Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Solubility of Water in Aprotic Heterocyclic Anion (AHA) Ionic Liquids

Bonilla, G. M. A.[Gabriela M. Avelar], Morales-Collazo, O.[Oscar], Brennecke, J. F.[Joan F.]
J. Chem. Eng. Data 2019, 64, 11, 4875-4881
ABSTRACT
The hydrophobic-hydrophilic character of a series of fifteen tetra-alkylphosphonium ionic liquids with aprotic heterocyclic anions (AHAs) was studied by measuring their liquid-liquid equilibrium with water. Specifically, the solubility of water in the ionic liquid rich phase was determined at room temperature by Karl Fischer titration. The effect of the tetra-alkyl-phosphonium cation was studied by varying alkyl chain length; as expected, hydrophobicity increases with increasing alkyl chain length. The effect of the anion was studied by pairing the tetra-alkyl-phosphonium cation with different AHAs and by adding different substituents on the anion. The anion nature, basicity and electron withdrawing effect of different substituents proved to have a significant impact on the IL's hydrophobicity. Changes in the alkyl chain length of the cation and the nature of the anion are able to tune the solubility of water in the ILs over an order of magnitude.
Compounds
# Formula Name
1 C34H70N3P trihexyl(tetradecyl)phosphonium 1,2,4-triazolide
2 C34H70N3P trihexyl(tetradecyl)phosphonium 1,2,3-triazolide
3 C35H71N2P trihexyl(tetradecyl)phosphonium imidazolide
4 C39H73N2P trihexyl(tetradecyl)phosphonium benzimidazolide
5 C33H69N4P trihexyl(tetradecyl)phosphonium tetrazolide
6 C37H72F3N2P trihexyl(tetradecyl)phosphonium 3-methyl-5-trifluoromethylpyrazolide
7 C39H72BrN2P trihexyl(tetradecyl)phosphonium 5-bromobenzimidazolide
8 C35H70N3O2P trihexyl(tetradecyl)phosphonium 4-nitropyrazolide
9 C36H70F3N2P trihexyl(tetradecyl)phosphonium 3-trifluoromethylpyrazolide
10 C40H75N2PS trihexyl(tetradecyl)phosphonium 2-(methylthio)benzimidazolide
11 C35H67N2P tributyl(octadecyl)phosphonium 2-cyanopyrrolide
12 C34H68F6NO4PS2 trihexyl(tetradecyl)phosphonium bis[(trifluoromethyl)sulfonyl]imide
13 C37H71N2P trihexyl(tetradecyl)phosphonium 2-cyanopyrrolide
14 C19H35N2P triethyl(octyl)phosphonium 2-cyanopyrrolide
15 H2O water
16 C41H73N2P trihexyl(tetradecyl)phosphonium 5-cyanoindolide
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 14
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 11
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 13
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 1
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 2
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 3
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 4
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 5
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 6
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 7
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 8
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 9
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 10
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 16
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1
  • POMD
  • 12
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Titration method
  • 1