Acidic Ionic Liquids

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ACIDIC IONIC LIQUIDS

REFERENCES ACIDIC IONIC LIQUIDS

1-(4-sulfobutyl)-3-methylimidazolium trifluoromethanesulfonate, 98% [(CH₂)₄SO₃HMlm][CF₃SO₃]
ImSF1705c
1-(4-sulfobutyl)-3-methylimidazolium hydrogen sulfate, 98% [(CH₂)₄SO₃HMlm][HSO₄]
ImSF1213c ImSF1808c
1-(4-sulfobutyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 98% [(CH₂)₄SO₃HMlm][N(CF₃SO₂)₂]

Experimental aspect :



Hydrophilic Liquid at room temperature Brønsted acids Stable with water and oxygen Non-corrosive Easily recyclable

Solubility :

SOLVENT
MISCIBILITY

Water
Miscible

Hexane Ester immiscible immiscible

Applications :

These ionic liquids are used as acid catalysts in the following reactions : Esterification, Oxidation,

Alkylation, Beckmann Rearrangement, Cyclotrimerisation…

Esterification of ethanol by acetic acid¹:

Catalyzed by a Brønsted acidic ionic liquid

CH₃COOC₂H₅
Ethyl acetate
Conversion = 60.3% Selectivity = 98.2%

+
OH ₂

H₂SO₄

CH₃COOH
+
C
₂H₅OH

60°C, 4 h

Acetic acid
Ethanol

[(CH₂)H₄SO₃HMIm] [HSO₄]
CH₃COOC₂H₅
Ethyl acetate
Conversion = 92.8% Selectivity = 100%

+
OH ₂

The 1-(4-sulfobutyl)-3-methylimidazoliumhydrogensulfate is a more effective catalyst than a conventional catalyst (sulphuric acid H₂SO₄). The ester formed is extracted by a simple separation and the acidic ionic liquid may then be recycled without any loss of activity (at the 5^threcycling, Conversion=88.5% and Selectivity=100%).

Cyclotrimerization of aldehydes²:

Catalyzed by an acidic ionic liquid with no addition of any organic solvent

[(CH₂)₄SO₃HMIm] [CF SO₃]

25°C, 1 h

2, 4, 6-triisopropyl-1, 3, 5-trioxane Conversion = 93% Selectivity = 100%
Isobutyraldehyde

The Isobutyraldehyde (60 mol) is catalyzed by the 1-(4-sulfobutyl)-3-methylimidazolium trifluoromethanesulfonate (1 mol) in only one hour at room temperature. The product from the reaction is isolated by liquid-liquid extraction with hexane ant the acidic ionic liquid is easily recycled without any loss of activity (at the 5^threcycling, Conversion=93% and Selectivity=100%).

¹Jianzhou Gui, Xiaohui Cong, Dan Liu, Xiaotong Zhang, Zhide Hu b, Zhaolin Sun, Catalysis Communications, 5, 473–477, (2004) ²Jianzhou Gui, Dan Liu, Xiaomei Chen, Xiaotong Zhang, Lijuan Song, and Zhaolin Sun, React.Kinet.Catal.Lett., Vol. 90, No. 1,35−43 (2007)

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