Halide free synthesis of energetic azolium azolate salts

PHYS 522

Marcin Smiglak, smigl001@bama.ua.edu1, David Drab2, C. Corey Hines, cchines@bama.ua.edu2, W. Matthew Reichert, reich003@bama.ua.edu2, Robin D. Rogers, rdrogers@bama.ua.edu2, Kostyantyn Kirichenko, konstant@chem.ufl.edu3, and Adam Vincek3. (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
A new synthetic route to the formation of energetic azolium azolate salts, utilizing proton transfer from a neutral azole and the decarboxylation reaction of azolium-2-carboxylate zwitterionic salts, with a singular byproduct; gaseous CO2, has been developed. The salt was analyzed in terms of its thermal stability, melting point, and solid state behavior. The described protocol allows for the synthesis of azolium based ionic liquids via the halide free, clean, and efficient reaction. As our investigation shows this reaction is dependent on the pKa of the neutral azole vs. the pKa of the zwitterionic salt.

 

Poster Session
7:30 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Physical Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006