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PCB and PCNFate and Source
Takeshi Nakano(Hyogo Pref. Inst. of Env. Sci.)
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Dr. Imagawa / Dioxin symposium in Kyoto (1994)
Sudden Deathof Dr. Imagawa
on 19th Feb. 2001
It is truly a shame to lose him at such
a young age,and
I thank for hishelp to my study
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0.00001
0.0001
0.001
0.01
0.1
1
0 1 2 3 4 5 6 7 8 9 10
Atmospheric PCN (pg-TEQ/m3) in Japan (JEPA)
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Homologue distribution of PCN in Ambient air
0.000
0.100
0.200
0.300
0.400
0.500
0.600
Cl1 Cl2 Cl3 Cl4 Cl5 Cl6 Cl7 Cl8
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Homologue distribution of PCN in Ambient air
0.01.02.03.04.05.06.0
Cl1 Cl2 Cl3 Cl4 Cl5 Cl6 Cl7 Cl8
0.05.0
10.015.020.025.0
Cl1 Cl2 Cl3 Cl4 Cl5 Cl6 Cl7 Cl8
Kobe
On the mountain
Industrial site
0.0000.1000.2000.3000.4000.5000.600
Cl1 Cl2 Cl3 Cl4 Cl5 Cl6 Cl7 Cl8
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Homologue distribution in Ambient air
0.0000.1000.2000.3000.4000.5000.600
Cl1 Cl2 Cl3 Cl4 Cl5 Cl6 Cl7 Cl8
PUF
0
10
20
30
40
50
M1C
B
D2C
B
Tr3
CB
Te4
CB
P5C
B
Hx6
CB
Hp7
CB
O8C
B
N9C
B
D10
CB
PCN (vapor+particle)
PCB(gas phase)
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Homologue distribution in Ambient air
0.0000.1000.2000.3000.4000.5000.600
Cl1 Cl2 Cl3 Cl4 Cl5 Cl6 Cl7 Cl8
PCN
PUF
0
10
20
30
40
50
M1C
B
D2C
B
Tr3
CB
Te4
CB
P5C
B
Hx6
CB
Hp7
CB
O8C
B
N9C
B
D10
CB
PCB
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Atmospheric level of PCB/PCN/PCDD/PCDF
1
10
100
1000
PCB PCN PCDD PCDF 0.001
0.01
0.1
1PCB PCN PCDD PCDF
Ambient air (pg/m3) Ambient air (pg-TEQ/m3)
Total concentration TEQ concentration
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Air, Rain
1,2,6,7- (#39)
1,2,3,4,6- (#50) 1,2,3,6,7- (#54)
1,6,7- (#25)
2,3,6- (#26)1,2,3,4- (#27)
2,3- (#10) 1,2,3,7- (#30)
Air ・ Rain
Air
1,4,6- (#24) 1,3,7- (#21)
Water ・ sediment
β
Selected PCN isomers from result of PCA
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Daily variation of PCB in ambient air
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0
5 0 0
10 0 0
15 0 0
20 0 0
PC
B C
onc.
(pg
/m3)
0
5
1 0
1 5
2 0
2 5
3 0
Air
tem
p.(d
egC)
PC B (Q MF)PCB (P UF)T emp.
0
5 0
1 0 0
Rai
n (m
m)
0
5 0 0
10 0 0
15 0 0
20 0 0
4 9 19
24
24 3 13
23 3
S ampl ing Date
PC
B C
onc.
(pg
/m3)
9 8 0
9 9 0
10 0 0
10 1 0
10 2 0
10 3 0
10 4 0
Air
Pre
ss.(
hPa)
PC B (Q MF)
PCB (P UF)Pres s .
Figure 1. Changes of PCB concentrations in air with average temperature (°C), atmospheric pressure(hPa), and precipitation (mm) on the sampling date.
