1-ETHYL-3-METHYLIMIDAZOLIUM BIS(TRIFLUOROMETHYLSULFONYL)IMIDE

Description

It is a typical ionic liquid usually used as the solvent in the organic synthesis and chemical industry. For example, this chemical can act as the solvent for dissolving CO2 gas.¹ This substance may also function as the solvent for dissolving the electroactive oxygen, thus allowing for the study of electrochemical reduction of oxygen by cyclic voltammetry at a gold microdisk electrode.² Moreover, determination of ammonia based on electro-oxidation of hydroquinone has been carried out by using this compound as the solvent.³ Besides, nanoparticles of ZnO with the wurtzite structure have been synthesized via a microwave through the decomposition of zinc acetate dihydrate in 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide as a solvent.⁴

Referrence

1. Schilderman, A. M.; Raeissi, S.; Peters, C. J., Solubility of carbon dioxide in the ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Fluid Phase Equilib. 2007, 260, 19-22.
2. Buzzeo, M. C.; Klymenko, O. V.; Wadhawan, J. D.; Hardacre, C.; Seddon, K. R.; Compton, R. G., Voltammetry of oxygen in the room-temperature ionic liquids 1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide and hexyltriethylammonium bis((trifluoromethyl)sulfonyl)imide: One-electron reduction to form superoxide. Steady-state and transient behavior in the same cyclic voltammogram resulting from widely different diffusion coefficients of oxygen and superoxide. J. Phys. Chem. A 2003, 107, 8872-8878.
3. Giovanelli, D.; Buzzeo, M. C.; Lawrence, N. S.; Hardacre, C.; Seddon, K. R.; Compton, R. G., Determination of ammonia based on the electro-oxidation of hydroquinone in dimethylformamide or in the room temperature ionic liquid, 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Talanta 2004, 62, 904-911.
4. Goharshadi, E. K.; Ding, Y.; Nancarrow, P., Green synthesis of ZnO nanoparticles in a room-temperature ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. J. Phys. Chem. Solids 2008, 69, 2057-2060.

Conductivity

6.63 mS/cm

Chemical Properties

Clear colorless liquid

Uses

1-Ethyl-3-methylimidazolium bis(Trifluoromethylsulfonyl)imide is an ionic liquid; used in method for regulating thermal response temperature of ionic liquid gel and thermal response ionic liquid gel.

Uses

Ionic Liquids for Energy Storage Applications

General Description

1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [EMIM][N(Tf)₂] is a room temperature ionic liquid (RTIL). ([EMIM][N(Tf)₂]) as a non-aqueous solvent, is advantageous over traditional aprotic polar organic solvents in electrochemical investigation of electroactive species since it has low vapor pressure, high thermal stability, good conductivity and a wide electrochemical window. [EMIM][N(Tf)₂] shows good solubility in CO₂.

Synthesis

I. 200g of diethyl sulfate was added drop by drop to the toluene solution of 1-methylimidazole (118g of 1-methylimidazole, 400g of toluene), cooled in an ice bath, and operated under nitrogen atmosphere to ensure that the reaction temperature was between 20 and 30, and the ionic liquid formed in the reaction made the solution from clarification to turbidity, and the titration was finished, and the solution was static layered after stirring for 2h at room temperature to obtain 309g of crude 1-ethyl-3-methylimidazole ethyl sulfate. Ethyl methylimidazole sulfate crude 309g.

Two, with toluene washing three times to get 289g more pure 1-ethyl-3-methylimidazole sulfate ethyl ester, will be in the rotary evaporator on the decompression distillation for 1h to maintain the temperature of 60 , to remove residual toluene, and finally in 80 vacuum drying oven drying for 24h, to get 1-ethyl-3-methylimidazole sulfate ethyl ester finished product 280g, the detection purity of 99.9%. The purity was 99.9%.

Third, 200g of 1-ethyl-3-methylimidazolium ethyl sulfate, 243g of lithium bis(trifluoromethylsulfonyl)imide, 500g of pure water were put into the reaction kettle, warmed up to 60 , stirred and reacted for 2h, and then left to separate the phases, and 335g of 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide was obtained as crude product.

Fourth, 1-ethyl-3-methyl Imidazoline bis(trifluoromethylsulfonyl)imine crude product was washed with pure water for three times to obtain 312g of relatively pure 1-ethyl-3-methylimidazoline bis(trifluoromethylsulfonyl)imine, which was distilled under reduced pressure on a rotary evaporator for 2h, maintained at a temperature of 80 , most of the water was removed, and finally dried at 110 in a vacuum drying oven for 12h, to obtain the target product 1-ethyl-3-methylimidazoline bis ( Trifluoromethylsulfonyl)imide finished product 301g.