Selective enzymatic synthesis of amide surfactants from diethanolamine

Enzyme and Microbial Technology

Volumn 33, Issue 5, 2003, Pages 650-660

  Fernández Pérez, Mónica ^a   Otero, Cristina ^a  

^a INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

Author keywords

Amide surfactants; Diethanolamine; Emulsifiers; Enzymatic synthesis; N Acyldiethanolamine; O Acyldiethanolamine; Viscosity

Indexed keywords

ACYLATION; PRODUCTIVITY; SURFACE ACTIVE AGENTS; SYNTHESIS (CHEMICAL); VISCOSITY;

AMIDE SURFACTANTS;

ENZYMES;

AMIDE; DIETHANOLAMINE; DIOXANE; ENZYME; FATTY ACID; HEXANE; SURFACTANT;

ACYLATION; ARTICLE; BIOCATALYST; CONCENTRATION (PARAMETERS); ENZYME SYNTHESIS; KINETICS; NONHUMAN; TEMPERATURE; VISCOSITY;

EID: 0042381534     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(03)00184-4     Document Type: Article

References (22)

1. Raymond B.E., Prislinger A. Alkanolamides. Soap Cosmet. Chem. Spec. 4:1989;46-48.
2. Maag H. Fatty acid derivatives: important surfactants for household, cosmetic and industrial purposes. J. Am. Oil Chem. Soc. 61:1984;259-266.
3. 22 tricarboxylic acids. J. Am. Oil Chem. Soc. 68:1991;133-137.
4. Khemelnitsky Y.U., Levashov A.V., Klyachko N.L., Martinek K. Engineering biocatalytic systems in organic media with low water content. Enzyme Microb. Technol. 10:1988;710-724.
5. Wescott C.R., Klibanov A.M. The solvent dependence of enzyme specificity. Biochim. Biophys. Acta. 1206:1994;1-9.
6. Arcos J.A., Bernabé M., Otero C. Quantitative enzymatic production of 6-O-acylglucose esters. Biotechnol. Bioeng. 37:1998a;505-509.
7. Arcos J.A., Bernabé M., Otero C. Quantitative enzymatic production of 1,6-diacyl sorbitol esters. Biotechnol. Bioeng. 60:1998;53-60.
8. Torres C., Otero C. Part 1. Enzymatic synthesis of lactate and glycolate esters of fatty alcohols. Enzyme Microb. Technol. 25:1999a;745-752.
9. Torres C., Bernabé M., Otero C. Part 2. Two enzymatic procedures for the synthesis of malic acid monoesters. Enzyme Microb. Technol. 25:1999;753-761.
10. Paiva A.L., Balcao V.M., Malcata F.X. Kinetics and mechanisms of reactions catalysed by immobilized lipases. Enzyme Microb. Technol. 27:2000;187-204.
11. Zaks A., Klibanov A.M. Enzymatic catalysis in organic media at 100 °C. SCI. 224:1984;1249-1251.
12. Zaks A., Klibanov A.M. Enzyme catalyzed processes in organic solvents. Proc. Natl. Acad. Sci. U.S.A. 82:1985;3192-3196.
13. García M.J., Rebolledo F., Gotor V. Chemoenzymatic aminolysis and ammonolysis of β-ketoesters. Tetrahedron Lett. 34:1993;6141-6142.
14. Gotor V., Brieva R., Rebolledo F. A simple procedure for the preparation of chiral amides. Tetrahedron Lett. 29:1988;6973-6974.
15. Quirós M., Sánchez V.M., Brieva R., Rebolledo F., Gotor V. Lipase-catalyzed synthesis of optically active amides in organic media. Tetrahedron Asymm. 4:1993;1105-1112.
16. Zoete M.C., Kock-Van Dalen A.C., Van Rantwijk F., Sheldon R.A. Lipase-catalysed ammoniolysis of lipids. A facile synthesis of fatty acid amides. J. Mol. Catal. B. 1:1996;109-113.
17. Maugard T., Remaud-Simeon M., Petre D., Monsan P. Enzymatic synthesis of glycamide surfactants by amidification reaction. Tetrahedron. 53(14):1997a;5185-5194.
18. Maugard T., Remaud-Simeon M., Petre D., Monsan P. Lipase-catalyzed chemoselective N-acylation of amino-sugar derivatives in hydrophobic solvent: acid-amine ion-pair effects. Tetrahedron. 53(22):1997;7587-7594.
19. Fernández-Pérez M., Otero C. Enzymatic synthesis of amide surfactants from ethanolamine. Enzyme Microb. Technol. 28:2001;527-536.
20. Klibanov A.M. Enzymatic catalysis in anhydrous organic solvents. Trends Biochem. Sci. 14:1989;141-144.
21. Shinichirou T., Klibanov A.M. Chemoselectivity of enzymes in anhydrous media is strongly solvent dependent. Biocatalyst. 8:1993;3-19.
22. Kanerva L.T., Kosonen M., Vänttinen E., Huuhtanen T., Dahlqvist M. Studies of the chemo- and enantio-selectivity of the enzymatic monoacylations of amino alcohols. Acta Chem. Scand. 46:1992;1101-1105.