Skip to main content
Log in

Kitchen Waste Oil Convert to Biodiesel via W/O Interface Biocatalysis with Thermomyces Lanuginosus Lipase–PNIPAAm Conjugates

  • Original Paper
  • Published:
Waste and Biomass Valorization Aims and scope Submit manuscript

Abstract

Due to the scarcity of resources, alternatives to non-renewable resources have become more important. Chemical catalysts react violently and the conditions are harsh. Using biocatalysts at the water/oil (W/O) interface remains technically challenging and is rewarding. In this study, the Thermomyces lanuginosus lipase-poly coupling biocatalyst was prepared by the atom transfer radical polymerization “grafting-from” method. The TL–PNIPAAm conjugate was successfully prepared and circular dichroism showed a negligible change between the free enzyme and conjugated enzyme by sodium dodecyl sulfate–polyacrylamide gel electrophoresis and transmission electron microscopy. Furthermore, the temperature and pH stability of the conjugate was better than that of free TL. The remaining activity of the TL–PNIPAAm conjugate for 10 h was approximately 20% higher than that of free TL after heat treatment (55 °C) and higher pH stability was obtained in the pH 4–10. The remaining activity of the TL–PNIPAAm conjugates was above 60% after recycling 7 times. In addition, the conversion of biodiesel from kitchen waste oil was 92.6% at 50 °C for 25 h with a conversion efficiency of 0.04 g/mL/h. Thus, a high stability and reusability biocatalyst and stabilizer at the interface of water-in-oil Pickering emulsions was successfully prepared.

Graphical Abstract

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

Similar content being viewed by others

Data Availability

Data available within the article or its supplementary materials.

References

  1. Hossain, M.N., Bhuyan, M., Alam, A., Seo, Y.C.: Optimization of biodiesel production from waste cooking oil using S-TiO2/SBA-15 heterogeneous acid catalyst. Catalysts 9, 1 (2019)

    Google Scholar 

  2. Zhou, G.X., Chen, G.Y., Yan, B.B.: Biodiesel production in a magnetically-stabilized, fluidized bed reactor with an immobilized lipase in magnetic chitosan microspheres. Biotechnol. Lett. 36, 63–68 (2014)

    Article  Google Scholar 

  3. Felix, C., Ubando, A., Madrazo, C.: Investigation of direct biodiesel production from wet microalgae using definitive screening design. Energy Procedia 158, 1149–1154 (2019)

    Article  Google Scholar 

  4. Chen, C.Y., Li, D.S., Sun, N., Ma, X.F., Xiao, G.Q., Zhou, J.: Oil recovery from drilling cuttings by biosurfactant from kitchen waste oil. Energy Source Part A 43, 314–325 (2021)

    Article  Google Scholar 

  5. Patsalou, M., Chrysargyris, A., Tzortzakis, N.: A biorefinery for conversion of citrus peel waste into essential oils, pectin, fertilizer and succinic acid via different fermentation strategies. Waste Manage. 113, 469–477 (2020)

    Article  Google Scholar 

  6. Paul, A.A.L., Adewale, F.J.: Data on optimization of production parameters on persea americana (Avocado) plant oil biodiesel yield and quality. Data Brief. 20, 855–863 (2018)

    Article  Google Scholar 

  7. Wan, Y., Zheng, C.C., Lei, X.C, Lei, X.C., Zhuang, M.Q., Lin, J.H., Hu, W.D., Lin, J.D., Wan, S.L., Wan, Y.: Oxidative esterification of acetol with methanol to methyl pyruvate over hydroxyapatite supported gold catalyst: Essential roles of acid-base properties. Chin. J. Catal. 40, 1810–1819 (2019)

    Article  Google Scholar 

  8. Zhang, B.B., Weng, Y.D., Xu, H., Mao, Z.P.: Enzyme immobilization for biodiesel production. Appl. Microbiol. Biotechnol. 93, 61–70 (2012)

    Article  Google Scholar 

  9. Mateo, C., Palomo, J.M., Fernandez-Lorente, G.: Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb. Technol. 40, 1451–1463 (2007)

    Article  Google Scholar 

  10. Ben, L.K., Daud, W., Ghasemi, M., Leong, J.X., Lim, W.S., Ismail, M.: Non-Pt catalyst as oxygen reduction reaction in microbial fuel cells: a review. Int. J. Hydrogen Energ. 39, 4870–4883 (2014)

    Article  Google Scholar 

  11. Chen, C., Ng, D.Y.W., Weil, T.: Polymer bioconjugates: modern design concepts toward precision hybrid materials. Prog. Polym. Sci. 105, 101241 (2020)

    Article  Google Scholar 

  12. Kovaliov, M., Cheng, C., Cheng, B.: Grafting-from lipase: utilization of a common amino acid residue as a new grafting site. Polym. Chem. UK 9, 4651–4659 (2018)

