Abstract
In this work, the behavior of the polycyclic musks 6-acetyl-1,1,2,4,4,7-hexamethyltetraline (AHTN) and 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-γ-2-benzopyran (HHCB) was investigated upon disinfection by using sodium hypochlorite as disinfectant in a model disinfection basin in order to find new disinfection by-products (DBP). In the case of AHTN, the carboxylic acid 3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (AHTN-COOH) was generated by a haloform reaction, being the origin for two new chlorinated DBPs. In the case of HHCB, disinfection via hypochlorite led to the HHCB-lactone. All reaction products and intermediates were synthesized and isolated. The relevant degradation mechanisms are discussed in detail.
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Acknowledgements
The authors wish to thank Prof. Dr. Mügge and Ms. Thiesies (Humboldt University, Berlin, Department of Chemistry) for measuring NMR samples. David Siegel, Stefan Merkel, Sebastian Schmidt, and Robert Rothe (Federal Institute for Materials Research and Testing, Berlin, Germany) are thanked for valuable discussion and technical support. Dr. Franziska Emmerling and Werner Kraus (Federal Institute for Materials Research and Testing, Berlin, Germany) are acknowledged for measuring and obtaining X-ray crystal structures.
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Kuhlich, P., Göstl, R., Teichert, P. et al. Transformations of polycyclic musks AHTN and HHCB upon disinfection with hypochlorite: two new chlorinated disinfection by-products (CDBP) of AHTN and a possible source for HHCB-lactone. Anal Bioanal Chem 399, 3579–3588 (2011). https://doi.org/10.1007/s00216-011-4674-3
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DOI: https://doi.org/10.1007/s00216-011-4674-3