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Issue 5, 2012
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A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent

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Abstract

First, the electrochemical characteristics of Fenton's reagent (Fe(III), Fe(II) and hydrogen peroxide), including its catalytic (EC′) behaviour were investigated. Second, the electrogeneration of hydrogen peroxide by a two-electron reduction of dissolved oxygen was conducted at a carbon electrode in a divided electrolysis cell and the concentration of hydrogen peroxide obtained was determined by the titration. The two approaches were then combined to give a one-pot, relatively green approach to aromatic hydroxylation reactions, with the electro-Fenton method allowing the iron to be used catalytically and the oxygen/water employed as the hydroxylation reagent by the in situ production of hydrogen peroxide. In particular, the preparative-scale hydroxylation of salicylic acid has been studied in an oxygen-saturated 0.1 M Na2SO4 pH 3.0 solution containing 5 mM Fe(II) and 5 mM salicylic acid at the controlled potential of −1.0 V vs. SCE. The study showed that after the attack of the hydroxyl radical produced in situ by the electro-Fenton process on salicylic acid, 2,3- and 2,5-dihydroxybenzoic acids were detected as primary monohydroxylated products with the highest yield of ca. 21.6 ± 2.5%.

Graphical abstract: A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent

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Supplementary files

Article information


Submitted
02 Dec 2011
Accepted
28 Feb 2012
First published
15 Mar 2012

New J. Chem., 2012,36, 1265-1272
Article type
Paper

A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent

J. Panchompoo, L. Aldous, M. Kabeshov, B. S. Pilgrim, T. J. Donohoe and R. G. Compton, New J. Chem., 2012, 36, 1265
DOI: 10.1039/C2NJ21007J

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