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Investigation of reaction mechanisms by electrospray ionization mass spectrometry: characterization of intermediates in the degradation of phenol by a novel iron/magnetite/hydrogen peroxide heterogeneous oxidation system
Author(s) -
Moura Flávia C. C.,
Araujo Maria H.,
Dalmázio Ilza,
Alves Tânia M. A.,
Santos Leonardo S.,
Eberlin Marcos N.,
Augusti Rodinei,
Lago Rochel M.
Publication year - 2006
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2523
Subject(s) - chemistry , chlorobenzene , hydroquinone , phenol , electrospray ionization , hydrogen peroxide , mass spectrometry , benzene , tandem mass spectrometry , quinone , radical , peroxide , photochemistry , organic chemistry , catalysis , chromatography
Electrospray ionization (ESI) mass spectrometry (MS) and tandem mass spectrometry (MS/MS) were used to monitor the oxidation of phenol by a novel heterogeneous Fenton system based on a Fe 0 /Fe 3 O 4 composite and H 2 O 2 . On‐line ESI‐MS(/MS) shows that this heterogeneous system promotes prompt oxidation of phenol to hydroquinone, which is subsequently oxidized to quinone, other cyclic poly‐hydroxylated intermediates and an acyclic carboxylic acid. A peroxide‐type intermediate, probably formed via an electrophilic attack of HOO . on the phenol ring, was also intercepted and characterized. ESI‐MS(/MS) monitoring of the oxidation of two other model aromatic compounds, benzene and chlorobenzene, indicates the participation of analogous intermediates. These results suggest that oxidation by the heterogeneous system is promoted by highly reactive HO . and HOO . radicals generated from H 2 O 2 on the surface of the Fe 0 /Fe 3 O 4 composite via a classical Fenton‐like mechanism. Copyright © 2006 John Wiley & Sons, Ltd.