Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Phase behavior of ternary mixtures {aliphatic hydrocarbon + aromatic hydrocarbon + ionic liquid}: Experimental LLE data and their modeling by COSMO-RS

Dominguez, I.[Irene], Gonzalez, E. J.[Emilio J.], Palomar, J.[Jose], Dominguez, A.[Angeles]
J. Chem. Thermodyn. 2014, 77, 222-229
ABSTRACT
Separation of aromatic and aliphatic hydrocarbons is a complex process in the petrochemical industry due to overlapping boiling points and azeotrope formation. In this paper, liquid extraction of aromatic compounds (toluene and ethylbenzene) from aliphatic compounds (hexane and cyclohexene) using ionic liquids (1-butyl-3-methylimidazolium methylsulfate, BMimMSO4, 1-propyl-3-methylimidazolium bis{trifluoromethylsulfonyl}imide, PMimNTf2, and 1-butyl-3-methylimidazolium bis{trifluoromethylsulfonyl} imide, BMimNTf2) as solvent was studied. (Liquid + liquid) equilibrium (ELL) data for the ternary systems {hexane (1) + ethylbenzene (2) + BMimMSO4, or BMimNTf2, or PMimNTf2 (3)}, {hexane (1) + toluene (2) + BMimMSO4 (3)} and {cyclohexene (1) + ethylbenzene (2) + BMimMSO4 (3)} were experimentally determined at T = 298.15 K and atmospheric pressure. Moreover, an analysis of the influence of the structure of each compound on the phase behavior was also carried out. The ability of the studied ILs to separate aromatic from aliphatic compounds was evaluated in terms of the solute distribution ratio, b, and the selectivity, S. The Non Random Two-Liquid (NRTL) and UNIversal QUAsiChemical (UNIQUAC) thermodynamic models were used to correlate the experimental LLE data. Furthermore, the COnductorlike Screening MOdel for Real Solvents (COSMO-RS) was applied to predict the (liquid + liquid) equilibrium. The suitability of this model to describe the phase behavior of the studied mixtures was evaluated comparing the experimental and calculated data.
Compounds
# Formula Name
1 C9H18N2O4S 1-butyl-3-methylimidazolium methyl sulfate
2 C10H15F6N3O4S2 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
3 C9H13F6N3O4S2 1-methyl-3-propylimidazolium bis[(trifluoromethyl)sulfonyl]imide
4 C6H14 hexane
5 C6H10 cyclohexene
6 C7H8 toluene
7 C8H10 ethylbenzene
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
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 1
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 1
  • POMD
  • 2
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 2
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 1
  • POMD
  • 3
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 3
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 1
  • POMD
  • 4
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 4
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 1
  • POMD
  • 5
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 5
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 1
  • POMD
  • 6
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 6
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 1
  • POMD
  • 7
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 7
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 1
  • POMD
  • 6
  • 4
  • 1
  • Mole fraction - 4 ; Liquid mixture 1
  • Mole fraction - 4 ; Liquid mixture 2
  • Mole fraction - 6 ; Liquid mixture 2
  • Mole fraction - 6; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Density calibration data
  • Density calibration data
  • Density calibration data
  • 11
  • POMD
  • 7
  • 4
  • 1
  • Mole fraction - 4 ; Liquid mixture 1
  • Mole fraction - 4 ; 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
  • Density calibration data
  • Density calibration data
  • Density calibration data
  • 12
  • POMD
  • 7
  • 5
  • 1
  • Mole fraction - 5 ; Liquid mixture 1
  • Mole fraction - 5 ; 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
  • Density calibration data
  • Density calibration data
  • Density calibration data
  • 11
  • POMD
  • 7
  • 4
  • 2
  • Mole fraction - 4 ; Liquid mixture 1
  • Mole fraction - 4 ; 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
  • Density calibration data
  • Density calibration data
  • Density calibration data
  • 12
  • POMD
  • 7
  • 4
  • 3
  • Mole fraction - 4 ; Liquid mixture 1
  • Mole fraction - 4 ; 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
  • Density calibration data
  • Density calibration data
  • Density calibration data
  • 13
  • POMD
  • 4
  • 1
  • Mole fraction - 4 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Density calibration data
  • 1
  • POMD
  • 6
  • 1
  • Mole fraction - 6 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Density calibration data
  • 1
  • POMD
  • 7
  • 1
  • Mole fraction - 7 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Density calibration data
  • 1
  • POMD
  • 5
  • 1
  • Mole fraction - 5 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Density calibration data
  • 1
  • POMD
  • 4
  • 2
  • Mole fraction - 4 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Density calibration data
  • 1
  • POMD
  • 7
  • 2
  • Mole fraction - 7 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Density calibration data
  • 1
  • POMD
  • 4
  • 3
  • Mole fraction - 4 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Density calibration data
  • 1
  • POMD
  • 7
  • 3
  • Mole fraction - 7 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Density calibration data
  • 1