Enzymatic synthesis of farnesyl laurate in organic solvent: Initial water activity, kinetics mechanism, optimization of continuous operation using packed bed reactor and mass transfer studies

Bioprocess and Biosystems Engineering

Volumn 34, Issue 6, 2011, Pages 687-699

  Rahman, N K ^a   Kamaruddin, A H ^a   Uzir, M H ^a  

^a SCHOOL OF CHEMICAL ENGINEERING   (Malaysia)

Author keywords

Esterification; Mass transfer; Ordered Bi Bi mechanism; Packed bed reactor; Water activity

Indexed keywords

CONTINUOUS OPERATION; DEAD-END COMPLEX; ENZYMATIC SYNTHESIS; EXPERIMENTAL DATA; FARNESOL; INFLUENCE OF WATER; KINETICS MECHANISM; KINETICS STUDIES; LAURATE; LAURIC ACID; LIPOZYME; MASS TRANSFER STUDIES; MOLAR CONVERSION; OPTIMUM CONDITIONS; ORDERED-BI-BI MECHANISM; PACKED BED REACTOR; REACTION MEDIUM; WATER ACTIVITY;

CHEMICAL REACTORS; ENZYMES; ESTERIFICATION; ESTERS; KINETICS; MASS TRANSFER; ORGANIC SOLVENTS; RATE CONSTANTS; SATURATED FATTY ACIDS; SYNTHESIS (CHEMICAL); WATER CONTENT;

PACKED BEDS;

FARNESYL LAURATE; FUNGAL ENZYME; ORGANIC SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CONTINUOUS FLOW REACTOR; CONTROLLED STUDY; ENZYME IMMOBILIZATION; ENZYME KINETICS; ENZYME SUBSTRATE; ENZYME SYNTHESIS; ESTERIFICATION; FLOW RATE; GAS CHROMATOGRAPHY; HYDRATION; NONHUMAN; PACKED BED REACTOR; PRIORITY JOURNAL; PROCESS OPTIMIZATION; RESPONSE SURFACE METHOD; RHIZOMUCOR; RHIZOMUCOR MIEHEI; TEMPERATURE; WATER CONTENT;

ALGORITHMS; BIOCATALYSIS; BIOREACTORS; ENZYMES, IMMOBILIZED; ESTERIFICATION; FARNESOL; KINETICS; LAURATES; LIPASE; MODELS, CHEMICAL; SOLVENTS; WATER;

EID: 79960458632     PISSN: 16157591     EISSN: 16157605     Source Type: Journal    
DOI: 10.1007/s00449-011-0518-y     Document Type: Article

References (65)

