Skip to main content
Log in

Heterogeneous Biocatalytic Processes of the Low-Temperature Synthesis of Esters: Selecting an Organic Solvent

  • BIOCATALYSIS
  • Published:
Catalysis in Industry Aims and scope Submit manuscript

Abstract

A study is performed of the processes of low-temperature enzymatic synthesis of esters in nonaqueous media of organic solvents with the participation of heterogeneous biocatalysts produced by the adsorptive immobilization of recombinant Thermomyces lanuginosus lipase (produced by Pichia pastoris) on macroporous carbon aerogel. Esterification is conducted in individual organic solvents of different polarities, namely nonpolar (lоg P > 2.5) solvents hexadecane, hexane, and toluene; the polar (lоg P < 1) diethyl ether, tert-butanol, and acetone; binary mixtures with different compositions (e.g., hexane with diethyl ether in volume ratio 1 : (1/5–3)). Comparative studies are made of the effect the nature of the solvent and co-solvent on the properties of the prepared biocatalysts (such as enzymatic activity and operational stability) in the batch esterification of heptanoic acid (C7:0) with alcohols such as polar ethanol and n‑butanol, and nonpolar n-octanol and n-hexadecanol. The activity of the biocatalysts is found to depend largely on the polarity of both the solvents used in the reaction and the alcohol substrates. The maximum activity (400 U g−1; 1 U (unit of activity) = 1 μmol min−1) is observed in a medium of nonpolar and inviscid hexane (lоg P = 2.9), while the minimum activity (4 U g−1) is detected in acetone (lоg P = 0.4). There is virtually no esterification of heptanoic acid in the presence of tert-butanol (lоg P = 0.6). The activity of the biocatalysts is found to depend nonmonotonically on the lоg P of individual solvent. In binary mixtures of such organic solvents as hexane and diethyl ether, the biocatalytic activity increases linearly as lоg Pmix increases. The biocatalysts have the maximum operational stability in binary mixture of hexane and diethyl ether.

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.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.

Similar content being viewed by others

REFERENCES

  1. Voitkevich, S.A., 865 dushistykh veshchestv dlya parfyumerii i bytovoi khimii (865 Fragrances for Perfumery and Household Detergents), Moscow: Pishchevaya promyshlennost’, 1994.

  2. Soldatenkov, A.T., Kolyadina, N.M., and Le Tuan Anh, Osnovy organicheskoi khimii dushistykh veshchestv dlya prikladnoi estetiki i aromaterapii (Foundations of Organic Chemistry of Fragrances for Applied Aesthetics and Aromatherapy), Moscow: Akademkniga, 2006.

  3. De Almeida, R.M., Souza, F.T.C., Junior, M.A.C., Albuquerque, N.J.A., Meneghetti, S.M.P., and Meneghetti, M.R., Catal. Commun., 2014, vol. 46, pp. 179–182.

    Article  CAS  Google Scholar 

  4. Chang, S.W. and Shaw, J.F., New Biotechnol., 2009, vol. 26, nos. 3–4, pp. 109–116.

  5. Stergiou, P.Y., Foukis, A., Filippou, M., Koukouritaki, M., Parapouli, M., Theodorou, L.G., Hatziloukas, E., Afendra, A., Pandey, A., and Papamichael, E.M., Biotechnol. Adv., 2013, vol. 31, pp. 1846–1859.

    Article  CAS  Google Scholar 

  6. Gumel, A.M., Annuar, M.S.M., Heidelberg, T., and Chisti, Y., Process Biochem., 2011, vol. 46, no. 11, pp. 2079–2090.

    Article  CAS  Google Scholar 

  7. Sun, J., Lee, L.W.W., and Liu, S.Q., Aust. J. Chem., 2014, vol. 67, no. 10, pp. 1373–1381.

    Article  CAS  Google Scholar 

  8. Villeneuve, P., Biotechnol. Adv., 2007, vol. 25, no. 6, pp. 515–536.

    Article  CAS  Google Scholar 

  9. Bezborodov, A.M. and Zagustina, N.A., Appl. Biochem. Microbiol., 2014, vol. 50, no. 4, pp. 313–337.

    Article  CAS  Google Scholar 

  10. Nguyen, P.C., Nguyen, M.T.T., Lee, C.-K., Oh, I.-N., Kim, J.-H., Hong, S.-T., and Park, J.-T., Carbohydr. Polym., 2019, vol. 218, pp. 126–135.

    Article  CAS  Google Scholar 

  11. Janssen, A.E.M., Sjursnes, B.J., Vakurov, A.V.U., and Halling, P.J., Enzyme Microb. Technol., 1999, vol. 24, nos. 8–9, pp. 463–470.

