Thermodynamics Research Center / ThermoML | Fluid Phase Equilibria

Ammonium ionic liquids as green solvents for drugs

Melo, C. I.[Catarina I.], Bogel-Lukasik, R.[Rafal], Nunes da Ponte, M.[Manuel], Bogel-Lukasik, E.[Ewa]
Fluid Phase Equilib. 2013, 338, 209-216
ABSTRACT
A high solubility of antituberculosis antibiotic drugs: isoniazid and pyrazinecarboxamide in ammonium ionic liquids shown in this work, demonstrates the promising perspectives in the drug processing. Solid liquid equilibrium (SLE) measurements have been made using a dynamic (synthetic) method. Thermophyscial properties such as melting point, enthalpy of fusion, temperatures of phase transitions and corresponding enthalpies for both isoniazid and pyrazinecarboxamide as well as for three ammonium salts were acquired using differential scanning calorimetry (DSC). The solubility of isoniazid in analysed ILs was found to be higher than that of pyrazinecarboxamide. Considering ammonium salts examined in this work, didecyldimethylammonium nitrate is the best solvent for both antibiotics. The solid liquid phase equilibria were described using six different correlation equations which revealed a relatively good description with an acceptable standard deviation temperature range.
Compounds
# Formula Name
1 C22H48N2O3 Didecyldimethylammonium nitrate
2 C21H38N2O3 Benzyllauryldimethylammonium nitrate
3 C23H42N2O3 (Benzyl)(dimethyl)(tetradecyl)ammonium nitrate
4 C6H7N3O isonicotinic acid hydrazide
5 C5H5N3O pyrazinecarboxamide
6 C8H16F6N2O5S2 ethyl(2-hydroxyethyl)dimethylammonium bis{(trifluomethyl)sulfonyl}imide
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
  • 4
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 5
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 5
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 6
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • Triple point temperature, K ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • Triple point temperature, K ; Crystal 3
  • Crystal 3
  • Crystal 2
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 6
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 2
  • Crystal 2
  • Crystal 1
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 6
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal 3
  • Crystal 3
  • Crystal 2
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 4
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS
  • 14
  • POMD
  • 4
  • 2
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Solvent: Mass fraction - 2; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS
  • 12
  • POMD
  • 4
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • VISOBS
  • 11
  • POMD
  • 5
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • VISOBS
  • 13
  • POMD
  • 5
  • 2
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Solvent: Mass fraction - 2; Liquid
  • Liquid
  • Crystal - 5
  • VISOBS
  • 13
  • POMD
  • 5
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • VISOBS
  • 9
  • POMD
  • 2
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mass fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal 1
  • DTA
  • 1