Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Solubility and preferential solvation of 2-methyl-4-nitroaniline in mixed solvents of ethyl acetate + (methanol, ethanol, n-propanol and isopropanol)

Li, X.[Xinbao], Cong, Y.[Yang], Li, C.[Congcong], Du, C.[Cunbin], Zhao, H.[Hongkun]
J. Chem. Thermodyn. 2017, 113, 71-80
ABSTRACT
The mole fraction solubility of 2-methyl-4-nitroaniline in binary mixed solvents of (ethyl acetate + methanol), (ethyl acetate + ethanol), (ethyl acetate + n-propanol) and (ethyl acetate + isopropanol) was determined experimentally by using static method at temperatures from (278.15 to 313.15) K under atmospheric pressure. The solubility increased with increasing temperature and mass fraction of ethyl acetate. At the same temperature and mass fraction of ethyl acetate, the mole fraction solubility in (ethyl acetate + methanol) was greater than those in the other mixed solvents. The solubility values were correlated with Jouyban Acree model, van t Hoff-Jouyban-Acree model, modified Apelblat-Jouyban-Acree model, Ma model, and Sun model. The maximum values of relative average deviations and root-meansquare deviations were 0.47 10 2 and 2.26 10 4, respectively. Preferential solvation parameters of the solute were also derived by means of the inverse Kirkwood-Buff integrals (IKBI) method. The preferential solvation parameters dx1,3 are negative in alcohol-rich composition, but positive in intermediate and ethyl acetate-rich composition. The ethyl acetate action may be related to the breaking of the ordered structure of alcohol around the polar moieties of 2-methyl-4-nitroaniline. The positive dx1,3 values could be explained based on the higher acidic behaviour of 2-methyl-4-nitroaniline molecules interacting with the hydrogen acceptor groups present in ethyl acetate. This work expands the physicochemical information about solid in binary solvent mixtures.
Compounds
# Formula Name
1 C7H8N2O2 2-methyl-4-nitroaniline
2 CH4O methanol
3 C2H6O ethanol
4 C3H8O propan-1-ol
5 C3H8O propan-2-ol
6 C4H8O2 ethyl acetate
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
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 72
  • POMD
  • 3
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 72
  • POMD
  • 4
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 72
  • POMD
  • 5
  • 1
  • 6
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 6; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 72