Lipase catalyzed synthesis of cinnamyl acetate via transesterification in non-aqueous medium

Process Biochemistry

Volumn 47, Issue 3, 2012, Pages 496-502

  Yadav, Ganapati D ^a   Devendran, Saravanan ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Cinnamyl acetate; Novozym 435; Organic media; Ternary complex mechanism; Transesterification

Indexed keywords

CHEMICAL CATALYSIS; CINNAMYL ACETATE; CINNAMYL ALCOHOLS; COSMETIC INDUSTRY; EFFICIENT PROCESS; ENZYMATIC SYNTHESIS; FLAVOR AND FRAGRANCES; IMMOBILIZED LIPASE; LIPASE-CATALYZED; LIPASE-CATALYZED SYNTHESIS; MOLE RATIO; NON-AQUEOUS MEDIUM; NON-LINEAR REGRESSION ANALYSIS; NOVOZYM435; ORGANIC MEDIA; TERNARY COMPLEX MECHANISM; VINYL ACETATES;

CATALYSIS; CATALYSTS; LIPASES; ORGANIC SOLVENTS; REACTION KINETICS; REGRESSION ANALYSIS; SYNTHESIS (CHEMICAL); TOLUENE; TRANSESTERIFICATION;

VOLATILE FATTY ACIDS;

INSECTIVORA;

EID: 84856218515     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2011.12.008     Document Type: Article

References (41)

