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Enzymatic Synthesis of Citronellyl Palmitate in Organic Media: Process Optimization and Kinetic Evaluation
Corresponding Author(s) : Ahmad Adnan
Asian Journal of Chemistry,
Vol. 28 No. 2 (2016): Vol 28 Issue 2
Abstract
Kinetics of citronellyl palmitate ester formation from citronellol-palmitic acid was studied by using immobilized lipase Novozym 435 Candida antarctica. Lipase immobilized onto macroporous acrylic resin gave the best results. Different parameters like reaction medium, temperature, substrate concentration were optimized for the enzymatic synthesis of citronellyl palmitate. The optimum temperature was 30 °C, optimum molar ratio of alcohol to acid was 1:1. The best solvent for maximum esterification was n-hexane. At higher concentration of alcohol enzyme inhibition took place.
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- J.M.R. da Silva and M.G. Nascimento, Process Biochem., 47, 517 (2012); doi:10.1016/j.procbio.2011.12.019.
- N.A. Serri, A.H. Kamaruddin and K.Y.T. Len, Food Bioprod. Process., 88, 327 (2010); doi:10.1016/j.fbp.2008.12.002.
- M. Habulin, S. Sabeder, M. Paljevac, M. Primozic and Z. Knez, J. Supercrit. Fluids, 43, 199 (2007); doi:10.1016/j.supflu.2007.05.001.
- G.D. Yadav and P.S. Lathi, J. Mol. Catal. B, 27, 113 (2004); doi:10.1016/j.molcatb.2003.10.004.
- J. Tramper, M.H. Bermue, H.H. Beeftink and U. Von Stokar, Biocatalysis in Non-Conventional Media, Elsevier Science Publishers B.V., Amsterdam, The Netherlands (1992).
- T. Garcia, A. Coteron, M. Martinez and J. Aracil, Chem. Eng. Sci., 55, 1411 (2000); doi:10.1016/S0009-2509(99)00425-X.
- D. Mukesh, S. Jadhav, A.A. Banerji, K. Thakkar and H.S. Bevinakatti, J. Chem. Technol. Biotechnol., 69, 179 (1997); doi:10.1002/(SICI)1097-4660(199706)69:2<179::AID-JCTB697>3.0.CO;2-4.
- J.A. Arcos, C.G. Hill and C. Otero, Biotechnol. Bioeng., 73, 104 (2001); doi:10.1002/bit.1042.
- G.D. Yadav and P.S. Lathi, Biochem. Eng. J., 16, 245 (2003); doi:10.1016/S1369-703X(03)00026-3.
- G.D. Yadav and K.M. Devi, Biochem. Eng. J., 10, 93 (2002); doi:10.1016/S1369-703X(01)00164-4.
- R.Y. Kharisov, N.I. Petukhova, A.R. Davletova, N.M. Ishmuratova, V.V. Zorin, G.Y. Ishmuratov and G.A. Tolstikov, Chem. Nat. Comp., 36, 210 (2000); doi:10.1007/BF02236433.
- T.H. Chao, L. Ehrman, A. Permaul, R. Vincent, L. Sattaur and D. Brandt, J. Chem. Ecol., 36, 933 (2010); doi:10.1007/s10886-010-9838-7.
- G. Haniotakis, W. Francke, K. Mori, H. Redlich and V. Schurig, J. Chem. Ecol., 12, 1559 (1986); doi:10.1007/BF01012372.
- A. Daneshfar, H.S. Ghaziaskar, L. Shiri, M.H. Manafi, M. Nikorazm and S. Abassi, Biochem. Eng. J., 37, 279 (2007); doi:10.1016/j.bej.2007.05.007.
- P. Pires-Cabral, M.M.R. da Fonseca and S. Ferreira-Dias, Biochem. Eng. J., 33, 148 (2007); doi:10.1016/j.bej.2006.10.015.
- A.E.M. Janssen, A.M. Vaidya and P.J. Halling, Enzyme Microb. Technol., 18, 340 (1996); doi:10.1016/0141-0229(95)00075-5.
- P. Pires-Cabral, M.M.R. da Fonseca and S. Ferreira-Dias, Biochem. Eng. J., 43, 327 (2009); doi:10.1016/j.bej.2008.11.002.
- L. Azocar, G. Ciudad, H.J. Heipieper, R. Munoz and R. Navia, J. Biosci. Bioeng., 112, 583 (2011); doi:10.1016/j.jbiosc.2011.08.001.
- T. Issariyakul, M.G. Kulkarni, L.C. Meher, A.K. Dalai and N.N. Bakhshi, Chem. Eng. J., 140, 77 (2008); doi:10.1016/j.cej.2007.09.008.
- M. Samad, A.B. Salleh, C.N.A. Razak, K. Ampon, W.M.Z.W. Yunus and M. Basri, World J. Microbiol. Biotechnol., 6, 390 (1990); doi:10.1007/BF01202120.
