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6PPD-Quinone

From The Bioremediation Network

6PPD-Quinone (6PPD-Q)[edit]

Pollutant Information[edit]

Chemical Formula: C18H23N2O2
Pollutant Family: Tire rubber-derived quinones
CAS Number: 2754428-18-5
Molecular Weight: 299.39 g/mol
Solubility: Water-soluble
Persistence: Persistent in environment
Regulatory Status: EPA emerging contaminant priority

Overview[edit]

6PPD quinone (6PPD-Q) is a toxic transformation product formed when the tire preservative chemical 6PPD reacts with ozone in the air. First identified in 2020, 6PPD-Q has been linked to the mysterious die-offs of coho salmon in urban streams across the Pacific Northwest that had puzzled scientists for 25 years. This emerging contaminant is now recognized as one of the most toxic chemicals to aquatic life and represents a significant threat to sensitive fish species and aquatic ecosystems.

Characteristics[edit]

Physical Properties[edit]

  • State at room temperature: Solid
  • Color/Appearance: Dark-colored crystalline solid
  • Odor: Characteristic quinone odor
  • Melting point: Research ongoing
  • Boiling point: Decomposes before boiling
  • Density: Higher than water

Chemical Properties[edit]

  • pH effects: Stability varies with pH; more persistent at neutral to alkaline pH
  • Oxidation states: Quinone form is primary environmental concern
  • Reactivity: Reactive quinone structure; forms DNA adducts
  • Stability: Persistent in aquatic environments
  • Bioavailability: Highly bioavailable to aquatic organisms

Environmental Behavior[edit]

  • Mobility in soil: Moderate to high mobility
  • Water solubility: Sufficiently water-soluble to enter waterways via runoff
  • Volatility: Low volatility
  • Adsorption: Can bind to organic matter and sediments
  • Half-life: Research ongoing, appears persistent in environment

Sources & Contamination Pathways[edit]

Industrial Sources[edit]

  • Tire manufacturing facilities
  • Rubber processing plants
  • Automotive manufacturing

Transportation Sources[edit]

  • Vehicle tire wear on roadways (primary source)
  • Tire wear particles from highways and urban roads
  • Parking lots and heavily trafficked areas
  • Bridge crossings over waterways

Urban/Residential Sources[edit]

  • Urban stormwater runoff
  • Road dust containing tire wear particles
  • Atmospheric deposition from roadway areas

Natural Sources[edit]

  • None - 6PPD-Q is entirely anthropogenic

Environmental & Health Impacts[edit]

Effects on Land/Soil[edit]

  • Soil chemistry: May alter soil pH and nutrient cycling
  • Soil biology: Potential impacts on soil microorganisms and invertebrates
  • Plant uptake: Limited research on plant uptake mechanisms
  • Groundwater contamination: Can leach into groundwater systems
  • Ecosystem disruption: Disrupts food webs starting with sensitive fish species

Effects on Water Systems[edit]

  • Aquatic toxicity: Extremely toxic to coho salmon (LC50: 95 ng/L), brook trout, rainbow trout
  • Bioaccumulation: Accumulates in fish tissue, especially liver
  • Water quality: Degrades water quality in urban streams and rivers
  • Widespread distribution: Found from urban rivers to deep-sea environments

Human Health Effects[edit]

Acute Exposure[edit]

  • Limited human data available
  • Potential respiratory irritation from tire dust

Chronic Exposure[edit]

  • DNA adduct formation observed in laboratory studies
  • Potential liver toxicity and metabolic disruption
  • Neurotoxicity and developmental concerns under investigation
  • Inflammatory pathways activation

Vulnerable Populations[edit]

  • Children: Higher exposure risk due to smaller body size
  • Pregnant women: Potential placental transfer to developing fetus
  • Communities near highways: Higher exposure from tire wear particles
  • Workers: Tire manufacturing and automotive workers

Detection & Testing[edit]

Sampling Methods[edit]

  • Water sampling: Grab samples during storm events for highest concentrations
  • Stormwater sampling: Event-composite sampling recommended
  • Sediment sampling: Core samples from urban waterways
  • Biological sampling: Fish tissue analysis for bioaccumulation studies

Analytical Methods[edit]

  • LC-MS/MS (Liquid Chromatography-Tandem Mass Spectrometry) - Detection limit ~1 ng/L
  • EPA Draft Method 1634 for surface water and stormwater
  • High-resolution mass spectrometry for metabolite identification

Regulatory Limits[edit]

  • EPA screening values: Developed for protecting sensitive salmon species
  • Acute toxicity threshold: 95 ng/L for coho salmon (revised 2022)
  • No established drinking water standards yet
  • State guidelines: Washington State developing water quality criteria

Bioremediation Organisms[edit]

Fungi[edit]

  • Phanerochaete chrysosporium - Multifunctional enzyme degradation, 99% removal in 7 days
  • White-rot fungi - Lignin peroxidase, manganese peroxidase, laccase enzymes

Bacteria[edit]

  • Research ongoing - bacterial degradation pathways under investigation
  • Biological sludge systems - 85% reduction observed over 14 days

Plants (Phytoremediation)[edit]

