Microbial biofilm metabolization of benzalkonium compounds (benzyl dimethyl dodecyl ammonium & benzyl dimethyl tetradecyl ammonium chloride)

J Hazard Mater. 2024 Feb 5:463:132834. doi: 10.1016/j.jhazmat.2023.132834. Epub 2023 Oct 28.

Abstract

Benzalkonium chlorides (BACs) are quaternary ammonium compounds (QUATs) that are used as biocides. The degradation of these compounds in wastewater treatment plants is essential to reduce their spread into the environment and thus prevent the development of QUAT-resistant genes. The biodegradation of two BACs (BAC-12 and BAC-14) was investigated in moving bed biofilm reactors (MBBRs). Degradation half-lives of 12 and 20 h for BAC-12 and - 14, respectively, were detected as well as the formation of 42 metabolites. Two new degradation pathways for the BACs were identified in this study: 1) one involving an ω-oxidation, followed by β-oxidation and 2) one via an ω-oxidation followed by an α-oxidation that was succeeded by β-oxidation. Similar metabolites were detected for both BAC-12 and BAC-14. Additional metabolites were detected in the study, that could not be assigned to the above-mentioned pathways, revealing even more metabolic pathways in the MBBR which is probably due to the complexity of the microbial community in the biofilm. Interestingly, both TP194 (Benzyl-(carboxymethyl)-dimethylazanium) and TP208B (Benzyl-(2-carboxyethyl)-dimethylazanium) were identified as end products of the ω/β-pathway and the α/β-pathway. TP208B, TP152 and TP250 that were identified in this study, as well as the known BDMA were discovered in the effluent of a wastewater treatment plant.

Keywords: High resolution mass spectrometry; MBBR; Micropollutants; Moving bed biofilm reactor; Structural elucidation; Transformation products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ammonium Chloride
  • Benzalkonium Compounds* / metabolism
  • Biofilms*
  • Bioreactors

Substances

  • dimethyldodecylbenzylammonium
  • Benzalkonium Compounds
  • Ammonium Chloride