Prediction of partition coefficients using COSMO-RS: Solvent screening for maximum conversion in biocatalytic two-phase reaction systems

Chemical Engineering and Processing: Process Intensification

Volumn 47, Issue 6, 2008, Pages 1034-1041

  Spieß, Antje C ^a   Eberhard, Werner ^a   Peters, Martina ^a   Eckstein, Marrit F ^a   Greiner, Lasse ^a   Büchs, Jochen ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

COSMO RS prediction; Thermodynamics; Two phase systems

Indexed keywords

CATALYSIS; EXTRACTION; SOLUTIONS; SUBSTRATES;

COSMO-RS PREDICTION; TWO-PHASE SYSTEMS;

SOLVENTS;

CATALYSIS; EXTRACTION; SOLUTIONS; SOLVENTS; SUBSTRATES;

EID: 41449115770     PISSN: 02552701     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cep.2007.02.007     Document Type: Article

References (45)

1. Straathof A.J.J. Thermodynamics in Multiphase Biocatalysis, in: Thermodynamics for biochemical engineers, Course book (11-16 December, 2005), Mürren, Switzerland 22 pages
2. Hernandez-Justiz O., Fernandez-Lafuente R., Terreni M., and Guisan J.M. Use of aqueous two-phase systems for in situ extraction of water soluble antibiotics during their synthesis by enzymes immobilized on porous supports. Biotechnol. Bioeng. 59 (1998) 73-79
3. Bauer M., Griengl H., and Steiner W. Parameters influencing stability and activity of a S-hydroxynitrile lyase from Hevea brasiliensis in two-phase systems. Enzyme Microb. Tech. 24 (1999) 514-522
4. Sandford V., Breuer M., Hauer B., Rogers P., and Rosche B. (R)-Phenylacetylcarbinol production in aqueous/organic two-phase systems using partially purified pyruvate decarboxylase from Candida utilis. Biotechnol. Bioeng. 91 (2005) 190-198
5. Cull S.G., Holbrey J.D., Vargas-Mora V., Seddon K.R., and Lye G.J. Room-temperature ionic liquids as replacements for organic solvents in multiphase bioprocess operations. Biotechnol. Bioeng. 69 (2000) 227-233
6. Reetz M.T., Wiesenhofer W., Francio G., and Leitner W. Biocatalysis in ionic liquids: batchwise and continuous flow processes using supercritical carbon dioxide as the mobile phase. Chem. Commun. (2002) 992-993
7. M.H. Vermue, J. Tramper, Biocatalysis in non-conventional media-Medium engineering aspects (Technical report), Pure Appl Chem 67 (1995) 345-373.
8. Bruce L.J., and Daugulis A.J. Solvent selection strategies for extractive biocatalysis. Biotechnol. Progr. 7 (1991) 116-124
9. Villela Filho M., Stillger T., Müller M., Liese A., and Wandrey C. Is log P a convenient criterion to guide the choice of solvents for biphasic enzymatic reactions?. Angew. Chem. Int. Ed. 42 (2003) 2993-2996
10. Janssen A.E.M., and Halling P.J. Specificities of enzymes corrected for solvation depend on the choice of the standard state. J. Am. Chem. Soc. 116 (1994) 9827-9830
11. Janssen A.E.M., Sjursnes B.J., Vakurov A.V., and Halling P.J. Kinetics of lipase-catalyzed esterification in organic media: Correct model and solvent effects on parameters. Enzyme Microb. Technol. 24 (1999) 463-470
12. Halling P.J. Thermodynamic predictions for biocatalysis in nonconventional media-Theory, tests, and recommendations for experimental design and analysis. Enzyme Microb. Technol. 16 (1994) 178-206
13. Eckstein M., Peters M., Lembrecht J., Spiess A.C., and Greiner L. Maximise your equilibrium conversion in biphasic catalysed reactions: mathematical description and practical guideline. Ad. Synth. Catal. 348 (2006) 1591-1596
14. Martinek K., Klibanov A.M., Samokhin G.P., Semenov A.N., and Berezin I.V. Preparative enzymatic synthesis in biphasic aqueous-organic system. Bioorg. Khim+ 3 (1977) 696-702
15. Martinek K., Semenov A.N., and Berezin I.V. Enzymatic synthesis in biphasic aqueous-organic systems 1. Chemical equilibrium shift. Biochim. Biophys. Acta 658 (1981) 76-89
16. Antczak T., Hiler D., Krystynowicz A., Bielecki S., and Galas E. Mathematical modelling of ester synthesis by lipase in biphasic system. J. Mol. Catal. B-Enzym 11 (2001) 1043-1050
17. Eggers D.K., Blanch H.W., and Prausnitz J.M. Extractive catalysis: Solvent effects on equilibria of enzymatic reactions in two-phase systems. Enzyme Microb. Tech. 11 (1989) 84-89
18. Janssen A.E.M., Wessels Boer N., and Van't Riet K. Solvent effects on the equilibirum position of lipase-catalyzed esterification of decanoic acid and various alcohols. Biocatalysis 8 (1993) 133-153
19. Lye G.J., Dalby P.A., and Woodley J.M. Better biocatalytic processes faster: new tools for the implementation of biocatalysis in organic synthesis. Org. Process Res. Dev. 6 (2002) 434-440
20. Straathof A.J.J., Panke S., and Schmid A. The production of fine chemicals by biotransformations. Curr.Opin.Biotechnol. 13 (2002) 548-556
