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Detection of methylquinoline transformation products in microcosm experiments and in tar oil contaminated groundwater using LC-NMR

 
: Reineke, A.-K.; Preiss, A.; Elend, M.; Hollender, J.

:

Chemosphere 70 (2008), No.11, pp.2118-2126
ISSN: 0045-6535
ISSN: 0366-7111
English
Journal Article
Fraunhofer ITEM ()
Methylquinoline; tar oil; LC-NMR; metabolite; biodegradation; groundwater

Abstract
N-heterocyclic compounds are known pollutants at tar oil contaminated sites. Here we report the degradation of methyl-, and hydroxy-methyl-substituted quinolines under nitrate-, sulfate- and iron-reducing conditions in microcosms with aquifer material of a former coke manufacturing site. Comparison of degradation potential and rate under different redox conditions revealed highest degradation activities under sulfate-reducing conditions, the prevailing conditions in the field. Metabolites of methylquinolines, with the exception of 2-methylquinolines, were formed in high amounts in the microcosms and could be identified by (1)H NMR spectroscopy as 2(1H)-quinolinone analogues. 4-Methyl-, 6-methyl-, and 7-methyl-3,4-dihydro-2(1H)-quinolinone, the hydrogenated metabolites in the degradation of quinoline compounds, were identified by high resolution LC-MS. Metabolites of methylquinolines showed persistence, although for the first time a transformation of 4-methylquinoline and its metabolite 4-methyl-2(1H)-quinolinone is described. The relevance of the identified metabolites is supported by the detection of a broad spectrum of them in groundwater of the field site using LC-NMR technique. LC-NMR allowed the differentiation of isomers and identification without reference compounds. A variety of methylated 2(1H)-quinolinones, as well as methyl-3,4-dihydro-2(1H)-quinolinone isomers were not identified before in groundwater.

: http://publica.fraunhofer.de/documents/N-67520.html