Geranyl acetate synthesis in a packed-bed reactor catalyzed by novozym in supercritical carbon dioxide and in supercritical ethane

Industrial and Engineering Chemistry Research

Volumn 50, Issue 4, 2011, Pages 1938-1946

  Couto, Ricardo ^a   Vidinha, Pedro ^a   Peres, Célia ^a   Ribeiro, Adriano S ^b   Ferreira, Olga ^c   Oliveira, Manuela V ^b   MacEdo, Eugénia A ^b   Loureiro, José M ^b   Barreiros, Susana ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b UNIVERSITY OF PORTO   (Portugal)

^c INSTITUTO POLITÉCNICO DE BRAGANÇA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

CANDIDA ANTARCTICA LIPASE B; ENZYME PERFORMANCE; ENZYME STABILITY; ESTERIFICATION REACTIONS; GERANYL ACETATE; NOVOZYM435; NOVOZYMES; OPERATING REGIONS; PACKED BED REACTOR; REACTION MIXTURE; REASONABLE ACCURACY; STEADY-STATE CONVERSIONS; STIRRED TANK REACTORS; SUPERCRITICAL CARBON DIOXIDES; SUPERCRITICAL ETHANE; WATER ACTIVITY;

ACETIC ACID; BATCH REACTORS; CARBON DIOXIDE; CATALYSIS; ENZYME ACTIVITY; ENZYMES; ESTERIFICATION; ESTERS; ETHANE; KINETIC PARAMETERS; PACKED BEDS; PEBBLE BED REACTORS; STATE ESTIMATION; SYNTHESIS (CHEMICAL);

SUPERCRITICAL FLUID EXTRACTION;

EID: 79951488864     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie101489j     Document Type: Article

References (45)

