Thermodynamics Research Center, ThermoML : Journal of Chemical and Engineering Data

Solubility Increment and Thermodynamic Analysis of Bioactive Antofloxacin Hydrochloride in Aqueous ChCl/PTS Deep Eutectic Solvent and Cosolvent Mixtures

Zhang, Y.[Ying], Du, C.[Cunbin], Cong, Y.[Yang], Xue, Y.[Yi], Qiao, B.[Bin], Ye, T.[Tingting], Wang, M.[Mingliang]
J. Chem. Eng. Data 2019, 64, 12, 5748-5754
ABSTRACT
The solubility of antofloxacin hydrochloride in deep eutectic solvent (DES) aqueous solutions between choline chloride (ChCl) and p-toluenesulfonic acid (PTS), (ethanol + water) and (ethanol + acetonitrile) co-solvent mixtures were investigated by means of the isothermal dissolution equilibrium method at (273.15-318.15) K under pressure condition of 101.3 kPa. Experimental solubility was strongly increased more than about 560 folds in aqueous ChCl/PTS system with the increasing temperature and mass fraction of DES, and it is 404 times in (ethanol + water) and 60 times in (ethanol + acetonitrile). The solubility maximum 0.01226 (318.15 K, in mole fraction) was obtained in wDES = 0.6 of the aqueous ChCl/PTS DES. X-ray power diffraction (XPRD) was employed to examine the equilibrium solid phase samples of antofloxacin hydrochloride in three systems resulting in no polymorphic transformation, solvate formation or crystal transition compared to the raw sample. The modified Apelblat equation was exclusively used to correlate the equilibrium solubility. Results show that the RAD and RMSD highest were, 2.35x10-2 and 3.45x10-5, respectively. The modified Apelblat equation could be used to correlate the results. Data obtained elucidated that the ChCl/PTS DES is an effective additive for enhancing the antofloxacin hydrochloride solubility.
Compounds
# Formula Name
1 C18H22ClFN4O4 antofloxacin hydrochloride
2 C7H8O3S 4-methylbenzenesulfonic acid
3 C5H14ClNO choline chloride
4 C7H8 toluene
5 H2O water
6 C7H6O2 benzoic acid
7 C2H6O ethanol
8 C2H3N acetonitrile
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
  • 6
  • 4
  • Mole fraction - 6 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • Chromatography
  • 7
  • POMD
  • 1
  • 5
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 10
  • POMD
  • 1
  • 3
  • 2
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Amount ratio of component to other component of binary solvent - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 10
  • POMD
  • 1
  • 7
  • 5
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 100
  • POMD
  • 1
  • 7
  • 8
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mass fraction - 7; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Chromatography
  • 90