Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Stability of Ion Pairs of Bis(trifluoromethanesulfonyl)amide-Based Ionic Liquids in Dichloromethane

Katsuta, S.[Shoichi], Shiozawa, Y.[Yuta], Imai, K.[Kazuo], Kudo, Y.[Yoshihiro], Takeda, Y.[Yasuyuki]
J. Chem. Eng. Data 2010, 55, 4, 1588-1593
ABSTRACT
The ion pair formation constants at infinite dilution (KIP0) of bis(trifluoromethanesulfonyl)amide ([NTf2]-) salts in dichloromethane were determined conductometrically at 298.2 K. The cations used were nine monovalent organic ions having similar molecular size, i.e., 1-butyl-3-methylimidazolium ([BuMeIm]+), 1-butyl-2,3-dimethylimidazolium ([BuMe2Im]+), 1-butylpyridinium ([BuPy]+), 1-propyl-2,3,5-trimethylpyrazolium ([Me3PrPyra]+), 1-butyl-1-methylpyrrolidinium ([BuMePyrr]+), 1-methyl-1-propylpiperidinium ([MePrPip]+), methyltripropylammonium ([MePr3N]+), propyltrimethylammonium ([Me3PrN]+), and tetraethylammonium ([Et4N]+), where the results for [BuMeIm]+, [BuMe2Im]+, and [Et4N]+ were cited from our previous study. It was found from the KIP0 values that the ion pair stability varies with the cation in the order [BuMeIm]+ greater than [Me3PrN]+ greater than [BuPy]+ ? [BuMePyrr]+ ? [MePrPip]+ greater than [MePr3N]+ ? [Et4N]+ ? [BuMe2Im]+ ? [Me3PrPyra]+, which was explained on the basis of the structures of the cations. For the salts used, the fundamental properties as ionic liquids, such as density, viscosity, and electric conductivity, were also measured. The activation energies for viscous flow were determined from the temperature dependence of the viscosity, and their relation with the KIP0 values was discussed.
Compounds
# Formula Name
1 C10H15F6N3O4S2 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
2 C11H14F6N2O4S2 1-butylpyridinium bis[(trifluoromethyl)sulfonyl]imide
3 C11H20F6N2O4S2 1-butyl-1-methylpyrrolidinium bis[(trifluoromethyl)sulfonyl]imide
4 C11H17F6N3O4S2 1-butyl-2,3-dimethyl-1H-imidazolium bis(trifluoromethylsulfonyl)amide
5 C11H17F6N3O4S2 2,3,5-trimethyl-1-propyl-1H-pyrazolium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide
6 C11H20F6N2O4S2 1-methyl-1-propylpiperidinium bis(trifluoromethylsulfonyl)imide
7 C12H24F6N2O4S2 methyltripropylammonium bis[(trifluoromethyl)sulfonyl]amide
8 C8H16F6N2O4S2 N,N,N-trimethylpropanaminium bis((trifluoromethyl)sulfonyl)amide
9 C10H20F6N2O4S2 tetraethylammonium bis[(trifluoromethyl)sulfonyl]imide
10 CH2Cl2 dichloromethane
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
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 1
  • Kinematic viscosity, m2/s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CAPTUB:UFactor:4
  • 4
  • POMD
  • 1
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 14
  • POMD
  • 3
  • Kinematic viscosity, m2/s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CAPTUB:UFactor:4
  • 4
  • POMD
  • 3
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 19
  • POMD
  • 4
  • Kinematic viscosity, m2/s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CAPTUB:UFactor:4
  • 4
  • POMD
  • 4
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 18
  • POMD
  • 5
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 5
  • Kinematic viscosity, m2/s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CAPTUB:UFactor:4
  • 4
  • POMD
  • 5
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 10
  • POMD
  • 6
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 6
  • Kinematic viscosity, m2/s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CAPTUB:UFactor:4
  • 4
  • POMD
  • 6
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 21
  • POMD
  • 7
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 8
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 8
  • Kinematic viscosity, m2/s ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • CAPTUB:UFactor:4
  • 4
  • POMD
  • 8
  • Mass density, kg/m3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Vibrating tube method
  • 10
  • POMD
  • 9
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 10
  • 2
  • Molar conductivity, S*m2/mol ; Liquid
  • Amount concentration (molarity), mol/dm3 - 2; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Linear-bridge conductometer
  • 9
  • POMD
  • 10
  • 5
  • Molar conductivity, S*m2/mol ; Liquid
  • Amount concentration (molarity), mol/dm3 - 5; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Linear-bridge conductometer
  • 7
  • POMD
  • 10
  • 3
  • Molar conductivity, S*m2/mol ; Liquid
  • Amount concentration (molarity), mol/dm3 - 3; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Linear-bridge conductometer
  • 10
  • POMD
  • 10
  • 6
  • Molar conductivity, S*m2/mol ; Liquid
  • Amount concentration (molarity), mol/dm3 - 6; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Linear-bridge conductometer
  • 8
  • POMD
  • 10
  • 7
  • Molar conductivity, S*m2/mol ; Liquid
  • Amount concentration (molarity), mol/dm3 - 7; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Linear-bridge conductometer
  • 8
  • POMD
  • 10
  • 8
  • Molar conductivity, S*m2/mol ; Liquid
  • Amount concentration (molarity), mol/dm3 - 8; Liquid
  • Pressure, kPa; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Linear-bridge conductometer
  • 7