Kinetics of synthesis of butyl butyrate by esterification and transesterification in supercritical carbon dioxide

Journal of Chemical Technology and Biotechnology

Volumn 83, Issue 8, 2008, Pages 1135-1144

  Varma, Mahesh N ^a   Madras, Giridhar ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Butyl butyrate; Esterification; Novozym 435; Ping Pong Bi Bi mechanism; Transesterification

Indexed keywords

ALCOHOLS; CANNING; CARBON DIOXIDE; ESTERIFICATION; ESTERS; FATTY ACIDS; FOOD PRESERVATION;

BUTYL BUTYRATE; BUTYRIC ACIDS; ENZYMATIC ESTERIFICATION; ETHYL BUTYRATE; FOOD INDUSTRIES; GREEN-CHEMISTRY; NOVOZYM 435; PING-PONG BI-BI MECHANISM; SUPERCRITICAL CARBON DIOXIDE; TRANSESTERIFICATION;

SUPERCRITICAL FLUID EXTRACTION;

BUTANOL; BUTYL BUTYRIC ACID; BUTYRIC ACID; BUTYRIC ACID DERIVATIVE; CARBON DIOXIDE; ETHYL BUTYRIC ACID; SUPERCRITICAL CARBON DIOXIDE; TRIACYLGLYCEROL LIPASE;

ANALYTICAL PARAMETERS; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; ESTERIFICATION; HYDROLYSIS; MODEL; SYNTHESIS; TEMPERATURE DEPENDENCE; TRANSESTERIFICATION;

ANANAS COMOSUS;

EID: 48449086301     PISSN: 02682575     EISSN: 10974660     Source Type: Journal    
DOI: 10.1002/jctb.1897     Document Type: Article

References (48)

