Original Paper

Analytical and Bioanalytical Chemistry

, Volume 399, Issue 10, pp 3579-3588

First online:

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

  • Paul KuhlichAffiliated withBAM Federal Institute for Materials Research and Testing Email author 
  • , Robert GöstlAffiliated withDepartment of Chemistry, Humboldt-University Berlin
  • , Philip TeichertAffiliated withBAM Federal Institute for Materials Research and Testing
  • , Christian PiechottaAffiliated withBAM Federal Institute for Materials Research and Testing
  • , Irene NehlsAffiliated withBAM Federal Institute for Materials Research and Testing

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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.

Keywords

Musk AHTN HHCB HHCB-lactone Chlorination Disinfection