Abstract
n-Butyl dipheyl methyl mercapto acetate is an important pharmaceutical intermediate, having applications in the synthesis of Modafinil, a CNS stimulant drug. The current process is highly polluting and requires alternate green processes. Synthesis of it was carried out via lipase in the presence of microwave irradiation. Optimization of reaction conditions, such as catalyst loading, mole ratio of reactants, reaction temperature, water concentration and reusability of catalysts under the microwave irradiation was done. Among all, the commercially available lipases Novozym 435 was found best and gives the conversion 34% in 24 h at 60°C. A ping–pong bi–bi model with substrate n-butanol inhibition at higher concentration was found to be suitable for kinetics of the reaction.
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References
Astorga C, Robolledo F, Gotor V (1991) Synthesis of hydrazides through an enzymic hydrzinolysis reaction. Synthesis 5:350–352
Carceller E, Merlos M, Giral M, Almansa C, Bartroli J, Garcia-Rafanell J, Forn J (1993) Synthesis and structure-activity relationships of 1-acyl-4-((2-methyl-3-pyridyl)cyanomethyl)piperazines as PAF antagonists. J Med Chem 2984–2997
Carrea G, Riva S (2000) Properties and synthetic applications of enzymes in organic solvents. Angew Chem Int Ed 39:2226–2254
Carrillo-Munoz J, Bouvet D, Guibe-Jampel E, Loupy A, Petit A (1996) Microwave-promoted lipase-catalyzed reactions. Resolution of (±)-1-phenylethanol. J Org Chem 61:7746–7749
Edin M, Bäckvall J, Córdova A (2004) Tandem enantioselective organo- and biocatalysis: a direct entry for the synthesis of enantiomerically pure aldols. Tertrahedron Lett 45:7697–7701
Fernandes MLM, Krieger N, Baron AM, Zamora PP, Ramos LP, Mitchell DA (2004) Hydrolysis and synthesis reactions catalysed by Thermomyces lanuginosa lipase in the AOT/Isooctane reversed micellar system. J Mol Catal B Enzym 30:43–49
Gelo-Pujic M, Guibe-Jampel E, Loupy A, Galema S, Mathe D (1996) Enzymic glycosidation in dry media under microwave irradiation. J Che Soc Perkin Trans 1:2777
Gotor V, Brieva R, Gonzalez C, Rebolledo F (1991) Enzymatic aminolysis and transamidation reactions. Tetrahedron 47:9207–9214
Gourari-Kriouile S, Zoulalian A, Roussy G, Thiebaut J (1991) Gas-solid catalytic reaction in presence of microwave radiation. Recents Progres en Genie des Procedes 5:235–40
Kidwai M, Goel Y, Kumar P (1998) Microwave assisted synthesis of new bioactive 1,3,4-thiadiazolyl substituted 1,3,4-oxadiazoles. Indian J Pharm Sci 60(6):396–399
Lafon L (1977) Phloroglucinol derivatives. Ger Offen 2,642, 511
Lin G, Lin W (1998) Microwave-promoted lipase-catalyzed reactions. Tetrahedron Lett 39:4333–4336
Loupy A (2006) Microwaves in organic synthesis. Wiley-VCH, Weinheim
Parker M, Besson T, Lamare S, Legoy M (1996) Microwave radiation can increase the rate of enzyme-catalysed reactions in organic media. Tetrahedron Lett 37:8383–8386
Patel RN (2002) Microbial/enzymatic synthesis of chiral intermediates for pharmaceuticals. Enzyme Microb Technol 31:804–826
Segel IH (1975) Enzyme kinetics. Wiley, New York
Tramper LCJ, Lilly MD (1987) Biocatalysis in organic solvents. Elsevier, Amsterdam, pp 147–153
Varma RS (2001) Solvent-free accelerated organic syntheses using microwaves. Pure Appl Chem 73:190–198
Xavier Malcata F, Reyes HR, Garcia HS, Hill CG Jr, Amundson CH (1992) Kinetics, and mechanisms of reactions catalysed by immobilized lipases. Enzyme Microb Technol 14:426–444
Yadav GD, Lathi PS (2003) Kinetics and mechanism of synthesis of butyl isobutyrate over immobilised lipases. Biochem Eng J 16:245–252
Yadav GD, Lathi PS (2004) Synergism between microwave and enzyme catalysis in intensification of reactions and selectivities: transesterification of methyl acetoacetate with alcohols. J Mol Cat A Chem 223:51–56
Yadav GD, Lathi PS (2005) Synergism of microwaves and immobilized enzyme catalysis in synthesis of adipic acid esters in nonaqueous media. Synthetic Commun 35:1699–1705
Yadav GD, Manjula Devi K (2001) A kinetic model for the enzyme-catalyzed self-epoxidation of oleic acid. J Am Oil Chem Soc 78:347–351
Yadav GD, Manjula Devi K (2002) Enzymatic synthesis of perlauric acid using Novozym 435. Biochem Eng J 10(2):93–101
Yadav GD, Manjula Devi K (2004a) Kinetics of hydrolysis of tetrahydrofurfuryl butyrate in a three phase system containing immobilized lipase from Candida antarctica. Biochem Eng J 17:57–63
Yadav GD, Manjula Devi K (2004b) Immobilized lipase-catalysed esterification and transesterification reactions in non-aqueous media for the synthesis of tetrahydrofurfuryl butyrate: comparison and kinetic modeling. Chem Eng Sci 59:373–383
Yadav GD, Trivedi AH (2003) Kinetic modeling of immobilized-lipase catalyzed transesterification of n-octanol with vinyl acetate in non-aqueous media. Enzyme Microb Technol 32:783–789
Yadav GD, Subramanian S (2006) Indian Patent Application
Yang K, Wang Y (2004) Lipase-catalyzed transesterification in aqueous medium under thermodynamic and kinetic control using carboxymethyl cellulose acetylation as the model reaction. Enzyme Microb Technol 35:223–231
Zhang J, Wu J, Yang L (2004) The kinetic study on lipase-catalyzed asymmetric alcoholysis of α-cyano-benzyl acetate in organic media. J Mol Catal B Enzym 31:67–72
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PSL thanks University Grant Commission (UGC) for SRF, which enabled this work to be carried out. GDY acknowledges support from the Darbari Set Professorship Endowment for personal Chair.
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Yadav, G.D., Lathi, P.S. Microwave assisted enzyme catalysis for synthesis of n-butyl dipheyl methyl mercapto acetate in non-aqueous media. Clean Techn Environ Policy 9, 281–287 (2007). https://doi.org/10.1007/s10098-006-0082-3
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DOI: https://doi.org/10.1007/s10098-006-0082-3