1. MS Shintre RS Ghadge SB Sawant 2002 Lipolase catalyzed synthesis of benzyl esters of fatty acids Biochem Eng J 12 131 141 10.1016/S1369-703X(02) 00066-9 1:CAS:528:DC%2BD38XntVajtL0%3D (Pubitemid 35167949)
2. SW Chang JF Shaw CK Yang CJ Shieh 2007 Optimal continuous biosynthesis of hexyl laurate by a packed bed bioreactor J Process Biochem 42 1362 1366 10.1016/j.procbio.2007.06.008 1:CAS:528:DC%2BD2sXpsFKisr4%3D (Pubitemid 47268824)
3. MBA Rahman UH Zaidan M Basri MZ Hussien RNZRA Rahman AB Salleh 2008 Enzymatic synthesis of methyl adipate ester using lipase from Candida rugosa immobilized on Mg, Zn and Ni of layered double hydroxides (LDHs) J Mol Cat B Enzym 50 33 39 10.1016/j.molcatb.2007.09.020 (Pubitemid 350123115)
4. DY Ganapati BD Shrikant 2009 Immobilized lipase-catalysed synthesis of cinnamyl laurate in non-aqueous media J Mol Cat B Enzym 57 34 39 10.1016/j.molcatb.2008.06.013
5. H Horchani NB Salem Z Zarai A Sayari Y Gargouri M Chaabouni 2010 Enzymatic synthesis of eugenol benzoate by immobilized Staphylococcus aureus lipase: optimization using response surface methodology and determination of antioxidant activity Bioresource Technol 101 2809 2817 10.1016/j.biortech.2009. 10.082 1:CAS:528:DC%2BC3cXjvVentQ%3D%3D
6. G Carrea G Ottolina S Riva 1995 Role of solvents in the control of enzyme selectivity in organic media Trends Biotechnol 13 63 69 10.1016/S0167-7799(00) 88907-6 1:CAS:528:DyaK2MXktFWis7g%3D
7. PJ Halling 1992 Salt hydrates for water activity control in biocatalysts in organic media Biotechnol Tech 6 271 276 10.1007/BF02439357 1:CAS:528:DyaK38XmtFSlt74%3D
8. ZQ Duan W Du DH Liu 2010 The pronounced effect of water activity on the positional selectivity of Novozym 435 during 1, 3-diolein synthesis by esterification Catal Commun 11 356 358 10.1016/j.catcom.2009.10.030 1:CAS:528:DC%2BC3cXktlSjtA%3D%3D
9. F Chamouleau D Coulon M Girardin M Ghoul 2001 Influence of water activity and water content on sugar esters lipase-catalyzed synthesis in organic media J Mol Cat B Enzym 11 949 954 10.1016/S1381-1177(00)00166-1 1:CAS:528: DC%2BD3MXptlWntQ%3D%3D (Pubitemid 32114282)
10. S Panke MG Wubbolts 2002 Enzyme technology and bioprocess engineering Curr Opin Biotechnol 13 111 116 10.1016/S0958-1669(02)00302-6 1:CAS:528:DC%2BD38Xis1Clt7o%3D (Pubitemid 34310368)
11. M Adamczack UT Bornscheuer 2009 Improving ascorbyl oleate synthesis catalyzed by Candida antartica lipase B in ionic liquids and water activity control by salts hydrates J Process Biochem 44 257 261 10.1016/j.procbio.2008. 10.014
12. P Pires-Cabral MMR da Fonseca S Ferreira-Dias 2009 Synthesis of ethyl butyrate in organic media catalyzed by Candida rugosa lipase immobilized in polyurethane foams: a kinetic study Biochem Eng J 43 327 332 10.1016/j.bej.2008.11.002 1:CAS:528:DC%2BD1MXhtVeisb0%3D
13. A Daneshfar HS Ghaziaskar L Shiri MH Manafi M Nikorazm S Abassi 2007 Synthesis of 2-ethylhexyl-2-ethylhexanoate catalyzed by immobilized lipase in n-hexane: a kinetic study Biochem Eng J 37 279 284 10.1016/j.bej.2007.05.007 1:CAS:528:DC%2BD2sXht1KjsrrF (Pubitemid 350019039)
14. JW Swarts P Vossenberg MH Meerman AEM Janssen RM Boom 2008 Comparison of two-phase lipase-catalysed esterification on micro and bench-scale Biotechnol Bioeng 99 855 861 10.1002/bit.21650 1:CAS:528:DC%2BD1cXit1Kqsr4%3D (Pubitemid 351316627)
15. Elfanso E, Garland M, Loh KC, Talukder MMR, Widjaja E (2009) In situ monitoring of turbid immobilized lipase-catalyzed esterification of oleic acid using fiber-optic Raman spectroscopy. Catal Today (in Press, Corrected Proof)
16. P Znidarsic-Plazl I Plazl 2009 Modelling and experimental studies on lipase-catalyzed isoamyl acetate synthesis in a microreactor Process Biochem 44 1115 1121 10.1016/j.procbio.2009.06.003 1:CAS:528:DC%2BD1MXhtVKlsLfF
