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

Mixtures of Pyridine and Nicotine with Pyridinium-Based Ionic Liquids

Pereiro, A. B., Rodriguez, A., Blesic, M., Shimizu, K.[Kenji], Canongia Lopes, J. N., Rebelo, L. P. N.
J. Chem. Eng. Data 2011, 56, 12, 4356-4363
ABSTRACT
The melting temperatures of [Cnmpy]Cl (4 = even n = 18) were determined by a dynamic method and confirmed by differential scanning calorimetry. The latter technique was also used to measure the corresponding enthalpies of fusion. The temperatures marking the onset of decomposition of the eight ionic liquids were determined by thermogravimetry. The solid liquid and liquid liquid phase equilibria of binary mixtures of pyridine or nicotine with four ionic liquids of the 1-alkyl-3-methylpyridinium chloride family ([Cnmpy]Cl with n = 4, 6, 10, 16) were investigated. The T x phase diagrams were measured at atmospheric pressure using turbidimetry in the (280 to 378) K temperature range. The diagrams show that pyridine is miscible in all proportions with the four studied ionic liquids while nicotine is only partially miscible with [C4mpy]Cl and [C6mpy]Cl. Data were interpreted using molecular dynamics simulations. The study illustrates, once again, the unique structural and solvent properties of ionic liquids.
Compounds
# Formula Name
1 C5H5N pyridine
2 C10H14N2 (-)-3-(N-methylpyrrolidino)pyridine
3 C10H16ClN 1-butyl-3-methylpyridinium chloride
4 C12H20ClN 1-hexyl-3-methylpyridinium chloride
5 C14H24ClN 1-octyl-3-methylpyridinium chloride
6 C16H28ClN 1-decyl-3-methylpyridinium chloride
7 C18H32ClN 1-dodecyl-3-methylpyridinium chloride
8 C20H36ClN 1-tetradecyl-3-methylpyridinium chloride
9 C22H40ClN 1-hexadecyl-3-methylpyridinium chloride
10 C24H44ClN 3-methyl-1-octadecylpyridinium chloride
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
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 3
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 3
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS:UFactor:4
  • 1
  • POMD
  • 4
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 4
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 4
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS:UFactor:4
  • 1
  • POMD
  • 5
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 5
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 5
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS:UFactor:4
  • 1
  • POMD
  • 6
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 6
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 6
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS:UFactor:4
  • 1
  • POMD
  • 7
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 7
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 7
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS:UFactor:4
  • 1
  • POMD
  • 8
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 8
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 8
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS:UFactor:4
  • 1
  • POMD
  • 9
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 9
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 9
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS:UFactor:4
  • 1
  • POMD
  • 10
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 10
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 10
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS:UFactor:4
  • 1
  • POMD
  • 1
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS:UFactor:16
  • 10
  • POMD
  • 1
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS:UFactor:32
  • 9
  • POMD
  • 1
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • VISOBS:UFactor:16
  • 11
  • POMD
  • 1
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 9; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 9
  • VISOBS:UFactor:32
  • 16
  • POMD
  • 2
  • 3
  • Quadruple (quintuple) point temperature, K ; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Crystal - 3
  • Air at 1 atmosphere
  • OTHER:::sMethod:Visual inspection
  • 1
  • POMD
  • 2
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS:UFactor:16
  • 2
  • POMD
  • 2
  • 4
  • Quadruple (quintuple) point temperature, K ; Liquid mixture 1
  • Liquid mixture 1
  • Liquid mixture 2
  • Crystal - 4
  • Air at 1 atmosphere
  • OTHER::sMethod:Visual inspection, average of SLE observations
  • 1
  • POMD
  • 2
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS:UFactor:16
  • 1
  • POMD
  • 2
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS:UFactor:16
  • 4
  • POMD
  • 2
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • VISOBS:UFactor:16
  • 15
  • POMD
  • 2
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 9; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 9
  • VISOBS:UFactor:32
  • 18