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R2 = 0 .1 7 93
R2 = 0 .0 077
0
10
20
30
40
50
60
10 1 00 1 0 00 1 0 0 00
g as eous -PC B (PUF)(pg / m3)
( °C)
9 80
9 90
1 0 00
1 0 10
1 0 20
1 0 30
1 0 40(h Pa)
T em p.( °C) P ress ure(h Pa)
R2 = 0 .3 2 74
R2 = 0 .3 315
0
10
20
30
40
50
60
0.1 1 10 1 00 1 000
parti cu late -PCB (Q M F)(pg / m3)
( °C)
9 80
9 90
1 0 00
1 0 10
1 0 20
1 0 30
1 0 40(h Pa)
T em p.( °C) P ress ure(h Pa)
Relation between distribution of gase and particulate-PCB with temperature (C) and atmospheric pressure (hPa).
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KC 300-600
0
10
20
30
PUF
0
10
20
30
QMF
0
10
20
30
#11
#12/
#13
#15
#35
#37
#74
#70
#66
#80/
#55
#56
#77
#107
#123
#118
#114
#105
#126
#156
#157
#169
#180
#193
#191
#170
#190
#189
Co-PCB in air and technical PCB
Gas phase
particulate
HeptaHexaPentaTetraTriDi
3,4,
3’-
3,4,
4’-
3,3’
-
4,4’
-3,
4-/ 3
,4’-
3,4,
3’,4
’-
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PCB
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PCN
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Isomer spescific analysis
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Source estimation
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PCB
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production 60,000t in Japan
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Source Fate Sediment Ambient air
PCB
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source Fate Ambient air Congener profiles
PCN
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O
Cl
ClCl
O
ClCl
Cl
OH
Cl
OH
Cl
Cl
2,3,8-
1,2,8-+
4-MCP
3,4-DCP 2,3,8-TrCDF
1,2,8-TrCDF
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O
Cl
O
OH
OH
Cl
1,4,7-
1,4,9- Cl
Cl
Cl
Cl
Cl
Cl
Cl
OH
OH
O
Cl
1,4,6- Cl
O
Cl
1,4,8- Cl
Cl
Cl
Cl
Cl
Synthesis of 1,4,X-T3CDF isomers from chlorophenol
Authentic standard (1,4,7- : NMR)
2,5-DCP
4-MCP
3-MCP2-MCP
O-m-
p-
1,4,6-TrCDF
1,4,8-TrCDF
1,4,9-TrCDF
1,4,7-TrCDF
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0.000.100.200.300.400.50
PUF- 1 PUF-2 PUF- 3
2-F
0.000.200.400.600.801.00
PUF- 1 PUF-2 PUF- 3
23-F
0.000.200.400.600.801.00
PUF-1 PUF-2 PUF-3
248-F
0.000.200.400.600.801.001.20
PUF-1 PUF- 2 PUF-3
2378- F
0.000.200.400.600.801.001.20
PUF- 1 PUF-2 PUF- 3
12 3 78 - F
0.000.200.400.600.801.001.20
PUF- 1 PUF- 2 PUF- 3
234 6 78 - F
0.000.100.200.300.400.50
PUF- 1 PUF-2 PUF-3
2-D
0.00
0.20
0.40
0.60
0.80
PUF- 1 PUF- 2 PUF-3
23-D
0.000.200.400.600.801.001.20
PUF-1 PUF- 2 PUF-3
237-D
0.000.200.400.600.801.001.20
PUF-1 PUF- 2 PUF- 3
2378- D
0.000.200.400.600.801.001.20
PUF- 1 PUF-2 PUF- 3
12 3 78 - D
0.000.200.400.600.801.001.20
PUF- 1 PUF-2 PUF-3
123789-D
0.000.200.400.600.801.00
PUF- 1 PUF-2 PUF-3
12346 78 - D
0.000.200.400.600.801.001.20
PUF- 1 PUF-2 PUF-3
12346789 - D
0.000.200.400.600.801.001.20
PUF-1 PUF- 2 PUF-3
12346 78 - F
0.000.200.400.600.801.001.20
PUF- 1 PUF-2 PUF-3
12346789 - F
13C12-MCDF
13C12-OCDF
13C12-HpCDF
13C12-DiCDF
13C12-TrCDF
13C12-TeCDF
13C12-PeCDF
13C12-HxCDF
13C12-MCDD
13C12-OCDD
13C12-HpCDD
13C12-DiCDD
13C12-TrCDD
13C12-TeCDD
13C12-PeCDD
13C12-HxCDD
Breakthrough from PUF plug using High volume air sampler