1. Liese, A.; Seelbach, K.; Buchholz, A., Haberland, J. Processes. In Industrial Biotransformations, 2nd ed.; Liese, A., Seelbach, K., Wandrey, C., Eds.; Wiley-VCH: Weinheim, Germany, 2006; pp 147 513.
2. Klibanov, A. M. Improving Enzymes by Using them in Organic Solvents Nature 2001, 409, 241-246 (Pubitemid 32144293)
3. Garcia, S.; Lourenĉo, N. M. T.; Lousa, D.; Sequeira, A. F.; Mimoso, P.; Cabral, J. M. S.; Afonso, C. M. A.; Barreiros, S. A Comparative Study of Biocatalysis in Non-Conventional Solvents: Ionic Liquids, Supercritical Fluids and Organic Media Green Chem. 2004, 6, 466-470 (Pubitemid 39472344)
4. Cantone, S.; Hanefeld, U.; Basso, A. Biocatalysis in Non-Conventional Media - Ionic Liquids, Supercritical Fluids and the Gas Phase Green Chem. 2007, 9, 954-971
5. Sheldon, R. A. E Factors, Green Chemistry and Catalysis: An Odyssey Chem. Commun. 2008, 3352-3365 (Pubitemid 352009192)
6. Buchholz, K.; Kasche, V.; Bornscheuer, U. T. Biocatalysts and Enzyme Technology; Wiley-VCH: Weinheim, Germany, 2005.
7. Hyde, J. R.; Licence, P.; Carter, D.; Poliakoff, M. Continuous Catalytic Reactions in Supercritical Fluids Appl. Catal., A 2001, 222, 119-131 (Pubitemid 34086246)
8. Halling, P. J. Thermodynamic Predictions for Biocatalysis in Nonconventional Media: Theory, Tests, and Recommendations for Experimental Design and Analysis Enzyme Microb. Technol. 1994, 16, 178-206 (Pubitemid 24102654)
9. Vázquez Lima, F.; Pyle, D. L.; Asenjo, J. A. Factors Affecting the Esterification of Lauric Acid Using an Immobilized Biocatalyst: Enzyme Characterization and Studies in a Well-Mixed Reactor Biotechnol. Bioeng. 1995, 46, 69-97
10. Mensah, P.; Gainer, J. L.; Carta, G. Adsorptive Control of Water in Esterification with Immobilized Enzymes. II. Fixed-bed Reactor Behavior Biotechnol. Bioeng. 1998, 60, 445-453 (Pubitemid 28489509)
11. Whetje, E.; Svensson, I.; Adlercreutz, P.; Mattiasson, B. Continuous Control of Water Activity During Biocatalysis in Organic Media Biotechnol. Tech. 1993, 7, 873-878 (Pubitemid 2016796)
12. Wehtje, E.; Kaur, J.; Adlercreutz, P.; Chand, S.; Mattiasson, B. Water Activity Control in Enzymatic Esterification Processes Enzyme Microb. Technol. 1997, 21, 502-510 (Pubitemid 27489046)
13. Bartling, K.; Thompson, J. U. S.; Pfromm, P. H.; Czermak, P.; Rezac, M. E. Lipase-Catalyzed Synthesis of Geranyl Acetate in n-Hexane with Membrane-Mediated Water Removal Biotechnol. Bioeng. 2001, 75, 676-681 (Pubitemid 33115759)
14. Dumond, T.; Barth, D.; Perrut, M. Continuous Synthesis of Ethyl Myristate by Enzymatic Reaction in Supercritical Carbon Dioxide J. Supercrit. Fluids 1993, 6, 85-89
15. Marty, A.; Dossat, V.; Condoret, J. S. Continuous Operation of Lipase-Catalyzed Reactions in Nonaqueous Solvents: Influence of the Production of Hydrophilic Compounds Biotechnol. Bioeng. 1997, 56, 232-237 (Pubitemid 27430901)
16. Mensah, P.; Gainer, J. L.; Carta, G. Adsorptive Control of Water in Esterification with Immobilized Enzymes. I. Batch Reactor Behavior Biotechnol. Bioeng. 1998, 60, 435-444
17. Omar, I. C.; Nishio, N.; Nagai, S. The Role of Water on the Equilibrium of Esterification by Immobilized Lipase Packed-Bed Column Reactor Biotechnol. Lett. 1988, 11, 799-804
18. Mensah, P.; Carta, G. Adsorptive Control of Water in Esterification with Immobilized Enzymes. Continuous Operation in a Periodic Counter-Current Reactor Biotechnol. Bioeng. 1999, 66, 137-146 (Pubitemid 30010337)
19. Trusek-Holownia, A.; Noworyta, A. An Integrated Process: Ester Synthesis in an Enzymatic Membrane Reactor and Water Sorption J. Biotechnol. 2007, 130, 47-56 (Pubitemid 46634653)
20. Engasser, J. M.; Hisland, P. Diffusional Effects on the Heterogeneous Kinetics of Two-Substrate Enzymic Reactions J. Theor. Biol. 1979, 77, 427-440
21. Bódalo, A.; Gómez, J. L.; Gómez, E.; Bastida, J.; Ḿximo, M. F. Fluidized Bed Reactors Operating with Immobilized Enzyme Systems: Design Model and its Experimental Verification Enzyme Microb. Technol. 1995, 17, 915-922
