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

Solubility of Benzimidazoles in Alcohols

Domanska, U.[Urszula], Bogel-Lukasik, E.[Ewa]
J. Chem. Eng. Data 2003, 48, 4, 951-956
ABSTRACT
The solid-liquid equilibrium (SLE) has been measured from 270 K to 445 K for 10 binary mixtures of benzimidazoles (benzimidazole and 2-methylbenzimidazole) with alcohols (1-propanol, 1-butanol, 2-butanol, 2-methyl-2-propanol, 1-hexanol) using a dynamic method. The melting point, enthalpy of fusion, and heat capacity change at the melting temperature were determined by differential scanning calorimetry (DSC). The solubility of benzimidazoles in alcohols (C3-C6) is higher than in water and in 1-octanol and generally decreases with an increase of the alkyl chain length of the alcohol. The intermolecular solute- solvent interaction is higher for the 1-alcohol than for the secondary or tertiary alcohol. The solubility of 2-methylbenzimidazole in alcohols (C3-C6) is higher than that of benzimidazole. Experimental results of solubility were correlated by means of the Wilson, UNIQUAC ASM, and NRTL 1 equations utilizing parameters derived from SLE results. The existence of a solid-solid first-order phase transition in benzimidazole and 2-methylbenzimidazole has been observed in the DSC measurements and has been taken into consideration in the solubility calculation. The best correlation of the solubility data has been obtained by the NRTL 1 equation.
Compounds
# Formula Name
1 C7H6N2 benzimidazole
2 C3H8O propan-1-ol
3 C4H10O butan-1-ol
4 C4H10O butan-2-ol
5 C6H14O hexan-1-ol
6 C8H8N2 2-methylbenzimidazole
7 C4H10O 2-methylpropan-2-ol
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
  • DTA
  • 1
  • POMD
  • 1
  • Molar heat capacity at constant pressure, J/K/mol ; Crystal
  • Temperature, K; Crystal
  • Pressure, kPa; Crystal
  • Crystal
  • Small sample (50 mg) DSC
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Temperature, K; Crystal
  • Crystal
  • Crystal of unknown type
  • DSC
  • 2
  • POMD
  • 6
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • Molar heat capacity at constant pressure, J/K/mol ; Crystal
  • Temperature, K; Crystal
  • Pressure, kPa; Crystal
  • Crystal
  • Small sample (50 mg) DSC
  • 1
  • POMD
  • 6
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Temperature, K; Crystal
  • Crystal
  • Crystal of unknown type
  • DSC
  • 2
  • POMD
  • 7
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • VISOBS
  • 1
  • POMD
  • 1
  • 2
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 1
  • VISOBS:UFactor:16
  • 20
  • POMD
  • 1
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 1
  • VISOBS:UFactor:16
  • 25
  • POMD
  • 1
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 1
  • VISOBS:UFactor:16
  • 27
  • POMD
  • 1
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 1
  • VISOBS:UFactor:16
  • 17
  • POMD
  • 1
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 1 - 7
  • VISOBS:UFactor:16
  • 10
  • POMD
  • 1
  • 5
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 1
  • VISOBS:UFactor:16
  • 22
  • POMD
  • 2
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 6
  • VISOBS:UFactor:16
  • 24
  • POMD
  • 3
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 6
  • VISOBS:UFactor:16
  • 20
  • POMD
  • 4
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 6
  • VISOBS:UFactor:16
  • 18
  • POMD
  • 7
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 6
  • VISOBS:UFactor:16
  • 19
  • POMD
  • 7
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 1 - 7
  • VISOBS:UFactor:16
  • 15
  • POMD
  • 5
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 2 - 6
  • VISOBS:UFactor:16
  • 29