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

Solubility of 1-Alkyl-3-ethylimidazolium-Based Ionic Liquids in Water and 1-Octanol

Domanska, U.[Urszula], Rekawek, A.[Anna], Marciniak, A.[Andrzej]
J. Chem. Eng. Data 2008, 53, 5, 1126-1132
ABSTRACT
The liquid liquid phase equilibria (LLE) of the following imidazolium ionic liquids (ILs), {1-ethyl-3- ethylimidazolium,or1-butyl-3-ethylimidazolium,or1-hexyl-3-ethylimidazoliumbis{(trifluoromethyl)sylfonyl}imide [EEIM][Tf2N], or [BEIM][Tf2N], or [HEIM][Tf2N], + water or + 1-octanol}, and {1-butyl-3-ethylimidazolium hexafluorophosphate [BEIM][PF6] + water or + 1-octanol}, have been measured. The effect of anion type ([Tf2N]- compared to [PF6]-) and the effect of structural components of an ionic liquid including alkyl chain length on the cation and the ethyl substituent instead of methyl at the cation on the physicalchemical properties of the IL and on the phase behavior were studied. An upper critical solution temperature (UCST) was observed in every system. An increase in the alkyl chain length increases the mutual solubility with 1-octanol and partly with water. Ionic liquids with the ethyl substituent on the cation [HEIM][Tf2N] show higher solubility in 1-octanol in comparison with the methyl substituent. After the synthesis, the characterization and purity of the compounds were obtained by nuclear magnetic resonance (NMR), elemental analysis, water content (Fischer method), and differential scanning microcalorimetry (DSC). From DSC, the melting point, enthalpy of fusion, and the temperatures of glass transition of all the investigated ionic liquids were determined. The experimental LLE data were correlated by means of the NRTL equation.
Compounds
# Formula Name
1 C9H13F6N3O4S2 1,3-diethylimidazolium bis[(trifluoromethyl)sulfonyl]imide
2 C11H17F6N3O4S2 1-butyl-3-ethylimidazolium bis[(trifluoromethyl)sulfonyl]imide
3 C13H21F6N3O4S2 1-hexyl-3-ethylimidazolium bis(trifluoromethylsulfonyl)imide
4 C9H17F6N2P 1-butyl-3-ethylimidazolium hexafluorophosphate
5 H2O water
6 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
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Triple point temperature, K ; Glass
  • Glass
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 1
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 1
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 2
  • Triple point temperature, K ; Glass
  • Glass
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 2
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 3
  • Triple point temperature, K ; Glass
  • Glass
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 3
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 4
  • Triple point temperature, K ; Glass
  • Glass
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 5
  • 1
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS:UFactor:128
  • 25
  • POMD
  • 5
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS:UFactor:8
  • 12
  • POMD
  • 5
  • 3
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 3; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS:UFactor:8
  • 13
  • POMD
  • 5
  • 4
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 4; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS:UFactor:48
  • 10
  • POMD
  • 6
  • 1
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS:UFactor:8
  • 16
  • POMD
  • 6
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS:UFactor:8
  • 15
  • POMD
  • 6
  • 3
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 3; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS:UFactor:8
  • 18
  • POMD
  • 6
  • 4
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 4; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS:UFactor:8
  • 19