Skip to main content
Log in

Efficient lipase-catalyzed production of tailor-made emulsifiers using solvent engineering coupled to extractive processing

  • Published:
Journal of the American Oil Chemists' Society

Abstract

Within the framework of enzymatic biosurfactant synthesis, the development of reaction processes leading to a selective and efficient production is of crucial interest. In this work, we proposed an enzymatic method for producing 1(3)-monooleoyl-rac-glycerol using a commercial immobilized lipase, the Lipozyme®. To avoid the blockage of the enzyme by the presence of insoluble glycerol, the latter was adsorbed onto dried silica gel. The selective monoester production (83%) was obtained using 2-methyl-2-butanol amended n-hexane (90:10, vol/vol) as reaction medium. The observed decrease in the substrate conversion, in a medium containing 2-methyl-2-butanol, was countered by coupling to the reaction an inline selective recovery method for the produced monoester by adsorption onto a silica gel column located at the outflow of the reaction vessel. This process leads to an efficient monooleoyl glycerol production with a high oleic acid conversion (71%) and to the recovery of a 100% pure monooleoyl glycerol.

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.

Similar content being viewed by others

References

  1. Ducret, A., A. Giroux, M. Trani, and R. Lortie, Enzymatic Preparation of Biosurfactants from Sugars or Sugar Alcohols and Fatty Acids in Organic Media Under Reduced Pressure, Biotechnol. Bioeng. 48:214–221 (1995).

    Article  CAS  Google Scholar 

  2. Liu, K.J., and J.F. Shaw, Synthesis of Propylene Glycol Monoesters of Docosahexaenoic Acid and Eicosapentaenoic Acid by Lipase-Catalyzed Esterification in Organic Solvents, J. Am. Oil Chem. Soc. 72:1271–1274 (1995).

    Article  CAS  Google Scholar 

  3. Nieendick, C., and K.H. Schmid, Alkyl Polyglycosides—A New Generation of Surfactants for the Use in Manual Dishwashing Agents, Agro-Food Industry Hi-Tech:27–30 (1995).

  4. McNeill, G.P., S. Shimizu, and T. Yamane, Solid Phase Enzymatic Glycerolysis of Beef Tallow Resulting in a High Yield in Monoglyceride, J. Am. Oil Chem. Soc. 67:779–783 (1990).

    Article  CAS  Google Scholar 

  5. Ducret, A., A. Giroux, M. Trani, and R. Lortie, Characterization of Enzymatically Prepared Biosurfactants, Ibid.:109–113 (1996).

    Article  CAS  Google Scholar 

  6. Akoh, C.C., Lipase-Catalyzed Synthesis of Partial Glyceride, Biotechnol. Lett. 15:949–954 (1993).

    Article  CAS  Google Scholar 

  7. Bornscheuer, U.T., and T. Yamane, Activity and Stability of Lipase in the Solid-Phase Glycerolysis of Triolein, Enzyme Microb. Technol. 16:864–865 (1994).

    Article  CAS  Google Scholar 

  8. Castillo, E., A. Marty, D. Combes, and J.S. Condoret, Polar Substrates for Enzymatic Reactions in Supercritical CO2: How to Overcome the Solubility Limitation, Biotechnol. Lett. 16:169–174 (1994).

    Article  CAS  Google Scholar 

  9. Park, H.O., D.S. Lee, and S.C. Shim, Sugar Solubilization Agent for Enzymatic Condensation of Glucose in Organic Solvents, Ibid.:111–116 (1992).

    Article  CAS  Google Scholar 

  10. Ferrier, R.J., Applications of Phenylboronic Acid in Carbohydrate Chemistry, Methods Carbohydr. Chem. 6:419–426 (1972).

    CAS  Google Scholar 

  11. Berger, M., K. Laumen, and M.P. Schneider, Lipase Catalyzed Esterification of Hydrophilic Diols in Organic Solvents, Biotechnol. Lett. 14:553–558 (1992).

    Article  CAS  Google Scholar 

  12. Castillo, E., V. Dossat, A. Marty, J.S. Condoret, and D. Combes, The Role of Silica Gel in Lipase-Catalyzed Esterification Reactions of High Polar Substrates, J. Am. Oil Chem. Soc. 74:77–85 (1997).

    Article  CAS  Google Scholar 

  13. Berger, M., K. Laumen, and M.P. Schneider, Enzymatic Esterification of Glycerol I. Lipase-Catalyzed Synthesis of Regioisomerically Pure 1,3-sn-Diacylglycerols, Ibid.:955–960 (1992).

    Article  CAS  Google Scholar 

  14. Kwon, S.J., J.J. Han, and J.S. Rhee, Production and in situ Separation of Mono- or Diacylglycerol Catalyzed by Lipases in n-Hexane, Enzyme Microb. Technol. 17:700–704 (1995).

    Article  CAS  Google Scholar 

  15. Dordick, J.S., Designing Enzymes for Use in Organic Solvents, Biotechnol. Prog. 8:259–267 (1992).

    Article  PubMed  CAS  Google Scholar 

  16. Janssen, A.E.M., M. Hadini, N. Wessels Boer, R. Walinga, A. Van der Padt, H.M. Van Sonsbeek, and K. Van’t Riet, The Effect of Organic Solvents on Enzymatic Esterification of Polyols, in Biocatalysis in Non Conventional Media, edited by J. Tramper, et al., Elsevier Science Publishers B.V., Amsterdam, 1992, pp. 155–161.

    Google Scholar 

  17. Ergan, F., and G. André, Simple High Performance Liquid Chromatography Methods for Monitoring Lipase Reactions, Lipids 24:76–78 (1989).

    Article  PubMed  CAS  Google Scholar 

  18. Valivety, R.H., G.A. Johnston, C.J. Suckling, and P.J. Halling, Solvent Effects on Biocatalysis in Organic Systems: Equilibrium Position and Rates of Lipase Catalyzed Esterification, Biotechnol. Bioeng. 38:1137–1143 (1991).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

About this article

Cite this article

Edmundo, C., Valérie, D., Didier, C. et al. Efficient lipase-catalyzed production of tailor-made emulsifiers using solvent engineering coupled to extractive processing. J Amer Oil Chem Soc 75, 309–313 (1998). https://doi.org/10.1007/s11746-998-0046-3

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-998-0046-3

Key words

Navigation