    Article  Google Scholar 

  13. Wang, Y., Wu, C.: Site-specific conjugation of polymers to proteins. Biomacromol 19, 1804–1825 (2018)

    Article  Google Scholar 

  14. Sołowiej, B.G., Nastaj, M., Szafrańska, J.O.: Effect of emulsifying salts replacement with polymerised whey protein isolate on textural, rheological and melting properties of acid casein model processed cheeses. Int. Dairy J. 105, 104694 (2020)

    Article  Google Scholar 

  15. Zhu, B.B., Lu, D.N., Ge, J., Liu, Z.: Uniform polymer–protein conjugate by aqueous AGET ATRP using protein as a macroinitiator. Acta Biomater. 7, 2131–2138 (2011)

    Article  Google Scholar 

  16. Nady, D., Zaki, A.H., Raslan, M.: Enhancement of microbial lipase activity via immobilization over sodium titanate nanotubes for fatty acid methyl esters production. Int. J. Biol. Macromol. 146, 1169–1179 (2020)

    Article  Google Scholar 

  17. Kim, J.Y., Lee, B.S., Choi, J.: Cytocompatible polymer grafting from individual living cells by atom-transfer radical polymerization. Angew. Chem. Int. Ed. 55, 15306–15309 (2016)

    Article  Google Scholar 

  18. Wang, Y., Fantin, M., Matyjaszewski, K.: Synergy between electrochemical ATRP and RAFT for polymerization at low copper loading. Macromol. Rapid Commun. 39, e1800221 (2018)

    Article  Google Scholar 

  19. Mendonça, P.V., Averick, S.E., Konkolewicz, D.: Straightforward Arget ATRP for the synthesis of primary amine polymethacrylate with improved chain-end functionality under mild reaction conditions. Macromolecules 47, 4615–4621 (2014)

    Article  Google Scholar 

  20. Hu, Y., Shi, C.Y., Xun, X.M., Huang, B.R., You, S., Wu, F.A., Wang, J.: Xylanase-polymer conjugates as new catalysts for xylooligosaccharides production from lignocellulose. Biochem. Eng. J. 171, 108025 (2021)

    Article  Google Scholar 

  21. Van Schie, M.M.C.H., Ebrahimi, K.H., Hagen, W.R.: Fast and accurate enzyme activity measurements using a chip-based microfluidic calorimeter. Anal. Biochem. 544, 57–63 (2018)

    Article  Google Scholar 

  22. Teng, Y., Xu, Y.: A modified para-nitrophenyl palmitate assay for lipase synthetic activity determination in organic solvent. Anal. Biochem. 363, 297–299 (2007)

    Article  Google Scholar 

  23. Gupta, N., Rathi, P., Gupta, R.: Simplified para-nitrophenyl palmitate assay for lipases and esterases. Anal. Biochem. 311, 98–99 (2002)

    Article  Google Scholar 

  24. Yan, C.H., Xun, X.M., Wang, J., Wang, J.Z., You, S., Wu, F.A., Wang, J.: An alternative solution for alpha-linolenic acid supplements: in vitro digestive properties of silkworm pupae oil in a pH-stat system. Food Funct. 12, 2428–2441 (2021)

    Article  Google Scholar 

  25. Zhou, X.J., Zhu, C.T., Hu, Y., You, S., Wu, F.A., Wang, J.: A novel microfluidic aqueous two-phase system with immobilized enzyme enhances cyanidin-3-O-glucoside content in red pigments from mulberry fruits. Biochem. Eng. J. 158, 107556 (2020)

    Article  Google Scholar 

  26. Glassman, M.J., Olsen, B.D.: Arrested phase separation of elastin-like polypeptide solutions yields stiff, thermoresponsive gels. Biomacromol 16, 3762–3773 (2015)

    Article  Google Scholar 

  27. Yao, M.L., Hua, X.F.: Enzyme–polymer hybrid nanocatalyst prepared by microemulsion polymerization. Catal. Lett. 144, 1240–1244 (2014)

    Article  Google Scholar 

  28. Qu, Y.N., Huang, R.L., Qi, W., Qu, Q., Su, R.X., He, Z.M.: Structural insight into stabilization of pickering emulsions with Fe3o4@SiO2 nanoparticles for enzyme catalysis in organic media. Part. Part. Syst. Charact. 34, 1700117 (2017)

    Article  Google Scholar 

  29. Yang, J.J., Ma, X.X., Zhang, Z.S., Chen, B., Li, S.A., Wang, G.J.: Lipase immobilized by modification-coupled and adsorption-cross-linking methods: a comparative study. Biotechnol. Adv. 28, 644–650 (2010)

    Article  Google Scholar 

  30. Rahman, M.S., Brown, J., Murphy, R.: Polymer modification of lipases, substrate interactions, and potential inhibition. Biomacromol 22, 309–318 (2021)