  • Research in early stages - plant uptake and metabolism being studied
  • Potential for constructed wetland applications

Bioremediation Strategies[edit]

Bioretention Systems[edit]

  • High-performance bioretention soil mix: Enhanced soil media for stormwater treatment
  • Green infrastructure: Bioswales and rain gardens with amended soil
  • Engineered wetlands: Constructed wetlands for tire particle capture
  • Mycofiltration: Fungal-based filter systems

Advanced Biological Treatment[edit]

  • Fungal bioreactors: P. chrysosporium enzyme systems
  • Activated sludge enhancement: Biological treatment plant modifications
  • Biofilm systems: Fixed-film biological treatment

Alternative Treatment Methods[edit]

Physical Treatment[edit]

  • Mobile stormwater filters: Bridge-mounted filtration systems
  • Tire particle capture: Source control at roadways
  • Sedimentation: Settling ponds for tire wear particle removal

Chemical Treatment[edit]

  • Advanced oxidation: UV-activated periodate, ozone treatment
  • Peroxymonosulfate (PMS): Unactivated oxidation generates singlet oxygen
  • Activated carbon: Adsorption treatment
  • Metal-organic frameworks: Novel 3D framework materials for adsorption

Source Reduction[edit]

  • Tire chemistry alternatives: Research into safer 6PPD replacements
  • Tire design improvements: Reduced wear particle generation
  • Road surface modifications: Less abrasive pavement materials

Case Studies[edit]

Nisqually Tribe Mobile Stormwater Filter - Ohop Valley, Washington[edit]

  • Location: Bridge crossing in Ohop Valley, Washington
  • Contamination source: Highway runoff containing tire wear particles
  • Treatment method: Mobile stormwater filtration system
  • Organisms used: Physical filtration (pre-biological treatment)
  • Duration: Installed 2022, ongoing monitoring
  • Results: Reduces tire particle loads entering salmon habitat
  • Partners: Nisqually Tribe, Long Live the Kings nonprofit
  • Source: EPA 6PPD-quinone fact sheet, 2024

P. chrysosporium Laboratory Treatment Study[edit]

  • Location: Laboratory-scale study
  • Contamination source: Synthetic 6PPD-Q solutions
  • Treatment method: White-rot fungal degradation
  • Organisms used: Phanerochaete chrysosporium
  • Duration: 7 days
  • Results: 99.06% removal efficiency, detoxified metabolites
  • Innovation: Multifunctional enzyme system breaks down quinone toxicity
  • Source: ScienceDirect research paper, 2025

Prevention Strategies[edit]

Source Reduction[edit]

  • Development of safer tire antioxidant alternatives to 6PPD
  • Improved tire manufacturing to reduce wear particle generation
  • Traffic reduction strategies in sensitive watersheds

Infrastructure Best Management Practices[edit]

  • Green infrastructure implementation in urban areas
  • Bioretention systems along transportation corridors
  • Road design modifications to capture runoff
  • Bridge runoff treatment systems

Groups & Projects Working on This Pollutant[edit]

  • University of Washington Tacoma - Environmental Chemistry Lab - Tire wear particle research - Multiple publications on 6PPD-Q discovery
  • EPA Office of Research and Development - Chemical Safety Research - 6PPD-Q Action Plan development - National coordination
  • Washington State Department of Ecology - Toxic Chemicals Program - Stormwater treatment guidance - State regulatory development
  • Nisqually Tribe Environmental Department - Watershed protection - Mobile filter installation - Tribal leadership on solutions
  • Long Live the Kings - Salmon conservation - Stormwater treatment projects - Community partnerships
  • Interstate Technology Regulatory Council (ITRC) - Multi-state coordination - Technical guidance development - Regulatory collaboration

Resources[edit]

Scientific Literature[edit]

  • Tian et al. (2021). "A Ubiquitous Tire Rubber–Derived Chemical Induces Acute Mortality in Coho Salmon." Science 371:185-89
  • Tian et al. (2022). "6PPD-Quinone: Revised Toxicity Assessment and Quantification with a Commercial Standard." Environmental Science & Technology Letters
  • Yu et al. (2025). "6PPD-quinone degradation by unactivated peroxymonosulfate via direct oxidation." Chemical Engineering Journal

Government Resources[edit]

  • EPA 6PPD-quinone Research and Action Plan (2024)
  • Washington State Department of Ecology 6PPD Fact Sheet
  • USGS 6PPD-quinone Environmental Health Program

Testing & Analysis[edit]

  • ALS Environmental - 6PPD-Q analytical services - LC-MS/MS analysis
  • TestAmerica Laboratories - Emerging contaminant testing - EPA Method 1634
  • University research labs - Contact state environmental agencies for testing resources

Related Pollutants[edit]

  • 6PPD (parent compound) - Source chemical that transforms to 6PPD-Q
  • Other PPD-quinones - Related tire rubber-derived transformation products
  • 1,3-Diphenylguanidine (DPG) - Co-occurring tire additive
  • Benzothiazoles - Other tire-derived chemicals in stormwater
  • PAHs (Polycyclic Aromatic Hydrocarbons) - Co-contaminants in tire wear particles

Last updated: June 24, 2025
Page maintainer: Bioremmy