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Source Fate Sediment Ambient air
PCB
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source Fate Ambient air Congener profiles
PCN
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0.0
2.0
4.0
6.0
8.0
10.0
12.0
42
37/3
3/34
44/4
7
45/3
6
28/4
3
27/3
0 39 32
48/3
5
38/4
0 46 31 41
TeCN
0.0
0.2
0.4
0.6
0.8
1.0
1.2
1.452
/60 58 61 50 51 54 57 62
53/5
5 59 49 56
66/6
7
64/6
8 69
71/7
2 63 65 70
PeCN HxCN
0.0
2.0
4.0
6.0
8.0
10.0
12.0
4
5/7
6/12
11/8 3 10 9
20/1
9
21/2
4 14 15 16 17
25/2
6 13 22 23 18
DiCN TrCN
PCN congener distribution in ambient air.
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0
5
10
15
20
25
4
5/7
6/12
11/8 3 10 9
20/1
9
21/2
4 15 16 17
25/2
6/13 22 23 18 42
37/3
3/34
44/4
7
45/3
6
30/2
7 32
35/4
8
38/4
0 46 41
52/6
0 58 61 50 51 54 57 62
53/5
5 59 49 56
66/6
7
64/6
8 69
71/7
2 63 65 70
PCN congener distribution in ambient air.
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PCN isomer distribution in air, dry-deposition, rain particle, Halowax, sediment and landfil sludge.
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Air Sampling
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Water Sampling 100L High volume water sampler
•Qurtz Micro Fiber for particulate•Poly Urethane Foam for dissolved
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0.0
2.0
4.0
6.0
8.0
10.0
12.0
42
37/3
3/34
44/4
7
45/3
6
28/4
3
27/3
0 39 32
48/3
5
38/4
0 46 31 41
TeCN
0.0
0.2
0.4
0.6
0.8
1.0
1.2
1.452
/60 58 61 50 51 54 57 62
53/5
5 59 49 56
66/6
7
64/6
8 69
71/7
2 63 65 70
PeCN HxCN
0.0
2.0
4.0
6.0
8.0
10.0
12.0
4
5/7
6/12
11/8 3 10 9
20/1
9
21/2
4 14 15 16 17
25/2
6 13 22 23 18
DiCN TrCN
PCN congener distribution in ambient air.
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0
5
10
15
20
25
4
5/7
6/12
11/8 3 10 9
20/1
9
21/2
4 15 16 17
25/2
6/13 22 23 18 42
37/3
3/34
44/4
7
45/3
6
30/2
7 32
35/4
8
38/4
0 46 41
52/6
0 58 61 50 51 54 57 62
53/5
5 59 49 56
66/6
7
64/6
8 69
71/7
2 63 65 70
PCN congener distribution in ambient air.
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PCN isomer distribution in air, dry-deposition, rain particle, Halowax, sediment and landfil sludge.
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Analytical Method of Environmental Samples
Sampling
Extraction
Cleanup
Daily Variation
L/L -> SPE
Removal Interference
Measurement GC/MS, LC/MS
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Importance of Low chlorinated DD/DF
formation mechanism
PCB PCN PCDD PCDF
MCDF > TCDF
水系、大気系
degration mechanism
origin estimation
Monitoring of stack gas
Monitoring of Environment
on site analysis
Isomer distribution
Bio degradation pathway
Important information
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23478-PeCDF
3453’4’- Co-PCB
2378- TCDD
123567-HxCN
7575
135
209
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Air depo sediment water soil
Contribution in TEQ value
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Ambient air
0.001
0.01
0.1
1PCB PCN PCDD PCDF
pg-TEQ/m3
1
10
100
1000
PCB PCN PCDD PCDF
pg/m3
Contribution in TEQ value
TEQ value
Total conc.