17. DY Ganapati KM Devi 2002 Enzymatic synthesis of perlauric acid using Novozym 435 Biochem Eng J 10 93 101 10.1016/S1369-703X(01)00164-4 (Pubitemid 34272909)
18. DY Ganapati PS Lathi 2004 Synthesis of citronellyl laurate in organic media catalyzed by immobilized lipases: kinetic studies J Mol Cat B Enzym 27 113 119 10.1016/j.molcatb.2003.10.004 (Pubitemid 38084948)
19. NA Serri AH Kamaruddin WS Long 2006 Studies of reaction parameters on synthesis of citronellyl laurate ester via immobilized candida rugosa lipase in organic media Bioprocess Biosyst Eng 29 253 260 10.1007/s00449-006-0074-z 1:CAS:528:DC%2BD28XpsFWmtrk%3D (Pubitemid 44394709)
20. PA Claon CC Akoh 1994 Effect of reaction parameters on SP435 lipase-catalyzed synthesis of citronellyl acetate in organic solvent Enzym Microb Technol 15 835 838 10.1016/0141-0229(94)90056-6 (Pubitemid 24306278)
21. H Stamatis P Christakopoulos D Kekos BJ Marcis FN Kolisis 1998 Studies on the synthesis of short-chain geranyl esters catalyzed by Fusarium oxysporum esterase in organic solvents J Mol Cat B Enzym 4 229 236 10.1016/S1381-1177(98) 00003-4 1:CAS:528:DyaK1cXjvVSktLw%3D (Pubitemid 28303939)
22. T Chattarjee DK Bhattacharyya 1998 Synthesis of monoterpene esters by alcoholysis reaction with Mucor miehei lipase in a solvent-free medium J Am Oil Chem Soc 75 651 655 10.1007/s11746-998-0079-7 (Pubitemid 128553470)
23. CG Laudani M Habulin Z Knez GD Porta E Reverchon 2007 Immobilized lipase-mediated long-chain fatty acid esterification in dense carbon dioxide: bench scale packed bed reactor study J Supercrit Fluids 41 74 81 10.1016/j.supflu.2006.08.017 1:CAS:528:DC%2BD2sXjsVOjtbo%3D (Pubitemid 46441775)
24. N Khaled D Montet M Pina J Graille 1991 Fructose oleate synthesis in a fixed catalyst bed reactor Biotechnol Lett 13 167 172 10.1007/BF01025812 1:CAS:528:DyaK3MXitVGnu78%3D
25. JH Xu Y Kato Y Asano 2001 Efficient preparation of (R)-α- monobenzoyl glycerol by lipase catalysed asymmetric esterification: optimization and operation in a packed bed reactor Biotechnol Bioeng 73 493 499 10.1002/bit.1084 1:CAS:528:DC%2BD3MXktVSltbY%3D (Pubitemid 32574324)
26. I Petzelbauer B Kuhna B Splechtna KD Kulbe B Nidetzky 2002 Development of an ultrahigh-temperature process for the enzymeatic hydrolysis of lactose IV: immobilization of two thermostable β-glycosidases and optimization of packed bed reactor for lactose conversion Biotechnol Bioeng 77 619 631 10.1002/bit.10110 1:CAS:528:DC%2BD38XitFSgu7w%3D (Pubitemid 34712325)
27. WW Xi JH Xi 2005 Preparation of enantiopure (S)-ketoprofen by immobilized Candida rugosa lipase in packed bed reactor Proc Biochem 40 2161 2166 10.1016/j.procbio.2004.08.003 1:CAS:528:DC%2BD2MXhsVOhtL4%3D (Pubitemid 40257043)
28. Y Watanabe Y Shimada A Sugihara Y Tominaga 2001 Enzymatic conversion of waste edible oil to biodiesel fuel in a fixed bed bioreactor J Am Oil Chem Soc 78 703 707 10.1007/s11746-001-0329-5 1:CAS:528:DC%2BD3MXmt12htrg%3D (Pubitemid 32932256)
29. K Nie F Xie F Wang T Tan 2006 Lipase catalyzed methanolysis to produce biodiesel: optimization of the biodiesel production J Mol Cat B Enzym 43 142 147 10.1016/j.molcatb.2006.07.016 1:CAS:528:DC%2BD28Xht1SgsbzI (Pubitemid 44693436)
30. D Royon M Daz G Ellenrieder S Locatelli 2007 Enzymatic production of biodiesel from cotton seed oil using t-butanol as a solvent Biores Technol 98 648 653 10.1016/j.biortech.2006.02.021 1:CAS:528:DC%2BD28Xps1Wks78%3D (Pubitemid 44375010)
31. E Roca N Minander B Hahn-Hagerdal 1996 Xylitol production by immobilized recombinant Saccharomyces cerevisiae in a continuous packed bed bioreactor Biotechnol Bioeng 51 317 326 10.1002/(SICI)1097-0290(19960805)51:3<317::AID- BIT7>3.0.CO;2-G 1:CAS:528:DyaK28XksVCms70%3D (Pubitemid 26286400)
