Reaction Kinetics and Catalysis Letters

, Volume 95, Issue 2, pp 257–264 | Cite as

Study on the alcoholysis of isoflavone catalyzed by ionic liquids

  • Zuojun Wei
  • Yong Huang
  • Shuguang Deng
  • Dipendu Saha
  • Yingxin Liu
  • Qilong Ren
Article
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Abstract

Alcoholysis of soybean isoflavone glucosides by butanol catalyzed by acidic ionic liquids was studied. The effects of the ionic liquid catalyst type, catalyst concentration, reaction time and reaction temperature on glycoside conversions, and aglycons yields were investigated. The optimum reaction conditions are found to be as follows: 0.036 g mL−1 of ionic liquid [BIM]HSO4 as catalyst, reaction temperature at 104±1°C, reaction time of 100 min. Under these optimum reaction conditions near complete conversions of the three kinds of glycosides (daidzin, glycitin and genistin) are obtained. Furthermore, the kinetics parameters for the alcoholysis were estimated. The activation energies of alcoholysis for the three kinds of isoflavone glucosides are 124 kJ mol−1, 67 kJ mol−1 and 115 kJ mol−1, respectively.

Keywords

Alcoholysis ionic liquid isoflavone activation energy reaction kinetics 
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References

  1. 1.
    C.L. Holder, M.I. Churchwell, D.R. Doerge: J. Agr. Food Chem., 47, 3764 (1999).CrossRefGoogle Scholar
  2. 2.
    P. Chuankhayan, T. Rimlumduan, J. Svasti, J.R.K. Cairns: J. Agr. Food Chem., 55, 2407 (2007).CrossRefGoogle Scholar
  3. 3.
    S.S. Li, C.J. Wu, B.G. Su, Q.L. Ren: Chin. Fats, 29, 28 (2004).Google Scholar
  4. 4.
    M. Richelle, S. Pridmore-Merten, S. Bodenstab, M. Enslen, E.A. Offord: J. Nutr., 132, 2587 (2002).Google Scholar
  5. 5.
    Y.B. Choi, K.S. Kim, J.S. Rhee: Biotechnol. Lett., 24, 2113 (2002).CrossRefGoogle Scholar
  6. 6.
    T. Welton: Coord. Chem. Rev., 248, 2459 (2004).CrossRefGoogle Scholar
  7. 7.
    H.E. Lanman, R.V. Nguyen, X.Q. Yao, T.H. Chan, C.J. Li: J. Mol. Catal. A: Chem., 279, 218 (2008).CrossRefGoogle Scholar
  8. 8.
    A. Fernicola, S. Panero, B. Scrosati, M. Tamada, H. Ohno: Chem. Phys. Chem., 8, 1103 (2007).Google Scholar
  9. 9.
    Z.Y. Duan, Y.L. Gu, Y.Q. Deng: Catal. Commun., 7, 651 (2006).CrossRefGoogle Scholar
  10. 10.
    Q.W. Yang, Z.J. Wei, H.B. Xing, Q.L. Ren: Catal. Commun., 9, 1307 (2008)CrossRefGoogle Scholar
  11. 11.
    M. Miyazawa, K. Sakano, S.I. Nakamura, H. Kosaka: J. Agr. Food Chem., 47, 1346 (1999).CrossRefGoogle Scholar
  12. 12.
    G.P. Fenner: J. Agr. Food Chem., 44, 3727 (1996).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC. 2008

Authors and Affiliations

  • Zuojun Wei
    • 1
  • Yong Huang
    • 1
  • Shuguang Deng
    • 2
  • Dipendu Saha
    • 2
  • Yingxin Liu
    • 3
  • Qilong Ren
    • 1
  1. 1.Department of Chemical and Biochemical Engineering, College of Materials Science and Chemical EngineeringZhejiang UniversityHangzhouChina
  2. 2.Department of Chemical EngineeringNew Mexico State UniversityLas CrucesUSA
  3. 3.College of Pharmaceutical Science, State Key Laboratory Breeding Base of Green Chemistry Synthesis TechnologyZhejiang University of TechnologyHangzhouChina

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