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.
Similar content being viewed by others
References
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).
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).
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).
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).
Ducret, A., A. Giroux, M. Trani, and R. Lortie, Characterization of Enzymatically Prepared Biosurfactants, Ibid.:109–113 (1996).
Akoh, C.C., Lipase-Catalyzed Synthesis of Partial Glyceride, Biotechnol. Lett. 15:949–954 (1993).
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).
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).
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).
Ferrier, R.J., Applications of Phenylboronic Acid in Carbohydrate Chemistry, Methods Carbohydr. Chem. 6:419–426 (1972).
Berger, M., K. Laumen, and M.P. Schneider, Lipase Catalyzed Esterification of Hydrophilic Diols in Organic Solvents, Biotechnol. Lett. 14:553–558 (1992).
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).
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).
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).
Dordick, J.S., Designing Enzymes for Use in Organic Solvents, Biotechnol. Prog. 8:259–267 (1992).
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.
Ergan, F., and G. André, Simple High Performance Liquid Chromatography Methods for Monitoring Lipase Reactions, Lipids 24:76–78 (1989).
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).
Author information
Authors and Affiliations
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
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11746-998-0046-3