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Precursor of PCDD/DF formation
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Phenol 2-MCP 3-MCP 4-MCP 23-DCP 24-DCP 25-DCP
Phenol 4-F 1/3-F 2-F 34-F 24-F 14-F
2-MCP 46-F 16/36-F 26-F 346-F 246-F 146-F
3-MCP 17/37/19-F 18/27-F 167/347-F 168/247-F 147/149-F
4-MCP 28-F 267-F 248-F 148-F
Precursor of PCDD/DF formation
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Landfil
4
5/7
6/1211/8 310
9 20/19
21/24
15 16 1725/26/1322
23
1842
37/33/34
4447
45/3628/43
30/27 39 32 35/48
38/40
463141
52/60
58
6150
51 5457
6253/55 59
49 5666/67
64/6869 71/72
63 6570
020406080
4
5/7
6/12
11/8 3 10 9
20/1
9
21/2
4 15 16 17
25/2
6/13 22 23 18 42
37/3
3/34 44 47
45/3
6
28/4
3
30/2
7 39 32
35/4
8
38/4
0 46 31 41
52/6
0 58 61 50 51 54 57 62
53/5
5 59 49 56
66/6
7
64/6
8 69
71/7
2 63 65 70
Sediment
4
5/7
6/1211/8 3
10 920/19
21/24
15 16 1725/26/132223
18
4237/33/34
44
47
45/3628/43
30/27 39 32 35/4838/40
46 3141
52/60
5861
5051 54
57 62 53/55 5949 5666/67
64/68
6971/72 63
6570
020406080
HALOWAX
4
5/7
6/1211/83
10 9 20/19
21/24
15 16 1725/26/1322
23
18 42
37/33/34
4447
45/3628/43
30/27 39 3235/48
38/4046
314152/60
58
6150 51 54
57 62 53/55
59
49 5666/6764/68
69
71/72
6365
700
20406080
dry-depos i ti o n
4
5/7
6/1211/8 3
10 920/19
21/24
15
161725/26/13
2223
18 4237/33/34
44 4745/3628/43
30/27 39 3235/48
38/40
463141
52/60 5861 50
51
5457 62 53/55
59
49 5666/6764/68
6971/72
63 6570
020406080
rain particle
4
5/7
6/1211/8
310 9 20/19
21/24
15 16 1725/26/1322
2318 42
37/33/34
444745/3628/4330/27
39 3235/48
38/4046
314152/60
5861
5051
54 57 62 53/55 5949 56
66/67
64/6869
71/72
63 6570
020406080
Air
4
5/76/1211/8
310 920/19
21/24
15 16 17
25/26/13
22 23 18 42
37/33/34
44 4745/3628/43
30/27
39 3235/4838/4046 3141
52/60
58 61
50
51 5457 6253/5559 49 56
66/67
64/6869
71/72
63 6570
020406080
PCN isomer distribution
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Annual inventory of Dioxin from Incinerator
1. Hyogo pref 2. Japan
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Hyogo pref
Japan
Emision (g-TEQ/year)
Emission (g-TEQ/year)
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Homologue Distribution
十五社橋
020406080
100120140
T4CD
Ds
P5CD
Ds
H6CD
Ds
H7CD
Ds
O8CD
D
T4CD
Fs
P5CD
Fs
H6CD
Fs
H7CD
Fs
O8CD
F
River water
PCDD PCDF
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PCDD
脇田橋
0100200300400500600700800900
1000T4
CDDs
P5CD
Ds
H6CD
Ds
H7CD
Ds
O8CD
D
T4CD
Fs
P5CD
Fs
H6CD
Fs
H7CD
Fs
O8CD
F
PCDF
River sediment
Homologue Distribution
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辰巳橋
0200400600800
10001200140016001800
T4CD
Ds
P5CD
Ds
H6CD
Ds
H7CD
Ds
O8CD
D
T4CD
Fs
P5CD
Fs
H6CD
Fs
H7CD
Fs
O8CD
F
PCDD PCDF
Incineration pattern
Homologue Distribution
River sediment
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脇田橋
0100200300400500600700800900
1000
T4CD
Ds
P5CD
Ds
H6CD
Ds
H7CD
Ds
