Acetic Acid → 1-Ethyl-3-methylimidazolium acetate

HRID 889664Notes

Reaction equation

HRID 889664 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]>>[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

3

Reactant 2

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

Product 1

HCID 116583531-Ethyl-3-methylimidazolium acetateYield 93.1%

Conditions

Temperature
80 °C

Procedure

226.8 g (0.72 mol) of Ba(OH)2 (octahydrate) are suspended in 600 g of water. The suspension is heated to 80° C., resulting in the barium salt melting and forming an aqueous emulsion. 149.8 g (0.72 mol) of 1-methyl-3-ethylimidazolium hydrogensulfate are added dropwise to this emulsion, with the temperature rising to 100° C. Despite the barium sulfate which precipitates, the suspension remains readily stirrable. The reaction mixture is stirred for another 2 hours at 80° C., cooled 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. Drying under reduced pressure gives 113.3 g (0.67 mol) of 1-methyl-3-ethylimidazolium acetate (yield: 92%). The chloride content is 4 ppm.

Workup

  1. customforming an aqueous emulsion
  2. customrising to 100° C
  3. customDespite the barium sulfate which precipitates
  4. temperaturecooled
  5. filtrationthe precipitated BaSO4 is filtered off
  6. filtrationas filter aid
  7. customthe water is removed on a rotary evaporator
  8. extractionthe oil which remains is extracted with ethyl acetate
  9. customDrying under reduced pressure

Sources & evidence

ORD record
ord-9b19c61056a1475187216e64e530f8e1
Source dataset
uspto-grants-2012_08
Patent number
US08252943B2

Reaction notes

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