The phase behavior of five ?-adrenergic blocking agents (acebutolol, atenolol, nadolol, pindolol, and propranolol) were explored in liquid and supercritical carbon dioxide at (298, 308, and 318) K and at pressures between (80 and 275) bar. The solubility of the solids in carbon dioxide was experimentally determined by observing the cloud point using a variable-volume stirred vessel with visual access. Although these compounds are very similar structurally, each containing a secondary amine, alcohol, aromatic ring, and ether group, only pindolol was soluble in carbon dioxide under the conditions explored. The other four ? blockers were observed to form yellow-brown salt complexes with carbon dioxide and did not show any appreciable solubility. It is believed that pindolol?s lower basicity (having a Kb an order of magnitude lower than the other four compounds) prevented it from reacting with carbon dioxide, a Lewis acid, and salting out as the other four ? blockers did.
Compounds
#
Formula
Name
1
CO2
carbon dioxide
2
C14H20N2O2
pindolol
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.