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

Liquid Phase Behavior of Ionic Liquids with Water and 1-Octanol and Modeling of 1-Octanol/Water Partition Coefficients

Chapeaux, A.[Alexandre], Simoni, L. D.[Luke D.], Stadtherr, M. A. A.[Mark A.], Brennecke, J. F.[Joan F.]
J. Chem. Eng. Data 2007, 52, 6, 2462-2467
ABSTRACT
This study examines the effect of structural components of an ionic liquid (IL), including the choice of the anion, alkyl chain length on the cation, and substitution on the cation, on the mutual solubility with water and with 1-octanol. This is important because ionic liquids have been shown to be good replacements for organic extraction solvents in some liquid separations. In addition, we use the measured data to predict 1-octanol/water partition coefficients for the ionic liquids using the nonrandom two liquid (NRTL) and electrolyte nonrandom two liquid (eNRTL) excess Gibbs energy models. Specifically, the mutual solubilities of 15 different imidazolium, pyridinium, and quaternary ammonium ionic liquids with water were measured at (23.5 +/- 1) deg C. An increase in the alkyl chain length or the substitution decreases the mutual solubility with water. The [BF4]- and [B(CN)4]- anions are significantly more hydrophilic than [PF6]-, [(CF3SO2)2N]-, and [(CF3SO2)3C]-. The mutual solubilities of 10 ILs with 1-octanol were measured at (23.5 ( 1) deg C. For these systems, the longer the alkyl chain, the more soluble the IL was in the alcohol, while ring substitution has little effect. From this data, 1-octanol/water partition coefficients of 10 ionic liquids were predicted using the NRTL and eNRTL models.
Compounds
# Formula Name
1 C8H11F6N3O5S2 1-(2-hydroxyethyl)-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
2 C12H19F6N3O4S2 1-hexyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
3 C13H21F6N3O4S2 1-hexyl-2,3-dimethylimidazolium bis[(trifluoromethyl)sulfonyl]imide
4 C14H23F6N3O4S2 1-octyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
5 C12H15F9N2O6S3 1-butyl-3-methylimidazolium tris[(trifluoromethyl)sulfonyl]methide
6 C10H11BN6 1-ethyl-3-methylimidazolium tetracyanoborate
7 C7H14F6N2O5S2 choline bis(trifluoromethylsulfonyl)imide
8 C12H16F6N2O4S2 1-butyl-3-methylpyridinium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
9 C13H18F6N2O4S2 1-hexylpyridinium bis(trifluromethylsulfonyl)imide
10 C14H20F6N2O4S2 1-hexyl-3-methylpyridinium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
11 C15H22F6N2O4S2 1-hexyl-3,5-dimethylpyridinium bis(trifluoromethylsulfonyl)imide
12 C17H26F6N2O4S2 1-hexyl-2-ethyl-3,5-dimethylpyridinium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
13 C16H24F6N2O4S2 1-octyl-3-methylpydridinium bis(trifluoromethylsulfonyl)imide
14 C15H23F6N3O4S2 4-(dimethylamino)-1-hexyl-pyridinium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
15 C16H25F6N3O4S2 1-hexyl-3-methyl-4-(dimethylamino)pyridinium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
16 H2O water
17 C8H18O octan-1-ol
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
  • 16
  • 6
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 6
  • Mass fraction - 6 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 1
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 1
  • Mass fraction - 1 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 5
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 5
  • Mass fraction - 5 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 2
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 2
  • Mass fraction - 2 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 4
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 4
  • Mass fraction - 4 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 3
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 3
  • Mass fraction - 3 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 8
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 8
  • Mass fraction - 8 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 9
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 9
  • Mass fraction - 9 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 10
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 10
  • Mass fraction - 10 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 11
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 11
  • Mass fraction - 11 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 13
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 13
  • Mass fraction - 13 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 14
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 14
  • Mass fraction - 14 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 12
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Titration method
  • 1
  • POMD
  • 16
  • 12
  • Mass fraction - 12 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 16
  • 15
  • Mass fraction - 16 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • 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
  • spectroscopy
  • 1
  • POMD
  • 17
  • 6
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 6
  • Mass fraction - 6 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 8
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 8
  • Mass fraction - 8 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 9
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 9
  • Mass fraction - 9 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 10
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 10
  • Mass fraction - 10 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 11
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 11
  • Mass fraction - 11 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 12
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 12
  • Mass fraction - 12 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 13
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 13
  • Mass fraction - 13 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 14
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 14
  • Mass fraction - 14 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 15
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 15
  • Mass fraction - 15 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1
  • POMD
  • 17
  • 7
  • Mass fraction - 17 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 17
  • 7
  • Mass fraction - 7 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • spectroscopy
  • 1