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Envr 210. Tues. and Thurs- 3 credit hours, room 1001 Hooker-SPH 11am to ~12:15 pm Snow days call 942 4880 or cell 919 614 4730 http://www.unc.edu/courses/2006spring/envr/210/001/Envr210.html Rich Kamens; 966 5452 [email protected] http://airsite.unc.edu/~kamens/. Textbook

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Envr 210 l.jpg
Envr 210

  • Tues. and Thurs- 3 credit hours, room 1001 Hooker-SPH

  • 11am to ~12:15 pm

  • Snow days call 942 4880

    or cell 919 614 4730

  • http://www.unc.edu/courses/2006spring/envr/210/001/Envr210.html

  • Rich Kamens; 966 5452

  • [email protected]

  • http://airsite.unc.edu/~kamens/


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  • Textbook

  • Environmental Organic Chemistry by René P. Schwarzenbach, Philip M. Gschwend, and Dieter M. Imboden, John Wiley & Sons, Inc., New York, 2003, ISBN 0-471-35053-2, pages:1313.





Dual 270m 3 chamber fine particle t 1 2 17 h l.jpg
Dual 270m aerosols3 chamber fine particle t 1/2 >17 h


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From a Modeling perspective Equilibrium Organic Gas-particle partitioning provides a context for addressing SOA Formation

  • Numerical fitting

  • Semi-explicit


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cis-pinonaldhyde Gas-particle partitioning provides a context for addressing SOA Formation

Gas phase reactions

C=O

C=O

O

O

particle

Link gas and particle phases


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k Gas-particle partitioning provides a context for addressing SOA Formationon

koff

particle

C=O

O

kon

koff

  • [ igas] + [part] [ipart]

Kp = kon/koff


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+ CO, HO Gas-particle partitioning provides a context for addressing SOA Formation

OH

2,

CHO

O

norpinonaldehyde

COOH

O

O

O

O

norpinonic

O

acid

Criegee1

3

COOH

O

O

O

pinonic acid

O

a

-pinene

CH

CHO

O

3

+ other

O

COOH

products

Criegee2

COOH

pinic acid

Mechanism


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pinonaldehyde Gas-particle partitioning provides a context for addressing SOA Formation


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Overall kinetic Mechanism Gas-particle partitioning provides a context for addressing SOA Formation

  • linked gas and particle phase rate expressions


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Particle Phase reactions Gas-particle partitioning provides a context for addressing SOA Formation

cis-pinonaldhyde

Gas phase reactions

C=O

C=O

O

O

polymers

particle


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Particle Phase reactions Gas-particle partitioning provides a context for addressing SOA Formation

cis-pinonaldhyde

C=O

C=O

O

O

Gas phase reactions

particle

polymers


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Particle Phase reactions Gas-particle partitioning provides a context for addressing SOA Formation

cis-pinonaldhyde

C=O

C=O

O

O

Gas phase reactions

polymers


Particle phase pinonaldehyde dimers from acid a pinene o 3 l.jpg
Particle phase pinonaldehyde dimers from Gas-particle partitioning provides a context for addressing SOA Formationacida-pinene +O3

M Na+(ESI-QTOF Tolocka et al, 2003)


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Chemical System Gas-particle partitioning provides a context for addressing SOA Formation

+ NOx+ sunlight + ozone----> aerosols

a-pinene


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data Gas-particle partitioning provides a context for addressing SOA Formation

NO

model

O3

NO2

ppmV

NO2

Time in hours EST

0.95 ppm a-pinene + 0. 44ppm NOx


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O Gas-particle partitioning provides a context for addressing SOA Formation

O

3

mg/m

Gas phase pinonaldehdye

Time in hours EST


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3 Gas-particle partitioning provides a context for addressing SOA Formation

mg/m

Measured particle mass vs. model

Particle phase

Particle phase

data

3

mg/m

model TSP

model TSP

Time in hours EST


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UNC outdoor chamber group Gas-particle partitioning provides a context for addressing SOA Formation


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Air Pollution in Northern Gas-particle partitioning provides a context for addressing SOA FormationThailand


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Introduction to Environmental Physical Organic Chemistry Gas-particle partitioning provides a context for addressing SOA Formation

  • Environmental chemistry may be defined as "the study of sources, reactions, transport, effects, and fates of chemical species in water, soil, and air environments, and the effects of technology thereon.” Manahan, 1994


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Class objectives: Gas-particle partitioning provides a context for addressing SOA Formation

  • Highlight some important areas in environmental chemistry

  • present some of the common techniques that environmental chemists use to quantify process that occur in the environment

  • It is assumed that everyone has courses in organic and physical chemistry.


