Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Determination, correlation and prediction of the solubilities of niflumic acid, clofenamic acid and tolfenamic acid in supercritical CO2

Li, H.[Hongru], Jia, D.[Dongdong], Zhu, Q.[Qianqian], Shen, B.[Bingqian]
Fluid Phase Equilib. 2015, 392, 95-103
ABSTRACT
In this paper, the solubilities of niflumic acid, clofenamic acid and tolfenamic acid were experimentally determined and correlated with the semi-empirical models. Meanwhile, their solubilities were also correlated and estimated using the compressed gas model combined with the reference solubilities and the modified expanded liquid model combined with the group contribution method. In solubility determination, the dynamic method was adopted and the solubilities under the pressures and temperatures of 12-36MPa and 313-333 K were measured. The semi-empirical models containing Teja model, Chrastil model, Bartle model and Kumar-Johnston (K-J) model were used to correlate the solubilities of these fenamate medicines and the correlation results show a good consistency with the measured solubilities. The solubilities of the three fenamate medicines in sc-CO2 were correlated and estimated using the compressed gas model. With the experimental reference solubilities known, their solubilities can be correlated and predicted satisfactorily. The average absolute relative deviations (AARD %) are 5.0% and 11.9% respectively. Using the modified expanded liquid model, the solubilities of the three fenamate medicines were correlated and the average AARD% is 9.6%. Combined with the group contribution method, this model can estimate the solubilities of the three fenamate medicines in the order of magnitude.
Compounds
# Formula Name
1 C13H9F3N2O2 2-[[3-(trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic acid
2 C13H9Cl2NO2 clofenamic acid
3 C14H12ClNO2 2-[(3-chloro-2-methylphenyl)amino]benzoic acid
4 CO2 carbon dioxide
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
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 4
  • 1
  • Mole fraction - 1 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 1
  • UV-vis spectrophotometry
  • 24
  • POMD
  • 4
  • 2
  • Mole fraction - 2 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 2
  • UV-vis spectrophotometry
  • 24
  • POMD
  • 4
  • 3
  • Mole fraction - 3 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 3
  • UV-vis spectrophotometry
  • 24