Swift and efficient sono-hydrolysis of nitriles to carboxylic acids under basic condition: role of the oxide anion radical in the hydrolysis mechanism.
Carboxylic acids are promising candidates for new sustainable strategies in organic synthesis. In this paper, we ascertain the potential of ultrasound for the hydrolysis of nitriles into carboxylic acids through the study of key parameters of the reaction: pH, hydrolysis medium, reaction time and activation technique. The positive influence of ultrasound under basic conditions is due to more than mechanical effects of cavitation. Indeed, the rate of hydrolysis is dramatically increased under sonication in NaOH solutions. A radical mechanism involving the oxide anion radical O(*-) is proposed.
Lignier
Pascal
P
Université de Savoie, Laboratoire de Chimie Moléculaire et Environnement, Campus Scientifique de Savoie Technolac, 73376 Le Bourget du Lac Cedex, France.
Estager
Julien
J
Kardos
Nathalie
N
Gravouil
Lydie
L
Gazza
Julien
J
Naffrechoux
Emmanuel
E
Draye
Micheline
M
D000838:Anions / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D012972:Sodium Hydroxide / Q000737:chemistry*; D014465:Ultrasonics
D000838:Anions; D002264:Carboxylic Acids; D005609:Free Radicals; D009570:Nitriles; D012972:Sodium Hydroxide