  12. Laane, C., Boeren, S., Vos, R., and Veeger, C., Biotechnol. Bioeng., 1987, vol. 30, no. 1, pp. 81–87.

    Article  CAS  Google Scholar 

  13. Su, E. and Wei, D., J. Mol. Catal. B: Enzym., 2008, vol. 55, nos. 3–4, pp. 118–125. https://doi.org/10.1016/j.molcatb.2008.03.001

  14. Gamayurova, V.S., Zinov’eva, M.E., and Elizarova, E.V., Katal. Prom-sti, 2008, no. 3, pp. 54–58.

  15. Gamayurova, V.S., Zinov’eva, M.E., Kalachev, N.V., and Shnaider, K.L., Catal. Ind., 2015, vol. 7, no. 3, pp. 239–243.

    Article  Google Scholar 

  16. Gamayurova, V.S., Shnaider, K.L., and Jamai, M.J., Catal. Ind., 2017, vol. 8, no. 1, pp. 85–90.

    Article  Google Scholar 

  17. Abildskov, J., van Leeuwen, M.B., Boeriu, C.G., and van den Broek, L.A.M., J. Mol. Catal. B: Enzym., 2013, vols. 85–86, pp. 200–213. https://doi.org/10.1016/j.molcatb.2012.09.012

  18. Stamatis, H., Xenakis, A., Provelegiou, M., and Kolisis, F.N., Biotechnol. Bioeng., 1993, vol. 42, no. 1, pp. 103–110.

    Article  CAS  Google Scholar 

  19. Gandhi, N.N. and Mukherjee, K.D., J. Am. Oil Chem. Soc., 2001, vol. 78, no. 2, pp. 161–165.

    Article  CAS  Google Scholar 

  20. Arsan, J. and Parkin, K.L., Biotechnol. Bioeng., 2000, vol. 69, no. 2, pp. 222–226.

    Article  CAS  Google Scholar 

  21. Kovalenko, G.A., Perminova, L.V., Beklemishev, A.B., Mamaev, A.L., and Patrushev, Yu.V., Catal. Ind., 2018, vol. 10, no. 1, pp. 68–74.

    Article  Google Scholar 

  22. Kovalenko, G.A., Perminova, L.V., and Beklemishev, A.B., React. Kinet., Mech. Catal., 2019, vol. 128, no. 1, pp. 479–491. https://doi.org/10.1007/s11144-019-01648-z

    Article  CAS  Google Scholar 

  23. Kovalenko, G.A., Perminova, L.V., Krasnikov, D.V., and Kuznetsov, V.L., J. Porous Mater., 2018, vol. 25, no. 4, pp. 1017–1026. https://doi.org/10.1007/s10934-017-0512-0

    Article  CAS  Google Scholar 

  24. Bearden, J.C., Jr., Biochim. Biophys. Acta, 1978, vol. 533, pp. 525–529.

    Article  CAS  Google Scholar 

  25. Viswanadhan, V.N., Ghose, A.K., Revankar, G.N., and Robins, R.K., J. Chem. Inf. Comput. Sci., 1989, vol. 29, no. 3, pp. 163–172.

    Article  CAS  Google Scholar 

  26. Cea, M., González, M.E., Abarzúa, M., and Navia, R., J. Environ. Manage., 2019, vol. 242, pp. 171–177.

    Article  CAS  Google Scholar 

  27. Yadav, M.G.; Vadgama, R.N., Kavadia, M.R., Odaneth, A.A., and Lali, A.M., Biotechnol. Rep., 2019, vol. 23, article ID E00353.

    Article  Google Scholar 

  28. Sá, A.G.A., de Meneses, A.C., Lerin, L.A., de Araújo, P.H.H., Sayer, C., and de Oliveira, D., Bioprocess Biosyst. Eng., 2018, vol. 41, no. 5, pp. 585–591.

    Article  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors thank A.B. Beklemishev and M.B. Pykhtina of the Institute of Biochemistry, Siberian Branch, Russian Academy of Sciences, for providing a lyophilized sample of recombinant lipase rPichia/lip. We are also grateful to V.L. Kuznetsov and S.I. Moseenkov, Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences, for providing carbon aerogel samples.

Funding

This work was supported by the Russian Foundation for Basic Research, project no. AAA-A17-117041710075-0 “Scientific Foundations of Catalytic and Biotechnological Processes of the Transformation of Renewable Raw Materials for Chemistry and Power Engineering.”

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. V. Perminova.

Additional information

Translated by V. Glyanchenko

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kovalenko, G.A., Perminova, L.V. Heterogeneous Biocatalytic Processes of the Low-Temperature Synthesis of Esters: Selecting an Organic Solvent. Catal. Ind. 13, 90–98 (2021). https://doi.org/10.1134/S2070050421010074

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2070050421010074

Keywords:

Navigation