Criteria to design green enzymatic processes in ionic liquid/supercritical carbon dioxide systems

Biotechnology Progress

Volumn 20, Issue 3, 2004, Pages 661-669

  Lozano, Pedro ^a   De Diego, Teresa ^a   Gmouh, Said ^b   Vaultier, Michel ^b   Iborra, José L ^a  

^a UNIVERSITY OF MURCIA   (Spain)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CATALYSIS; ENZYMES; FREE ENERGY; HYDROPHOBICITY; MASS TRANSFER; SYNTHESIS (CHEMICAL);

ENZYME CATALYSIS; IONIC LIQUIDS (IL);

BIOTECHNOLOGY;

CARBON DIOXIDE; ION; LIPASE B, CANDIDA ANTARCTICA; PHENETHYL ALCOHOL; QUATERNARY AMMONIUM DERIVATIVE; SOLVENT; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; ESTERIFICATION; EVALUATION; METHODOLOGY; PHASE TRANSITION; SOLUTION AND SOLUBILITY; SUPERCRITICAL FLUID CHROMATOGRAPHY;

CARBON DIOXIDE; CHROMATOGRAPHY, SUPERCRITICAL FLUID; ESTERIFICATION; IONS; LIPASE; PHASE TRANSITION; PHENYLETHYL ALCOHOL; QUATERNARY AMMONIUM COMPOUNDS; SOLUTIONS; SOLVENTS;

CANDIDA; CANDIDA ANTARCTICA;

EID: 2942709868     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp0342497     Document Type: Article

References (36)

