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

Solubility Measurement and Modeling for 2-Benzoyl-3-chlorobenzoic Acid and 1-Chloroanthraquinone in Organic Solvents

You, Y.[Yujing], Gao, T.[Ting], Qiu, F.[Fangli], Wang, Y.[Yong], Chen, X.[Xiaoying], Jia, W.[Wenping], Li, R.[Rongrong]
J. Chem. Eng. Data 2013, 58, 6, 1845-1852
ABSTRACT
Solubilities of 2-benzoyl-3-chlorobenzoic acid and 1-chloroanthraquinone in organic solvents of ethyl acetate, acetone, 1,4-dioxane, and toluene were determined experimentally in the temperature range from (273.15 to 323.15) K by gravimetric method. The experimental results indicate that the solubility of 2-benzoyl-3-chlorobenzoic acid and 1-chloroanthraquinone in the solvents increased with an increase in temperature. The solubility data of 1-chloroanthraquinone in the different solvents accord with the following order toluene greater than ethyl acetate greater than 1,4-dioxane greater than acetone, whereas for 2-benzoyl-3-chlorobenzoic acid the order is toluene greater than 1,4-dioxane greater than ethyl acetate greater than acetone. The experimental data were correlated with the modified Apelblat equation, ?h equation, Wilson model, and NRTL model. The correlation results with the modified Apelblat equation, the ?h equation, and NRTL model are better than those with the Wilson model. The enthalpy, entropy, and the change of Gibbs free energy of 2-benzoyl-3-chlorobenzoic acid and 1-chloroanthraquinone in the selected organic solvents were calculated from the measured solubility data by using the modified van t Hoff equation. The experimental data and model parameters would be useful for optimizing the preparation and purification process of 1-chloroanthraquinone and 2-benzoyl-3-chlorobenzoic acid in industry.
Compounds
# Formula Name
1 C14H7ClO2 1-chloroanthraquinone
2 C14H9ClO3 2-benzoyl-3-chlorobenzoic acid
3 C4H8O2 ethyl acetate
4 C3H6O acetone
5 C4H8O2 1,4-dioxane
6 C7H8 toluene
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 enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 2
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • gravimetric method
  • 10
  • POMD
  • 4
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • gravimetric method
  • 10
  • POMD
  • 5
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • gravimetric method
  • 10
  • POMD
  • 6
  • 2
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • gravimetric method
  • 10
  • POMD
  • 1
  • 3
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • gravimetric method
  • 9
  • POMD
  • 4
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • gravimetric method
  • 9
  • POMD
  • 1
  • 5
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • gravimetric method
  • 9
  • POMD
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • gravimetric method
  • 9