A Solventless Route to 1-Ethyl-3-methylimidazolium Fluoride Hydrofluoride, [C₂mim][F]·xHF

Abstract

The ionic liquid 1-ethyl-3-methylimidazolium fluoride hydrofluoride, [C2mim][F] x xHF, has been synthesized through a new, solventless route that excludes halogen metathesis. The byproducts are salts, alcohols, and carbon dioxide.

Betaine Adducts of N‐Heterocyclic Carbenes: Synthesis, Properties, and Reactivity

“…Decomposition of the unstable methyl hydrogen carbonate into methanol and carbon dioxide would then provide the capping group for 1,3-dimethylimidazol-2-ylidene (Scheme 8). [57] This procedure was further extended to 1-ethylimidazole [58] and 1-butylimidazole [59] [Equation (24)]. Prolonged heating at high temperature (70-120°C) in sealed tubes was required to complete the transformation in all cases.…”

“…A solvent-less route to 1-ethyl-3-methylimidazolium fluoride that does not require the intervention of chloride salts has also been devised along the same lines. [58] (35)…”

“…The dihedral angle between the N 2 C + and N 2 C -moieties was found to be 85.6°and the molecule displays strongly basic properties toward Brønsted acids. [100] ( 58) In addition to heteroallenes of the X=C=Y type (X, Y = NR, O, S, Se), a few ketenes and allenes also afford stable zwitterions when treated with NHC precursors. Two examples of diphenylketene adducts have been reported by Regitz et al to illustrate the reactivity of electron-rich olefins [Equation (59)].…”

1-n-Butyl-3-methylimidazolium-2-carboxylate: a versatile precatalyst for the ring-opening polymerization of ε-caprolactone and rac-lactide under solvent-free conditions

“…Indeed, methylimidazolium-2-carboxylates can be easily synthesized with high yields by the one-pot reaction of dimethyl carbonate (DMC) with imidazole derivatives, making them very attractive and accessible compounds [35]. Therefore, they found applications as ligands in organometallic catalysis [36–41], as precursors of halide-free ionic liquids [42–45], and as organocatalysts in reactions involving carbon dioxide transfer in the formation of ketoacetates [46–47] and carboxylation of epoxides [48]. Some of us have recently reported a green application of BMIM-2-CO 2 , highlighting its efficiency for the conversion of raw glycerol to glycerol carbonate by transesterification [49].…”

Room-Temperature Fluorohydrogenate Ionic Liquids of Alkylpyridinium Cations and Allylated Quarternary Cyclic Ammonium Cations

“…9 Very recently, a different synthetic route for FHILs starting from the corresponding alkyl amine and dimethylcarbonate has been reported. 10 Recent work has investigated the application of FHILs as propellants for ion engines 11,12 and as electrolytes for the electrolytic production of porous silicon. 13,14 The authors have already reported some fundamental studies on the physical and chemical properties, electrochemical stability, [15][16][17][18][19][20] and structural characteristics [21][22][23] of FHILs, especially those composed of alkylated cyclic ammonium cations.…”