Research on Chemical Intermediates

, Volume 36, Issue 9, pp 1027–1035 | Cite as

Hydroesterification of ethylene oxide catalyzed by 1-butyl-3-methylimidazolium cobalt tetracarbonyl ionic liquid



In this paper, functional ionic liquid 1-butyl-3-methylimidazolium cobalt tetracarbonyl [Bmim][Co(CO)4] is prepared in a metathesis reaction between [Bmim]Cl and KCo(CO)4. The structure of [Bmim]+ is illustrated by 1H NMR, while [Co(CO)4] is confirmed by IR(νCO) spectrum. Methyl 3-hydroxypropionate(3-HPM), an intermediate to 1,3-propanediol (1,3-PDO), can be prepared in high yield by hydroesterification of ethylene oxide in the presence of a [Bmim][Co(CO)4] catalyst. Under a pressure of 3.7 MPa and at a temperature of 75 °C, the yield of 3-HPM can reach 90.8% in 10 h. Even after the catalyst is recycled three times, a yield of more than 80% can be obtained. A possible reaction mechanism has also been proposed.


Hydroesterification Methyl 3-hydroxypropionate Ethylene oxide 1-Butyl-3-methylimidazolium cobalt tetracarbonyl Functional ionic liquid 



This research was supported by National Natural Science Foundation of China (20776071) and Introduced Talents Starting Foundation of QUST.


  1. 1.
    H.S. Kim, J.Y. Bea, J.S. Lee et al., Appl. Catal. A 301, 75–78 (2006)CrossRefGoogle Scholar
  2. 2.
    K. Wang, M.C. Hawley, J.S. DeAthos, Ind. Eng. Chem. Res 42, 2913–2923 (2003)CrossRefGoogle Scholar
  3. 3.
    J.B. Powell, L.H. Slaugh, T.C. Forschner, T.B. Thomason, T.C. Semple, P.R. Weider, J.P. Arhancet, US Patent 5,777,182 (1998)Google Scholar
  4. 4.
    J.F. Knifton, L.H. Slaugh, P.R. Weider, T.G. James, J.B. Powell, K.D. Allen, T.S. Williams, US Patent 6,468,940 (2002)Google Scholar
  5. 5.
    H. Thomas, J. Bernd, S. Joerg, H. Willi, V. Ruolf, US Patent 6297408 (2001)Google Scholar
  6. 6.
    H. Thomas, J. Bernd, H. Willi, V. Rudolf. US Patent 6342646 (2002)Google Scholar
  7. 7.
    M.A. Murphy, B.L. Smith, A. Aguilo, et al. Process for making 1,3-diols from epoxides[P].US Patent Appl, US Patent 4873379 (1989)Google Scholar
  8. 8.
    J.F. Knifton, T.G. James, L.H. Slaugh, K.D. Allen, P.R. Weider, J.B. Powell, US Patent 7538061B2 (2009)Google Scholar
  9. 9.
    R.L.D. Aquino, Chem. Eng. 106(5), 56–62 (1999)Google Scholar
  10. 10.
    C.F. Thomas, R.W. Paul, H.S. Lynn, B.P. Joseph, US Patent 6191321 (2001)Google Scholar
  11. 11.
    F. Cui, J. Chen, J.H. Liu, Ch.G. Xia, J. Tong, CN Patent 101020635 (2007)Google Scholar
  12. 12.
    C.F. Thomas, R.W. Paul, H.S. Lynn, et al., US Patent 6191321 (2001)Google Scholar
  13. 13.
    P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39, 3772 (2000)Google Scholar
  14. 14.
    R. Sheldon, Chem. Commun. 2399–2407 (2001)Google Scholar
  15. 15.
    J. Dupont, R.F. de Souza, P.A. Suarez, Z. Chem. Rev. 102, 3667 (2002)CrossRefGoogle Scholar
  16. 16.
    C. Daguenet, P.J. Dyson, Organometallics 23, 6080–6083 (2004)CrossRefGoogle Scholar
  17. 17.
    E. Mizushima, T. Hayashi, M. Tanaka, Green Chem. 3(2), 76 (2001)CrossRefGoogle Scholar
  18. 18.
    C.J. Boxwell, P.J. Dyson, D.J. Ellis, T.J. Welton, Am. Chem. Soc. 124(32), 9334 (2002)CrossRefGoogle Scholar
  19. 19.
    L.C. Tamara, D.Y.L. Yutan, J. Am. Chem. Soc. 128(31), 10125 (2006)CrossRefGoogle Scholar
  20. 20.
    Y. Gok, I. Ozdemir, E. Cetinkaya, Chin. J. Catal. 28(6), 489 (2007)CrossRefGoogle Scholar
  21. 21.
    R.J.C. Brown, P.J. Dyson, D.J. Ellis et al. Chem. Commun. 1862–1863 (2001)Google Scholar
  22. 22.
    C.A. Ohlin, P.J. Dyson, G. Laurenezy, Chem. Commun. 7(9), 1070–1071 (2004)CrossRefGoogle Scholar
  23. 23.
    V. Mahadevan, Y.D.Y.L. Getzler, G.W. Coates, Angew. Chem. Int. Ed. 41, 2781 (2002)CrossRefGoogle Scholar
  24. 24.
    Y.D.Y.L. Getzler, V. Mahadevan, E.B. Lobkovsky, G.W. Coates, J. Am. Chem. Soc. 124, 1174 (2002)CrossRefGoogle Scholar
  25. 25.
    R.F. Heck, D.S. Breslow, J. Am. Chem. Soc. 83(19), 4023–4027 (1961)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  • Zhiguo Lv
    • 1
  • Hengsheng Wang
    • 1
  • Juan Li
    • 1
  • Zhenmei Guo
    • 1
  1. 1.College of Chemical EngineeringQingdao University of Science and TechnologyQingdaoPeople’s Republic of China

Personalised recommendations