O8CD
D
T4CD
Fs
P5CD
Fs
H6CD
Fs
H7CD
Fs
O8CD
F
Pesticide pattern CNP
PCP
辰巳橋
0200400600800
10001200140016001800
T4CD
Ds
P5CD
Ds
H6CD
Ds
H7CD
Ds
O8CD
D
T4CD
Fs
P5CD
Fs
H6CD
Fs
H7CD
Fs
O8CD
F
PCDD PCDF
Incineration pattern
Homologue Distribution River sediment
PCP
CNP
Pesticide pattern
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PCDD PCDF
燃焼系
神戸市東部沖
0200400600800
1000120014001600
T4CD
Ds
P5CD
Ds
H6CD
Ds
H7CD
Ds
O8CD
D
T4CD
Fs
P5CD
Fs
H6CD
Fs
H7CD
Fs
O8CD
F
Homologue Distribution
Sea sediment
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PCB concentration and TEQ value
KC300 KC400 KC500 KC600
2x10-
50.7 x10
-56x10-
53x10-
5
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Source estimation
KC 300
KC 400
KC 500
KC 600
Sediment A Sediment B
Ship paint
N.C.P.
Insulator
Insulator
capacitor
capacitor
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環境試料中のコプラナ PCBの相対比
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KC300
Isomer distribution and Source estimation
Sediment A Water A
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KC 4 00 KC 5 00
KC 6 00
Isomer distribution and Source estimation
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Co-PCB in sediment and PCA
P1 :#118,#105,#180
P2 : #180, #170
KC-600
P3 :#77,#105,#180
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Co-PCB isomer distribution and PCA
KC-600
KC-600
KC-500
KC-400
KC-300
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Co-PCB isomer ratio and Source
KC-600
KC-500
KC-400
KC-300
Sediment A
Sediment B
flyash
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Co-PCB isomer ratio in environmental sample
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PCDFパ ル プ 漂 白 漂 白 パ タ ー ン TeCDF (2,3,7,8-, 1,2,7,8-)ク ロ ル ア ル カ リ : PCDF (2,3,7,8-, 1,2,7,8-, 1,3,4,6,8-, 1,2,4,7,8-, 1,2,3,7,8-, 1,2,3,4,8-, 2,3,4,7,8-)燃焼起源 ( 流動床炉 ) : PCDF (2,4,6,7‐, 3,4,6,7-, 2,3,6,7-, 2,3,4,6-, 2,3,4,6,8-, 2,3,4,6,7-, 2,3,4,7,8-)農 薬 (CNP) : 24-F,246-F,248-F,2468-F,12468-F, 23468-F農薬 (PCP): OCDF, 1234689-F,1234678-F, 124689-F,12468-F農薬 (24-D) : TeCDF (2,4,6,8‐)
燃焼起源 農薬起源
特徴的な異性体
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PCB Incineration and PCB product(KC,AC)#118/#77ratio、 #77/#126 ratio
PCN Incineration and PCN product(HALOWAX)(Incineration)1267-N, 12367-N, (PCN product)1248-N
PCDDIncineration(FBI) : 2,6-PeCDD(xxx68, xxx79)pattern Incineration(stoker : 2,3-PeCDD patternPesticide(CNP) : PCDD(13-,136-,138-,137-,139-, 1368-,1379-,12479-, 12468-, 12368-, 12379-)Pesticide(PCP) : OCDD, HpCDD(1234678-)Pesticide(24-D) : D2CDD (2,7- , 2,8-)
Important Isomer for origin estimation
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quick cleanup methods
PCDD
PCDF
PCB
PCN
simultaneous analysis
analysis of low chlorinated DD/DF
origin estimation
Isomer distribution
排出源毎の特徴的分布を蓄積
Incineration
PCB ( KC 3~600)
Pesticide
PCN ( Halowax)
Homologue distribution