    Article  Google Scholar 

  31. Thushari, I., Babel, S.: Biodiesel production from waste palm cooking oil using solid acid catalyst derived from coconut meal residue. Waste Biomass Valori. 11, 4941–4956 (2020)

    Article  Google Scholar 

  32. Razack, S.A., Duraiarasan, S.: Response surface methodology assisted biodiesel production from waste cooking oil using encapsulated mixed enzyme. Waste Manage. 47, 98–104 (2016)

    Article  Google Scholar 

  33. Moovendhan, M., Vairamani, S., Shanmugam, A.: Utilization of cuttlefish liver waste for oil production: evaluation of quality characteristics and biological activity. Waste Biomass Valori. 10, 2959–2965 (2019)

    Article  Google Scholar 

  34. Neto, C., Sydney, E.B., Candeo, E.S., de Souza, E., Camargo, D., Sydney, A., de Carvalho, J.C., Letti, L., Pandey, A., Soccol, C.R.: New method for the extraction of single-cell oils from wet oleaginous microbial biomass: efficiency, oil characterisation and energy assessment. Waste Biomass Valori. 11, 3443–3452 (2020)

    Article  Google Scholar 

  35. Sadhukhan, S., Sarkar, U.: Production of biodiesel from Crotalaria juncea (sunn-hemp) oil using catalytic trans-esterification: process optimisation using a factorial and box-behnken design. Waste Biomass Valori. 7, 343–355 (2016)

    Article  Google Scholar 

  36. Siddeeg, A., Xia, W.S.: Oxidative stability, chemical composition and organoleptic properties of seinat (Cucumis melovar tibish) seed oil blends with peanut oil from China. J. Food Sci. Technol. Mys. 52, 8172–8179 (2015)

    Article  Google Scholar 

  37. Wang, C.M., Xie, S.Y., Zhong, M.X.: Effect of hydrothermal pretreatment on kitchen waste for biodiesel production using alkaline catalyst. Waste Biomass Valori. 8, 369–377 (2017)

    Article  Google Scholar 

  38. Tang, X.Y., Niu, S., Zhao, S., Zhang, X.Y., Yu, H.M., Lu, C.M.: Synthesis of sulfonated catalyst from bituminous coal to catalyze esterification for biodiesel production with promoted mechanism analysis. J. Ind. Eng. Chem. 77, 432–440 (2019)

    Article  Google Scholar 

  39. Ogata, T., Nagasako, T., Umeki, Y.: Synthesis, properties, and functions of thermosensitive copolymers having pyridyl and/or pyridinium groups. React. Funct. Polym. 67, 700–707 (2007)

    Article  Google Scholar 

  40. Lapuerta, M., Rodríguez-Fernández, J., Estevez, C.: Properties of fatty acid glycerol formal ester (FAGE) for use as a component in blends for diesel engines. Biomass Bioenerg. 76, 130–140 (2015)

    Article  Google Scholar 

  41. Wang, J.Z., Liu, X., Li, W.J., Song, W.M., Herman, R.A., Sheng, S., Wu, F.A., Wang, J.: One hour enzymatic synthesis of structure lipids enriched unsaturated fatty acids from silkworm pupae oil under microwave irradiation. J. Chem. Technol. Biotechnol. 95, 363–372 (2019)

    Article  Google Scholar 

  42. Wang, J.Z., Wu, C.K., Yan, C.H., Chen, H., You, S., Sheng, S., Wu, F.A., Wang, J.: Nutritional targeting modification of silkworm pupae oil catalyzed by a smart hydrogel immobilized lipase. Food Funct. 12, 6240–6253 (2021)

    Article  Google Scholar 

  43. Karmee, S.K.: Enzymatic biodiesel production from Manilkara zapota (L.) seed oil. Waste Biomass Valori. 9, 725–730 (2018)

    Article  Google Scholar 

  44. Hu, Y., Shi, C.Y., Xun, X.M., Chai, Y.L., Herman, R.A., You, S., Wu, F.A., Wang, J.: W/W droplet-based microfluidic interfacial catalysis of xylanase-polymer conjugates for xylooligosaccharides production. Chem. Eng. Sci. 248, 117110 (2022)

    Article  Google Scholar 

Download references

Funding

This work was supported by the National Natural Science Foundation of China (Grant No. 21978121) and the 333 High-level Talent Training Project of Jiangsu Province (Grant No. BRA2019281).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jun Wang.

Ethics declarations

Conflict of interest

The authors have declared no conflicts of interest.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1059 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shi, CY., Hu, Y., Chai, YL. et al. Kitchen Waste Oil Convert to Biodiesel via W/O Interface Biocatalysis with Thermomyces Lanuginosus Lipase–PNIPAAm Conjugates. Waste Biomass Valor 13, 3945–3956 (2022). https://doi.org/10.1007/s12649-022-01735-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12649-022-01735-8

Keywords

Navigation