Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Solubility of pharmaceutical compounds in ionic liquidsAna

Santos, A. D. d.[Ana Duarte dos], Morais, A. R. C.[Ana R.C.], Melo, C.[Catarina], Bogel-Lukasik, R.[Rafal], Bogel-Lukasik, E.[Ewa]
Fluid Phase Equilib. 2013, 356, 18-29
ABSTRACT
The solubility of N-acetyl-l-cysteine, coumarin and 4-hydroxycoumarin in alternative solvents was studied in this work. The solid-liquid equilibrium (SLE) measurements have been performed using a dynamic(synthetic) method. Melting points and enthalpies of fusion of the pharmaceutical compounds wereacquired using a differential scanning calorimetry (DSC). The solubility of N-acetyl-l-cysteine and 4-hydroxycoumarin in trifluoromethanesulfonate ionic liquids was found to be significantly higher thanin the studied bis(trifluoromethylsulfonyl)amide ionic liquids while coumarin exhibited the opposite behaviour.The solid-liquid phase equilibria were described using the six different correlation equations whichrevealed a good description with an acceptable standard deviation temperature range.Moreover, the solubility data were used to calculate the 1-octanol/water partition coefficients of the studied drugs. Coumarin has a high partition coefficient, which is considered to be favourable for a rapid absorption of compounds once they are in an aqueous solution. N-acetyl-l-cysteine showed opposite results for the system with 1-octanol/water.
Compounds
# Formula Name
1 C9H6O2 1,2-benzopyrone
2 C5H9NO3S N-acetyl-L-cysteine
3 C9H6O3 4-hydroxycoumarin
4 C8H11F6N3O4S2 1-ethyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide
5 C10H15F6N3O4S2 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
6 C12H19F6N3O4S2 1-hexyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
7 C16H27F6N3O4S2 1-decyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide
8 C7H11F3N2O3S 1-ethyl-3-methylimidazolium trifluoromethanesulfonate
9 C9H15F3N2O3S 1-butyl-3-methylimidazolium trifluoromethanesulfonate
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
  • 3
  • 8
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 10
  • POMD
  • 3
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 10
  • POMD
  • 3
  • 5
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • VISOBS
  • 7
  • POMD
  • 2
  • 8
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 20
  • POMD
  • 2
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 12
  • POMD
  • 2
  • 5
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 9
  • POMD
  • 2
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 9
  • POMD
  • 2
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • VISOBS
  • 11
  • POMD
  • 1
  • 9
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 9
  • POMD
  • 1
  • 8
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 8
  • POMD
  • 1
  • 4
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 8
  • POMD
  • 1
  • 5
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 7
  • POMD
  • 1
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 7
  • POMD
  • 1
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 1; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • VISOBS
  • 10