Acetic Acid → 1-Butyl-3-methylimidazolium Acetate

HRID 1611863Notes

Reaction equation

HRID 1611863 reaction equation
[Cl-].[CH2:2]([N+:6]1[CH:10]=[CH:9][N:8]([CH3:11])[CH:7]=1)[CH2:3][CH2:4][CH3:5].[C:12]([OH:15])(=[O:14])[CH3:13]>[Ni]>[C:12]([O-:15])(=[O:14])[CH3:13].[CH2:2]([N+:6]1[CH:10]=[CH:9][N:8]([CH3:11])[CH:7]=1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 178448538HCID 178448538, compound

Product 1

HCID 1784762761-Butyl-3-methylimidazolium AcetateYield 70%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

In a second example, a two-compartment cell was constructed, using a DSA anode, a cation exchange membrane (Nafion 902 from DuPont) and a Ni cathode. 10 liters each of 2 M 1-Butyl-3-Methylimidazolium Chloride and 1.5 M acetic acid were added to the two compartments, and 10 amps current was applied to the cell until the pH of the solution containing the acetic acid had risen to 7.0. The catholyte was then removed from the cell, and the 1-Butyl-3-Methylimidazolium Acetate product isolated by removing the water by rotary distillation as described above. The yield was 70% and had 329 ppm sodium and 893 ppm Cl. The product also contained 19% water, which could not easily be removed by vacuum evaporation. However, the 1-Butyl-3-Methylimidazolium Acetate product could be further dried by azeotropic distillation. The wet product was heated to reflux in a round bottom flask, fitted with a Dean-Stark trap with benzene was added. When no more water was collected in the trap, the benzene was removed by rotoevaporation. The product now contained <0.5% H2O.

Workup

  1. customThe catholyte was then removed from the cell

Sources & evidence

ORD record
ord-25143bc453d949ca8a292b1f5612b7a5
Source dataset
uspto-grants-2006_01
Patent number
US06991718B2

Reaction notes

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