32. H Mu X Xu CE Hoy 1998 Production of specific-structured triacylglycerols by lipase catalyzed interesterification in a laboratory scale continuous reactor J Am Oil Chem Soc 75 1187 1193 1:CAS:528:DyaK1cXmsVKis7Y%3D (Pubitemid 128567018)
33. X Xu S Balchen CE Hoy J Adler-Nissen 1998 Production of specific-structured lipids by enzymatic interesterification in a pilot continuous enzyme reactor J Am Oil Chem Soc 75 1573 1579 10.1007/s11746-998- 0096-6 1:CAS:528:DyaK1cXnvFOktLo%3D (Pubitemid 128607914)
34. Y Shimada M Suenaga A Sugihara S Nakai Y Tominaga 1996 Continuous production of structured lipid containing γ-linolenic and caprylic acids by immobilized Rhizopus delemar lipase J Am Oil Chem Soc 76 189 193 10.1007/s11746-999-0217-x
35. SFA Halim AH Kamaruddin WJN Fernando 2009 Continuous biosynthesis of biodiesel from waste cooking palm oil in a packed bed reactor: optimization using response surface methodology (RSM) and mass transfer studies Biores Technol 100 710 716 10.1016/j.biortech.2008.07.031 1:CAS:528:DC%2BD1cXht1OksbnF
36. Montgomery DC (2001) Design and analysis of experiments, 5th edn. John Wiley & Sons, New York
37. HA Aziz AH Kamaruddin MZA Bakar 2007 Process optimization studies on solvent extraction with naphthalene-2-boronic acid ion-pairing with trioctylmethylammonium chloride in sugar purification using design of experiments Sep Purif Technol 60 190 197 10.1016/j.seppur.2007.08.011 (Pubitemid 351389821)
38. VRC Murty J Bhat PKA Muniswaran 2004 Mass transfer effects in immobilized lipase packed bed reactor during the hydrolysis of rice bran oil Chem Biochem 18 177 182 1:CAS:528:DC%2BD2cXmtVyisb0%3D
39. VRC Murty J Bhat PKA Muniswaran 2005 External mass transfer effects during the hydrolysis of rice bran oil in immobilized lipase packed bed reactor Chem Biochem 19 57 61 1:CAS:528:DC%2BD2MXjt1Ois78%3D (Pubitemid 40479463)
40. Y Caro M Pina F Turon S Guilbert E Mougeot DV Fetsch P Attwool J Graille 2002 Plant lipase: biocatalyst aqueous environment in relation to optimal catalytic activity in lipase-catalyzed synthesis reactions Biotechnol Bioeng 77 693 703 10.1002/bit.10155 1:CAS:528:DC%2BD38XitFSnsr4%3D (Pubitemid 34712332)
41. LJL Giraldo M Laguerre J Lecomte MC Figueroa-Espinoza N Barouh B Barea Villeneuve 2007 Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium Enzym Microb Technol 41 721 726 10.1016/j.enzmictec.2007.06. 004 (Pubitemid 47371025)
42. CM Rosell AM Vaidya 1995 Twin-core packed bed reactors for organic phase enzymatic esterification with water activity control Appl Microbiol Biotechnol 44 283 286 10.1007/BF00169917 1:CAS:528:DyaK28XitVers7c%3D (Pubitemid 26024347)
43. C Humeau M Girardin B Rovel A Miclo 1998 Effect of the thermodynamic water activity and the reaction medium hydrophobicity on the enzymatic synthesis of ascorbyl palmitate J Biotechnol 63 1 8 10.1016/S0168-1656(98)00069-8 1:CAS:528:DyaK1cXltFWru7c%3D (Pubitemid 28375737)
44. BM Lue S Karboune FK Yeboah S Kermasha 2005 Lipase-catalyzed esterification of cinnamic acid and oleyl alcohol in organic solvent media J Chem Technol Biotechnol 80 462 468 10.1002/jctb.1237 1:CAS:528: DC%2BD2MXjtVeqtbc%3D (Pubitemid 40443678)
45. IJ Kang PH Pfromm ME Rezac 2005 Real time measurement and control of thermodynamic water activities for enzymatic catalysis in hexane J Biotechnol 119 147 154 10.1016/j.jbiotec.2005.04.002 1:CAS:528:DC%2BD2MXpslCht7c%3D (Pubitemid 41219543)
46. R Awang M Basri S Ahmad AB Salleh 2000 Enzymatic esterification of dihydroxystearic acid J Am Oil Chem Soc 77 609 612 10.1007/s11746-000-0098-1 1:CAS:528:DC%2BD3cXksVOgu78%3D
