Identification of novel tetrabromobisphenol A byproducts in industrial chemicals and 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 highest concentration of 1.56×102 ng g-1 dry weight, while in the river waters, only R1-R4 were detected with 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.