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Environmental Organic Chemistry Schwarzenbach, Gschwend, Imboden, 2a ed., Wiley, Hoboken, NJ, EUA, 2003. Captulos 1-8. Artigos
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Reaction Mechanisms in Environmental Organic Chemistry, Larson, Weber, 1a ed., Lewis Pub., Boca Raton, FL, EUA, 1994
Accumulation rate in the sediments of Lake Ontario (data from 2 different sediment cores) 1980 DDT (DDT+DDE+DDD) 1970
1970
DDT
1960
1960
1950
1950
1940 20 40 60 10 3 t 80 20 40 60 g . m -2 year-1 80
1940
Accumulation rate in the sediments of Lake Ontario (data from 2 different sediment cores) 1980
1970
1970
1960
1960
1950
Cl m Cl n
1940
10
20 103 t
30
100
Environmental Organic Chemistry, Schwarzenbach, Gschwend, Imboden, 2a ed., Wiley, Hoboken, NJ, EUA, 2003
Hidrocarbonetos
CH3CH3
etano
CH3CH2CH2CH3
butano
C23-C33
n-alcanos (impar) cera epicuticular de plantas ambientes limpos
C24-C30
alcanos ramificados combusto veicular
limoneno
derivados do benzeno
benzeno
tolueno
o, m e p-xileno
etil benzeno
estireno
bifenila
BTEX
evaporao de gasolina, combusto de diesel indeno tetralina
poliaromticos (HPA)
naftaleno
antraceno
fenantreno
perileno
pireno
benzo[a]pireno
OH
OH
CH3CH2OH
etanol
OH HO
etileno glicol
OH Clm
fenol clorofenol (m = 1-5)
HO
OH
OH
O
C9H19 O(CH2CH2O)nH (n = 5-10)
O O O
ter etlico 1,4-dioxano solventes MTBE metil-t-butil ter
O Cl
epicloridrina intermedirio qumico
Clm
Cln
C9H19
O(CH2CH2O)2H
+
C9H19 OH
+
C9H19 OCH2CH2OH
Brm
retardante de chama
Brn
Clm
Cln
O H
O H
acrolena
O H
formaldedo
intermedirio qumico benzaldedo solvente solvente intermedirio qumico intermedirio qumico produto secundrio do O tratamento de gua
O
acetona 2-butanona
OH O OH O
Cl O
acetofenona
Cl Cl
O
acetato de etila solvente
O O O
R1
solvente plastificante
Cl
(R,S)-mecoprop herbicida
R2
O
OH
Contendo nitrognio
NH2 R1 N H X,R NH R2
N,N'-dialquil/aril p-fenilenodiaminas antioxidantes trietilamina solvente, agente umectante, inibidor de corroso propelente
N H3C H3C
R N R
X-
Cl N N H N
atrazina herbicida
OH NO2
N N H O HN
N N
azobenzeno intermedirio qumico pesticida
NO2
NO2 O O N O O O O O2N
nitroglicerina 1-nitropireno combusto 2,4-dinitro-o-cresol herbicida
Br
O2N
N N NO2
Dispersive Blue 79 pigmento txtil
NO2 O2N
N N
NO2
NO2
RDX
explosivos
Contendo enxofre
SH
etilmercaptana agente de odor intermedirio qumico
Cl S
dimetilssulfeto solvente produto biognico
Sn-2
sulfeto e polissulfetos produto biognico
S SH
tiofenol intermedirio qumico
NH2 Cl
clortiamida herbicida
O S S
dimetilssulfxido (DMSO) solvente
SO3-
SO3-
SO3NH2 R
O O S O CO2H
sulfometuron herbicida
O O S O OH2N
O S O N
sulfadiazina frmaco
NH N
NH NH N N
SO3-O S 3
Contendo fsforo
HO Cl Cl Cl
O P O
triclorfon inseticida
O O HO P
OH O C P OH O P F O O O P O O
trifenilfosfato plastificante retardante de chama
OH CH3 OH
HEDP agente complexante
sarin gs neurotxico
S(O) O P O O S S O P O O2N
paration (paraoxon) inseticida, acaricida disulfoton inseticida, acaricida
Contendo halognios
CH3Cl
clorofrmio emisses vulcnicas fermentao combusto da vegetao tratamento de gua combusto veicular SN2 com CH3I (algas)
CH3Br
bromofrmio algas
CH3I
iodofrmio
CH2Cl2
diclorometano solvente
ClCH2CH2Cl
CH3CCl3
Clm Cln Clk Cln
terfenilas cloradas (PCTs) 8149 representantes
Cl2C=CCl2
tetracloroeteno
1,1,1-tricloroetano 1,1,2-tricloroeteno
Cl Clm Cl Cl
Cl
HCB
Cl Cl
HCH
Cl Cl Cl
Cl Cl
tintas para impresso papel carbono capacitores e tranformadores (ascarel) lmpadas fluorescentes, etc.
Cl Cl
Cl
pesticidas
Cl CCl3 Cl Cl Cl Cl C H
DDT
Cl Cl Cl Cl Cl
Cl Cl
Cl
Dieldrin
Cl O Cl
herbicidas
Cl
O
Endrin
Cl
Cl Cl Cl
O O
CN O
O CH3 O CH3 H H H O
O S N O N H H HO
17-etinil estradiol
CH3 H H
OH
O
17a-acetxi-progesterona hormnio
O O
H N
hormnio, anticoncepcional
O OH
S N
HO
O
penicilina V antibitico
I OH O
O I
levotiroxina hormnio
transporte e partio
mesma fase ou entre fases
ATMOSPHERE
wet + dry deposition of i i i products chem.+biol. transform. vertical and horizontal mixing of i i products. chem.+biol. transform. direct + indirect photolysis h
export of i by outflow
WATER SEDIMENTS
burial of i
sedimentation
i = composto
Environmental Organic Chemistry, Schwarzenbach, Gschwend, Imboden, 2a ed., Wiley, Hoboken, NJ, EUA, 2003
(a)
O
0.8 1.0/0
OH
pKa1 = 4.48
OH
pKa2 = 9.32
O
pKa1 = 6.61
pKa2 = 9.82
pK i a
log Cisat w log Cisat w
0.2
OH
0.4 0.6
OH
NH+
+
O