21. Prausnitz J.M. Biotechnology: a new frontier for molecular thermodynamics. Fluid Phase Equilibr. 53 (1989) 439-451
22. von Stockar U., and van der Wielen L.A.M. Back to Basics: Thermodynamics in Biochemical Engineering. in: Process Integration in Biochemical Engineering vol.80 (2003), Springer-Verlag, Berlin, Heidelberg 1-17
23. Arlt W., Spuhl O., and Klamt A. Challenges in thermodynamics. Chem. Eng. Process 43 (2004) 221-238
24. Franke R., Krissmann J., and Janowsky R. What can the process engineer expect of COSMO-RS?. Chem-Ing-Tech 74 (2002) 85-89
25. Spuhl O., Arlt W., and Hernandez A.D. Prediction of thermodynamic material properties with the COSMO-RS continuum model. Chem-Ing-Tech 75 (2003) 58-62
26. M.F. Eckstein, Alcohol dehydrogenase catalysed reductions in non-conventional media, Ph.D. Thesis, University of Rostock, 2004.
27. Eckstein M., Lembrecht J., Schumacher J., Eberhard W., Spiess A.C., Peters M., Roosen C., Greiner L., Leitner W., and Kragl U. Maximise your equilibrium conversion in biphasic catalysed reactions: How to obtain reliable data for equilibrium constants?. Adv. Synth. Catal. 348 (2006) 1597-1604
28. de Bruijn J., Busser F., Seinen W., and Hermens J. Determination of octanol/water partition coefficients for hydrophobic organic chemicals with the "slow-stirring" method. Environ. Toxicol. Chem. 8 (1989) 499-512
29. Fan K.K., Ouyang P., Wu X., and Lu Z. Prediction of aqueous phase pH for enzymatic synthesis of peptides in aqueous-organic biphasic systems. J. Chem. Technol. Biotechnol. 76 (2001) 851-856
30. Klamt A., and Schüürmann G. Cosmo - a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perk. T 2 (1993) 799-805
31. Schäfer A., Klamt A., Sattel D., Lohrenz J.C.W., and Eckert F. COSMO implementation in TURBOMOLE: Extension of an efficient quantum chemical code towards liquid systems. Phys. Chem. Chem. Phys. 2 (2000) 2187-2193
32. Klamt A. Conductor-like screening model for real solvents - a new approach to the quantitative calculation of solvation phenomena. J. Phys. Chem-Us 99 (1995) 2224-2235
33. Klamt A., Jonas V., Bürger T., and Lohrenz J.C.W. Refinement and parametrization of COSMO-RS. J. Phys. Chem. A 102 (1998) 5074-5085
34. Sorensen J.W., and Arlt W. Liquid-Liquid Equilibrium Data Collection. Binary Systems vol. 1, Part 1 (1979), DECHEMA, Frankfurt/Main
35. Gröger H., Hummel W., Rollmann C., Chamouleau F., Husken H., Werner H., Wunderlich C., Abokitse K., Drauz K., and Buchholz S. Preparative asymmetric reduction of ketones in a biphasic medium with an (S)-alcohol dehydrogenase under in situ-cofactor-recycling with a formate dehydrogenase. Tetrahedron 60 (2004) 633-640
36. Matos J.R., and Wong C.H. Biphasic one-pot synthesis of two useful and separable compounds using cofactor-requiring enzymatic reactions: Glutamate dehydrogenase catalyzed synthesis of l-α-aminoadipate coupled with alcohol dehydrogenase catalyzed synthesis of a chiral lactone. J. Org. Chem. 51 (1986) 2388-2389
37. Suye S.I., Kamiya K., Kawamoto T., and Tanaka A. Efficient repeated use of alcohol dehydrogenase with NAD(+) regeneration in an aqueous-organic two-phase system. Biocatal. Biotransfor. 20 (2002) 23-28
38. Eckstein M., Daußmann T., and Kragl U. Recent developments in NAD(P)H regeneration for enzymatic reductions in one- and two-phase systems. Biocatal. Biotransfor. 22 (2004) 89-96
39. Pfründer H., Amidjojo M., Kragl U., and Weuster-Botz D. Efficient whole-cell biotransformation in a biphasic ionic liquid/water system. Angew. Chem. Int. Ed. 43 (2004) 4529-4531
40. Heinemann M., Kümmel A., Giesen R., Ansorge-Schumacher M., and Büchs J. Experimental and theoretical analysis of phase equilibria in a two-phase system used for biocatalytic esterifications. Biocatal. Biotransfor. 21 (2003) 115-121
41. Stephenson R.M. Mutual solubilities: water-ketones, water-ethers, and water-gasoline-alcohols. J. Chem. Eng. Data 37 (1992) 80-95
42. Lin S.T., and Sandler S.I. A priori phase equilibrium prediction from a segment contribution solvation model. Ind. Eng. Chem. Res. 41 (2002) 899-913
43. Barcza L., and Foldeaki E. Distribution of monomeric and dimeric propionic acids between water and some organic solvents. Acta Chim. Hung. 95 (1977) 247-252
44. Voutsas E.C., Stamatis H., Kolisis F.N., and Tassios D. Solvent effects on equilibrium position and initial rate of lipase-catalyzed esterification reactions in organic solvents: Experimental results and prediction capabilities. Biocatal. Biotransfor. 20 (2002) 101-109
45. Eckert F., and Klamt A. Fast solvent screening via quantum chemistry: COSMO-RS approach. Aiche. J. 48 (2002) 369-385