Kinetics and gibbs function studies on lipase-catalyzed production of non-phthalate plasticizer
Loading...
Date
43912
Journal Title
Journal ISSN
Volume Title
Type
Article
Publisher
Japan Oil Chemists Society
Series Info
Journal of Oleo Science;Volume 69, Issue 7, 2020, Pages 727-735
Scientific Journal Rankings
Abstract
Petroleum based phthalate plasticizers encounter enormous claims to prohibit their production due to their harmful health impacts when they are mixed with plastics. That is why efforts are being done to find safer natural alternatives. We have investigated the reaction kinetics of the esterification epoxidation of oleic acid and 2-ethylhexanol in the presence of hydrogen peroxide catalyzed using Candida antarctica lipase (Novozym 435, Novozymes, Kobenhavn, Denmark). The product of this reaction is epoxidized 2-ethylhexyl oleate, a non-phthalate green plasticizer. The kinetic model for this reaction follows a multi-substrate Ping-Pong Bi-Bi mechanism with competitive inhibition by the alcohol. The reaction’s kinetic parameters were found to be 0.76 M, 0.37 M, 0.08 M, and 37.20 mM/min for Michalis-Menten constant for oleic acid (Kmo), Michalis-Menten constant for alcohol (Kma ), alcohol inhibition constant (Kia ), and maximum reaction velocity (Vmax), respectively. Then the Gibbs function analysis of the transition state based on the Arrhenius and Eyring equations was carried out. The internal diffusional limitations were found to be negligible as the effectiveness factor took the value of almost unity. While the external mass transfer resistance had no effect on the reaction due to operating at relatively high agitation speed and high temperature. This investigation confirms that this reaction was only kinetically controlled. © 2020 by Japan Oil Chemists’ Society
Description
Scopus
Keywords
Gibbs function, Ping-Pong Bi-Bi model, plasticizer, Novozym 435, esterification-epoxidation
Citation
Hosney, H., Nadiem, B., Ashour, I., Mustafa, I., El-Shibiny, A. Epoxidized vegetable oil and bio-based materials as PVC plasticizer (Open Access) (2018) Journal of Applied Polymer Science, 135 (20), art. no. 46270. Cited 23 times. http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1097-4628 doi: 10.1002/app.46270 View at Publisher 2 Samarth, N.B., Mahanwar, P.A. Modified vegetable oil based additives as a future polymeric material-Re-view (2015) Open J. Org. Polym. Mater, 5, pp. 1-22. Cited 46 times. 2 3 (2008) Regulation(EC)No 1272/2008 of the European Parlia-ment and of the council. Cited 43 times. 3 OJEU 4 (2012) 4)LO 2012-1442. OJFR 5 Borsato, D., Galvan, D., Pereira, J.L., Orives, J.R., Angilelli, K.G., Coppo, R.L. Kinetic and thermodynamic parameters of biodiesel oxidation with synthetic antioxidants: Simplex centroid mixture design (Open Access) (2014) Journal of the Brazilian Chemical Society, 25 (11), pp. 1984-1992. Cited 21 times. http://jbcs.sbq.org.br/imagebank/pdf/v25n11a08.pdf doi: 10.5935/0103-5053.20140182 View at Publisher 6 Omrani, I., Ahmadi, A., Farhadian, A., Shendi, H.K., Babanejad, N., Nabid, M.R. Synthesis of a bio-based plasticizer from oleic acid and its evaluation in PVC formulations (2016) Polymer Testing, 56, pp. 237-244. Cited 13 times. doi: 10.1016/j.polymertesting.2016.10.027 View at Publisher 7 Hosney, H., Mustafa, A. Semi-continuous production of 2-ethyl hexyl ester in a packed bed reactor: Optimization and economic evaluation (Open Access) (2020) Journal of Oleo Science, 69 (1), pp. 31-41. https://www.jstage.jst.go.jp/article/jos/69/1/69_ess19229/_pdf doi: 10.5650/jos.ess19229 View at Publisher 8 Abdelmoez, W., Mostafa, N.A., Mustafa, A. Utilization of oleochemical industry residues as substrates for lipase production for enzymatic sunflower oil hydrolysis (2013) Journal of Cleaner Production, 59, pp. 290-297. Cited 23 times. doi: 10.1016/j.jclepro.2013.06.032 View at Publisher 9 Mustafa, A., Karmali, A., Abdelmoez, W. Optimisation and economic assessment of lipase-catalysed production of monoesters using Rhizomucor miehei lipase in a solvent-free system (2016) Journal of Cleaner Production, 137, pp. 953-964. Cited 16 times. doi: 10.1016/j.jclepro.2016.07.056 View at Publisher 10 Abdelmoez, W., Mustafa, A. Oleochemical industry future through biotechnology (Open Access) (2014) Journal of Oleo Science, 63 (6), pp. 545-554. Cited 23 times. https://www.jstage.jst.go.jp/article/jos/63/6/63_ess14022/_pdf doi: 10.5650/jos.ess14022 View at Publisher 11 Galgali, A., Gawas, S.D., Rathod, V.K. Ultrasound assisted synthesis of citronellol laurate by using Novozym 435 (2018) Catalysis Today, 309, pp. 133-139. Cited 7 times. http://www.sciencedirect.com/science/journal/09205861 doi: 10.1016/j.cattod.2017.08.052 View at Publisher 12 Heeres, A., Vanbroekhoven, K., Van Hecke, W. Solvent-free lipase-catalyzed production of (meth)acrylate monomers: Experimental results and kinetic modeling (2019) Biochemical Engineering Journal, 142, pp. 162-169. Cited 2 times. www.elsevier.com/locate/bej doi: 10.1016/j.bej.2018.11.011 View at Publisher 13 Encinar, J.M., González, J.F., Sánchez, N., Nogales-Delgado, S. Sunflower oil transesterification with methanol using immobilized lipase enzymes (2019) Bioprocess and Biosystems Engineering, 42 (1), pp. 157-166. Cited 11 times. https://rd.springer.com/journal/449 doi: 10.1007/s00449-018-2023-z View at Publisher 14 Bansode, S.R., Hardikar, M.A., Rathod, V.K. Evaluation of reaction parameters and kinetic modelling for Novozym 435 catalysed synthesis of isoamyl butyrate (2017) Journal of Chemical Technology and Biotechnology, 92 (6), pp. 1306-1314. Cited 18 times. http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1097-4660 doi: 10.1002/jctb.5125 View at Publisher 15 Zarejousheghani, F., Kariminia, H.-R., Khorasheh, F. Kinetic modelling of enzymatic biodiesel production from castor oil: Temperature dependence of the Ping Pong parameters (2016) Canadian Journal of Chemical Engineering, 94 (3), pp. 512-517. Cited 10 times. http://www.interscience.wiley.com doi: 10.1002/cjce.22408 View at Publisher 16 Carnahan, B., Luther, H.A., Wilke, J.O. (1969) Applied nu-merical methods. Cited 3002 times. 16 Wiley, New York 17 Eyring, H. The activated complex in chemical reactions (1935) The Journal of Chemical Physics, 3 (2), pp. 63-71. Cited 2216 times. View at Publisher 18 Hosney, H., Al-Sakkari, E.G., Mustafa, A., Ashour, I., Mustafa, I., El-Shibiny, A. A cleaner enzymatic approach for producing non-phthalate plasticiser to replace toxic-based phthalates (2020) Clean Technologies and Environmental Policy, 22 (1), pp. 73-89. https://link.springer.com/journal/10098 doi: 10.1007/s10098-019-01770-5 View at Publisher 19 Ferrão-Gonzales, A.D., Véras, I.C., Silva, F.A.L., Alvarez, H.M., Moreau, V.H. Thermodynamic analysis of the kinetics reactions of the production of FAME and FAEE using Novozyme 435 as catalyst (Open Access) (2011) Fuel Processing Technology, 92 (5), pp. 1007-1011. Cited 16 times. doi: 10.1016/j.fuproc.2010.12.023 View at Publisher 20 Basri, M., Kassim, M.A., Mohamad, R., Ariff, A.B. Optimization and kinetic study on the synthesis of palm oil ester using Lipozyme TL im (2013) Journal of Molecular Catalysis B: Enzymatic, 85-86, pp. 214-219. Cited 33 times. doi: 10.1016/j.molcatb.2012.09.013 View at Publisher 21 Bansode, S.R., Hardikar, M.A., Rathod, V.K. Evaluation of reaction parameters and kinetic modelling for Novozym 435 catalysed synthesis of isoamyl butyrate (2017) Journal of Chemical Technology and Biotechnology, 92 (6), pp. 1306-1314. Cited 18 times. http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1097-4660 doi: 10.1002/jctb.5125 View at Publisher 22 Cavallaro, V., Tonetto, G., Ferreira, M.L. Optimization of the enzymatic synthesis of pentyl oleate with lipase immobilized onto novel structured support (Open Access) (2019) Fermentation, 5 (2), art. no. 48. Cited 3 times. https://www.mdpi.com/2311-5637/5/2/48/pdf doi: 10.3390/fermentation5020048 View at Publisher 23 Somashekar, B.R., Lohith, K., Manohar, B., Divakar, S. Inhibition of Rhizomucor miehei and Candida rugosa lipases by d-glucose in esterification between