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

Solubility of Imidazoles, Benzimidazoles, and Phenylimidazoles in Dichloromethane, 1-Chlorobutane, Toluene, and 2-Nitrotoluene

Domanska, U.[Urszula], Pobudkowska, A.[Aneta], Rogalski, M.[Marek]
J. Chem. Eng. Data 2004, 49, 4, 1082-1090
ABSTRACT
Solubilities of seven imidazoles (1H-imidazole, 2-methyl-1H-imidazole, benzimidazole, 2-methylbenzimidazole, 2-phenylimidazole, 4,5-diphenylimidazole, and 2,4,5-triphenylimidazole) in organic solvents (dichloromethane, 1-chlorobutane, toluene, and 2-nitrotoluene) have been measured using a synthetic method and liquid chromatography. The interactions of the imidazoles, benzimidazoles, or phenylimidazoles with different solvents are discussed. The solubilities of these imidazoles in chloroalkanes were very low. In all solvents studied, the solubility of phenylmidazoles was significantly lower than the solubility of 1H-imidazole or benzimidazoles. Experimental results of solubility were correlated by means of the Wilson, UNIQUAC, and NRTL equations utilizing parameters derived from solid-liquid equilibria results. The existence of a solid-solid first-order phase transition in the solute has been taken into consideration in the solubility calculation. The best correlation of the solubility data was obtained by the Wilson equation with the average root-mean-square deviation ?T equal to 3.2 K.
Compounds
# Formula Name
1 C3H4N2 1H-imidazole
2 C4H6N2 2-methylimidazole
3 C7H6N2 benzimidazole
4 C8H8N2 2-methylbenzimidazole
5 C9H8N2 2-phenyl-1H-imidazole
6 C21H16N2 2,4,5-triphenyl-1H-imidazole
7 CH2Cl2 dichloromethane
8 C4H9Cl 1-chlorobutane
9 C7H8 toluene
10 C7H7NO2 2-nitrotoluene
11 C15H12N2 4,5-diphenylimidazole
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
  • 2
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 3
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 4
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 11
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC:UFactor:2
  • 1
  • POMD
  • 11
  • Triple point temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA:UFactor:2
  • 1
  • POMD
  • 8
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 2
  • VISOBS:UFactor:4
  • 37
  • POMD
  • 7
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 2
  • VISOBS:UFactor:8
  • 43
  • POMD
  • 7
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 1 - 2
  • VISOBS:UFactor:8
  • 1
  • POMD
  • 9
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 2
  • VISOBS:UFactor:4
  • 38
  • POMD
  • 10
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 2
  • VISOBS:UFactor:8
  • 14
  • POMD
  • 10
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 1 - 2
  • VISOBS:UFactor:8
  • 18
  • POMD
  • 3
  • 8
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 3
  • VISOBS:UFactor:8
  • 46
  • POMD
  • 3
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 3
  • VISOBS:UFactor:8
  • 34
  • POMD
  • 3
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 3
  • VISOBS:UFactor:8
  • 25
  • POMD
  • 3
  • 10
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 3
  • VISOBS:UFactor:8
  • 18
  • POMD
  • 3
  • 10
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 1 - 3
  • VISOBS:UFactor:8
  • 16
  • POMD
  • 8
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 4
  • VISOBS:UFactor:8
  • 31
  • POMD
  • 7
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 4
  • VISOBS:UFactor:8
  • 30
  • POMD
  • 9
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 4
  • VISOBS:UFactor:8
  • 40
  • POMD
  • 10
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 4
  • VISOBS:UFactor:16
  • 36
  • POMD
  • 10
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 1 - 4
  • VISOBS:UFactor:8
  • 21
  • POMD
  • 8
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • CHROM:UFactor:8
  • 3
  • POMD
  • 7
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 4
  • POMD
  • 9
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 10
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 3
  • POMD
  • 8
  • 5
  • Mole fraction - 5 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • Chromatography
  • 3
  • POMD
  • 7
  • 5
  • Mole fraction - 5 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • Chromatography
  • 3
  • POMD
  • 9
  • 5
  • Mole fraction - 5 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • Chromatography
  • 3
  • POMD
  • 10
  • 5
  • Mole fraction - 5 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • Chromatography
  • 3
  • POMD
  • 8
  • 11
  • Mole fraction - 11 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 11
  • Chromatography
  • 3
  • POMD
  • 7
  • 11
  • Mole fraction - 11 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 11
  • Chromatography
  • 3
  • POMD
  • 9
  • 11
  • Mole fraction - 11 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 11
  • Chromatography
  • 3
  • POMD
  • 10
  • 11
  • Mole fraction - 11 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 11
  • Chromatography
  • 3
  • POMD
  • 8
  • 6
  • Mole fraction - 6 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • Chromatography
  • 3
  • POMD
  • 7
  • 6
  • Mole fraction - 6 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • Chromatography
  • 3
  • POMD
  • 9
  • 6
  • Mole fraction - 6 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • Chromatography
  • 3