Acetic Acid → 1-Ethyl-3-methylimidazolium acetate

HRID 889663Notes

Reaction equation

HRID 889663 reaction equation
S([O-])(O)(=O)=O.[CH3:6][N+:7]1[CH:11]=[CH:10][N:9]([CH2:12][CH3:13])[CH:8]=1.[C:14]([OH:17])(=[O:16])[CH3:15]>O>[C:14]([O-:17])(=[O:16])[CH3:15].[CH3:6][N+:7]1[CH:11]=[CH:10][N:9]([CH2:12][CH3:13])[CH:8]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 162172151-Ethyl-3-methylimidazolium hydrogen sulfate

Product 1

HCID 116583531-Ethyl-3-methylimidazolium acetateYield 88.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

149.8 g (0.72 mol) of 1-methyl-3-ethylimidazolium hydrogensulfate are dissolved in 600 ml of water, and 226.8 g (0.72 mol) of Ba(OH)2 (octahydrate) are subsequently added in portions over a period of 30 minutes. The temperature is increased to 60° C. and the reaction mixture is stirred for 2 hours at this temperature. It is allowed to cool overnight and the precipitated BaSO4 is filtered off using Celite as filter aid. After addition of 43.5 g (0.72 mol) of glacial acetic acid, the water is removed on a rotary evaporator and the oil which remains is extracted with ethyl acetate. To remove residual water, the oil is admixed with n-butanol and the n-butanol is subsequently distilled off under reduced pressure. This gives 108.3 g (0.636 mol) of 1-methyl-3-ethylimidazolium acetate (yield: 88% based on 1-methyl-3-ethylimidazolium hydrogensulfate). The chloride content is 4 ppm.

Workup

  1. temperatureto cool overnight
  2. filtrationthe precipitated BaSO4 is filtered off
  3. filtrationas filter aid
  4. customthe water is removed on a rotary evaporator
  5. extractionthe oil which remains is extracted with ethyl acetate
  6. customTo remove residual water
  7. distillationthe n-butanol is subsequently distilled off under reduced pressure

Sources & evidence

ORD record
ord-b748425a75eb4a76b033133c4c3362b7
Source dataset
uspto-grants-2012_08
Patent number
US08252943B2

Reaction notes

Loading…