Formation of PCB-like and PCDF-like transformation products from liquid crystal monomers in aqueous chlorination: Degradation, transformation and toxicity evaluation

Liquid crystal monomers (LCMs) are persistent, bioaccumulative and toxic emerging contaminants that are widely detected in various environmental compartments including wastewater. However, scarce information is available regarding the fate of LCMs upon wastewater treatment. The current work is the first study to investigate the degradation, transformation fate and toxicity of LCMs upon chlorination, using 4’-propoxy-4-biphenylcarbonitrile (3OCB) and 1-ethoxy-2,3-difluoro-4-(4-propylphenyl)benzene (2OdF3B) as model LCMs. A total of 34 transformation products (TPs) were identified and structurally elucidated, some of which possessed similar chemical structures to the legacy persistent organic pollutants (POPs) – “polychlorinated biphenyls” (PCBs) and “polychlorinated dibenzofurans” (PCDFs). With in silico toxicity assessment, most of the generated TPs showed potential developmental toxicity, mutagenicity, endocrine disruption and protein binding ability compared to the parent compounds. Further toxicity assessments, as well as epidemiology studies, to reveal the hazards of these PCB-like and PCDF-like TPs are urgently needed.