Journal of the American Oil Chemists’ Society

, Volume 73, Issue 1, pp 109–113 | Cite as

Characterization of enzymatically prepared biosurfactants

  • Amélie Ducret
  • André Giroux
  • Michael Trani
  • Robert Lortie
Article

Abstract

Various fatty monoesters of sugars and sugar alcohols were prepared enzymatically in organic solvent. Water produced during esterification was removed by refluxing through a dessicant under reduced pressure. Surface properties of these esters such as surface and interfacial tensions and their ability to stabilize emulsions at 30°C were evaluated: oleate esters of glucose, fructose, and sorbitol show similar behavior in reduction of surface and interfacial tensions, and values for the critical micelle concentration are about 8·10−5 M. It was also observed with sorbitol esters that the shorter the alkyl chain, the higher the critical micelle concentration. Generally, emulsions prepared with the emulsifier dissolved in the water or in the oil phase lead to oil-in-water or water-in-oil emulsions, respectively. Sorbitol monolaurate significantly increased the stability of oil-in-water emulsions, with only 5% separation of the phases after 48h at 30°C, compared to 10% for chemically prepared sorbitan monolaurate under the same conditions. Sorbitol monoerucate was very efficient in stabilizing water-in-oil emulsions, with only 1% separation of the phases.

Key words

Critical micelle concentration emulsifier emulsion stability enzymatic esterification lipase nonionic surfactant sugar alcohol esters sugar esters surface activity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Khan, R., The Chemistry of Sucrose,Advances in Carbohydrate Chem. and Biochem. 33:271–273 (1976).Google Scholar
  2. 2.
    Magg, H., Fatty Acid Derivatives: Important Surfactants for Household, Cosmetic and Industrial Purposes,J. Am. Oil. Chem. Soc. 61:259–267 (1984).Google Scholar
  3. 3.
    Bailey’s Industrial Oil and Fat Products, 4th edn., edited by D. Swern, John Wiley and Sons, New York, 1979, pp. 651–653.Google Scholar
  4. 4.
    Fregapane, G., B.D. Sarney, G. Greenberg, D. Knight, and E.N. Vulfson, Enzymatic Synthesis of Monosaccharide Fatty Acid Esters and Their Comparison with Conventional Products.J. Am. Oil Chem. Soc. 71:87–91 (1994).Google Scholar
  5. 5.
    Therisod, M., and A.M. Klibanov, Facile Enzymatic Preparation of Monoacylated Sugars in Pyridine,J. Am. Chem. Soc. 108:5638–5640 (1986).CrossRefGoogle Scholar
  6. 6.
    Chopineau, J., F.D. McCafferty, M. Therisod, and A.M. Klibanov, Production of Biosurfactants from Sugar Alcohols and Vegetable Oils Catalyzed by Lipases in a Nonaqueous Medium,Biotech. Bioeng. 31:208–214 (1988).CrossRefGoogle Scholar
  7. 7.
    Riva, S., J. Chopineau, A.P.G. Kieboom, and A.M. Klibanov, Protease-Catalyzed Regioselective Esterification of Sugars and Related Compounds in Anhydrous Dimethylformamide.J. Am. Chem. Soc. 110:584–589 (1988).CrossRefGoogle Scholar
  8. 8.
    Mutua, L.N., and C.C. Akoh, Synthesis of Alkyl Glycoside Fatty Acid Esters in Non-Aqueous Media byCandida sp. Lipase,J. Am. Oil Chem. Soc. 70:43–46 (1993).Google Scholar
  9. 9.
    Khaled, N., D. Montet, M. Pina, and J. Graille, Fructose Oleate Synthesis in a Fixed Catalyst Bed Reactor,Biotechnol. Lett. 13, 157–172 (1991).CrossRefGoogle Scholar
  10. 10.
    Oguntimein, G.B., H. Erdmann, and R.D. Schmid, Lipase Catalysed Synthesis of Sugar Ester in Organic Solvents,Ibid. 15:175–180 (1993).CrossRefGoogle Scholar
  11. 11.
    Schlotterbeck, A., S. Lang, V. Wray, and F. Wagner, Lipase-Catalyzed Monoacylation of Fructose,Ibid. 15:61–64 (1993).CrossRefGoogle Scholar
  12. 12.
    Guillardeau, L., D. Montet, N. Khaled, M. Pina, and J. Graille, Fructose Caprylate Biosynthesis in a Solvent-Free Medium,Tenside Surfactants Deterg. 25:342–344 (1992).Google Scholar
  13. 13.
    Fregapane, G., D.B. Sarney, and E.N. Vulfson, Enzymic Solvent-Free Synthesis of Sugar Acetal Fatty Acid Esters,Enzyme Microb. Technol. 13:796–800 (1991).CrossRefGoogle Scholar
  14. 14.
    Björkling, F., S.E. Godtfredsen, and O. Kirk, A Highly Selective Enzyme-Catalysed Esterification of Simple Glucosides,J. Chem. Soc. Commun. 14:934–935 (1989).CrossRefGoogle Scholar
  15. 15.
    Adelhorst, K., F. Björkling, S.E. Godtfredsen, and O. Kirk, Enzyme Catalysed Preparation of 6-O-Acylglucopyranosides,Synthesis 2:112–115 (1990).CrossRefGoogle Scholar
  16. 16.
    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).CrossRefGoogle Scholar
  17. 17.
    Zaks, A., and A.M. Klibanov, The Effect of Water on Enzyme Action in Organic Media,J. Biol. Chem. 263:8017–8021 (1988).Google Scholar
  18. 18.
    Rosen, M., The Relationship of Structure to Properties in Surfactants,J. Am. Oil Chem. Soc. 49:293–297 (1972).Google Scholar
  19. 19.
    Rosen, M.,Surfactants and Interfacial Phenomena, John Wiley and Sons, New York, 1978.Google Scholar
  20. 20.
    Rosen, M., Relationship of Structure to Properties in Surfactants: II. Efficiency in Surface or Interfacial Tension Reduction,J. Am. Oil Chem. Soc. 51:461–465 (1974).Google Scholar
  21. 21.
    Matsumura, S., K. Imai, S. Yoshikawa, K. Kawada, and T. Uchiborr, Surface Activities, Biodegradability and Antimicrobial Properties ofn-Alkyl Glucosides, Mannosides and Galactosides,Ibid. 67:996–1001 (1990).Google Scholar

Copyright information

© AOCS Press 1996

Authors and Affiliations

  • Amélie Ducret
    • 1
  • André Giroux
    • 1
  • Michael Trani
    • 1
  • Robert Lortie
    • 1
  1. 1.Bioprocess R & D Group, Biotechnology Research InstituteNational Research CouncilMontrealCanada

Personalised recommendations