Ionic liquids via reaction of the zwitterion 1,3-dimethylimidazolium-2-carboxylate with protic acids

I&EC 104

Marcin Smiglak, smigl001@bama.ua.edu1, W. Matthew Reichert, reich003@bama.ua.edu2, Scott T. Griffin, griff015@bama.ua.edu2, John D. Holbrey2, Robin D. Rogers, rdrogers@bama.ua.edu2, Kostyantyn Kirichenko, konstant@chem.ufl.edu3, Dazhi Zhang3, and Alan R. Katritzky, katritzky@chem.ufl.edu3. (1) Department of Chemistry and Center for Green Manufacturing, University of Alabama, Tuscaloosa, AL 35487, (2) Department of Chemistry and Center for Green Manufacturing, The University of Alabama, Tuscaloosa, AL 35487, (3) Department of Chemistry, Center for Heterocyclic Compounds, University of Florida, PO Box 117200, Gainesville, FL 32611-7200
New, halide free syntheses of ionic liquids (ILs) or IL precursors, by the reaction of 1,3-dimethylimidazolium-2-carboxylate with different acids has been investigated. By utilization of established synthetic protocols, new, fast, time- and cost-efficient formation of 1,3-dialkylimidazolium salts, from 1-alkylimidazoles, dimethyl carbonate, and protic acids in the presence of polar aprotic solvents can be obtained. Moreover, interesting behavior of the zwitterionic 1,3-dialkylimidazolium-2-carboxylate reacted with weaker acids, was noted, leading to the formation of two isomeric products: 2- or 4-hydroxycarbonyl-1,3-dialkylimidazolium salts, which, under specific conditions can undergo decarboxylation reactions. Here we present our experimental approaches to developing synthetic protocols which allow the formation of variety of ionic liquids via halide-free routes.
 

Ionic Liquids: Not Just Solvents Anymore OR Ionic Liquids: Parallel Futures (Sponsored by Green Chemistry and Engineering, Separation Science and Technology and Novel Chemistry with Industrial Applications Sub-Divisions)
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Industrial and Engineering Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006