Tetrahaloindate(III)-Based Ionic Liquids in the Coupling Reaction of Carbon Dioxide and Epoxides To Generate Cyclic Carbonates:  H-Bonding and Mechanistic Studies

Yong Jin Kim and Rajender S. Varma*
Sustainable Technology Division, National Risk Management Research Laboratory, U.S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 443, Cincinnati, Ohio 45268
J. Org. Chem., 2005, 70 (20), pp 7882–7891
DOI: 10.1021/jo050699x
Publication Date (Web): September 7, 2005
Copyright Not subject to U.S. Copyright. Published 2005 American Chemical Society
*

 To whom correspondence should be addressed. Tel:  (+1-513) 487-2701. Fax:  (+1-513) 569-7677.

, varma.rajender@epa.gov

Abstract

Abstract Image

The microwave reactions of InX3 with [Q]Y produce a series of tetrahaloindate(III)-based ionic liquids (ILs) with a general formula of [Q][InX3Y] (Q = imidazolium, phosphonium, ammonium, and pyridinium; X = Cl, Br, I; Y = Cl, Br). The reaction of CO2 with a variety of epoxides has been examined in the presence of these ILs wherein tetrahaloindate(III)-based ILs are found to exhibit high catalytic activities and evidence is presented that supports the significant role of H-bonding interactions in the [Q][InX3Y]-catalyzed coupling reactions. The effects of various parameters such as temperature, pressure, and molar ratio of propylene oxide to catalyst have been investigated, and the plausible reaction mechanism based on the 1H and 13C NMR studies is presented for the formation of propylene carbonate.

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History

  • Published In Issue September 30, 2005
  • Received April 7, 2005

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