Reaction #586085

Reaction equation

KCl

1-Butyl-3-methylimidazolium chloride

potassium 1,1,2-trifluoro-2-(perfluoroethoxy)ethanesulfonate

→

product

Yield 62.0%

1-butyl-3-methylimidazolium 1,1,2-trifluoro-2-(perfluoroethoxy)ethanesulfonate

Yield 62.0%

Solvents

acetone

acetone

Conditions

Workup

1. 1
   Otherto settle leaving a colorless solution above it
2. 2
   FiltrationThe reaction mixture was filtered once through a celite/acetone pad
3. 3
   Otheragain through a fritted glass funnel to remove the KCl
4. 4
   OtherThe acetone was removed in vacuo first on a rotovap
5. 5
   workup.WAITon a high vacuum line (4 Pa, 25 degrees C.) for 2 hr
6. 6
   OtherResidual KCl was still precipitating out of the solution, so methylene chloride (50 ml)
7. 7
   workup.ADDITIONwas added to the crude product, which
8. 8
   Washwas then washed with deionized water (2×50 ml)
9. 9
   DryingThe solution was dried over magnesium sulfate
10. 10
    Otherthe solvent was removed in vacuo

Procedure

1-Butyl-3-methylimidazolium chloride (Bmim-Cl, 7.8 g) and dry acetone (150 ml) were combined at room temperature in a 500 ml flask. At room temperature in a separate 200 ml flask, potassium 1,1,2-trifluoro-2-(perfluoroethoxy)ethanesulfonate (TPES-K, 15.0 g) was dissolved in dry acetone (300 ml). These two solutions were combined and allowed to stir magnetically for 12 hr under positive nitrogen pressure. The KCl precipitate was then allowed to settle leaving a colorless solution above it. The reaction mixture was filtered once through a celite/acetone pad and again through a fritted glass funnel to remove the KCl. The acetone was removed in vacuo first on a rotovap and then on a high vacuum line (4 Pa, 25 degrees C.) for 2 hr. Residual KCl was still precipitating out of the solution, so methylene chloride (50 ml) was added to the crude product, which was then washed with deionized water (2×50 ml). The solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give the product as a viscous light yellow oil (12.0 g, 62% yield).

Source