Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Separation of sulfur compounds from alkanes with 1-alkylcyanopyridinium-based ionic liquids

Domanska, U.[Urszula], Walczak, K.[Klaudia], Zawadzki, M.[Maciej]
J. Chem. Thermodyn. 2014, 69, 27-35
ABSTRACT
In this work, we studied the applicability of new 1-alkyl-cyanopyridinium-based ionic liquids (ILs) in the extraction of aromatic-sulfur compounds from aliphatic mixtures. The synthesis of new 1-alkyl-cyanopyridinium- based ionic liquids is presented. Experimental data for (liquid + liquid) equilibrium (LLE) were obtained for various binary and ternary mixtures of {IL (1) + thiophene, or benzothiophene (2) + heptane (3)} at T = 308.15 K and ambient pressure. Three ILs have been studied: 1-butyl-3-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide [BCN3Py][NTf2], 1-butyl-4-cyanopyridinium bis{(trifluoromethyl) sulfonyl}imide [BCN4Py][NTf2] and 1-hexyl-4-cyanopyridinium bis{(trifluoromethyl)sulfonyl} imide, [HCN4Py][NTf2]. One of the IL showed excellent results in terms of sulfur compounds selectivity and solute distribution ratio compared to what is currently used in industry. Chromatography analysis showed that the IL used as an entrainer was not present in the alkane layer. This eliminates the step needed for the separation of the solvent. A comparative study of the separation effectiveness of [BCN4Py][NTf2] in this work in comparison with other reported ILs was performed for choosing the best solvent for the intended separation. Density and viscosity of [BCN4Py][NTf2] were measured over a range of temperature from (278.15 to 358.15) K. 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 C12H13F6N3O4S2 1-butyl-3-cyanopyridinium bis(trifluoromethylsulfonyl)imide
2 C14H17F6N3O4S2 1-hexyl-4-cyanopyridinium bis(trifluoromethylsulfonyl)imide
3 C12H13F6N3O4S2 1-butyl-4-cyanopyridinium bis(trifluoromethylsulfonyl)imide
4 C4H4S thiophene
5 C8H6S benzo[b]thiophene
6 C7H16 heptane
7 C3H8O propan-1-ol
8 C3H6O acetone
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
  • 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
  • 9
  • POMD
  • 3
  • Viscosity, Pa*s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Falling or rolling sphere viscometry
  • 6
  • 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
  • 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
  • 13
  • 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
  • 8
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 8
  • Refractive index (Na D-line) ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Standard Abbe refractometry
  • 1
  • POMD
  • 4
  • 6
  • 1
  • Mole fraction - 1 ; Liquid mixture 1
  • Mole fraction - 4 ; Liquid mixture 2
  • Mole fraction - 1 ; Liquid mixture 2
  • Mole fraction - 4; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • Chromatography
  • Chromatography
  • 10
  • POMD
  • 4
  • 6
  • 2
  • Mole fraction - 2 ; Liquid mixture 1
  • Mole fraction - 4 ; Liquid mixture 2
  • Mole fraction - 2 ; Liquid mixture 2
  • Mole fraction - 4; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • Chromatography
  • Chromatography
  • 12
  • POMD
  • 4
  • 6
  • 3
  • Mole fraction - 3 ; Liquid mixture 1
  • Mole fraction - 4 ; Liquid mixture 2
  • Mole fraction - 3 ; Liquid mixture 2
  • Mole fraction - 4; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • Chromatography
  • Chromatography
  • 10
  • POMD
  • 5
  • 6
  • 3
  • Mole fraction - 3 ; Liquid mixture 1
  • Mole fraction - 5 ; Liquid mixture 2
  • Mole fraction - 3 ; Liquid mixture 2
  • Mole fraction - 5; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • Chromatography
  • Chromatography
  • 11
  • POMD
  • 5
  • 6
  • 2
  • Mole fraction - 2 ; Liquid mixture 2
  • Mole fraction - 2 ; Liquid mixture 1
  • Mole fraction - 5 ; Liquid mixture 1
  • Mole fraction - 5; 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
  • Mole fraction - 1 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • 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
  • Chromatography
  • 1
  • POMD
  • 6
  • 2
  • Mole fraction - 2 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 4
  • 2
  • Mole fraction - 4 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 6
  • 3
  • Mole fraction - 3 ; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 4
  • 3
  • Mole fraction - 4 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 5
  • 3
  • Mole fraction - 3 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • 1
  • POMD
  • 5
  • 3
  • Mole fraction - 5 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 2
  • Pressure, kPa; Liquid mixture 2
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 5
  • 2
  • Mole fraction - 2 ; Liquid mixture 2
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 2
  • Liquid mixture 1
  • Chromatography
  • 1
  • POMD
  • 5
  • 2
  • Mole fraction - 2 ; Liquid mixture 1
  • Temperature, K; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Chromatography
  • 1