Synergism between microwave and enzyme catalysis in intensification of reactions and selectivities: transesterification of methyl acetoacetate with alcohols

被引:79
作者
Yadav, GD [1 ]
Lathi, PS [1 ]
机构
[1] Univ Bombay, Inst Chem Technol, Dept Chem Engn, Bombay 400019, Maharashtra, India
关键词
microwave catalysis; lipase catalysis; beta-keto esters; methyl acetoacetate; synergism; intensification of rates; immobilized lipases; selectivities;
D O I
10.1016/j.molcata.2003.09.050
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
beta-Keto esters serve as important synthons since they can be easily transformed into chiral building blocks via enzymatic transformation. As a consequence, their inter-conversion into different esters has gained a great deal of attention. This work focuses on the transesterification of methyl acetoacetate, a beta-keto ester, with various alcohols in the presence of immobilized lipases the influence of microwave irradiation. A number of commercially available lipases such as Novozym 435, Lipozyme RM IM and Lipozyme TL IM were screened and Novozym, 435 was found to be the most active. The effect of chain length of alcohol was also studied. There is a synergism between the enzyme catalysis and microwaves. The reaction follows the ping pong bi-bi mechanism. The theoretical predictions and experimental data match very well. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:51 / 56
页数:6
相关论文
共 28 条
[11]   Microwave-promoted lipase-catalyzed reactions [J].
Lin, GL ;
Lin, WY .
TETRAHEDRON LETTERS, 1998, 39 (24) :4333-4336
[12]   TRANSESTERIFICATION [J].
OTERA, J .
CHEMICAL REVIEWS, 1993, 93 (04) :1449-1470
[13]   Microwave radiation can increase the rate of enzyme-catalysed reactions in organic media [J].
Parker, MC ;
Besson, T ;
Lamare, S ;
Legoy, MD .
TETRAHEDRON LETTERS, 1996, 37 (46) :8383-8386
[14]   Selective catalytic transesterification, transthiolesterification, and protection of carbonyl compounds over natural kaolinitic clay [J].
Ponde, DE ;
Deshpande, VH ;
Bulbule, VJ ;
Sudalai, A ;
Gajare, AS .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1058-1063
[15]   PREPARATION OF BETA-KETO-ESTERS BY 4-DMAP-CATALYZED ESTER EXCHANGE [J].
TABER, DF ;
AMEDIO, JC ;
PATEL, YK .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3618-3619
[16]   BIOCATALYSIS IN ORGANIC-CHEMISTRY .2. PRESENT AND FUTURE [J].
TURNER, MK .
TRENDS IN BIOTECHNOLOGY, 1995, 13 (07) :253-258
[17]   Selective enzymic esterification of free fatty acids with n-butanol under microwave irradiation and under classical heating [J].
Vacek, M ;
Zarevúcka, M ;
Wimmer, Z ;
Stránsky, K ;
Demnerová, K ;
Legoy, MD .
BIOTECHNOLOGY LETTERS, 2000, 22 (19) :1565-1570
[18]   Solvent-free accelerated organic syntheses using microwaves [J].
Varma, RS .
PURE AND APPLIED CHEMISTRY, 2001, 73 (01) :193-198
[19]   Preparation of long-chain acyl thioesters - thio wax esters - by the use of lipases [J].
Weber, N ;
Klein, E ;
Vosmann, K ;
Mukherjee, KD .
BIOTECHNOLOGY LETTERS, 1998, 20 (07) :687-691
[20]   Immobilized lipase-catalysed esterification and transesterification reactions in non-aqueous media for the synthesis of tetrahydrofurfuryl butyrate: comparison and kinetic modeling [J].
Yadav, GD ;
Devi, KM .
CHEMICAL ENGINEERING SCIENCE, 2004, 59 (02) :373-383