First Report on the Occurrence of N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) and 6PPD-Quinone as Pervasive Pollutants in Human Urine from South China

Environmental Science & Technology Letters, Journal Year: 2022, Volume and Issue: 9(12), P. 1056 - 1062

Published: Nov. 21, 2022

N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) and its quinone derivative, 6PPD-quinone (6PPD-Q), have been found to be prevalent in the environment, but there are currently no data on their presence humans. Herein, we conducted first human biomonitoring study of 6PPD 6PPD-Q by measuring 150 urine samples collected from three different populations (general adults, children, pregnant women) South China. Both were detected samples, with detection frequencies between 60% 100%. Urinary concentrations significantly higher than those correlated well (p < 0.01), indicating coexposure In vitro metabolic experiments demonstrated rapid depletion liver microsomes, which should responsible for lower urine. Additionally, women exhibited apparently (median 0.068 2.91 ng/mL, respectively) did adults (0.018 0.40 ng/mL) children (0.015 0.076 ng/mL). The high daily urinary excretion was estimated 273 (ng/kg bw)/day. Considering that a lethal toxicant multiple aquatic species, potential health risks posed long-term exposure require urgent attention.

Language: Английский

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Microplastics in urban runoff: Global occurrence and fate

Water Research, Journal Year: 2022, Volume and Issue: 225, P. 119129 - 119129

Published: Sept. 17, 2022

Language: Английский

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Widespread Occurrence and Transport of p-Phenylenediamines and Their Quinones in Sediments across Urban Rivers, Estuaries, Coasts, and Deep-Sea Regions

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(6), P. 2393 - 2403

Published: Jan. 31, 2023

p-Phenylenediamines (PPDs) are widely used as antioxidants in tire rubber, and their derived quinone transformation products (PPD-Qs) may pose a threat to marine ecosystems. A compelling example is N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD)-derived quinone, called 6PPD-Q, the causal toxicant for stormwater-linked acute mortality toward coho salmon. However, knowledge of co-occurrences PPDs PPD-Qs transport from freshwater oceanic waterbodies on large geographical scale remains unknown. Herein, we performed first large-scale survey these chemicals sediments across urban rivers, estuaries, coasts, deep-sea regions. Our results demonstrated that seven four ubiquitously present riverine, estuarine, coastal sediments, most them also occur sediments. The dominant concern were identified 6PPD 6PPD-Q. Total sedimentary concentrations presented clear spatial trend with decreasing levels rivers (medians: 39.7 15.2 ng/g) estuaries (14.0 5.85 then coasts (9.47 2.97 regions (5.24 3.96 ng/g). Interestingly, variation ratios 6PPD-Q (R6PPD/6PPD-Q) trend. field measurements implied riverine outflows be an important route rubber-derived open oceans.

Language: Английский

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Occurrence and risks of 23 tire additives and their transformation products in an urban water system

Environment International, Journal Year: 2022, Volume and Issue: 171, P. 107715 - 107715

Published: Dec. 22, 2022

Tire wear particles (TWPs) enter road surface with the friction between tires and surfaces. Under volatilization, leaching, transformation action on TWPs by sunlight rain, tire additives are released into urban water systems, such as rainfall runoff, wastewater treatment plants (WWTPs), receiving waters, drinking plant (DWTP). In this study, we investigated occurrence of 23 their products in system Pearl River Delta region, South China. Nineteen target compounds were detected 1,3-Diphenylguanidine (DPG) showing highest maximum concentration 58780 ng/L. Benzothiazole its at frequency 100 % total concentrations 480-42160 The antioxidant derivative N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine-quinone (6PPD-Q) was also up to 1562 ng/L, which considerably higher than that parent compound 6PPD (the 7.52 ng/L). Eleven 8 WWTPs influents effluents, respectively, removal rates - 62-100 %. Seventeen Zhujiang Dongjiang rivers, while 9 sources DWTP samples. Road 79200 is suggested main non-point source for effluents point due incomplete after accepting initial runoff. 6PPD-Q other 10 displayed median high ecological risks human daily intake estimated be 2.63 ×

Language: Английский

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Analysis, environmental occurrence, fate and potential toxicity of tire wear compounds 6PPD and 6PPD-quinone

Journal of Hazardous Materials, Journal Year: 2023, Volume and Issue: 452, P. 131245 - 131245

Published: March 21, 2023

Language: Английский

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The Tire-Derived Chemical 6PPD-quinone Is Lethally Toxic to the White-Spotted Char Salvelinus leucomaenis pluvius but Not to Two Other Salmonid Species

Environmental Science & Technology Letters, Journal Year: 2022, Volume and Issue: 9(12), P. 1050 - 1055

Published: Nov. 7, 2022

N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine-quinone, also known as 6PPD-quinone (6PPD-Q), was recently identified the toxic chemical that causes acute mortality in coho salmon following exposure to urban road runoff. Subsequent studies found there were large differences sensitivity 6PPD-Q (>100-fold) even among salmonid species. Here we performed 96 h toxicity tests of with three species (Salvelinus leucomaenis pluvius, Salvelinus curilus, and Oncorhynchus masou masou) lethally S. pluvius a 24 median lethal concentration (LC50) 0.51 μg/L but not other two at environmentally relevant concentrations (<3.8 μg/L). In addition, measured suspected monohydroxylated metabolite brain gill tissues for The internal (ILC50) estimated be 4.0 μg/kg wet weight 6.2 while tissue surviving exceeded ILC50 values pluvius. These results suggest might affected by toxicodynamic factors well toxicokinetics.

