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)

• Published in: Journal of chemical and engineering data 2010-09, Vol.55 (9), p.3863-3868
• Main Authors: Núñez, Gonzalo A, del Valle, José M, de la Fuente, Juan C
• Format: Article
• Language: English
• Subjects: Chemistry; Exact sciences and technology; General and physical chemistry; Solubility; Solutions
• ISSN: 0021-9568; 1520-5134
• DOI: 10.1021/je900957v

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 y 2 = 0.13·10−3 at 333 K and 11.4 MPa to y 2 = 1.91·10−3 at 333 K and 26.0 MPa for farnesol and from y 2 = 0.49·10−5 at 313 K and 10.3 MPa to y 2 = 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.