Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Phase behaviour of tricyanomethanide-based ionic liquids with alcohols and hydrocarbons

Domanska, U.[Urszula], Lukoshko, E. V.[Elena Vadimovna], Szydlowski, J.[Jerzy]
Fluid Phase Equilib. 2015, 387, 18-23
ABSTRACT
Ionic liquids (ILs) are known as attractive solvents showing high extraction capacity for aromatic hydrocarbons from aliphatic hydrocarbons and for sulfur compounds from alkanes. New experimental results on liquid liquid phase equilibrium (LLE) in the binary systems of {1-butyl-1-methylpyrrolidinium tricyanomethanide, [BMPYR][TCM] + an alcohol (1-octanol, 1-decanol), or + hydrocarbons (benzene, toluene, ethylbenzene, and heptane)} and of {1-butyl-1-methylmorpholinium tricyanomethanide, [BMMOR][TCM] + an alcohol (1-hexanol, 1-octanol, 1-decanol), or + hydrocarbons (benzene, toluene, ethylbenzene, thiophene, and heptane)} have been determined at atmospheric pressure using a dynamic method. Upper critical solution temperature type of phase behavior for alcohols and a visible tendency for heptane was observed. For aromatic hydrocarbons there is a visible tendency of the lower critical solution temperature phase behavior. Decrease of solubility of alcohol with an increase of its alkyl chain length and of aromatic hydrocarbons with an increase of the alkyl chain length of substituent for all studied systems was detected. The correlation of the experimental data has been carried out using the non-random two liquid (NRTL) equation. The influence of the cation structure on the phase behavior has been discussed. The phase diagrams reported here have been compared to the systems published earlier with the 1-butyl-1-methylpyrrolidinium, or TCM based ionic liquids.
Compounds
# Formula Name
1 C13H20N4 1-butyl-1-methylpyrrolidinium tricyanomethanide
2 C13H20N4O 4-butyl-4-methylmorpholinium tricyanomethanide
3 C6H14O hexan-1-ol
4 C8H18O octan-1-ol
5 C10H22O decan-1-ol
6 C6H6 benzene
7 C7H8 toluene
8 C8H10 ethylbenzene
9 C4H4S thiophene
10 C7H16 heptane
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
  • 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
  • 5
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 6
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 7
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 8
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 9
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 10
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 1
  • POMD
  • 4
  • 1
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 9
  • POMD
  • 5
  • 1
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 13
  • POMD
  • 6
  • 1
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 4
  • POMD
  • 7
  • 1
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 5
  • POMD
  • 8
  • 1
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 7
  • POMD
  • 10
  • 1
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 1; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 4
  • POMD
  • 3
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 10
  • POMD
  • 4
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 20
  • POMD
  • 5
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 19
  • POMD
  • 6
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 4
  • POMD
  • 7
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 5
  • POMD
  • 8
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 5
  • POMD
  • 9
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 5
  • POMD
  • 10
  • 2
  • Liquid-liquid equilibrium temperature, K ; Liquid mixture 1
  • Mole fraction - 2; Liquid mixture 1
  • Pressure, kPa; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • VISOBS
  • 4