1. Serra S, Fuganti C and Brenna E, Biocatalytic preparation of natural flavours and fragrances. Trends Biotechnol 23:193-198 (2005).
2. Munro IC, Kennepohl E and Kroes R, A procedure for the safety evaluation of flavouring substances. Food Chem Toxicol 37:207-232 (1999).
3. Huang S and Chang H, Kinetic study on the esterification of geraniol and acetic acid in organic solvents using surfactant-coated lipase. J Chem Technol Biotechnol 74:183-187 (1999).
4. Rassy HE, Perrard A and Pierre AC, Application of lipase encapsulated in silica aerogels to a transesterification reaction in hydrophobic and hydrophilic solvents: Bi-Bi Ping-Pong kinetics. J Mol Catal B: Enzym 30:137-150 (2004).
5. Maury S, Buisson P, Perrard A and Pierre AC, Compared esterification kinetics of the lipase from Burkholderia cepacia either free or encapsulated in a silica aerogel. J Mol Catal B: Enzym 32:193-203 (2005).
6. Yadav GD and Lathi PS, Kinetics and mechanism of synthesis of butyl isobutyrate over immobilised lipases. Biochem Eng J 16:245-252 (2003).
7. Santos JC and de Castro HF, Optimization of lipase-catalysed synthesis of butyl butyrate using a factorial design. World J Microbiol Biotechnol 22:1007-1011 (2006).
8. Abbas H and Comeau L, Aroma synthesis by immobilized lipase from Mucor sp. Enzyme Microb Technol 32:589-595 (2003).
9. Lozano P, Perez-Marin AB, De Diego T, Gomez D, Paolucci-Jeanjean D, Belleville MP, et al., Active membranes coated with immobilized Candida antarctica lipase B: preparation and application for continuous butyl butyrate synthesis in organic media. J Membr Sci 201:55-64 (2002).
10. 2 gel fibre. J Chem Technol Biotechnol 77:86-91 (2001).
11. De Castro HF, de Lima R and Roberto IC, Rice straw as a support for immobilization of microbial lipase. Biotechnol Prog 17:1061-1064 (2001).
12. Borzeix F, Monot F and Vandecasteele J, Strategies for enzymatic esterification in organic solvents: comparison of microaqueous, biphasic, and micellar systems. Enzyme Microb Technol 14:791-797 (1992).
13. Yadav GD and Manjula Devi K, Immobilized lipase-catalysed esterification and transesterification reactions in non-aqueous media for the synthesis of tetrahydrofurfuryl butyrate: comparison and kinetic modeling. Chem Eng Sci 59:373-383 (2004).
14. Yadav GD and Lathi PS, Lipase catalyzed transesterification of methyl acetoacetate with n-butanol. J Mol Catal B: Enzym 32:107-113 (2005).
15. Rizzi M, Stylos P, Riek A and Reuss M, A kinetic study of immobilized lipase catalysing the synthesis of isoamyl acetate by transesterification in n-hexane. Enzyme Microb Technol 14:709-714 (1992).
16. Romero MD, Calvo L, Alba C and Daneshfar A, A kinetic study of isoamyl acetate synthesis by immobilized lipase-catalyzed acetylation in n-hexane. J Biotechnol 127:269-277 (2007).
17. Zaidi A, Gainer JL, Carta G, Mrani A, Kadiri T, Belarbi Y, et al., Esterification of fatty acids using nylon-immobilized lipase in n-hexane: kinetic parameters and chain-length effects. J Biotechnol 93:209-216 (2002).
18. Yadav GD and Manjula Devi K, Kinetics of hydrolysis of tetrahydrofurfuryl butyrate in a three phase system containing immobilized lipase from Candida antarctica. Biochem Eng J 17:57-63 (2004).
19. Chulalaksananukui W, Condoret J and Combes D, Kinetics of geranyl acetate synthesis by iipase-catalysed transesterification in n-hexane. Enzyme Microb Technol 14:293-298 (1992).
20. Janssen AEM, Sjursnes BJ, Vakurov AV and Halling PJ, Kinetics of lipase-catalyzed esterification in organic media: correct model and solvent effects on parameters. Enzyme Microb Technol 24:463-470 (1999).
21. Romero MD, Calvo L, Alba C, Habulin M, Primozic M and Knez Z, Enzymatic synthesis of isoamyl acetate with immobilized Candida antarctica lipase in supercritical carbon dioxide. J Supercrit Fluids 33:77-84 (2005).
22. Srivastava S, Modak J and Madras G, Enzymatic synthesis of flavors in supercritical carbon dioxide. Ind Eng Chem Res 41:1940-1945 (2002).
23. Kumar R, Madras G and Modak J, Enzymatic synthesis of ethyl palmitate in supercritical carbon dioxide. Ind Eng Chem Res 43:1568-1573 (2004).
