Potential environmental fate and risk based on the hydroxyl radical-initiated transformation of atmospheric 1,2-dibromo-4-(1,2dibro-moethyl)cyclohexane stereoisomers

1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane (TBECH), as an emerging brominated flame retardant (EBFR) pollutant, has been often observed in the air, and to comprehend its fate in the environment is still challenging due to the diversity of its stereoisomers. In this work, the environmental transformation behavior and potential toxicological implications of TBECH stereoisomers under the oxidation of OH. in the gas phase were investigated by computational chemistry. Our results indicate the complexity of the TBECH transformation reactions and the diversity of its transformation products in the atmosphere. Although the reactions of TBECH enantiomers with OH. exhibit highly consistency, it is obvious that the reactions of the four diastereoisomers of TBECH with OH. and their subsequent reactions have both specificity and similarity. The dehydrogenation intermediates produced by H-abstraction of OH. in the initial reactions may undergo oxidative debromination, hydroxylation and decomposition reactions, leading to the transformation into low bromine and monohydroxy substituted compounds, as well as debrominated or unbrominated unsaturated fatty ketones. The toxicity assessments show that all transformation products are less toxic to aquatic organisms than TBECH, but some of them are still classified at toxic or harmful levels. More importantly, some transformation products still exhibit carcinogenic and teratogenic activity. To our knowledge, this study provides, for the first time, a deep insight into the transformation mechanism, kinetics, and environmental impacts of atmospheric TBECH by theoretical calculations.

Automated summary

This study investigates the environmental transformation and toxicological implications of TBECH stereoisomers under OH. oxidation in the gas phase using computational chemistry. The results reveal the complexity of TBECH transformation reactions and the diversity of its atmospheric transformation products, with lower toxicity to aquatic organisms but some remaining classified as toxic or harmful, and exhibiting carcinogenic and teratogenic activity. This study provides a deep insight into the transformation mechanism, kinetics, and environmental impacts of atmospheric TBECH for the first time through theoretical calculations.