- M.N. Tahir, A. Adnan, E. Strömberg and P. Mischnick, Bioprocess Biosyst. Eng., 35, 535 (2012); doi:10.1007/s00449-011-0626-8.
- M.N. Tahir, A. Adnan and P. Mischnick, Process Biochem., 44, 1276 (2009); doi:10.1016/j.procbio.2009.06.019.
References
J.M.R. da Silva and M.G. Nascimento, Process Biochem., 47, 517 (2012); doi:10.1016/j.procbio.2011.12.019.
N.A. Serri, A.H. Kamaruddin and K.Y.T. Len, Food Bioprod. Process., 88, 327 (2010); doi:10.1016/j.fbp.2008.12.002.
M. Habulin, S. Sabeder, M. Paljevac, M. Primozic and Z. Knez, J. Supercrit. Fluids, 43, 199 (2007); doi:10.1016/j.supflu.2007.05.001.
G.D. Yadav and P.S. Lathi, J. Mol. Catal. B, 27, 113 (2004); doi:10.1016/j.molcatb.2003.10.004.
J. Tramper, M.H. Bermue, H.H. Beeftink and U. Von Stokar, Biocatalysis in Non-Conventional Media, Elsevier Science Publishers B.V., Amsterdam, The Netherlands (1992).
T. Garcia, A. Coteron, M. Martinez and J. Aracil, Chem. Eng. Sci., 55, 1411 (2000); doi:10.1016/S0009-2509(99)00425-X.
D. Mukesh, S. Jadhav, A.A. Banerji, K. Thakkar and H.S. Bevinakatti, J. Chem. Technol. Biotechnol., 69, 179 (1997); doi:10.1002/(SICI)1097-4660(199706)69:2<179::AID-JCTB697>3.0.CO;2-4.
J.A. Arcos, C.G. Hill and C. Otero, Biotechnol. Bioeng., 73, 104 (2001); doi:10.1002/bit.1042.
G.D. Yadav and P.S. Lathi, Biochem. Eng. J., 16, 245 (2003); doi:10.1016/S1369-703X(03)00026-3.
G.D. Yadav and K.M. Devi, Biochem. Eng. J., 10, 93 (2002); doi:10.1016/S1369-703X(01)00164-4.
R.Y. Kharisov, N.I. Petukhova, A.R. Davletova, N.M. Ishmuratova, V.V. Zorin, G.Y. Ishmuratov and G.A. Tolstikov, Chem. Nat. Comp., 36, 210 (2000); doi:10.1007/BF02236433.
T.H. Chao, L. Ehrman, A. Permaul, R. Vincent, L. Sattaur and D. Brandt, J. Chem. Ecol., 36, 933 (2010); doi:10.1007/s10886-010-9838-7.
G. Haniotakis, W. Francke, K. Mori, H. Redlich and V. Schurig, J. Chem. Ecol., 12, 1559 (1986); doi:10.1007/BF01012372.
A. Daneshfar, H.S. Ghaziaskar, L. Shiri, M.H. Manafi, M. Nikorazm and S. Abassi, Biochem. Eng. J., 37, 279 (2007); doi:10.1016/j.bej.2007.05.007.
P. Pires-Cabral, M.M.R. da Fonseca and S. Ferreira-Dias, Biochem. Eng. J., 33, 148 (2007); doi:10.1016/j.bej.2006.10.015.
A.E.M. Janssen, A.M. Vaidya and P.J. Halling, Enzyme Microb. Technol., 18, 340 (1996); doi:10.1016/0141-0229(95)00075-5.
P. Pires-Cabral, M.M.R. da Fonseca and S. Ferreira-Dias, Biochem. Eng. J., 43, 327 (2009); doi:10.1016/j.bej.2008.11.002.
L. Azocar, G. Ciudad, H.J. Heipieper, R. Munoz and R. Navia, J. Biosci. Bioeng., 112, 583 (2011); doi:10.1016/j.jbiosc.2011.08.001.
T. Issariyakul, M.G. Kulkarni, L.C. Meher, A.K. Dalai and N.N. Bakhshi, Chem. Eng. J., 140, 77 (2008); doi:10.1016/j.cej.2007.09.008.
M. Samad, A.B. Salleh, C.N.A. Razak, K. Ampon, W.M.Z.W. Yunus and M. Basri, World J. Microbiol. Biotechnol., 6, 390 (1990); doi:10.1007/BF01202120.
M.N. Tahir, A. Adnan, E. Strömberg and P. Mischnick, Bioprocess Biosyst. Eng., 35, 535 (2012); doi:10.1007/s00449-011-0626-8.
M.N. Tahir, A. Adnan and P. Mischnick, Process Biochem., 44, 1276 (2009); doi:10.1016/j.procbio.2009.06.019.