Language: Английский

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Chiral perspective evaluations: Enantioselective hydrolysis of 6PPD and 6PPD-quinone in water and enantioselective toxicity to Gobiocypris rarus and Oncorhynchus mykiss

Environment International, Journal Year: 2022, Volume and Issue: 166, P. 107374 - 107374

Published: June 27, 2022

As a ubiquitous tire antidegradant, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD) is persistently released into the environment. It highly toxic to aquatic organisms, and its transformation product 6PPD-quinone (6PPD-Q), "very toxic" Oncorhynchus kisutch at median lethal concentration (LC50) of < 0.1 ng/mL. Notably, 6PPD 6PPD-Q are chiral compounds. Here, enantioselective evaluations, including hydrolysis acute toxicity were conducted after preparing enantiomer, confirming enantiomer absolute configuration establishing enantioseparation methods. In experiments, products 6PPD-Q, phenol, 4-[(1,3-dimethylbutyl)amino]- (4-DBAP) 4-hydroxydiphenylamine (4-HDPA) detected. different water solutions, 4-DBAP 4-HDPA was very fast (0.87-107 h), while half-lives (12.8-16.3 d) significantly longer than (4.83-64.1 h). At enantiomeric level, no conversion occurred. R-6PPD generated R-6PPD-Q, S-6PPD S-6PPD-Q, formation rate S-6PPD-Q 1.77 times faster R-6PPD-Q. terms toxicity, China-specific Gobiocypris rarus (LC50, 162-201 ng/mL), it had difference. 1.66-4.31 ng/mL) mykiss, which commercial importance, toxicities rac-6PPD-Q 1.9 2.6 higher Furthermore, concentrations R-6PPD-Q in solutions LC50 values O. species-specific, should raise concern. These results provide important information for environmental risk assessments especially from perspective enantiomers.

Language: Английский

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Tire-rubber related pollutant 6-PPD quinone: A review of its transformation, environmental distribution, bioavailability, and toxicity

Journal of Hazardous Materials, Journal Year: 2023, Volume and Issue: 459, P. 132265 - 132265

Published: Aug. 15, 2023

Language: Английский

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Uptake, Metabolism, and Accumulation of Tire Wear Particle-Derived Compounds in Lettuce

Environmental Science & Technology, Journal Year: 2022, Volume and Issue: 57(1), P. 168 - 178

Published: Dec. 28, 2022

Tire wear particle (TWP)-derived compounds may be of high concern to consumers when released in the root zone edible plants. We exposed lettuce plants TWP-derived diphenylguanidine (DPG), hexamethoxymethylmelamine (HMMM), benzothiazole (BTZ), N-phenyl-N′-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD), and its quinone transformation product (6PPD-q) at concentrations 1 mg L–1 hydroponic solutions over 14 days analyze if they are taken up metabolized by Assuming that TWP a long-term source plants, we further investigated effect leaching from on concentration leachate leaves adding constantly solutions. Concentrations leaves, roots, nutrient solution were quantified triple quadrupole mass spectrometry, metabolites identified Orbitrap resolution spectrometry. This study demonstrates readily with measured maximum leaf between ∼0.75 (6PPD) 20 μg g–1 (HMMM). Although these plant, several products, most which proved more stable than parent compounds. Furthermore, continuous led resupply replenishment leaves. The stability largely unknown toxicities is particularly concerning an important new aspect for impact assessment environment.

Language: Английский

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Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(14), P. 5621 - 5632

Published: March 30, 2023

6PPD, a tire rubber antioxidant, poses substantial ecological risks because it can form highly toxic quinone transformation product (TP), 6PPD-quinone (6PPDQ), during exposure to gas-phase ozone. Important data gaps exist regarding the structures, reaction mechanisms, and environmental occurrence of TPs from 6PPD ozonation. To address these gaps, ozonation was conducted over 24–168 h were characterized using high-resolution mass spectrometry. The probable structures proposed for 23 with 5 subsequently standard-verified. Consistent prior findings, 6PPDQ (C18H22N2O2) one major in (∼1 19% yield). Notably, not observed 6QDI (N-(1,3-dimethylbutyl)-N′-phenyl-p-quinonediimine), indicating that formation does proceed through or associated TPs. Other included multiple C18H22N2O C18H22N2O2 isomers, presumptive N-oxide, N,N′-dioxide, orthoquinone structures. Standard-verified quantified roadway-impacted samples, total concentrations 130 ± 3.2 μg/g methanol extracts tread wear particles (TWPs), 34 4 μg/g-TWP aqueous TWP leachates, 2700 1500 ng/L roadway runoff, 1900 1200 creeks. These demonstrate are likely an important ubiquitous class contaminants environments.

Language: Английский

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