Skip to main content
Log in

Synthesis and Characterization of Epoxidized Silkworm Pupae Oil and Its Application as Polyvinyl Chloride

  • Original Article
  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

More and more industries demand environmental friendliness. Silkworm pupae oil (SPO), extracted from the desilked silkworm pupae, can serve as a promising substrate alternative to use in plasticization. This study aimed to prepare epoxidized silkworm pupae oil (ESPO) and investigate their effects on the thermal stability and plasticization of polyvinyl chloride (PVC) films. A chemo-enzymatic method of ESPO was developed in the presence of Lipase SMG1-F278N and H2O2 in natural deep eutectic solvents (DESs). Lipase SMG1-F278N could initiate the epoxidation reaction effectively at room temperature with a negligible loss of activities 10 batches. A maximum oxirane value of 6.94% was obtained. The formation of oxirane ring in ESPO was confirmed by FTIR and 13C NMR spectra. Moreover, ESPO showed a better thermal stability and lower freezing point than epoxidized soybean oil (ESO). It was demonstrated that ESPO had a good frost resistance. In addition, ESPO showed a significantly improved plasticizing effect on flexible polyvinyl chloride (PVC). Compared with ESO, ESPO could increase the tensile elongation at break effectively. A significantly lower migration rate of plasticizer was observed in PVC plasticized with ESPO.

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

Access this article

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

Instant access to the full article PDF.

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

Similar content being viewed by others

References

  1. Zhang, C., Garrison, T. F., Madbouly, S. A., & Kessler, M. R. (2017). Recent advances in vegetable oil-based polymers and their composites. Progress in Polymer Science, 71, 91–143.

    Article  CAS  Google Scholar 

  2. Sahoo, S. K., Khandelwal, V., & Manik, G. (2018). Development of toughened bio-based epoxy with epoxidized linseed oil as reactive diluent and cured with bio-renewable crosslinker. Polymers for Advanced Technologies, 29(1), 565–574.

    Article  CAS  Google Scholar 

  3. Joshi, S. M., Gogate, P. R., & Kumar, S. (2018). Intensification of esterification of karanja oil for production of biodiesel using ultrasound assisted approach with optimization using response surface methodology. Chemical Engineering and Processing, 124, 186–198.

    Article  CAS  Google Scholar 

  4. Dodo, R. M., Ause, T., Dauda, E. T., Shehu, U., & Mudiare, E. (2020). Mechanical properties and microstructures data of aisi 1070 steel quenched in epoxidized transesterified cottonseed oil. Data Brief, 30(32), 106100.

    Article  Google Scholar 

  5. Choi, M. S., Rehman, S. U., Kim, H., Han, S. B., Lee, J., & Hong, J. (2017). Migration of epoxidized soybean oil from polyvinyl chloride/polyvinylidene chloride food packaging wraps into food simulants. Environmental Science and Pollution Research International, 25(5), 5033–5039.

    Article  Google Scholar 

  6. Li, J., Gu, G., He, Z., Kong, W., SO Economics, & Z University. (2018). Regional distribution and developing emphasis of china’s cocoon silk industry. Acta Sericol. Sin., 44(06), 936–946.

    Google Scholar 

  7. Wu, X., He, K., Velickovic, T. C., & Liu, Z. (2021). Nutritional, functional, and allergenic properties of silkworm pupae. Food Science & Nutrition, 9(8), 4655–4665.

    Article  Google Scholar 

  8. Wang, W., Xu, L., Zou, Y., Pang, D., Shi, W., Mu, L., Li, E., Lan, D., & Wang, Y. (2019) Comprehensive identification of principal lipid classes and tocochromanols in silkworm (Antheraea pernyi and Bombyx mori) Pupae Oils. European Journal of Lipid Science and Technology 122(2).

  9. Wei, Z. J., Liao, A. M., Zhang, H. X., Jian, L., & Jiang, S. T. (2009). Optimization of supercritical carbon dioxide extraction of silkworm pupal oil applying the response surface methodology. Bioresource Technology, 99(18), 4214–4219.

    Article  Google Scholar 

  10. Allauddin, S., Somisetti, V., Ravinder, T., Rao, B., Narayan, R., & Raju, K. (2016). One-pot synthesis and physicochemical properties of high functionality soy polyols and their polyurethane-Urea coatings. Industrial Crops and Products, 85, 361–371.

    Article  CAS  Google Scholar 

  11. Xia, Y., & Larock, R.C. (2010) Vegetable oil-based polymeric materials: Synthesis, properties, and applications. Green Chemistry. 12(11).

  12. Fenollar, O., Garcia-Sanoguera, D., Sanchez-Nacher, L., Lopez, J., & Balart, R. (2010). Effect of the epoxidized linseed oil concentration as natural plasticizer in vinyl plastisols. Journal of Materials Science, 45(16), 4406–4413.

    Article  CAS  Google Scholar 

  13. Fenollar, O., Sanchez-Nacher, L., Garcia-Sanoguera, D., López, J., & Balart, R. (2009). The effect of the curing time and temperature on final properties of flexible PVC with an epoxidized fatty acid ester as natural-based plasticizer. Journal of Materials Science, 44(14), 3702–3711.

    Article  CAS  Google Scholar 

  14. Quadrosjr, J. V. D., & Giudici, R. (2016). Epoxidation of soybean oil at maximum heat removal and single addition of all reactants. Chem. Eng. Processing., 100, 87–93.

    Article  Google Scholar 

  15. Zhou, P., Wang, X., Zeng, C., Wang, W., Yang, B., & Hollmann, F. (2017). Deep eutectic solvents enable more robust chemoenzymatic epoxidation reactions. ChemCatChem, 9(6), 934–936.

