Process intensification of immobilized lipase catalysis by microwave irradiation in the synthesis of 4-chloro-2-methylphenoxyacetic acid (MCPA) esters |
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| Institution: | 1. Department of Chemistry, Thamirabharani Engineering College, Tirunelveli, Tamil Nadu, India;2. Department of Chemistry, N.M.S.S.V.N. College, Madurai 625 019, Tamil Nadu, India;3. Department of Physics, Mother Teresa Women’s University, Kodaiakanal 624101, Tamil Nadu, India;4. UGC-DAE-CSR, University Campus, Khandwa Road, Indore 452017, India;5. Laboratory of Radical Pharmaco–Chemistry, UMR CNRS 6264, University of the Méditerranée, Faculty of Pharmacy, 27 Bd Jean Moulin, 13385 Marseille Cedex 5, France;6. Department of Physics, N.M.S.S.V.N. College, Madurai 625 019, Tamil Nadu, India;1. Enzyme and Fermentation Technology Laboratory, College of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037, PR China;2. State Key Laboratory of Bioreactor Engineering, New World Institute of Biotechnology, East China University of Science and Technology, Shanghai 200237, PR China;1. Technology Product Management, Astellas Pharma Inc., 2-5-1 Nihonbashi-Honcho, Chuo-ku, Tokyo 103-8411, Japan;2. Technology Development, Toyama Technology Center, Astellas Pharma Tech Co., Ltd., 2-5-1 Nihonbashi-Honcho, Chuo-ku, Tokyo 103-8411, Japan;3. Laboratory of Molecular Biotechnology, Division of Biotechnology, Department of Bioengineering Science, Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan;1. IFREMER Brest, Laboratoire de Dynamique de L’Environnement Côtier, CS 10070, 29280 Plouzane, France;2. UMR CNRS LOG 8187, Université Lille 1 Sciences et Technologies, Station Marine, 28 avenue Foch, 62930 Wimereux, France;1. Center for Computational Biology, Beijing Forestry University, Beijing 100083, China;2. Center for Statistical Genetics, The Pennsylvania State University, Hershey, PA 17033, USA;1. Department of Food and Nutrition, Korea University, Seoul 136-703, Republic of Korea;2. BK21PLUS Program in Embodiment: Health-Society Interaction, Department of Public Health Sciences, Graduate School, Korea University, Seoul 136-703, Republic of Korea;3. Department of Nutritional Science and Food Management, Ewha Womans University, Seoul 120-749, Republic of Korea |
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| Abstract: | 4-Chloro-2-methylphenoxyacetic acid (MCPA) is a selective systemic herbicide which is absorbed by leaves and roots. MCPA esters are preferred due to their low water solubility and environmental friendliness. Esterification of MCPA with n-butanol was investigated as a model reaction using immobilized enzymes under the influence of microwave irradiation. Different immobilized enzymes such as Novozym 435, Lipozyme TL IM, Lipozyme RM IM and Lipase AYS Amano were studied under microwave irradiation amongst which Novozym 435 (immobilized Candida antarctica lipase B) was the best catalyst. Effects of various parameters were systematically studied on rates and conversion. Under microwave irradiation, the initial rates were observed to increase up to 2-fold. Under optimized conditions of 0.1 mmol MCPA and 0.3 mmol n-butanol in 15 mL 1,4-dioxane as solvent, Novozym 435 showed a conversion of 83% at 60 °C in 6 h. Based on initial rate and progress curve data, the reaction was shown to follow the Ping Pong bi–bi mechanism with inhibition by MCPA and n-butanol. Esterification of MCPA was also studied with different alcohols such as isopropyl alcohol, n-pentanol, n-hexanol, benzyl alcohol and 2-ethyl-1-hexanol. |
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| Keywords: | Enzyme biocatalysis Immobilized enzymes Biotransformation Kinetic parameters 4-Chloro-2-methylphenoxyacetic acid esters Microwave irradiation |
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