1. K. Othmer Encyclopedia of chemical technology, vol 9. 1991 Wiley New York p. 781
2. G.D. Yadav, and P.H. Mehta Heterogeneous catalysis in esterification reactions: preparation of phenethyl acetate and cyclohexyl acetate by using a variety of solid acidic catalysts Ind Eng Chem Res 33 1994 2198 2208
3. V.V. Bokade, and G.D. Yadav Transesterification of edible and nonedible vegetable oils with alcohols over heteropolyacids supported on acid-treated clay Ind Eng Chem Res 48 2009 9408 9415
4. G.D. Yadav, A.D. Sajgure, and S.B. Dhoot Enzyme catalysis in fine chemical and pharmacuetical industries S.K. Bhattacharya, Enzyme mixtures and complex biosynthesis 2007 Landes Biosciences Austin, TX
5. K. Priya, and A. Chadha Synthesis of hydrocinnamic esters by Pseudomonas cepacia lipase Enzyme Microb Technol 32 2003 485 490 (Pubitemid 36136069)
6. G.D. Yadav, and I.V. Borkar Kinetic modelling of immobilized lipase catalysis in synthesis of n-butyl levulinate Ind Eng Chem Res 47 2008 3358 3363
7. G.D. Yadav, and I.V. Borkar Lipase-catalyzed hydrazinolysis of phenyl benzoate: kinetic modeling approach Process Biochem 45 2010 586 592
8. A. Zaidi, J.L. Gainer, and G. Carta Fatty acid esterification using nylon-immobilized lipase Biotechnol Bioeng 48 1995 601 605
9. M.S. Mahmud, T. Safinski, M.I. Nelson, H.S. Sidhu, and A.A. Adesina Kinetic analysis of oleic acid esterification using lipase as catalyst in a microaqueous environment Ind Eng Chem Res 49 2010 1071 1078
10. K.M. Chabouni, H. Ghamgui, S. Bezzine, A. Rekik, and Y. Gargouri Production of flavour esters by immobilized Staphylococcus simulans lipase in a solvent-free system Process Biochem 41 2006 1692 1698 (Pubitemid 43744535)
11. J.B. Kristensen, X.B. Xu, and H.B. Mu Process optimization using response surface design and pilot plant production of dietary diacylglycerols by lipase-catalyzed glycerolysis J Agric Food Chem 53 2005 7059 7066 (Pubitemid 41375315)
12. S.H. Krishna, S. Divakar, S.G. Prapulla, and N.G. Karanth Enzymatic synthesis of isoamyl acetate using immobilized lipase from Rhizomucor miehei J Biotechnol 87 2001 193 201 (Pubitemid 32378753)
13. G. Langrand, C. Triantaphylides, and J. Baratti Lipase catalyzed formation of flavour esters Biotechnol Lett 10 1988 549 554
14. S.Y. Huang, H.L. Chang, and M. Goto Preparation of surfactant-coated lipase for the esterification of geraniol and acetic acid in organic solvents Enzyme Microb Technol 22 1998 552 557 (Pubitemid 28265820)
15. G.D. Yadav, and P. Sivakumar Enzyme-catalysed optical resolution of mandelic acid via R/S (±)-methyl mandelate in non-aqueous media Biochem Eng J 19 2004 101 107 (Pubitemid 38595518)
16. G.D. Yadav, and P.S. Lathi Synthesis of citronellol laurate in organic media catalyzed by immobilized lipases: kinetic studies J Mol Catal B-Enzym 27 2004 113 119 (Pubitemid 38084948)
17. J.M.S. Rocha, M.H. Gil, and F.A.P. Garcia Optimization of the enzymatic synthesis of n-octyl oleate with immobilized lipase in the absence of solvent J Chem Technol Biotechnol 74 1999 607 612
18. Y. Kato, I. Fujiwara, and Y. Asano A novel method for preparation of optically active α-monobenzoyl glycerol via lipase catalyzed asymmetric transesterification of glycerol Bioorg Med Chem Lett 9 1999 3207 3210
19. G.D. Yadav, and I.V. Borkar Synthesis of n-butyl acetamide over Immobilized lipase J Chem Technol Biotechnol 84 2009 420 426
20. G.D. Yadav, and K.M. Devi Enzymatic synthesis of perlauric acid using Novozym 435 Biochem Eng J 10 2002 93 101 (Pubitemid 34272909)
21. F. Bjorkling, S.E. Godtfredsen, and O. Kirk Lipase-mediated formation of peroxycarboxylic acids used in catalytic epoxidation of alkenes J Chem Soc Chem Commun 19 1990 1301 1303
22. F. Bjorkling, H. Frykman, S.E. Godtfredsen, and O. Kirk Lipase catalyzed synthesis of peroxycarboxylic acids and lipase-mediated oxidations Tetrahedron 48 1992 4587 4592
23. G.D. Yadav, and I.V. Borkar Kinetic modeling of microwave assisted chemo-enzymatic epoxidation of styrene to styrene oxide AIChE J 52 2006 1235 1247
24. S.C. Lemoult, P.F. Richardsen, and S.M. Roberts Lipase-catalyzed Baeyer-Villiger reactions J Chem Soc Perkin Trans 1 1995 89 91
25. T. Oliver, I. Alfonso, and V. Gotor Lipase catalysed Michael addition of secondary amines to acrylonitrile Chem Commun 2004 1724 1725 (Pubitemid 39127853)
26. A. Jackson A global overview of the flavours and fragrances market, vol 4 2009 IAL Consultants London p. 14
27. J.M.R. Nogales, E. Roura, and E. Contreras Biosynthesis of ethyl butyrate using immobilized lipase: a statistical approach Process Biochem 40 2005 63 68 (Pubitemid 39197391)
28. S.P. Bhatia, G.A. Wellington, J. Cocchiara, J. Lalko, C.S. Letizia, and A.M. Api Fragrance material review on cinnamyl acetate Food Chem Toxicol 45 2007 S53 S57
29. Chuanfa Y, Ruhui Z, Miaomiao Y, Lingfei R, Haohao H. Method for preparing cinnamyl acetate. CN Patent 101260042.
30. V.G. Devulapelli, and H.S. Weng Synthesis of cinnamyl acetate by solid-liquid phase transfer catalysis: kinetic study with a batch reactor Catal Commun 10 2009 1638 1642
31. Novo Nordisk Product Sheet for Novozym 435, Lipozyme RM IM and Lipozyme TL IM.
32. H.K. Weber, H. Stecher, and K. Faber Sensitivity of microbial lipases to acetaldehyde formed by acyl-transfer reactions from vinyl esters Biotechnol Lett 17 1995 803 808
33. T. Yang, M. Rebsdorf, U. Engelrud, and X. Xu Enzymatic production of monoacylglycerols containing polyunsaturated fatty acids through an efficient glycerolysis system J Agric Food Chem 53 2005 1475 1478
34. M.D. Romero, L. Calvo, C. Alba, A. Daneshfar, and H.S. Ghaziaskar Enzymatic synthesis of isoamyl acetate with immobilized Candida antarctica lipase in n-hexane Enzyme Microb Technol 35 2005 42 48 (Pubitemid 40615642)
35. H. Segel Enzyme kinetics. In behaviour and analysis of rapid equilibrium and steady-state enzyme systems 1975 Wiley New York 309-319
36. G.D. Yadav, and P.S. Lathi Kinetics and mechanism of synthesis of butyl isobutyrate over immobilised lipases Biochem Eng J 16 2003 245 252 (Pubitemid 37288381)
37. R.H. Perry, and D.W. Green Perry's chemical engineers' handbook 6th ed. 1984 McGraw-Hill New York p. 226
38. J.A. Arcos, C.G. Hill, and C. Otero Kinetics of the lipase-catalyzed synthesis of glucose esters in acetone Biotech Bioeng 73 2001 104 110 (Pubitemid 32291399)
39. J.E. Puskas, C.K. Chiang, and M.Y. Sen Green cationic polymerizations and polymer functionalization for biotechnology R.T. Mathers, M.A.R. Meier, Green polymerization methods: renewable starting materials, catalysis and waste reduction 2011 Wiley-VCH Weinheim 313 347
40. G.D. Yadav, and A.H. Trivedi Kinetic modeling of immobilized-lipase catalyzed transesterification of n-octanol with vinyl acetate in non aqueous media Enzyme Microb Technol 32 2003 783 789 (Pubitemid 36589020)
41. G.D. Yadav, and I.V. Borkar Kinetic and mechanistic investigation of microwave-assisted lipase catalyzed synthesis of citronellyl acetate Ind Eng Chem Res 48 2009 7915 7922