    Article  CAS  Google Scholar 

  16. Zhang, T., Ma, Y., Tan, C. P., Hollmann, F., Wang, J., Yang, B., & Wang, Y. (2019). An efficient strategy for the production of epoxidized oils: Natural deep eutectic solvent-based enzymatic epoxidation. Journal of the American Oil Chemists Society, 96(6), 671–679.

    Article  CAS  Google Scholar 

  17. Zhao, Z., Lan, D., Tan, X., Hollmann, F., Bornscheuer, U. T., Yang, B., & Wang, Y. (2019). How to break the Janus effect of H2O2 in biocatalysis? Understanding inactivation mechanisms to generate more robust enzymes. ACS Catalysis, 9(4), 2916–2921.

    Article  CAS  Google Scholar 

  18. Li, X., Li, D., Wang, W., Durrani, R., & Yang, B. (2016). Immobilization of SMG1-F278N lipase onto a novel epoxy resin: Characterization and its application in synthesis of partial glycerides. Journal of Molecular Catalysis B-enzymatic, 133, 154–160.

    Article  CAS  Google Scholar 

  19. Xu, T., Lu, L., Hou, S., Xu, J., Yang, B., & Wang, Y. (2012). Crystal structure of a mono- and diacylglycerol lipase from Malassezia globosa reveals a novel lid conformation and insights into the substrate specificity. Journal of Structural Biology, 178(3), 363–369.

    Article  CAS  Google Scholar 

  20. Hu, B., Li, C., Zhang, Z., Zhao, Q., Zhu, Y., & Su, Z. (2017). Microwave-assisted extraction of silkworm pupal oil and evaluation of its fatty acid composition, physicochemical properties and antioxidant activities. Food Chemistry, 231, 348–355.

    Article  CAS  Google Scholar 

  21. Daniels, R. L., Kim, H. J., & Min, D. B. (2006). Hydrogenation and interesterification effects on the oxidative stability and melting point of soybean oil. Journal of Agriculture and Food Chemistry, 54(16), 6011–6015.

    Article  CAS  Google Scholar 

  22. Wang, X., Tang, Q., Grzegorz, M. P., Yang, B., & Wang, Y. (2015). A mechanistic study into the epoxidation of carboxylic acid and alkene in a mono, di-acylglycerol lipase. Biochemical and Biophysical Research Communications, 460(2), 392–396.

    Article  CAS  Google Scholar 

  23. Vlček, T., & Petrović, Z. S. (2006). Optimization of the chemoenzymatic epoxidation of soybean oil. Journal of the American Oil Chemists Society, 83(3), 247–252.

    Article  Google Scholar 

  24. Dinda, S., Goud, V. V., Patwardhan, A. V., & Pradhan, N. C. (2011). Selective epoxidation of natural triglycerides using acidic ion exchange resin as catalyst. Asia-Pacific Journal of Chemical Engineering, 6(6), 870–878.

    Article  CAS  Google Scholar 

  25. Eiichi, K. N., Kanako, Y., Mitsuyoshi, N., Kazuo, M., & Tsuyoshi, M. (2002). Lipid profiles and oxidative stability of silkworm pupal oil. Journal of Oleo Science, 51(11), 681–690.

    Article  Google Scholar 

  26. Kim, J. R., & Sharma, S. (2012). The development and comparison of bio-thermoset plastics from epoxidized plant oils. Industrial Crops and Products, 36(1), 485–499.

    Article  CAS  Google Scholar 

  27. González-Benjumea, A., Marques, G., Herold-Majumdar, O. M., Kiebist, J., & Gutiérrez, A. (2021). High epoxidation yields of vegetable oil hydrolyzates and methyl esters by selected fungal peroxygenases. Front Bioeng Biotechnol, 5(8), 605854.

    Article  Google Scholar 

  28. Shi, Y., Lu, S., Ma, B., Chen, S., & Wang, X. (2021). A new method for designing bis-uracil derivatives as highly efficient and transparent pvc thermal stabilizer with excellent migration resistance. Polym Degrad Stabil, 186(1), 109504.

    Article  CAS  Google Scholar 

Download references

Funding

The authors acknowledge funding from the National Key R&D Program of China (2019YFD1002403), National Science Fund for Key Program of National Natural Science Foundation of China (31930084), Distinguished Young Scholars of China (31725022), China Agriculture Research System (CARS-18-ZJ0503), Science and Technology Planning Project of Guangdong Province (2019A050503002), and Innovation and Entrepreneurship Team of Nanhai Talent Plan of Nanhai District, Foshan (201811070001).

Author information

Authors and Affiliations

Authors

Contributions

Yingrui Ji: Experimental activities, conceptualization, data curation, supervision, formal analysis, validation, writing—original draft.

Long Xu: Methodology, writing—review and editing.

Qingqing Xu: Investigation.

Xuan Liu: Supervision.

Sen Lin: Formal analysis.

Sentai Liao: Experimental activities.

Weifei Wang: Resources.

Dongming Lan: Funding acquisition.

Corresponding authors

Correspondence to Weifei Wang or Dongming Lan.

Ethics declarations

Ethics Approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Consent to Participate

The authors agreed to participate in this work.

Consent for Publication

The authors agreed to publish this work.

Conflict of Interest

The authors declare no competing interests.

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

Ji, Y., Xu, L., Xu, Q. et al. Synthesis and Characterization of Epoxidized Silkworm Pupae Oil and Its Application as Polyvinyl Chloride. Appl Biochem Biotechnol 194, 1290–1302 (2022). https://doi.org/10.1007/s12010-021-03715-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12010-021-03715-5

Keywords

Navigation