A Superior New Route to Methyl Phosphonate-based Ionic Liquids

Abstract

In the search for new ionic liquids (ILs) for biomass processing, analytical chemistry, or modern nonvolatile fire retarding agents, alkyl phosphonate-based ILs represent very promising candidates. A very practical synthesis of such ILs, which is superior to the conventional quaternization of 1-alkylimidazoles by dimethyl phosphite (DMP), was developed. 1,3-Dialkylimidazolium halide salts serve as convenient starting materials, and various 1,3-dialkylimidazolium methyl phosphonates are thus accessible by simple, fast, and solvent-free procedures with DMP, where the anion is methylated.

When Chlorides are the Most Reactive: A Simple Route towards Diverse Mono- and Dicationic Dimethyl Phosphate Ionic Liquids

“…10 Schottenberger et al have successfully applied a similar strategy for the synthesis of methyl phosphonate IL. 11 These previously reported approaches encouraged us to adapt this anion metathesis for the synthesis of several functionalized and nonfunctionalized monocationic and dicationic IL with a DMP counterion, thereby broadening the scope of the methodology. Furthermore, the possibility to design the cation has led us to novel IL.…”

“…Furthermore, the possibility to design the cation has led us to novel IL. Based on the results of preliminary studies, [9][10][11] chloride-containing IL were selected as the most reactive and thereby promising starting materials for efficient synthesis of halide-free DMP IL.…”