24. Olsen T, Kerton F, Marriott R and Grogan G, Biocatalytic esterification of lavandulol in supercritical carbon dioxide using acetic acid as the acyl donor. Enzyme Microb Technol 39:621-625 (2006).
25. Srivastava S, Madras G and Modak J, Esterification of myristic acid in supercritical carbon dioxide. J Superctit Fluids 27:55-64 (2003).
26. Chulalaksananukul W, Condoret J and Combes D, Geranyl acetate synthesis by lipase-catalyzed transesterification in supercritical carbon dioxide. Enzyme Microb Technol 15:691-398 (1993).
27. 2. Biotechnol Bioeng 39:273-280 (1992).
28. Blattner C, Zoumpanioti M, Kroner J, Schmeer G, Xenakis A and Kunz W, Biocatalysis using lipase encapsulated in microemulsion-based organogels in supercritical carbon dioxide. J Supercrit Fluids 36:182-193 (2006).
29. Varma MN and Madras G, Synthesis of biodiesel from castor oil and linseed oil in supercritical fluids. Ind Eng Chem Res 46:1-6 (2007).
30. Hernandez FJ, de los Rios AP, Gomez D, Rubio M and Villora G, A new recirculating enzymatic membrane reactor for ester synthesis in ionic liquid/supercritical carbon dioxide biphasic systems. Appl Catal B Environ 67:121-126 (2006).
31. Yasmin T, Jiang T, Han B, Zhang J and Ma J, Transesterification reaction catalysed by Novozym 435 in supercritical carbon dioxide. J Mol Catal B: Enzym 41:27-31 (2006).
32. Paiva AL, van Rossum D and Malcata FX, Upase-catalyzed synthesis of butyl butyrate by alcoholysis in an integrated liquid-vapor system. Biotechnol Prog 19:750-754 (2003).
33. Litjens MJJ, Sha M, Straathof AJJ, Jongejan JA and Heijnen JJ, Competitive lipase-catalyzed ester hydrolysis and ammoniolysis in organic solvents: equilibrium model of a solid-liquid-vapor System. Biotechnol Bioeng 65:347-356 (1999).
34. Garcia T, Coteron A, Martinez M and Aracil J, Kinetic model for the esterification of oleic acid and cetyl alcohol using an immobilized lipase as catalyst. Chem Eng Sci 55:1411-1423 (2000).
35. Nakamura K, Chi YM, Yamanda Y and Yano T, Lipase activity and stability in supercritical carbon dioxide. Chem Eng Commun 45:207-212 (1986).
36. Fayolle F, Marchal R, Monot F, Blancher D and Ballerini D, An example of production of natural esters: synthesis of butyl butyrate from wheat flour. Enzyme Microb Technol 13:215-220 (1991).
37. De Diego T, Lazano P, Gmouh S, Vaultier M and Iborra JL, Understanding structure-stability relationships of Candida antartica lipase B in ionic liquids. Biomacromolecules 6:1457-1464 (2005).
38. Mesiano AJ, Beckman EJ and Russell AJ, Supercritical biocatalysis. Chem Rev 99:623-633 (1999).
39. 2 in green chemical synthesis and processing. J Supercrit Fluids 28:121-191 (2004).
40. Hobbs HR and Thomas NR, Biocatalysis in supercritical fluids, in fluorous solvents, and under solvent-free conditions. Chem Rev 107:2786-2820 (2007).
41. Knez Z and Habulin M, Lipase-catalyzed esterification in supercritical carbon dioxide Prog Biotechnol 8:401-405 (1992).
42. Tewari YB, Hara T, Phinney KW and Mayhew MP, A thermodynamic study of the lipase-catalyzed transesterification of benzyl alcohol and butyl acetate in supercritical carbon dioxide media. J Mol Catal B: Enzym 30:131-135 (2004).
43. Hassan S, Ghaziaskar R and Nikravesh M, Solubility of hexanoic acid and butyl acetate in supercritical carbon dioxide. Fluid Phase Equilibr 206:215-221 (2003).
44. Sellapan S and Akoh CC, Enzymatic acidolysis of tristearin with lauric and oleic acid to produce coating lipids. J Am Oil Chem Soc 77:1127-1133 (2000).
45. Zhang H, Xu X, Mu H, Nilsson J, Adler-Nissen J and Hoy CE, Lipozyme IM catalysed interesterification for the production of margarine fats in a 1 Kg scale stirred tank reactor. Eur J Lipid Sci Technol 102:411-418 (2000).
46. Cheng YC and Tsai SW, Effects of water activity and alcohol concentration on the kinetic resolution of lipase catalyzed acyl transfer in organic solvents. Enzyme Microb Technol 32:362-368 (2003).
47. Wu JY and Liu SW, Influence of alcohol concentration on lipase catalyzed enantioselective esterification ofiracemic naproxen in isooctane under controlled water activity. Enzyme Microb Technol 26:124 (2000).
48. Chen JW and Wu WT, Regeneration of immobilized candida antartica lipase for transesterification. J Biosci Bioeng 95:466 (2003).