Environmental Science & Technology Letters,
Journal Year:
2022,
Volume and Issue:
9(4), P. 333 - 338
Published: March 2, 2022
N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine-quinone
(6PPD-quinone),
a
transformation
product
of
the
rubber
tire
antioxidant
6PPD,
has
recently
been
identified
as
chemical
responsible
for
urban
runoff
mortality
syndrome
in
coho
salmon,
with
median
lethal
concentration
(LC50)
<0.1
μg/L.
Subsequent
studies
have
failed
to
confirm
comparable
sensitivity
other
fish
species.
Here,
we
investigated
acute
toxicity
6PPD-quinone
rainbow
trout,
brook
Arctic
char,
and
white
sturgeon.
Fish
were
exposed
under
static
renewal
conditions,
exposure
concentrations
verified
analytically.
Mortalities
trout
occurred
between
1.2
20
h,
while
mortalities
began
after
7
h
spanned
60
trout.
The
LC50s
(24
h)
(72
0.59
1.00
μg/L,
respectively.
Both
species
showed
characteristic
symptoms
(increased
ventilation,
gasping,
spiraling,
loss
equilibrium)
shortly
before
death.
No
observed
either
char
or
sturgeon
96
at
measured
high
14.2
This
is
first
study
demonstrate
fishes
commercial,
cultural,
ecological
importance
environmentally
relevant
provides
urgently
needed
information
environmental
risk
assessments
this
contaminant
emerging
concern.
Water Research,
Journal Year:
2022,
Volume and Issue:
212, P. 118122 - 118122
Published: Jan. 25, 2022
The
antiozonant
N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine
(6-PPD)
is
added
to
tires
increase
their
lifetime
and
emitted
with
tire
road
wear
particles
into
the
environment.
Recently,
one
of
its
transformation
products
(TPs),
6-PPD
quinone
(6-PPDQ),
has
gained
attention
due
toxicity
towards
coho
salmon.
In
this
study,
abiotic
oxidative
investigated
by
a
series
ozonation
experiments
in
lab
followed
analysis
TPs
using
liquid
chromatography-high
resolution-mass
spectrometry
(LC-HRMS).
A
total
38
were
detected
tentatively
identified,
which
formed
either
directly
from
or
via
6-PPDQ
as
intermediate.
suspect
screening
LC-HRMS
showed
32
these
occur
snow
collected
urban
roads
surrogate
road-runoff,
where
6-PPDQ,
4-aminodiphenylamine
(4-ADPA),
TP
213,
249
most
prominent
besides
6-PPD.
More
than
90%
load
was
found
particulate
fraction
snow.
Thus,
retaining
runoff
before
discharge
surface
water
would
substantially
reduce
emission
many
TPs.
Some
prevailed
phase
higher
polarity.
13
dissolved
wastewater
treatment
plant
(WWTP)
influent.
Their
markedly
enhanced
during
day
snowmelt
(approx.
1100
g/d)
rainfall
2000
compared
dry
weather
190
g/d).
contributed
less
1%
(estimated
concentrations
max
0.1
µg/L).
elimination
estimated
loads
related
WWTP
ranged
22
67%
depending
on
conditions.
Eventually
249,
4-ADPA
259_2
dominated
effluent
concentration
0.5
up
2
Thus
are,
likely,
specific
stable
be
determined
Environmental Science & Technology,
Journal Year:
2022,
Volume and Issue:
56(4), P. 2421 - 2431
Published: Jan. 31, 2022
Tire
road
wear
particles
(TRWPs)
are
one
of
the
largest
sources
microplastics
to
urban
environment
with
recent
concerns
as
they
also
provide
a
pathway
for
additive
chemicals
leach
into
environment.
Stormwater
is
major
source
TRWPs
and
associated
additives
surface
water,
including
antioxidant
derivative
N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine-quinone
(6PPD-quinone)
demonstrating
links
aquatic
toxicity
at
environmentally
relevant
concentrations.
The
present
study
used
complementary
analysis
methods
quantify
both
suite
known
tire
(including
6PPD-quinone)
an
tributary
in
Australia
during
severe
storm
events.
Concentrations
increased
more
than
40
times
storms,
maximum
concentration
2760
ng/L
∑15additives,
88
6PPD-quinone,
similar
profile
observed
each
storm.
were
detected
peaks
between
6.4
18
mg/L,
concentrations
all
highly
correlated.
Contaminant
mass
loads
this
catchment
estimated
up
100
g/storm
3
252
730
kg
TRWPs/storm.
While
6PPD-quinone
lower
previous
studies,
elevated
post
suggest
prolonged
exposure.
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.
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.
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
×
Environmental Science & Technology,
Journal Year:
2022,
Volume and Issue:
56(15), P. 10629 - 10637
Published: July 14, 2022
Substituted
para-phenylenediamine
(PPD)
antioxidants
have
been
extensively
used
to
retard
oxidative
degradation
of
tire
rubber
and
were
found
pervade
multiple
environmental
compartments.
However,
there
is
a
paucity
research
on
the
occurrences
their
transformation
products.
In
this
study,
we
revealed
co-occurrence
six
PPD-derived
quinones
(PPD-Qs)
along
with
eight
PPDs
in
fine
particulate
matter
(PM2.5)
from
two
Chinese
megacities,
which
N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine
quinone
(77PD-Q)
was
identified
quantified
for
first
time.
Prevalent
these
emerging
PPD-Qs
Taiyuan
(5.59–8480
pg/m3)
Guangzhou
(3.61–4490
pg/m3).
Significantly
higher
levels
PPDs/PPD-Qs
observed
at
roadside
site,
implying
possible
contribution
vehicle
emissions.
Correlation
analysis
implied
potential
consistencies
fate
suggested
that
most
them
originated
parent
PPDs.
For
different
subpopulation
groups
under
exposure
scenarios,
estimated
daily
intakes
(0.16–1.25
ng
kgbw–1
day–1)
comparable
those
(0.19–1.41
day–1),
suggesting
an
important
but
overlooked
caused
by
novel
PPD-Qs.
Given
prolonged
derivatives
traffic-relevant
occupations,
further
investigations
toxicological
epidemiological
effects
are
necessary.