

  18. Koay GFL, Abdullah LC, Yunus R, Choong ST, Siwayanan P, Salmiah A (2006) Board, Crystallization of dihydroxystearic acid (dhsa) produced from commercial grade palm oil based crude oleic acid employing isopropyl alcohol as solvent. 3:115–124.

  19. Goud VV, Patwardhan AV, Pradhan NC (2007) Kinetics of in situ epoxidation of natural unsaturated triglycerides catalyzed by acidic ion exchange resin. Ind Eng Chem Res 46:3078–3085. https://doi.org/10.1021/ie060146s

    Article  CAS  Google Scholar 

  20. Sinadinović-Fišer S, Janković M, Borota O (2012) Epoxidation of castor oil with peracetic acid formed in situ in the presence of an ion exchange resin. Chem Eng Process Process Intensif 62:106–113. https://doi.org/10.1016/j.cep.2012.08.005

    Article  CAS  Google Scholar 

  21. Sinadinović-Fišer S, Janković M, Petrović ZS (2001) Kinetics of in situ epoxidation of soybean oil in bulk catalyzed by ion exchange resin. J Am Oil Chem Soc 78:725–731. https://doi.org/10.1007/s11746-001-0333-9

    Article  Google Scholar 

  22. Santacesaria E, Russo V, Tesser R, Turco R, Di Serio M (2017) Kinetics of Performic Acid Synthesis and Decomposition. Ind Eng Chem Res 56:12940–12952. https://doi.org/10.1021/acs.iecr.7b00593

    Article  CAS  Google Scholar 

  23. 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  CAS  Google Scholar 

Download references

Acknowledgements

The author would like to thank Universiti Teknologi MARA for financial supported with : RMI file no: 600-RMC/GIP 5/3 (099/2021).

Author information

Authors and Affiliations

  1. School of Chemical Engineering, College of Engineering, Cawangan Pulau Pinang, Universiti Teknologi MARA, Kampus Permatang Pauh, 13500 Permatang Pauh, Pulau Pinang, Malaysia

    Mohd Jumain Jalil & Abdul Hadi

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

    Intan Suhada Azmi

  3. School of Mechanical Engineering, College of Engineering, Cawangan Pulau Pinang, Universiti Teknologi MARA, Kampus Permatang Pauh, 13500 Permatang Pauh, Pulau Pinang, Malaysia

    Aliff Farhan Mohd Yamin

Authors
  1. Mohd Jumain Jalil
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Intan Suhada Azmi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abdul Hadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Aliff Farhan Mohd Yamin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohd Jumain Jalil.

Ethics declarations

Conflict of interest

This finding and work are free form conflict of interest.

Research involving human and animal participants

No human and animal rights involved.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jalil, M.J., Azmi, I.S., Hadi, A. et al. In situ hydrolysis of epoxidized oleic acid by catalytic epoxidation-peracids mechanism. J Polym Res 29, 102 (2022). https://doi.org/10.1007/s10965-022-02944-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-022-02944-4

Keywords

Search

Navigation