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Class objectives: Gas-particle partitioning provides a context for addressing SOA Formation

  • Partitioning is a thread that runs through the course

  • Linear free energy relationships will be used to help quantify equilibrium and kinetic processes


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Thermodynamics Gas-particle partitioning provides a context for addressing SOA Formation

  • ui = uo1 +RT ln pi/p*iL

  • fi = i Xipi*pure liquid

  • RT lnfi hx /fiopure liq = RT lnfi H2O/fiopure liqfihx = fi H2O

  • ln Kp = a 1/T+b


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Vapor pressure Gas-particle partitioning provides a context for addressing SOA Formation

How to calculate boiling points


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Vapor pressure and Henry’s law Gas-particle partitioning provides a context for addressing SOA Formation

sat

P

sat

sat

*

i

K

P

V

iL

iw

sat

iaw

iw

C

iw

Solubility and activity coefficients

Octanol-water partitioning coefficients


Additional principles l.jpg
Additional Principles Gas-particle partitioning provides a context for addressing SOA Formation

  • Organic Acid-bases and LFERs

  • diffusion

  • chemical spills and mass transfer

  • Organic reactions in the environment

  • Solid- liquid interactions

  • photochemistry


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Homework, quizzes, exams Gas-particle partitioning provides a context for addressing SOA Formation

  • To insure that most of us stay reasonably current with the lectures and readings, an option is to have 6-8 unannounced quizzes throughout the semester.

  • They will take ~10 minutes. The first quiz will be on Chapter 2 since we will not cover Chapter 2. Quizzes will count 10% of your grade.


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  • There will be a homework problem set associated with each assigned chapter of the book. It is due a week after the completion of the book chapter.

  • These problem sets should take between 3 and 10 hrs. Answers will graded and returned to you as soon as possible. These will count for 25% of your grade.


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Learning illustrative examples and problems

  • Read Chapter

  • Simple or short Homeworks

  • Lecture ???

  • Long Homeworks

  • Exams


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Why the interest? illustrative examples and problems

There are more than 70,000 synthetic chemicals that are in daily use:

solvents

components of detergents

dyes and varnishes

additives in plastics and textiles

chemicals used for construction

antifouling agents

herbicides, insecticides,fungicides


Polynuclear aromatic hc pahs dioxins ketones pcbs cfcs ddt o 3 no 2 aerosols so 2 l.jpg

Some examples of environmental chemicals illustrative examples and problems

Polynuclear Aromatic HC (PAHs)

Dioxins

Ketones

PCBs

CFCs

DDT

O3, NO2, aerosols, SO2


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PAHs illustrative examples and problems

Formed from small ethylene radicals “building blocks” produced when carbon based fuels are burned

Sources are all types of burning

in ChiangMai, Thailand:a) 2-stroke motorcycle engines b) cars- light diesels c) open burning d) barbecued meat??


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Combustion Formation of PAH illustrative examples and problems

Badger and Spotswood 1960


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PAHs illustrative examples and problems

Metabolized to epoxides which are carcinogenic; O PAH

are indirect acting mutagens in bacterial mutagenicity tests (Ames-TA98+s9)

methyl PAHs are often more biologically active than PAHs


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Carcinogenic tests with PAHs illustrative examples and problems

Professor Gernot Grimmer extracted different types of smoke particles

He then took the extract and applied it to mouse skin

and implanted it into rat lungs

How did he obtain extracts?

How did he fractionate his extracts??


