Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Ternary LLE measurements for the separation of hex-1-ene/hexane and cyclohexene/cyclohexane compounds with [DCA]-based ionic liquids

Domanska, Urszula, Karpinska, Monika, Wlazlo, Michal, Zawadzki, Maciej
Fluid Phase Equilib. 2018, 462, 65-72
ABSTRACT
The objective of this work was to explore the feasibility of separation of hex-1-ene from hexane and cyclohexene from cyclohexane with new ionic liquids (ILs) with [DCA](-) anion. With this aim, the liquid-liquid phase equilibrium (LLE) for three ternary systems of {IL (1) + hex-1-ene (2) + hexane (3)} and two {IL (1) + cyclohexene (2) + cyclohexane (3)} at T = 298.15 K were determined at ambient pressure. Three new ILs have been presented and used in LLE measurements: 3-(2-methoxyethyl)-1-methylimidazolium dicyanamide, [(C2OCH3)MIM][DCA], 1-(4-methoxy-4-oxobutyl)-3-methylimidazolium dicyanamide, [(C3COOMe)MIM][DCA] and choline dicyanamide, [Chol][DCA]. The anion of the ILs was chosen after a literature analysis and measurements of activity coefficient at infinite dilution in many ILs. Chosen ILs revealed large selectivity and very low solute distribution ratio. The results of the chromatography analysis indicated that the ILs used as an entrainers were not detected in the hydrocarbon-rich layer, which is convenient, because eliminates the step needed for the separation of the solvent. The well known NRTL activity coefficient model was used to correlate the LLE data.
Compounds
# Formula Name
1 C6H12 hex-1-ene
2 C6H14 hexane
3 C6H10 cyclohexene
4 C6H12 cyclohexane
5 C9H13N5O 1-(2-methoxyethyl)-3-methylimidazolium dicyanamide
6 C11H15N5O2 1-(4-methoxy-4-oxobutyl)-3-methylimidazolium dicyanamide
7 C7H14N4O choline dicyanamide
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
  • 5
  • 1
  • 2
  • Mole fraction - 5 ; Liquid mixture 2
  • Mole fraction - 5 ; Liquid mixture 1
  • Mole fraction - 1 ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 12
  • POMD
  • 6
  • 1
  • 2
  • Mole fraction - 6 ; Liquid mixture 2
  • Mole fraction - 6 ; Liquid mixture 1
  • Mole fraction - 1 ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 11
  • POMD
  • 7
  • 1
  • 2
  • Mole fraction - 7 ; Liquid mixture 2
  • Mole fraction - 7 ; Liquid mixture 1
  • Mole fraction - 1 ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 12
  • POMD
  • 5
  • 3
  • 4
  • Mole fraction - 5 ; Liquid mixture 2
  • Mole fraction - 5 ; Liquid mixture 1
  • Mole fraction - 3 ; Liquid mixture 1
  • Mole fraction - 3; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 10
  • POMD
  • 6
  • 3
  • 4
  • Mole fraction - 6 ; Liquid mixture 2
  • Mole fraction - 6 ; Liquid mixture 1
  • Mole fraction - 3 ; Liquid mixture 1
  • Mole fraction - 3; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 11