Design of phosphonium ionic liquids for lipase-catalyzed transesterification

被引：66
作者：
Abe, Yoshikazu [1 ]
Kude, Keisuke [1 ]
Hayase, Shuichi [1 ]
Kawatsura, Motoi [1 ]
Tsunashima, Katsuhiko [2 ]
Itoh, Toshiyuki [1 ]
机构：
[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6808552, Japan
[2] Nippon Chem Ind Co Ltd, Koto Ku, Tokyo 1368515, Japan
来源：
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 2008年 / 51卷 / 3-4期
关键词：
ionic liquid; phosphonium salt; lipase; transesterification; rapid reaction;
D O I：
10.1016/j.molcatb.2007.11.010
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Ionic liquids are now recognized as solvents for use in lipase-catalyzed reactions; however, there still remains a serious drawback in that the rate of reaction in an ionic liquid is slower than that in a conventional organic solvent. To overcome this problem, attempts have been made to evolve phosphonium ionic liquids appropriate for lipase-catalyzed reaction; several types of phosphonium salts have been prepared and their capability evaluated for use as solvent for the lipase-catalyzed reaction. Very rapid lipase PS-catalyzed transesterification of secondary alcohols was obtained when 2-methoxyethyl(tri-n-butyl)phosphonium bis(trifluoromethanesulfonyl)imide ([MEBu3P][NTf2]) was used as solvent, affording the first example of a reaction rate superior to that in diisopropyl ether. (C) 2007 Elsevier B.V. All rights reserved.
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页码：81 / 85
页数：5
相关论文
共 32 条
  • [1] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
    CHEN, CS
    FUJIMOTO, Y
    GIRDAUKAS, G
    SIH, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
  • [2] Application of hydrophilic ionic liquids as co-solvents in chloroperoxidase catalyzed oxidations
    Chiappe, Cinzia
    Neri, Lisa
    Pieraccini, Daniela
    [J]. TETRAHEDRON LETTERS, 2006, 47 (29) : 5089 - 5093
  • [3] Reactivity of ionic liquids
    Chowdhury, Shahana
    Mohan, Ram S.
    Scott, Janet L.
    [J]. TETRAHEDRON, 2007, 63 (11) : 2363 - 2389
  • [4] Understanding structure -: Stability relationships of Candida antartica lipase B in ionic liquids
    De Diego, T
    Lozano, P
    Gmouh, S
    Vaultier, M
    Iborra, JL
    [J]. BIOMACROMOLECULES, 2005, 6 (03) : 1457 - 1464
  • [5] Lipase-catalyzed access to enantiomerically pure (R)- and (S)-trans-4-phenyl-3-butene-2-ol
    Ghanem, A
    Schurig, V
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (01) : 57 - 62
  • [6] Enhanced enantioselectivity and remarkable acceleration on the lipase-catalyzed transesterification using novel ionic liquids
    Itoh, T
    Han, SH
    Matsushita, Y
    Hayase, S
    [J]. GREEN CHEMISTRY, 2004, 6 (09) : 437 - 439
  • [7] Novel supporting materials of lipase PS suitable for use in an ionic liquid solvent system
    Itoh, T
    Ouchi, N
    Nishimura, Y
    Hui, HS
    Katada, N
    Niwa, M
    Onaka, M
    [J]. GREEN CHEMISTRY, 2003, 5 (05) : 494 - 496
  • [8] Itoh T, 2003, ACS SYM SER, V856, P251
  • [9] 1-butyl-2,3-dimethylimidazolium tetrafluoroborate: the most desirable ionic liquid solvent for recycling use of enzyme in lipase-catalyzed transesterification using vinyl acetate as acyl donor
    Itoh, T
    Nishimura, Y
    Ouchi, N
    Hayase, S
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2003, 26 (1-2) : 41 - 45
  • [10] Lipase-catalyzed enantioselective acylation in a halogen free ionic liquid solvent system
    Itoh, T
    Ouchi, N
    Hayase, S
    Nishimura, Y
    [J]. CHEMISTRY LETTERS, 2003, 32 (07) : 654 - 655
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