Amine oxidation. Part 15. A product and stoicheiometric study of the oxidation of aminoalcohols by vanadium(V) ions in aqueous perchloric acid

Abstract

A study of the conditions under which aqueous diethanolamine (DEA) is oxidised by vanadium (V) ions reveals that in neutral or basic solution no reaction occurs at reflux or at lower temperature. However, in acid solution with pH < 4 oxidation takes place. The products and stoicheiometry of the oxidation of DEA and of some related compounds in aqueous perchloric acid show that the aminoalcohols are extensively degraded. The oxidations resemble those of simple alcohols and involve an initial loss of hydrogen from the C–H bond α to the hydroxy-group. The mechanisms of this and subsequent oxidations in this multistep process are discussed.