Solvent-free enzymatic synthesis of fatty alkanolamides

Biotechnology and Bioengineering

Volumn 97, Issue 3, 2007, Pages 447-453

  Tufvesson, Pär ^a   Annerling, Annika ^b   Hatti Kaul, Rajni ^a   Adlercreutz, Dietlind ^a  

^a LUND UNIVERSITY   (Sweden)

^b Akzo Nobel Surface Chemistry AB   (Sweden)

Author keywords

Amide; Biosurfactant; Ethanolamine; Immobilized lipase

Indexed keywords

BIOSURFACTANTS; ETHANOLAMINE; IMMOBILIZED LIPASE; MONOETHANOLAMINE;

BIOSYNTHESIS; CONDENSATION; ENZYME IMMOBILIZATION; FATTY ACIDS; TEMPERATURE DISTRIBUTION;

AMIDES;

ALKANOLAMIDE DERIVATIVE; AMIDE; ETHANOLAMINE; FATTY ACID DERIVATIVE; LAURIC ACID; LIPASE B; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYSIS; DEHYDRATION; DISTILLATION; ENZYME ACTIVITY; ENZYME STABILITY; ENZYME SYNTHESIS; ESTERIFICATION; MELTING POINT; SOLVENT EFFECT; TEMPERATURE SENSITIVITY;

AMIDES; CANDIDA; ETHANOLAMINES; FATTY ACIDS; LIPASE; SOLVENTS; SURFACE-ACTIVE AGENTS;

CANDIDA ANTARCTICA;

EID: 34249812929     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.21258     Document Type: Article

References (23)

1. De Zoete MC, van Rantwijk F, Sheldon RA. 1994. Lipase-catalysed transformations with unnatural acyl acceptors. Catal Today 22:563-590.
2. De Zoete MC, Kock-van Dalen AC, van Rantwijk F, Sheldon RA. 1996. Lipase-catalysed ammoniolysis of lipids. A facile synthesis of fatty acid amides. J Mol Catal B: Enzym 2:141-145.
3. Fernández-Pérez M, Otero C. 2001. Enzymatic synthesis of amide surfactants from ethanolamine. Enzyme Microb Technol 28:527-536.
4. Fernández-Pérez M, Otero C. 2003. Selective enzymatic synthesis of amide surfactants from diethanolamine. Enzyme Microb Technol 33:650-660.
5. Fodor G, Kiss J. 1950. Acyl migration O-N in the diastereomeric 2-aminocyclohexyl benzoates. J Am Chem Soc 72:3495-3497.
6. Furutani T, Furui M, Ooshima H, Kato J. 1996. N-Acylation of β-amino alcohol by acyl migration following enzyme-catalysed esterification. Enzyme Microb Technol 19:578-584.
7. Gotor-Fernández V, Busto E, Gotor V. 2006. Candida antarctica Lipase B: An ideal biocatalyst for the preparation of nitrogenated organic compounds. Advan Syn Catal 348:797-812.
8. Irimescu R, Kato K. 2004a. Investigation of ionic liquids as reaction media for enzymatic enantioselective acylation of amines. J Mol Catal B: Enzym 30:189-194.
9. Irimescu R, Kato K. 2004b. Lipase-catalysed enantioselective reaction of amines with carboxylic acids under reduced pressure in non-solvent system and in ionic liquids. Tetrahedron Lett 45:523-525.
10. Johansson I. 2003. Amides, fatty acid. Kirk-Othmer encyclopedia of chemical technology. New York: John Wiley & Sons.
11. Kanerva LT, Kosonen M, Vänttinen E, Huuhtanen TT, Dahlqvist M. 1992. Studies on the chemo- and enantio-selectivity of the enzymatic monoacylations of amino alcohols. Acta Chem Scand 46:1101-1105.
12. Lancaster M. 2002. Green chemistry: An introductory text. Cambridge: Royal Society of Chemistry.
13. Levinson WE, Kuo TM, Kurtzman CP. 2005. Lipase-catalysed production of novel hydroxylated fatty amides in organic solvent. Enzyme Microb Technol 37:126-130.
14. Litjens MJJ, Sha M, Straathof AJJ, Jongejan JA, Heijnen JJ. 1999. Competitive lipase-catalysed ester hydrolysis and ammoniolysis in organic solvents; equilibrium model of a solid-liquid-vapour system. Biotechnol Bioeng 65:347-356.
15. Litjens MJJSM, Straathof AJJ, Jongejan JA. 2002. Primary amide synthesis from carboxylic acids with a lipase. WO0058490.
16. Maag H. 1984. Fatty acid derivatives: Important surfactants for household and industrial purposes. J Am Oil Chem Soc 61:259-266.
17. Maisonneuve B, Steichen D, Franklin R, Overkempe K. 2000. Process for making carboxylic amides. US6107498.
18. Maugard T, Remaud-Simeon M, Petre D, Monsan P. 1997. Lipase-catalysed chemoselective N-acylation of amino-sugar derivatives in hydrophobic solvent: Acid-amine ion-pair effects. Tetrahedron 53: 7587-7594.
19. Montet D, Pina M, Graille J, Renard G, Grimaud J. 1989. Synthesis of N-lauryloleylamide by the Mucor miehei lipase in an organic medium. Fett Wiss Technol 91:14-18.
20. Prasad AK, Husain M, Singh BK, Gupta RK, Manchanda VK, Olsen CE, Parmar VS. 2005. Solvent-free biocatalytic amidation of carboxylic acids. Tetrahedron Lett 46:4511-4514.
21. Rantwijk F, Hacking MAPJ, Sheldon RA. 2000. Lipase-catalysed synthesis of carboxylic amides: Nitrogen nucleophiles as acyl acceptor. Monatsh Chem 131:549-569.
22. Slotema WF, Sandoval G, Guieysse D, Straathof AJJ, Marty A. 2003. Economically pertinent continuous amide formation by direct lipase- catalysed amidation with ammonia. Biotechnol Bioeng 82: 664-669.
23. Zaks A, Klibanov AM. 1984. Enzymatic catalysis in organic media at 100°C. Science 224:1249-1251.