Abstract
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.
Similar content being viewed by others
References
H.S. Kim, J.Y. Bea, J.S. Lee et al., Appl. Catal. A 301, 75–78 (2006)
K. Wang, M.C. Hawley, J.S. DeAthos, Ind. Eng. Chem. Res 42, 2913–2923 (2003)
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)
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)
H. Thomas, J. Bernd, S. Joerg, H. Willi, V. Ruolf, US Patent 6297408 (2001)
H. Thomas, J. Bernd, H. Willi, V. Rudolf. US Patent 6342646 (2002)
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)
J.F. Knifton, T.G. James, L.H. Slaugh, K.D. Allen, P.R. Weider, J.B. Powell, US Patent 7538061B2 (2009)
R.L.D. Aquino, Chem. Eng. 106(5), 56–62 (1999)
C.F. Thomas, R.W. Paul, H.S. Lynn, B.P. Joseph, US Patent 6191321 (2001)
F. Cui, J. Chen, J.H. Liu, Ch.G. Xia, J. Tong, CN Patent 101020635 (2007)
C.F. Thomas, R.W. Paul, H.S. Lynn, et al., US Patent 6191321 (2001)
P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39, 3772 (2000)
R. Sheldon, Chem. Commun. 2399–2407 (2001)
J. Dupont, R.F. de Souza, P.A. Suarez, Z. Chem. Rev. 102, 3667 (2002)
C. Daguenet, P.J. Dyson, Organometallics 23, 6080–6083 (2004)
E. Mizushima, T. Hayashi, M. Tanaka, Green Chem. 3(2), 76 (2001)
C.J. Boxwell, P.J. Dyson, D.J. Ellis, T.J. Welton, Am. Chem. Soc. 124(32), 9334 (2002)
L.C. Tamara, D.Y.L. Yutan, J. Am. Chem. Soc. 128(31), 10125 (2006)
Y. Gok, I. Ozdemir, E. Cetinkaya, Chin. J. Catal. 28(6), 489 (2007)
R.J.C. Brown, P.J. Dyson, D.J. Ellis et al. Chem. Commun. 1862–1863 (2001)
C.A. Ohlin, P.J. Dyson, G. Laurenezy, Chem. Commun. 7(9), 1070–1071 (2004)
V. Mahadevan, Y.D.Y.L. Getzler, G.W. Coates, Angew. Chem. Int. Ed. 41, 2781 (2002)
Y.D.Y.L. Getzler, V. Mahadevan, E.B. Lobkovsky, G.W. Coates, J. Am. Chem. Soc. 124, 1174 (2002)
R.F. Heck, D.S. Breslow, J. Am. Chem. Soc. 83(19), 4023–4027 (1961)
Acknowledgments
This research was supported by National Natural Science Foundation of China (20776071) and Introduced Talents Starting Foundation of QUST.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lv, Z., Wang, H., Li, J. et al. Hydroesterification of ethylene oxide catalyzed by 1-butyl-3-methylimidazolium cobalt tetracarbonyl ionic liquid. Res Chem Intermed 36, 1027–1035 (2010). https://doi.org/10.1007/s11164-010-0215-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-010-0215-5