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Unusual polar metabolites in the groundwater of a contaminated waste site indicate a new pathway of mononitrotoluene transformation

: Preiss, Alfred; Berger-Preiss, Edith; Elend, Manfred; Reineke, Anne-Kirsten; Hollender, Juliane


Chemosphere 84 (2011), No.11, pp.1650-1657
ISSN: 0045-6535
ISSN: 0366-7111
Journal Article
Fraunhofer ITEM ()
mononitrotoluenes; polar metabolites; HPLC-NMR; HPLC-MS; groundwater

At a mononitrotoluene-contaminated waste disposal site, the groundwater was screened for polar transformation products of mononitrotoluenes, by means of HPLC-MS, HPLC-NMR and further off-line NMR and MS techniques. Besides expected metabolites such as aminotoluenes (ATs) and nitrobenzoic acids (NBAs), three unknowns (di- and tetrahydro-derivatives of (2-oxo-quinolin-3-yl) acetic acid) could be identified which, in the context of explosives and related compounds, are new metabolites. Evidence could be provided by microcosm experiments with 2-nitrotoluene (2-NT) that these metabolites are microbial transformation products of 2-NT under anaerobic conditions. The NMR and MS data are presented and the possible pathway for the formation of these metabolites after addition of 2-NT to fumarate is discussed.