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MeCl2


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Heat





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Heat


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Professor grimmer fractionated the exhaust extracts57 l.jpg
Professor Grimmer fractionated the exhaust extracts by evaporation by a

HPLC

column (silica gel)


Professor grimmer fractionated the exhaust extracts58 l.jpg
Professor Grimmer fractionated the exhaust extracts by evaporation by a

HPLC

hexane

MeCl2


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Professor Grimmer fractionated the exhaust extracts by evaporation by a

HPLC

uv orfluorescencedetector

hexane

MeCl2


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Professor Grimmer fractionated the exhaust extracts by evaporation by a

HPLC

uv orfluorescencedetector

Totalextract

hexane

MeCl2


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Professor Grimmer fractionated the exhaust extracts by evaporation by a

HPLC

uv orfluorescencedetector

Total

hexane

PAH 2&3 rings


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Professor Grimmer fractionated the exhaust extracts by evaporation by a

HPLC

uv orfluorescencedetector

Total

hexane

MeCl2

PAHs>3 rings


Professor grimmer fractionated the exhaust extracts63 l.jpg
Professor Grimmer fractionated the exhaust extracts by evaporation by a

HPLC

uv orfluorescencedetector

Total

ACN

Total-PAHs


Professor grimmer fractionated the exhaust extracts64 l.jpg
Professor Grimmer fractionated the exhaust extracts by evaporation by a

HPLC

uv orfluorescencedetector

Total

Total

PAH 2&3 rings

PAHs>3 rings

Total-PAHs


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What did Grimmer see when exposed rats and mice to the different fractions?

  • skin painted mice

  • implanted rat lungs


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Total minus the PAH fraction different fractions?


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Analysis of reaction products different fractions?

  • soxhlet extraction for 3 hours

    • blow up with dry gentle flow of nitrogen to about 0.5 to 1 ml

  • evaporation to about 0.5 to 1 ml

  • 1 to 2 ul injected directly to GC-MS (EI and CI)

  • The remainder solution: derivatization


Pfbha o 2 3 4 5 6 pentafluorobenzyl hydroxylamine for carbonyl groups l.jpg
PFBHA different fractions? O-(2,3,4,5,6-pentafluorobenzyl) -hydroxylamine for carbonyl groups


Pentafluorobenzyl bromide pfbbr derivatization for carboxylic and hydroxyl groups l.jpg
Pentafluorobenzyl bromide different fractions?(PFBBr)derivatization for carboxylic and hydroxyl groups

P

F

B

B

r

F

F

H

C

C

H

3

3

O

O

H

C

H

C

O

H

C

O

F

C

H

B

r

2

2

F

F

F

F

H

C

C

H

O

3

3

O

C

H

C

O

C

H

F

H

O

C

H

B

r

2

2

F

F

F

F

F

F

C

H

C

H

O

O

3

3

C

H

C

O

C

H

F

O

C

2

H

B

r

F

C

H

2

2

2

F

F

F

F



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GC- different fractions?EIMS for Oxygenated Terpenoids


Thermal desorption particle beam mass spectrometry paul ziemann l.jpg
Thermal desorption particle different fractions? beam mass spectrometry (Paul Ziemann)

Particle generator or smog chamber


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Chlorinated dibenzo dioxins and Furans different fractions?

These are some of the most toxic organics in the environment - LD50

Created by burning organics which have chlorine; incineration is a big source of atmospheric dioxins and furans

bleaching in making paper is another source


Combustion formation of dioxins from polychlorinated phenol l.jpg
Combustion Formation of Dioxins from Polychlorinated phenol different fractions?

O

H

Clx

.

OH

Clx

Flame

.

O

O

H

+

Polychlorinated

Phenol

C

l

y

O

+ OH

O

Cly

Cly

Clx

O

Clx

O

H

Chlorinated dibenzo dioxin

Shaub & Tsang, ES&T 1983.


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They have the following general structures different fractions?

O

Cl

x

O

Cl

y

chlorinated dioxin


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Cl different fractions?

x

Cl

y

They have the following general structures

O

Cl

x

O

Cl

y

chlorinated dioxin

O

chlorinated furan


The most toxic is either the 2 3 7 8 tetrachlorodibeno dioxin or furan l.jpg

O different fractions?

