Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Separation of hex-1-ene/hexane and cyclohexene/cyclohexane compounds with [EMIM]-based ionic liquids

Domanska, U.[Urszula], Karpinska, M.[Monika], Wlazlo, M.[Michal]
Fluid Phase Equilib. 2016, 427, 421-428
ABSTRACT
In this work we studied the applicability of three imidazolium-based ionic liquids (ILs) with different anions in the separation of hex-1-ene/hexane and cyclohexene/cyclohexane compounds. Experimental data for liquid-liquid equilibrium (LLE) were obtained for various binary and ternary mixtures of {IL (1) + hex-1-ene (2) + hexane (3)} or {IL (1) + cyclohexene (2) + cyclohexane (3)} at T = 298.15 K and ambient pressure. Three ILs have been studied: 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)-imide, [EMIM][NTf2], 1-ethyl-3-methylimidazolium dicyanamide, [EMIM][DCA] and 1-ethyl-3-methylimidazolium tricyanomethanide, [EMIM][TCM]. ILs were chosen after a literature analysis and measurements of activity coefficient at infinite dilution in many ILs. Chosen ILs showed excellent results in terms of selectivity and solute distribution ratio. The chromatography analysis revealed that the ILs used as an entrainers were not present in the hydrocarbon-rich layer. This is convenient for planned technology, because eliminates the step needed for the separation of the solvent. A comparative study of the separation effectiveness of the [EMIM][TCM] in comparison with two other reported ILs was chosen as the best solvent for the intended two separation processes. The non-random two liquid NRTL model was used successfully to correlate the experimental tie-lines and to calculate the phase composition error in mole fraction in the ternary systems.
Compounds
# Formula Name
1 C8H11F6N3O4S2 1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide
2 C8H11N5 1-ethyl-3-methylimidazolium dicyanamide
3 C10H11N5 1-ethyl-3-methyl-1H-imidazolium tricyanomethanide
4 C6H14 hexane
5 C6H12 hex-1-ene
6 C6H12 cyclohexane
7 C6H10 cyclohexene
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
  • 4
  • 5
  • 1
  • Mole fraction - 1 ; Liquid mixture 2
  • Mole fraction - 1 ; Liquid mixture 1
  • Mole fraction - 5 ; Liquid mixture 1
  • Mole fraction - 5; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 17
  • POMD
  • 4
  • 5
  • 2
  • Mole fraction - 5 ; Liquid mixture 2
  • Mole fraction - 2 ; Liquid mixture 1
  • Mole fraction - 5 ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 12
  • POMD
  • 4
  • 5
  • 3
  • Mole fraction - 3 ; Liquid mixture 2
  • Mole fraction - 3 ; Liquid mixture 1
  • Mole fraction - 5 ; Liquid mixture 1
  • Mole fraction - 5; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 16
  • POMD
  • 6
  • 7
  • 1
  • Mole fraction - 1 ; Liquid mixture 2
  • Mole fraction - 1 ; Liquid mixture 1
  • Mole fraction - 7 ; Liquid mixture 1
  • Mole fraction - 7; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 15
  • POMD
  • 6
  • 7
  • 2
  • Mole fraction - 7 ; Liquid mixture 2
  • Mole fraction - 2 ; Liquid mixture 1
  • Mole fraction - 7 ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • Chromatography
  • Chromatography
  • 17
  • POMD
  • 6
  • 7
  • 3
  • Mole fraction - 3 ; Liquid mixture 1
  • Mole fraction - 3 ; Liquid mixture 2
  • Mole fraction - 7 ; Liquid mixture 2
  • Mole fraction - 7; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • Chromatography
  • Chromatography
  • 14