Organic Chemistry

Biography

Biography: Joanna Feder Kubis

Abstract

Academic research on ionic liquids, across many varied applications, is strong and still growing area of interest. New chiral imidazolium-based ionic liquids containing (1R,2S,5R)-(–)-menthol substituent, having symmetrical structure of the salts, have been synthesized and characterized. Monocyclic terpen alcohol: (1R,2S,5R)-(–)-menthol, obtained from a variety of mint (Menthae L.), was used as a substrate in two different reactions to obtain 1,3-bis[(1R,2S,5R)-(–)-menthoxymethyl]imidazolium chloride [1], which is a prototype of chiral ionic liquids. After that, metathesis of this symmetrical imidazolium chloride with various organic and inorganic salts in menthol or water/menthol solution was carried out. The ion exchange reaction goes smoothly, with the satisfactory exceed (from 94 to 99%). Discussed symmetrical salts belong to Chiral Ionic Liquids (CILs) where the chirality resides in the cation and is associated with the presence of optical active (1R,2S,5R)-(–)-menthol. Obtained symmetrical salts are hydrophobic, and air- and moisture-stable under ambient conditions. Moreover, they are non-volatile and non-flammable. Some of the 1,3-bis[(1R,2S,5R)-(–)-menthoxymethyl]imidazolium salts [i.e.: chloride, bis(trifluoromethanesulfonyl) imide, acesulfame, saccharinate] possess excellent antielectrostatic properties and their ability to drain the surface charge is similar to these of a known antistatic agent (Catanac 609: American Cyanamin Co.).