Cl

Cl

Cl

Cl

O

More than 200 different structures are possible

The most toxic is either the 2,3,7,8 tetrachlorodibeno dioxin or furan


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These types of compounds produce toxic enzymes: arylhydrocarbon hydroxylase and 7-ethoxyresorufin deethylase

At low concentrations they may behave as environmental estrogens


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Environmentally, they are unreactive and can be transported long distances

They did not start to show up in the environment until the 1920s when there was a big increase in the production of chloro-organics (Professor Ron Hites, and students)


Environmental fate of chlorinated dioxins and furans czuczwa and hites 1984 l.jpg
Environmental Fate of Chlorinated Dioxins and Furans long distances(Czuczwa and Hites, 1984)

  • Collected core sediment samples from southern Lake Huron in the USA

  • Based on sedimentation rates they established age vs. concentration profiles for chlorinated dioxins and furans



Chlorinated aromatic production vs dioxin and furan conc in lake core samples l.jpg
Chlorinated aromatic production vs dioxin long distancesand furan conc. in lake core samples


Pcbs in the u s great lakes l.jpg
PCBs in the U.S. Great Lakes long distances

  • PCBs were banned in the early 1970s

  • In 1980 Eisenreich and co-workers estimated that still 85% of the PCBs in the US great lakes came from atmospheric sources.


Polychlorinated biphenyls pcbs l.jpg
Polychlorinated biphenyls (PCBs) long distances

  • Total Flux = Jair + Jrain + Jparticles

  • Jair = vw ( Cw-P/KH)if resistance to mass transfer is in the water phase

  • Jair = va (Cw KH - P)/RT if resistance is in the gas phase


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In the late 1980s a fugacity model was used to represent the distribution of PCBs in different environmental compartments

  • RT lnfair /fiopure liquid = RT lnf H2O/fiopure liquid

  • fair= f H2O


Slide89 l.jpg

  • In 1990 Eisenreich and co-workers reported that ambient measurements over the great lakes were generally constant for the past 10 years.

  • For the past 15 years sources to the lakes had declined because of the PCB ban.

  • Based on mass transfer calculations it was proposed that during the summer months the lakes were actually a source of atmospheric PCBs.


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Polychlorinated biphenyls (PCBs) measurements over the great lakes were generally constant for the past 10 years.

used as coolants - insulation fluids in transformers, capacitors , plastercisers, additives to epoxy paints

are thermally stable and biologically stable

can exist in the gas and particle phases


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Cl measurements over the great lakes were generally constant for the past 10 years.

x

Cl

y

PCB structures

  • Environmentally, they used to be considered unreactive, but there is evidence for some bio-degradation; they can be transported long distances


What do we do now when new compounds are introduced into the environment l.jpg
What do measurements over the great lakes were generally constant for the past 10 years.we do now, when new compounds are introduced into the environment...??

  • toxicity??

  • low concentration health effects?

  • damage to the ecosystem ?

  • where will it show up in the environment?

  • how is it transported in the environment and what is its life-time?


An example is a new compound called d5 it is a silicon oxygen compound l.jpg
An example is a new compound called measurements over the great lakes were generally constant for the past 10 years.D5. It is a silicon-oxygen compound

  • It is used to make silicone plastics.

  • It is possible that it could be used to replace toxic solvents like toluene and dichloro-methane.

  • Before it can be put into use in the US, we need to know its toxicity, chemical reactivity , environmental half-life, etc.


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New compounds are introduced into the environment ... measurements over the great lakes were generally constant for the past 10 years. Toxicity? Where will it go?

OH.

D4TOH


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Some examples of environmental exposures measurements over the great lakes were generally constant for the past 10 years.


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1. There is a general concern that if we observe measurements over the great lakes were generally constant for the past 10 years.abnormalities in wildlife, similar kinds of mechanisms may exist in humans.


Mercury poisoning off the coast of minamata japan is an example l.jpg
Mercury poisoning measurements over the great lakes were generally constant for the past 10 years.off the coast of Minamata, Japan is an example

  • Fishermen in the 1950s noticed sea birds were dying and feral cats that scavenged fish from the docks were “stiff legged”

  • Cerebral palsy and mental retardation started showing up in children.


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2. Toxic loads measurements over the great lakes were generally constant for the past 10 years.

