Identification of novel tetrabromobisphenol A byproducts in industrial chemicals and the environment near a manufacturing site: an overlooked source of novel pollutants†

Abstract

To evaluate the migration, transformation, and fate of tetrabromobisphenol A (TBBPA) in the environment, the transformation/degradation (T/D) products of TBBPA and byproducts of industrial production should be distinguished. Herein, 7 reported T/D products (R1–R7) and 7 novel byproducts (N1–N7) of TBBPA were identified in industrial-grade TBBPA chemicals by using high-performance liquid chromatography coupled ion trap mass spectrometry and high-resolution mass spectrometry with a suspect screening strategy. The possible formation pathways of these byproducts were attributed to the bromination, debromination, methylation, demethylation, hydroxylation, substitution, and radical coupling reactions of bisphenol A (BPA), BPA impurities, and TBBPA. The detection frequencies of R1–R7 and N3 (80–100%) were higher than those of N1, N2, and N4–N7 (20–60%) in industrial-grade TBBPA chemicals, with contents extended to 2.29% and 0.0989%, respectively. In the soils and sediments near the TBBPA plants, R1–R4 and N1 were detected with the highest concentration of 1.56 × 10² ng g⁻¹ dry weight, while in the river waters, only R1–R4 were detected with the highest concentration of 4.57 × 10² ng L⁻¹. An in silico analysis indicated the potential toxicity of these compounds, including their hepatotoxicity and carcinogenicity. To accurately estimate the environmental effects of the T/D products of TBBPA, the contributions of byproducts in industrial-grade TBBPA chemicals should be considered separately.