1. Ionic Liquids in Synthesis; Wassercheid, P., Welton, T., Eds.; Wiley-VCH. Weiheim, 2002.
2. Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Ionic liquids (moltent salts) phase organometallic catalysis. Chem. Rev. 2002, 102, 3667-3692.
3. Brennecke, J. F.; Maginn, E. J. Ionic liquids: Innovative fluids for chemical processing. AIChE J. 2001, 47, 2384-2389.
4. Gordon, C. M. New developments in catalysis using ionic liquids. Appl. Catal., A 2001, 222, 101-117.
5. 2 systems. J. Phys. Chem. B 2001, 105, 2437-2444.
6. Mesiano, A. J. Beckman, E. J.; Russell, A. J. Supercritical biocatalysis. Chem. Rev. 1999, 99, 623-633.
7. Blanchard, L. A.; Brennecke, J. F. Recovery of organic products from ionic liquids using supercritical carbon dioxide. Ind. Eng. Chem. Res. 2001, 40, 287-292.
8. Lozano, P.; de Diego, T., Carrié, D.; Vaultier, M.; Iborra, J. L. Continuous green biocatalytic processes using ionic liquids and supercritical carbon dioxide. Chem. Commum. 2002, 692-693.
9. Reetz, M.; Wiesenhöfer, W.; Franciò, G.; Leitner, W. Biocatalysis in ionic liquids: batchwise and continuous flow processes using supercritical, carbon dioxide as the mobile phase. Chem. Commun. 2002, 992-993
10. 2 systems. Angew. Chem., Int. Ed. 2003, 42, 148-150.
11. van Rantwijk, F.; Madeira-Lau, R.; Sheldon, R. A. Biocatalytic transformations in ionic liquids. TIBTECH 2003, 21, 131-138.
12. Kragl, U.; Eckstein, M.; Kaftzik, N. Enzyme catalysis in ionic liquids. Curr. Opin. Biotechnol. 2002, 13, 565-571.
13. Lozano, P.; de Diego, T., Carrié, D.; Vaultier, M.; Iborra, J. L. Enzymatic ester synthesis in ionic liquids. J. Mol. Catal., B 2003, 21, 9-13.
14. Shöfer, S. H.; Kaftzik, N.; Wasserscheid, P.; Kragl, U. Enzymatic catalysis in ionic liquids: lipase catalysed kinetic resolution of 1-phenylethanol with improved enantioselectivity. Chem. Commun. 2001, 425-426.
15. Park, S.; Kazlauskas, R. J. Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantioand regioseletive acylation. J. Org. Chem. 2001, 66, 8395-8401.
16. Kaar, J. L.; Jesionowski, A. M.; Berberich, J. A.; Moulton, R.; Russell, A. J. Impact of ionic liquid physical properties on lipase activity and stability. J. Am. Chem. Soc. 2003, 125, 4125-4131.
17. Lozano, P.; de Diego, T.; Guegan, J. P.; Vaultier, M.; Iborra, J. L. Stabilization of α-chymotrypsin by ionic liquids in transesterification reactions. Biotechnol. Bioeng. 2001, 75, 563-569.
18. Lozano, P.; de Diego, T.; Carrié, D.; Vaultier, M.; Iborra, J. L. Over-stabilization of Candida antarctica lipase B by ionic liquids in ester synthesis. Biotechnol. Lett. 2001, 23, 1529-1533.
19. Persson, M.; Bornscheuer, U. T. Increased stability of an esterase from Bacillus stearothermophilus in ionic liquids as compared to organic solvents. J. Mol. Catal., B 2003, 22, 21-27.
20. Kamat, S.; Critchley, G.; Beckman, E. J.; Russell, A. J. Biocatalytic synthesis of acrylates in organic solvents and supercritical fluids: III. Does carbon dioxide covalently modify enzymes? Biotechnol. Bioeng. 1995, 46, 610-620.
21. Lozano, P.; Avellaneda, A.; Pascual, R.; Iborra, J. L. Stability of immobilized α-chymotrpysin in supercritical carbon dioxide. Biotechnol. Lett. 1996, 18, 1345-1350.
22. Lozano, P.; de Diego, T., Carrié, D.; Vaultier, M.; Iborra, J. L. Lipase catalysis in ionic liquids and supercritical carbon dioxide at 150°C. Biotechnol. Prog. 2003, 19, 380-382.
23. Bonhôte, P.; Dias, A. P.; Papageorgiou, N. Kalyanasundaram, K.; Grätztel, M. Hydrophobic, highly conductive ambient-temperature molten salts. Inorg. Chem. 1996, 35, 1168-1178.
24. Carmichael, A. J.; Seddon, K. R. Polarity study of some 1-alkyl-3-methylimidazolium ambient-temperature ionic liquids with the solvatochromic dye, Nile Red. J. Phys. Org. Chem. 2000, 13, 591-595.
25. Hagiwara, R.; Ito, Y. Room-temperature ionic liquids of imidazolium cations and fluoroanions. J. Fluorine Chem. 2000, 105, 221-227.
26. Aki, S. N. V. K.; Brennecke, J. F.; Samanta, A. How polar are room-temperature ionic liquids? Chem. Commun. 2001, 413-414.
27. Sun, J.; Forsyth, M.; MacFarlane, D. R. Room-temperature molten salts based on the quaternary ammonium ion. J. Phys. Chem. B 1998, 102, 8858-8864
28. Matsumoto, H.; Kageyama, H.; Miyakazi, Y. Chem. Commun. 2002, 1726-1727.
29. Kim, K. J.; Diwekar, U. M.; Joback, K. G. Greener solvent selection under uncertainty. In Clean Solvents. Alternative Media for Chemical Reactions and Processing; Abraham, M. A., Moens, L., Eds.; ACS Symposium Series 819; American Chemical Society: Washington, DC, 2002; pp 224-237.
30. Eckstein, M.; Wassercheid, P.; Kragl, U. Enhanced enantioselectivity of lipase from Pseudomonas sp. at high temperatures and fixed water activity in the ionic liquid, 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulphonyl]amide. Biotechnol. Lett. 2002, 24, 763-767.
31. Berberich, J. A.; Kaar, J. L.; Russell, A. J. Use of salt hydrate pairs to control water activity for enzyme catalysis in ionic liquids. Biotechnol. Prog. 2003, 19, 1029-1032.
32. Lozano, P.; de Diego, T.; Iborra, J. L. Dynamic structure/function relationships in the α-chymotrypsin deactivation process by heat and pH. Eur. J. Biochem. 1996, 248, 80-85.
33. Sadana, A.; Henley, J. P. Single-step unimolecular non-first-order enzyme deactivation. Biotechnol. Bioeng. 1987, 30, 717-723.
34. Gekko, K.; Timasheff, S. N. Themodynamic and kinetic examination of protein stabilization by glycerol. Biochemistry 1981, 20, 4677-4686.
35. Arsan, J.; Parkin, K. L. Selectivity of Rhyzomucor miehei lipase as affected by choice of cosubstrate system in ester modification reactions in organic media. Biotechnol. Bioeng. 2000, 69, 222-226.
36. Lai, D. T.; O'Connor, C. J. Studies on synthesis of short chain alkyl esters catalyzed by goat pregastric lipase. J. Mol. Catal. B 1999, 6, 411-420.