  • Scientists have hypothesized that the fetus is sharing the mother’s toxic load, and may actually provide some protection to the mother by reducing her internal exposure.


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2. Toxic loads measurements over the great lakes were generally constant for the past 10 years.

  • Children get 12% of their lifetime exposure to dioxins during the 1st year.

  • Their exposure is 50 times greater than an adult during a very critical developmental period.


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2. Toxic loads measurements over the great lakes were generally constant for the past 10 years.

  • Firstborns from dolphins off the coast of Florida usually die before they separate from their mothers


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2. Toxic loads measurements over the great lakes were generally constant for the past 10 years.

  • It is speculated that mother dolphins unload 80% of their accumulated pollutants into their calves, probably during nursing.

  • The greatest exposures occurs with the 1st born

  • Does this have any implications for humans?


3 pesticide exposures l.jpg
3. Pesticide exposures measurements over the great lakes were generally constant for the past 10 years.

  • Children of farm families in the western Minnesota area of the US have significantly higher rates of birth defects than the general population.

  • The highest rates are among children conceived in the spring when spraying of pesticides is most intense; male babies had far more birth defects than females


4 the end points may not only be cancer but compromised immune systems and generally poorer health l.jpg
4. measurements over the great lakes were generally constant for the past 10 years.The end points may not only be cancer, but compromised immune systems and generally poorer health.


4 immune systems mother s milk l.jpg
4. Immune systems & Mother’s milk measurements over the great lakes were generally constant for the past 10 years.

  • In the Netherlands researchers have found that children with higher levels of dioxins and PCBs in their bodies have more health problems (immune system and hormonal changes) than children with lower levels.

  • This was linked to levels of PCBs in Mother’s milk.


4 mother s milk l.jpg
4. Mother’s milk measurements over the great lakes were generally constant for the past 10 years.

  • Mother’s milk from Inuit Indians in the Canadian Arctic has 7 times the PCBs as mother’s milk from women in the urban industrialized areas of southern Quebec.


4 mother s milk106 l.jpg
4. Mother’s milk measurements over the great lakes were generally constant for the past 10 years.

  • During the first year, Inuit babies suffer through 20 times more colds than babies in southern Quebec.

  • Acute ear infections are rampant.


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4. Mother’s milk measurements over the great lakes were generally constant for the past 10 years.

  • Babies nursed by mothers with the highest contamination levels in their milk are afflicted with more acute ear infections than bottle fed Inuit babies.

  • Many of these children don’t seem to produce enough antibodies for childhood vaccinations to take.


5 pcbs and lower intelligence l.jpg
5. PCBs and lower intelligence measurements over the great lakes were generally constant for the past 10 years.

  • There is evidence of lower intelligence in babies exposed to PCBs.

  • In adults, a blood-brain barrier insulates the brain from many potentially harmful chemicals circulating through the body

  • In a human child this barrier is not fully developed until 6 months after birth.


5 pcbs and lower intelligence109 l.jpg
5. PCBs and lower intelligence measurements over the great lakes were generally constant for the past 10 years.

  • In 1979 in Taiwan, more than 2000 people were exposed to PCB-contaminated cooking oil.

  • In the 1st 3 months many babies died outright. As the surviving children grew up, many were slower intellectually than other kids their age, were hyperactive and had behavioral problems.


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5. PCBs and lower intelligence measurements over the great lakes were generally constant for the past 10 years.

  • Similar observations were made in "high-PCB kids" in the Lake Michigan area.

  • This was associated with mothers eating salmon and trout from the Lake during the years before their children were born.


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5. PCBs and lower intelligence measurements over the great lakes were generally constant for the past 10 years.

  • At age 4 the high exposure group had poor short term memories. At age 11 the 30 most highly exposed kids had average IQ scores that were 6 points lower than the lowest-exposed group.

  • biomarker-metabolites???


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6. DDT and immune system damage measurements over the great lakes were generally constant for the past 10 years.

  • In a recent study (1998), residents whose homes are within a mile of Aberdeen, Texas pesticide sites show elevated DDE levels in their blood.


6 ddt and immune system damage113 l.jpg
6. DDT and immune system damage measurements over the great lakes were generally constant for the past 10 years.