47. Piszkiewicz D (1977) Kinetics of chemical and enzyme-catalyzed reactions. Oxford University Press, New York
48. Segel IH (1975) Enzyme kinetics: behavior and analysis of rapid equilibrium and steady-state enzyme system. John Wiley & Sons Inc., New York
49. K Faber S Riva 1992 Enzyme-catalyzed irreversible acyl transfer Synthesis 10 895 910 10.1055/s-1992-26255
50. DY Ganapati AH Trivedi 2003 Kinetic modeling of immobilized lipase-catalyzed transesterification of n-octanol with vinyl acetate in non-aqueous media Enzym Microb Technol 32 783 789 (Pubitemid 36589020)
51. Kula MR (2002) In: Druz K, Waldmann H (eds) Introduction: in enzyme catalysis in organic synthesis. Wiley-VCH, Germany
52. P Ye ZK Xu AF Che J Wu P Seta 2005 Chitosan-tethered poly(acylonitrile- co-maleic acid) hollow fiber membrane for lipase immobilization Biomaterials 26 6394 6403 10.1016/j.biomaterials.2005.04.019 1:CAS:528:DC%2BD2MXlsVCktLY%3D (Pubitemid 40828395)
53. Shuler ML, Kargi F (1992) Basic concepts: bioprocess engineering. Prentice Hall, New Jersey
54. Liese A (2000) Industrial Biotransformations. Wiley-VCH, Germany
55. KT Lee AM Mohtar NF Zainuddin S Bhatia 2005 Optimum condition for preparation of flue gas desulfurization absorbent rice husk ash Fuel 84 143 151 10.1016/j.fuel.2004.08.018 1:CAS:528:DC%2BD2cXptV2lur0%3D
56. X Yuan J Liu G Zheng J Shi J Tong G Huang 2008 Optimization of conversion of waste rapeseed oil with high FFA to biodiesel using response surface methodology Renew Energy 33 1678 1684 10.1016/j.renene.2007.09.007 1:CAS:528:DC%2BD1cXjvFehsbo%3D (Pubitemid 351417439)
57. Q Beg V Sahai R Gupta 2003 Statistical media optimization and alkaline protease production from Bacillus mojavensis in bioreactor Proc Biochem 39 203 209 10.1016/S0032-9592(03)00064-5 1:CAS:528:DC%2BD3sXotVOqtrw%3D (Pubitemid 38033682)
58. ON Ciftci S Fadlloglu F Gogus 2008 Conversion of olive pomace oil to cocoa butter-like fat in a packed bed enzyme reactor Biores Technol 100 324 329 10.1016/j.biortech.2008.05.035
59. O Tepe AY Dursun 2008 Combined effects of external mass transfer and biodegradation rates on removal of phenol by immobilized Ralstonia eutropha in a packed bed reactor J Hazard Mat 151 9 16 10.1016/j.jhazmat.2007.05.049 1:CAS:528:DC%2BD1cXnvVemtA%3D%3D
60. T Watanabe M Sugiura M Sato N Yamada K Nakanishi 2005 Diacylglycerol production in a packed bed bioreactor Proc Biochem 40 637 643 10.1016/j.procbio.2004.01.046 1:CAS:528:DC%2BD2cXpt1WgsLo%3D (Pubitemid 39437863)
61. YM Xia Y Fang ZG Xu HY Hu YA Shen J Brown Jr 2004 A novel process for enzymatic synthesis of N-lauroyl-β-amino propionitrile using a packed bed reactor coupled with on-line separation J Mol Cat B Enzym 31 111 115 10.1016/j.molcatb.2004.08.003 1:CAS:528:DC%2BD2cXpsFeqt7c%3D (Pubitemid 39505291)
62. LB Formuso CC Akoh 2002 Lipase-catalyzed acidolysis of olive oil and caprylic acid in a bench-scale packed bed bioreactor Food Res Intern 35 15 21 10.1016/S0963-9969(00)00158-7 (Pubitemid 34775857)
63. NN Gandhi SB Sawant JB Joshi 1995 Study on the Lipozyme catalyzed synthesis of butyl laurate Biotechnol Bioeng 46 1 12 10.1002/bit.260460102 1:CAS:528:DyaK2MXktlGmsbs%3D
64. MD Ramero L Calvo C Alba A Daneshfar HS Ghaziaskar 2005 Enzymatic synthesis of isoamyl acetate with immobilized Candida antartica lipase in n-hexane Enzym Microb Technol 37 42 48 10.1016/j.enzmictec.2004.12.033 (Pubitemid 40615642)
65. N Chaibakhsh MBA Rahman SA Aziz M Basri AB Salleh RNZRA Rahman 2009 Optimized lipase-catalyzed synthesis of adipate ester in a solvent-free system J Indust Microb Biotechnol 36 1149 1155 10.1007/s10295-009-0596-x 1:CAS:528:DC%2BD1MXhtVaitrnO