Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Solid Liquid Equilibrium of d- and l-Tartaric Acid and Their Importance for Enantioseparation

Wang, X.[Xiaofang], Zhang, X.[Xiangyang], Black, S.[Simon], Dang, L.[Leping], Wei, H.[Hongyuan]
J. Chem. Eng. Data 2012, 57, 6, 1779-1786
ABSTRACT
The solid liquid phase equilibrium of d- and l-tartaric acid (TA) was investigated in this work. Based on the solubility data, the dissolution enthalpy and entropy of the monohydrate racemic tartaric acid (race-TA) and enantiomer were calculated using van't Hoff plots. Binary melting point phase diagrams of d- and l-TA and ternary phase diagrams of d-TA/water/l-TA were also described. The results show that TA exhibits a racemic compound behavior. Furthermore, the influence of temperature on the eutectic points between enantiomer and racemic compounds was investigated. Finally, the importance of solid liquid equilibrium on the purification and separation of enantiomers was discussed.
Compounds
# Formula Name
1 C4H6O6 (2S,3S)-(-)-tartaric acid
2 H2O water
3 C4H6O6 (2R,3R)-2,3-dihydroxybutanedioic acid
4 C4H6O6 (R*,R*)-2,3-dihydroxybutanedioic acid
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
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • Chromatography
  • 1
  • POMD
  • 4
  • Normal melting temperature, K ; Crystal 1
  • Crystal 1
  • Liquid
  • Air at 1 atmosphere
  • Chromatography
  • 1
  • POMD
  • 3
  • 1
  • 2
  • Mass fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Crystal of intercomponent compound 1
  • Chromatography
  • 5
  • POMD
  • 3
  • 1
  • 2
  • Mass fraction - 2 ; Liquid
  • Temperature, K; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Crystal of intercomponent compound 1
  • Chromatography
  • 5
  • POMD
  • 3
  • 1
  • 2
  • Mass fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Mass fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • Chromatography
  • 7
  • POMD
  • 3
  • 1
  • 2
  • Mass fraction - 3 ; Liquid
  • Temperature, K; Liquid
  • Mass fraction - 2; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal of intercomponent compound 1
  • Chromatography
  • 34
  • POMD
  • 3
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 3; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal of intercomponent compound 1
  • DTA
  • 1