22. Abu-Reesh, I. M. Predicting the Performance of Immobilized Enzyme Reactors Using Reversible MichaelisMenten Kinetics Bioprocess Eng. 1997, 17, 131-137
23. 2 as Solvent: Approximation of System Kinetics J. Chem. Technol. Biotechnol. 2000, 75, 715-721 (Pubitemid 30621113)
24. Xiu, G.-H.; Jiang, L.; Li, P. Mass-Transfer Limitations for Immobilized Enzyme-Catalyzed Kinetic Resolution of Racemate in a Batch Reactor Ind. Eng. Chem. Res. 2000, 39, 4054-4062
25. Van Roon, J. L.; Arntz, M. M.; Kallenberg, A. I.; Paasman, M. A.; Tramper, J.; Schroen, C. J.; Beeftink, H. H. A Multicomponent Reaction-Diffusion Model of a Heterogeneously Distributed Immobilized Enzyme Appl. Microbiol. Biotechnol. 2006, 72, 263-278 (Pubitemid 44273049)
26. Yahya, A. R. M.; Anderson, W. A.; Moo-Young, M. Ester Synthesis in Lipase-Catalyzed Reactions Enzyme Microb. Technol. 1998, 23, 438-450 (Pubitemid 29070746)
27. 2 Gel Fiber J. Am. Oil Chem. Soc. 2001, 78, 1099-1103 (Pubitemid 34125340)
28. Abbas, H.; Comeau, L. Aroma Synthesis by Immobilized Lipase from Mucor sp Enzyme Microb. Technol. 2003, 32, 589-595 (Pubitemid 36324347)
29. Peres, C.; Gomes da Silva, M. D. R.; Barreiros, S. Water Activity Effects on Geranyl Acetate Synthesis Catalyzed by Novozym in Supercritical Ethane and in Supercritical Carbon Dioxide J. Agric. Food Chem. 2003, 51, 1884-1888
30. Larios, A.; García, H. S.; Oliart, R. M.; Valerio-Alfaro, G. Synthesis of Flavor and Fragrance Esters Using Candida antarctica Lipase Appl. Microbiol. Biotechnol. 2004, 65, 373-376 (Pubitemid 39281089)
31. 6 Biotechnol. Bioeng. 2005, 93, 318-324
32. Greenspan, L. Humidity Fixed Points of Binary Saturated Aqueous Solutions J. Res. Natl. Bur. Stand. (U.S.A.) 1977, 81A, 89-96
33. Fontes, N.; Partridge, J.; Halling, P. J.; Barreiros, S. Zeolite Molecular Sieves Have Dramatic Acid-Base Effects on Enzymes in Nonaqueous Media Biotechnol. Bioeng. 2002, 77, 296-305 (Pubitemid 34094157)
34. Gandhi, N. N.; Patil, N. S.; Sawant, S. B.; Joshi, J. B. Lipase-Catalyzed Esterification Catal. Rev. - Sci. Eng. 2000, 42, 439-480
35. Segel, I. H. Enzyme Kinetics; Wiley-Interscience: New York, 1993.
36. Claon, P. A.; Akoh, C. C. Enzymatic Synthesis of Geranyl Acetate in n -Hexane with Candida antarctica Lipase J. Am. Oil Chem. Soc. 1994, 71, 575-578
37. Froment, G. F.; Bischoff, K. B. Chemical Reactor Analysis and Design, 2nd ed.; John Wiley and Sons: New York, 1990.
38. Hindmarsh, A. C. ODEPACK, a Systematized Collection of ODE Solvers. In Scientific Computing; Stepleman, R. S., Ed.; North-Holland: Amsterdam, 1983, pp 55 64.
39. Petzold, L. R. Automatic Selection of Methods for Solving Stiff and Nonstiff Systems of Ordinary Differential Equations SIAM J. Sci. Stat. Comput. 1983, 4, 136-148
40. Levenberg, K. A Method for the Solution of Certain Problems in Least Squares Q. Appl. Math. 1944, 2, 164-168
41. Marquardt, D. W. An Algorithm for Least-Squares Estimation of Nonlinear Parameters SIAM J. Appl. Math. 1963, 11, 431-441
42. Parker, M. C.; Moore, B. D.; Blacker, A. J. Measuring Enzyme Hydration in Nonpolar Organic Solvents Using NMR Biotechnol. Bioeng. 1995, 46, 452-458
43. Colombié, S.; Tweddell, R. J.; Condoret, J. S.; Marty, A. Water Activity Control: A Way to Improve the Efficiency of Continuous Lipase Esterification Biotechnol. Bioeng. 1998, 60, 362-368 (Pubitemid 28446898)
44. Sanchéz, A.; Valero, F.; Lafuente, X.; Solà, C. Highly Enantioselective Esterification of Racemic Ibuprofen in a Packed Bed Reactor Using Immobilized Rhizomucor miehei Lipase Enzyme Microb. Technol. 2000, 27, 157-166 (Pubitemid 30345501)
45. Valivety, R. H.; Johnston, G. A.; Suckling, C. J.; Halling, P. J. Solvent Effects on Biocatalysis in Organic Systems: Equilibrium Position and Rates of Lipase Esterification Biotechnol. Bioeng. 1991, 38, 1137-1143