Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Separation of pyridine from heptane with tricyanomethanide-based ionic liquids

Domanska, U.[Urszula], Lukoshko, E. V.[Elena Vadimovna]
Fluid Phase Equilib. 2015, 395, 9-14
ABSTRACT
Recent approaches employ three tricyanomethanide-based ionic liquids (ILs) as selective solvents of the extraction of pyridine as a model compound of nitrogen compounds in fuels from heptane at T = 298.15 K and ambient pressure. Experimental data for liquid liquid phase equilibrium (LLE) were obtained for three ternary systems. The 1-butyl-3-methylimidazolium tricyanomethanide, [BMIM][TCM], 1-butyl-1- methylmorpholinium tricyanomethanide, [BMMOR][TCM] and 1-butyl-1-methylpyridinium tricyanomethanide, [BMPY][TCM] were used due to their immiscibility with gasoline and diesel, negligible vapor pressure, and high selectivity to sulfur- and nitrogen-containing compounds. All of proposed ILs showed similar excellent selectivity with the best Smax = 609.3 for and similar high distribution ratio with bmax = 9.2 for [BMMOR][TCM] in the extraction of pyridine from heptane and much higher to what is currently published for different ILs. Chromatography analysis showed that IL was not present in the heptane layer. This eliminate the process of the separation of the solvent from the raffinate layer. The data obtained have been correlated with the non-random two liquid NRTL model. The experimental tie-lines and the phase composition in mole fraction in the ternary systems were calculated with an average root mean square deviation (RMSD) of 0.004.
Compounds
# Formula Name
1 C12H15N5 1-butyl-3-methylimidazolium tricyanomethane
2 C13H20N4O 4-butyl-4-methylmorpholinium tricyanomethanide
3 C14H16N4 1-butyl-4-methylpyridinium tricyanomethanide
4 C5H5N pyridine
5 C7H16 heptane
6 C3H8O propan-1-ol
7 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
  • 3
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 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
  • 4
  • 5
  • 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
  • 7
  • POMD
  • 4
  • 5
  • 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
  • 13
  • POMD
  • 4
  • 5
  • 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
  • 7