Solubility of Collinin and Isocollinin in Pressurized
Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium
Measurements
Posted on 2019-08-21 - 20:04
Collinin
is a derivative of coumarin that has shown remarkable
potential against cancer, tuberculosis, periodontitis, and other prevalent
diseases, and is usually extracted from plants of the Rutaceae family
at a very low yield. In this work, collinin and a position-isomer
herein called isocollinin were synthesized at different scales (from
1 to 50 g of precursor) by a route consisting of two parallel and
two sequential chemical reactions. The isomers were characterized
by 1H NMR, 13C NMR, nuclear Overhauser enhancement
spectroscopy NMR, melting temperature, and melting enthalpy. For each
isomer, the Hansen solubility parameters and the radius of its solubility
sphere were experimentally determined by solubility tests in 15 common
solvents and two solvent blends. The solubility of each isomer in
pressurized CO2 was determined at 30 and 50 °C from
72.2 to 112.9 bar, by an in situ high-pressure spectrometry technique,
which was validated with the anthracene–CO2 system.
The solubility of both isomers in CO2 increased with pressure
in the range of temperatures and pressures considered, but that of
collinin exhibited an asymptotic behavior around 80.8 and 104.8 bar,
at 30 and 50 °C, respectively.
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Pardo-Castaño, Camilo; García, Andrés C.; Benavides, Paola; Bolaños, Gustavo (2019). Solubility of Collinin and Isocollinin in Pressurized
Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium
Measurements. ACS Publications. Collection. https://doi.org/10.1021/acs.jced.9b00234
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AUTHORS (4)
CP
Camilo Pardo-Castaño
AG
Andrés C. García
PB
Paola Benavides
GB
Gustavo Bolaños