Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Measurement and correlation of the solubility of rivaroxaban (form I) in binary mixtures of ethyl acetate with tetrahydrofuran, N,N-dimethylformamide, and N,N-dimethylacetamide from T = (278.15 to 318.15) K

Zhang, M.[Mudan], Fang, Z.[Zhenxuan], Zhai, J.[Jinghuan], Mao, S.[Shimin], Zhang, L.[Lijuan], Rohani, S.[Sohrab], Lu, J.[Jie]
J. Chem. Thermodyn. 2016, 94, 1-6
ABSTRACT
In this work, the solubility of rivaroxaban (form I) in binary solvent mixtures of ethyl acetate (EA) with N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA) and tetrahydrofuran (THF) was firstly experimentally measured over the temperature range from (278.15 to 318.15) K. Then the measured solubility data were correlated with such semiempirical thermodynamic models as Jouyban Acree (JA) equation and Buchowski (kh) equation. The crystal form of the residual solids in equilibrium with liquids was identified by powder X-ray diffraction (PXRD). The melting temperature and fusion enthalpy were determined using differential scanning calorimetry (DSC). The results show that, the solubility of rivaroxaban generally increases with the temperature and decreases with the increase in the content of EA in the binary solvent mixtures. Furthermore, when kh equation is used to correlate the solubility of rivaroxaban with the temperature in each solvent mixture, the average relative deviation (ARD) between the experimental and calculated values is about 0.0671, while it is about 0.0905 when JA equation is employed to correlate the solubility with the temperature and the composition of solvent mixtures simultaneously.
Compounds
# Formula Name
1 C19H18ClN3O5S Rivaroxaban
2 C4H8O2 ethyl acetate
3 C4H8O tetrahydrofuran
4 C3H7NO dimethylformamide
5 C4H9NO N,N-dimethylethanamide
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
  • 2
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Gravimetric method
  • 54
  • POMD
  • 5
  • 2
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Gravimetric method
  • 54
  • POMD
  • 3
  • 2
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Solvent: Mole fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Gravimetric method
  • 54
  • POMD
  • 4
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Gravimetric method
  • 9
  • POMD
  • 2
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Gravimetric method
  • 9
  • POMD
  • 5
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Gravimetric method
  • 9
  • POMD
  • 3
  • 1
  • Mole fraction - 1 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • Gravimetric method
  • 9