First insights into electrochemical transformations of two triazine-based brominated flame retardants in model systems

Abstract

In this work, a study of electrochemical conversion was performed to elucidate different degradation pathways of the heterocyclic brominated flame retardants 1,3,5-tris-(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione (TDBP-TAZTO) and 2,4,6-tris-(2,4,6-tribromo-phenoxy)-1,3,5-triazine (TTBP-TAZ). EC/MS was used to simulate the (bio)-transformation processes and to identify possible transformation products (TPs) which have never been reported before. For TDBP-TAZTO, six new TPs were observed after the electrochemical oxidation (applied potential of 0 to 1800 mV vs. Pd/H₂). In the case of TTBP-TAZ, seven debromination products were generated with an applied potential of 0 to 2200 mV vs. Pd/H₂. The main degradation pathways confirmed by high resolution mass spectrometry for both compounds were hydroxylation, debromination and dehydrobromination.