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

Solubilities of Phosphoramidic Acid, N-(phenylmethyl)-, Diphenyl Ester in Selected Solvents

Wang, L.[Lijuan], Du, C.[Chaojun], Wang, X.[Xiaojie], Zeng, H.[Hongyan], Yao, J.[Jun], Chen, B.[Baokuan]
J. Chem. Eng. Data 2015, 60, 6, 1814-1822
ABSTRACT
Phosphoramidic acid, N-(phenylmethyl)-, diphenyl ester (PANDE) was synthesized, and its thermostability was measured by thermogravimetric analysis. The melting temperature and the fusion enthalpy of PANDE were evaluated by a differential scanning calorimeter. The solubilities of PANDE in chloroform, tertrahydrofuran, dichloromethane, acetone, methyl acetate, ethyl acetate, acetonitrile, methanol, and toluene were measured by a gravimetric method at different temperatures. The solubilities of PANDE in different solvents at low temperatures are in the order of chloroform greater than tetrahydrofuran greater than dichloromethane greater than acetone greater than methyl acetate greater than ethyl acetate greater than acetonitrile greater than methanol greater than toluene. At higher temperatures the order is the same except that acetonitrile now becomes the least soluble. The solubility data of PANDE in nine selected solvents were well fitted by the Wilson, nonrandom two-liquid (NRTL), and universal quasichemical equations. The Wilson model and the NRTL model show better agreement in general. Finally, the solubility parameters of PANDE were evaluated by the Scatchard Hildebrand model, and meanwhile, the standard dissolution enthalpy, the standard dissolution entropy, and the standard molar Gibbs energy of PANDE in the selected solvents were also calculated by the van t Hoff model and the Gibbs Helmholtz equation. The results show that the dissolution process is endothermic and entropy-driven.
Compounds
# Formula Name
1 CH4O methanol
2 CH2Cl2 dichloromethane
3 C2H3N acetonitrile
4 C4H8O2 ethyl acetate
5 C4H8O tetrahydrofuran
6 CHCl3 trichloromethane
7 C3H6O2 methyl ethanoate
8 C7H8 toluene
9 C3H6O acetone
10 C19H18NO3P diphenyl benzylphosphoramidate
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
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 9
  • POMD
  • 9
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 7
  • POMD
  • 5
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 7
  • POMD
  • 4
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 9
  • POMD
  • 6
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 9
  • POMD
  • 2
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 5
  • POMD
  • 7
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 8
  • POMD
  • 8
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 11
  • POMD
  • 3
  • 10
  • Mole fraction - 10 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 10
  • Gravimetric
  • 10