l-alanine and d-glucose (2007) Journal of Bioscience and Bioengineering, 103 (2), pp. 122-128. Cited 9 times. doi: 10.1263/jbb.103.122 View at Publisher 24 Liu, W., Duan, F. Lipase-catalyzed transesterification of epoxidized soybean oil to prepare epoxy methyl esters (Open Access) (2018) Grasas y Aceites, 69 (2), art. no. e247. Cited 2 times. http://grasasyaceites.revistas.csic.es/index.php/grasasyaceites/article/view/1714/2261 doi: 10.3989/gya.1103172 View at Publisher 25 Chowdary, G.V., Prapulla, S.G. Kinetic study on lipase-catalyzed esterification in organic solvents (2005) Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 44 (11), pp. 2322-2327. Cited 30 times. 26 Sim, J.H., Harun Kamaruddin, A., Bhatia, S. Effect of mass transfer and enzyme loading on the biodiesel yield and reaction rate in the enzymatic transesterification of crude palm oil (2009) Energy and Fuels, 23 (9), pp. 4651-4658. Cited 18 times. http://pubs.acs.org/doi/pdfplus/10.1021/ef900474e doi: 10.1021/ef900474e View at Publisher 27 Geankoplis, C.J. (1993) Transport processes and unit oper-ations. Cited 1378 times. 28 3rd ed., Prentice-Hall International Inc., USA 28 Macleod, C. (2008) 29 Ph.D. thesis. Newcastle University, School of Chemical Engineering and Advanced Materials, Newcastle, UK 29 Todero, L.M., Bassi, J.J., Lage, F.A.P., Corradini, M.C.C., Barboza, J.C.S., Hirata, D.B., Mendes, A.A. Enzymatic synthesis of isoamyl butyrate catalyzed by immobilized lipase on poly-methacrylate particles: optimization, reusability and mass transfer studies (2015) Bioprocess and Biosystems Engineering, 38 (8). Cited 21 times. https://rd.springer.com/journal/449 doi: 10.1007/s00449-015-1402-y View at Publisher 30 Basir, F.A., Datta, S., Roy, P.K. Studies on biodiesel production from Jatropha Curcas oil using chemical and biochemical methods - A mathematical approach (2015) Fuel, 158, art. no. 9278, pp. 503-511. Cited 20 times. http://www.journals.elsevier.com/fuel/ doi: 10.1016/j.fuel.2015.05.048 View at Publisher 31 Bansode, S.R., Hardikar, M.A., Rathod, V.K. Evaluation of reaction parameters and kinetic modelling for Novozym 435 catalysed synthesis of isoamyl butyrate (2017) Journal of Chemical Technology and Biotechnology, 92 (6), pp. 1306-1314. Cited 18 times. http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1097-4660 doi: 10.1002/jctb.5125 View at Publisher 32 Calabrò, V., Ricca, E., De Paola, M.G., Curcio, S., Iorio, G. Kinetics of enzymatic trans-esterification of glycerides for biodiesel production (2010) Bioprocess and Biosystems Engineering, 33 (6), pp. 701-710. Cited 28 times. doi: 10.1007/s00449-009-0392-z View at Publisher 33 Dang, H.T., Obiri, O., Hayes, D.G. Feed batch addition of saccharide during saccharide-fatty acid esterification catalyzed by immobilized lipase: Time course, water activity, and kinetic model (2005) JAOCS, Journal of the American Oil Chemists' Society, 82 (7), pp. 487-493. Cited 20 times. doi: 10.1007/s11746-005-1098-x View at Publisher 34 Mahmud, M.S., Safinski, T., Nelson, M.I., Adesina, A.A. Enhancement of heterogeneous ethyl oleate synthesis using hydrous ethanol (2017) Aust. J. Basic Appl. Sci, 11 (3), pp. 160-164. 35 35 Ferreira, H.V., Rocha, L.C., Severino, R.P., Viana, R.B., Da Silva, A.B.F., Porto, A.L.M. Enzymatic resolution of racemic sulcatol by lipase from Candida antarctica in a large scale (2010) Journal of the Iranian Chemical Society, 7 (4), pp. 883-889. Cited 10 times. http://www.ics-ir.org/jics/archive/v7/4/article/pdf/JICS-7-4-Article-13.pdf doi: 10.1007/BF03246083 View at Publisher 36 Ghori, M.I., Iqbal, M.J., Hameed, A. Characterization of a novel lipase from bacillus sp. isolated from tannery wastes (Open Access) (2011) Brazilian Journal of Microbiology, 42 (1), pp. 22-29. Cited 35 times. http://www.scielo.br/pdf/bjm/v42n1/v42n1a03.pdf doi: 10.1590/S1517-83822011000100003 View at Publisher 37 Sharma, A., Dalai, A.K., Chaurasia, S.P. Thermodynamic study of hydrolysis and esterification reactions with immobilized lipases (2015) Eur. Int. J. Sci. Technol, 4, pp. 128-136