Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Solubilities of pharmaceutical and bioactive compounds in trihexyl(tetradecyl)phosphonium chloride ionic liquid

Faria, R. A.[Ricardo A.], Bogel-Lukasik, E.[Ewa]
Fluid Phase Equilib. 2015, 397, 18-25
ABSTRACT
The solubility of pharmaceutical and bioactive compounds, such as N-Acetyl-L-Cysteine, isoniazid, pyrazine-2-carboxamide, coumarin, 4-hydroxycoumarin, 4 -isobutylacetophenone, ibuprofen and thymoquinone, was tested in trihexyl(tetradecyl)phosphonium chloride. Hydrophobicity/hydrophilicity feature and melting point affected the solubility of the solutes in [P6,6,6,14][Cl]. 4 -Isobutylacetophenone, thymoquinone, coumarin and ibuprofen exhibited the best solubility in the IL due to their hydrophobicity. Then, N-Acetyl-L-Cysteine was found to be less soluble, and later on isoniazid, 4-hydroxycoumarin and pyrazinecarboxamide showed limited solubility in IL. The solid liquid phase equilibria of all investigated systems were described using the six different correlation equations. Considering the correlation of the phase equilibrium data, the satisfactory results which revealed a good description with an acceptable standard deviation temperature range were collected for systems with: N-Acetyl-LCysteine, coumarin, thymoquinone and ibuprofen. The solubilities of the studied compounds were approximately 2 times higher in trihexyl(tetradecyl)phosphonium chloride than in trihexyl(tetradecyl)phosphonium bis[(trifluoromethyl)sulfonyl]amide ionic liquid.
Compounds
# Formula Name
1 C32H68ClP trihexyl(tetradecyl)phosphonium chloride
2 C5H9NO3S N-acetyl-L-cysteine
3 C6H7N3O isonicotinic acid hydrazide
4 C5H5N3O pyrazinecarboxamide
5 C9H6O2 1,2-benzopyrone
6 C9H6O3 4-hydroxycoumarin
7 C10H12O2 2-isopropyl-5-methylcyclohexa-2,5-diene-1,4-dione
8 C13H18O2 ibuprofen
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
  • 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
  • 6
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 7
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 8
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 2
  • 1
  • Mole fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 2
  • visual
  • 14
  • POMD
  • 3
  • 1
  • Mole fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • visual
  • 9
  • POMD
  • 4
  • 1
  • Mole fraction - 4 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • visual
  • 9
  • POMD
  • 5
  • 1
  • Mole fraction - 5 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • visual
  • 10
  • POMD
  • 6
  • 1
  • Mole fraction - 6 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • visual
  • 10
  • POMD
  • 8
  • 1
  • Mole fraction - 8 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 8
  • visual
  • 16
  • POMD
  • 7
  • 1
  • Mole fraction - 7 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 7
  • visual
  • 15