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

Solubilities in Supercritical Carbon Dioxide of (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol (Farnesol) and (2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one (Naringenin)

Nunez, G. A.[Gonzalo A.], del Valle, J. M.[Jose M.], de la Fuente, J. C.[Juan C.]
J. Chem. Eng. Data 2010, 55, 9, 3863-3868
ABSTRACT
We measured the solubility in supercritical carbon dioxide (CO2) of farnesol [(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol] and naringenin [(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one] using a static-analytic method (a high-pressure static equilibrium cell coupled to an HPLC). The molar fraction of farnesol in the saturated CO2-rich phase increased between y2 = 0.13*10-3 at 333 K and 11.4 MPa to y2 = 1.91*10-3 at 333 K and 26.0 MPa for farnesol and from y2 = 0.49*10-5 at 313 K and 10.3 MPa to y2 = 1.65*10-5 at 333 K and 44.5 MPa for naringenin. The average error of our measurements was about 25 %. Farnesol had an end-temperature crossover point at approximately 17 MPa, whereas naringenin exhibited a monotonous increase in solubility with both temperature and pressure. The differences in solubility between farnesol, naringenin, and other sesquisterpenes or flavonoids reported in the literature were partially explained by differences in molecular weight and polarity between solutes. We correlated experimental data as a function of the system temperature and pressure and the density of the solvent using a literature model that also showed the autoconsistency of the data for CO2 densities above 412 kg*m-3 for naringenin.
Compounds
# Formula Name
1 C15H26O 3,7,11-trimethyldodeca-2,6,10-trien-1-ol
2 C15H12O5 4',5,7-trihydroxyflavanone
3 CO2 carbon dioxide
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
  • 1
  • Mole fraction - 1 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 1
  • Chromatography
  • 58
  • POMD
  • 3
  • 2
  • Mole fraction - 2 ; Fluid (supercritical or subcritical phases)
  • Temperature, K; Fluid (supercritical or subcritical phases)
  • Pressure, kPa; Fluid (supercritical or subcritical phases)
  • Fluid (supercritical or subcritical phases)
  • Crystal - 2
  • Chromatography
  • 59