Issue 5, 2023

Chemical characteristics, leaching, and stability of the ubiquitous tire rubber-derived toxicant 6PPD-quinone

Abstract

We here report chemical characteristics relevant to the fate and transport of the recently discovered environmental toxicant 6PPD-quinone (2-((4-methylpentan-2-yl)amino)-5-(phenylamino)cyclohexa-2,5-diene-1,4-dione or “6PPDQ”). 6PPDQ is a transformation product of the tire rubber antioxidant 6PPD that is ubiquitous in roadway environments, including atmospheric particulate matter, soils, runoff, and receiving waters, after dispersal from tire rubber use and wear on roadways. The aqueous solubility and octanol–water partitioning coefficient (i.e. log KOW) for 6PPDQ were measured to be 38 ± 10 μg L−1 and 4.30 ± 0.02, respectively. Within the context of analytical measurement and laboratory processing, sorption to various laboratory materials was evaluated, indicating that glass was largely inert but loss of 6PPDQ to other materials was common. Aqueous leaching simulations from tire tread wear particles (TWPs) indicated short term release of ∼5.2 μg 6PPDQ per gram TWP over 6 h under flow-through conditions. Aqueous stability tests observed a slight-to-moderate loss of 6PPDQ over 47 days (26 ± 3% loss) for pH 5, 7 and 9. These measured physicochemical properties suggest that 6PPDQ is generally poorly soluble but fairly stable over short time periods in simple aqueous systems. 6PPDQ can also leach readily from TWPs for subsequent environmental transport, posing high potential for adverse effects in local aquatic environments.

Graphical abstract: Chemical characteristics, leaching, and stability of the ubiquitous tire rubber-derived toxicant 6PPD-quinone

Supplementary files

Article information

Article type
Paper
Submitted
04 feb 2023
Accepted
27 mar 2023
First published
28 mar 2023

Environ. Sci.: Processes Impacts, 2023,25, 901-911

Author version available

Chemical characteristics, leaching, and stability of the ubiquitous tire rubber-derived toxicant 6PPD-quinone

X. Hu, H. (. Zhao, Z. Tian, K. T. Peter, M. C. Dodd and E. P. Kolodziej, Environ. Sci.: Processes Impacts, 2023, 25, 901 DOI: 10.1039/D3EM00047H

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