Solubility and salting behavior of several B-Adrenergic blocking agents in liquid and supercritical carbon dioxide.

The phase behavior of five a-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. Althoug 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 a 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 a blockers did.

Main Author: Weinstein, Randy.
Other Authors: Gribbin, Joseph., Muske, Kenneth.
Format: Villanova Faculty Authorship
Language: English
Published: 2005
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