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

Solubility of 4-Chloro-2,5-dimethoxynitrobenzene, 4-Chloro-2,5-dimethoxyaniline, and 2,5-Dimethoxyaniline in Binary and Pure Solvents: Determination and Modeling

Liu, X.[Xin], Liu, B.[Bo], Xu, Y.-S.[Yong-Sheng], Zhang, G.-L.[Guo-Liang], Xia, Q.[Qing], Zhang, F.-B.[Feng-Bao]
J. Chem. Eng. Data 2019, 64, 8, 3270-3279
ABSTRACT
Using the dynamic method over the temperature range of (277 to 340) K at atmosphere pressure, solubility of 4-chloro-2,5-dimethoxynitrobenzene (CDMB) and 4-chloro-2,5-dimethoxyaniline (CDMA) in methanol water and ethanol water solvent mixtures, where solute-free mass fraction of methanol and ethanol range from 0.2 to 0.8, and solubility of CDMB, CDMA, and 2,5-dimethoxyaniline (DMAn) in 2-methoxyethanol, 2-ethoxyethanol, 1-methoxy-2-propanol, and diethylene glycol have been investigated. In all solvents, there exists a direct relationship between solubility and temperature. In mixture solvents, the experimental data are correlated using the Wilson and the NRTL models. The solubility of CDMB and CDMA increases with the added amount of methanol or ethanol. In pure organic solvents, significant differences are discerned for the solubility of CDMB, CDMA, and DMAn, and data are correlated with the Wilson, the NRTL, the modified Apelblat, and the h models. The solubility of DMAn is strongly dependent on temperature, whereas CDMB is weakly dependent. On the basis of the solubility data and the solubility differences among CDMB, CDMA, and DMAn, ethanol water solution is preferred to be the solvent for the reduction of CDMB, and diethylene glycol is suggested to be the recrystallization solvent used to separate DMAn from the system.
Compounds
# Formula Name
1 C8H10ClNO2 4-chloro-2,5-dimethoxyaniline
2 C8H8ClNO4 1-chloro-2,5-dimethoxy-4-nitrobenzene
3 C8H11NO2 2,5-dimethoxyaniline
4 CH4O methanol
5 C2H6O ethanol
6 C3H8O2 2-methoxyethan-1-ol
7 C4H10O2 2-ethoxyethan-1-ol
8 C4H10O2 1-methoxy-2-propanol
9 C4H10O3 diethylene glycol
10 H2O water
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
  • Triple point temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • Triple point temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • Triple point temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • 5
  • 10
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Solvent: Mass fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 52
  • POMD
  • 2
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 11
  • POMD
  • 2
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 12
  • POMD
  • 2
  • 8
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 11
  • POMD
  • 2
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 11
  • POMD
  • 1
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 12
  • POMD
  • 1
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 12
  • POMD
  • 1
  • 8
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 11
  • POMD
  • 1
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 12
  • POMD
  • 3
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 11
  • POMD
  • 3
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 15
  • POMD
  • 3
  • 8
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 14
  • POMD
  • 3
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 17
  • POMD
  • 2
  • 4
  • 10
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Solvent: Mass fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 41
  • POMD
  • 1
  • 4
  • 10
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Solvent: Mass fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 56
  • POMD
  • 1
  • 5
  • 10
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Solvent: Mass fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 79