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7. measurements over the great lakes were generally constant for the past 10 years.Sexual impairment

  • There is evidence for sexual impairment in both animals and humans from high PCB exposures and other environmental chemicals.

  • Male beluga whales in the very polluted St. Lawrence River have exhibited female organs.


7 sexual impairment115 l.jpg
7. measurements over the great lakes were generally constant for the past 10 years.Sexual impairment

  • Highly exposed humans, alligators and panthers exhibit smaller male sex organs and low sperm counts.

  • Testicular cancers have nearly doubled among older teenagers in the US between 1973 and 1992.

  • In previous lectures I have said these have been linked to toxic exposures....long way from finding proof.


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7a. measurements over the great lakes were generally constant for the past 10 years.Sexual impairment

  • In a new study (Hardwell et al, Environ Presp, 2003) woman who’ve had substantial exposure to certain environmental pollutants are more likely to bear sons who develop testicular cancers (men ~ 30 years of age)

  • From 1973-1999 testicular cancers up 67%

  • Men with test-cancers had high cis nona chloridane, not PCBs, etc

  • Mothers, however, had high PCBs, HCB (hexa-chlorobenzenes) and cis nona chloridane


7b sexual impairment l.jpg
7b. measurements over the great lakes were generally constant for the past 10 years.Sexual impairment

  • These same mothers probably had high exposures when environmental contaminates peaked in Scandinavia in the 1970s

  • Richard Sharpe of Edinburogh and Niels Skakkebek (Denmark) propose that exposure to endocrine disruptors before birth can alter testicular-cell development and some of these cells may be cancerous after puberty.

  • This may also may explain rising rates of male infertility, and other sexual deformities


8 endocrine disrupters l.jpg
8. measurements over the great lakes were generally constant for the past 10 years.Endocrine disrupters

  • These studies have led to the notion of environmental "endocrine disrupters".

  • In the lock and key relationship between hormone and receptor molecules, these "hormone impostors" can:


8 endocrine disrupters119 l.jpg
8. measurements over the great lakes were generally constant for the past 10 years.Endocrine disrupters

  • bind with receptors and trigger biological processes

  • or bind with receptors and tie up an active hormone site

  • Some of these have been called environmental estrogens


9 other chemicals l.jpg
9. measurements over the great lakes were generally constant for the past 10 years.Other chemicals

  • From a historical perspective, everyone is now carrying at last 250 measurable chemicals that were not part of human chemistry before the 1920s (Peter Myers, 1996)

  • The most basic toxicity testing results cannot be found in the public record for nearly 75% of the top volume chemicals in commercial use in the USA


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9. measurements over the great lakes were generally constant for the past 10 years.Other chemicals

  • In other words, the public cannot tell whether a large majority of the highest-use chemicals in the United States pose health hazards or not (Amicus Journal, p23, Spring 1998).

  • An example are phthalates that go into many types of plastics which have been shown to reduce the sperm counts in mice.


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9. measurements over the great lakes were generally constant for the past 10 years.Other chemicals

  • Bisphenol-A (BPA) is an additive in polycarbonate plastics used in food liners, dental sealants, and dental fillings.

  • BPA causes increased prostate size in mice exposed to tiny doses while in the womb. These doses were 25,000 times smaller than the EPA threshold.


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9. measurements over the great lakes were generally constant for the past 10 years.Phthalates

  • Exposure of female rates to 200 to 1000 mg/kg body weight results in much lower testosterone in male offspring( L. Earl Gray. Jr. EPA, RTP, J. Tox and Ind. Health, Mar, 1999).

  • Exposures to the herbicide linuron made the epididymis (sperm-storing organ in rats) much smaller in male rats.


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epididymus measurements over the great lakes were generally constant for the past 10 years.


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Recommendations measurements over the great lakes were generally constant for the past 10 years.

  • During the insecticide spraying season, farmers should not try to have children.

  • Limit exposures to pesticides around the home.

  • When possible, buy foods that were grown without pesticides.

  • Governments must try to limit PCB introduction into the environment.

  • If incineration is used, chlorinated plastics should be removed, along with modern technology.


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