Ferrate(VI) oxidation of propranolol: Kinetics and products

The oxidation of propranolol (PPL), a β-blocker by ferrate(VI) (Fe(VI)) was studied by performing kinetics, stoichiometry, and analysis of the reaction products. The rate law for the oxidation of PPL by Fe(VI) was first-order with respect to each reactant. The dependence of second-order rate constants of the reaction of Fe(VI) and PPL on pH was explained using acid–base equilibrium of Fe(VI) and PPL. The required molar stoichiometry for the complete removal of PPL was determined to be 6:1 ([Fe(VI)]:[PPL]). The identified products using liquid chromatography–tandem mass spectrometry were oxidized product (OP)-292, OP-308, and OP-282. The formed OPs could possibly compete with the parent molecule to react with Fe(VI) and thus resulted in a non-linear relationship between degradation of PPL and the added amount of Fe(VI). Rate and removal studies indicate the Fe(VI) is able to oxidize PPL and hence can also oxidize other β-blockers, e.g., atenolol and metoprolol.

► Reaction kinetics of Fe(VI) and propranolol is similar to secondary amines.
► Complete transformation of propranolol by Fe(VI) in water.
► Opening of aromatic ring of propranolol by Fe(VI).
► Hydroxylation of amine moiety of propranolol by Fe(VI).