Nuclear chemistry

Medicinal chemistry

Organic chemistry

Environmental chemistry

Quinone

Environmental science

Chemistry

Ozone

Environmental Pollution

A recently identified chemical, 2-((4-Methylpentan-2-yl)amino)-5-(phenylamino)cyclohexa-2,5-diene-1,4-dione (6PPD-quinone; 6PPD-Q), is a transformation product of an additive used in the manufacture of tire rubber and causes acute lethality in coho salmon (Oncorhynchus kisutch) in urban watersheds. Despite its potential presence and ecotoxicity in receiving waters worldwide, information on the occurrence and fate of 6PPD-Q is limited. Here, we investigated the concentrations of 6PPD-Q and its parent chemical, 6PPD, in road dust collected from arterial and residential roads in Tokyo, Japan from May to October 2021. 6PPD-Q concentrations were highest from May to June, when atmospheric ozone concentrations are the highest in Japan; a correlation between 6PPD-Q and photochemical oxidants, as an alternative to ozone, corroborated this finding. We also found that 6PPD-Q concentrations at photochemical oxidant concentrations ranging from 35 to 47 ppbv were higher in dust collected from roads with high traffic volumes (i.e., arterial roads; median: 8.6 μg/g-OC) than in dust collected from roads with lower traffic volumes (i.e., residential roads; median: 6.3 μg/g-OC), indicating that 6PPD-Q is generated from traffic-related sources. We also found that 6PPD-Q was leached from dust particles within a few hours, with a log partitioning coefficient between organic carbon and water (KOC) of 3.2-3.5. The present results will help to understand the environmental occurrence, fate, and behavior of 6PPD-Q.

Concentration and leachability of N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) and its quinone transformation product (6PPD-Q) in road dust collected in Tokyo, Japan