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23478-TCDF
3453’4’- Co-PCB
2378- TCDD
123567-HxCN
7575
135
209
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海域底質中 PCBの鉛直分布
海域底質中 PCBの水平分布
PCB 汚染の時間的・経年変化
PCBは汚染拡散の重要な指標
環境中で分解しない。:難分解性
使用期間 10 ~ 20 年の環境負荷
PCB汚染の空間的移動
異性体 209 : 情報量が多い
熱安定性
化学的
生物学的
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海域底質の水平分布と鉛直分布
Production of N.C.P
Annual production Sediment core
PCB concentration
Annual production and Vertical distribution in sediment
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海底の地形・水深
播磨灘 大阪湾
スープ皿のような地形 東半分:陸、西半分:海
Horizontal distribution in sea sediment
Osaka Bay Harima nada
Sea bottom and water depth
like a soup dish Independent area
western and eastern part
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silt
sand
sand
Channel : fast stream
Central part: slow stream
silt
Horizontal distribution in sea sediment
Particle size in sea sediment
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海域底質の粒度分布を考慮しない場合
High
Low
Low
High
High
濃度の単調減少
Inmost part
鳴門 Osaka Bay
coast
Central part : High
channel
NAKANO (1979)
Horizontal distribution in sea sediment
Harima nada
Before normalization by particle size distribution
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海域底質の粒度分布を考慮した場合
海域底質中 PCBの水平分布
恒流図と濃度分布
粒径・微細粒子・比表面積で規格化
Constant flow map and PCB distribution
After normalization by particle size distribution
Horizontal distribution in sea sediment
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海域底質の水平分布
大阪湾
PCB濃度の距離減衰
神戸港周辺
Horizontal distribution in sea sediment
Osaka bay
Around Kobe port
PCB concentration and Distance from source
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9 10 11 12 13 14 15 16 17 18 19 20 21 22
9 10 11 12 13 14 15 16 17 18 19 20 21 22
9 10 11 12 13 14 15 16 17 18 19 20 21 22
1
42
3
MCDF
13 1714
1816
1237
2736
46
342628
24
19
23
137
DiCDF
TrCDF
138
346
129
267
347/
236
137
237/
149
246
248
136 16
813
412
4/14
7
178
148
126
128
247
167
139/
127
146
123
環境大気Ambient air
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環境大気
0
0.05
0.1
0.15
0.2
0.25
0.3
1 3 2 4 13 17 14 18 1612
, 24 37 27 23
36, 2
8 2619
, 34 46 137
138
136
168
134
124,
147
178
148
123
139,
127
146
167
247
128
126
248
246
237,
149
234,
238
347,
236
267
129
346
燃焼起源
0
0.05
0.1
0.15
0.2
0.25
0.3
0.35
1 3 2 4 13 17 14 18 1612
, 24 37 27 23
36, 2
8 2619
, 34 46 137
138
136
168
134
124,
147
178
148
123
139,
127
146
167
247
128
126
248
246
237,
149
234,
238
347,
236
267
129
346
環境大気の異性体分布 (MCDF~ TrCDF)
Ambient air
Incineration ( f lyash)
Isomer distribution of ambient air(MCDF-TrCDF)
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環境大気
00.10.20.30.40.50.60.70.8
2 1 1327
, 23,
2814
, 17 18 16 12 19 137
138
136
124
139,
237
147
123
178
127
128
146
126
129
燃焼起源
0
0.1
0.2
0.3
0.4
0.5
0.6
2 1 1327
, 23,
2814
, 17 18 16 12 19 137
138
136
124
139,
237
147
123
178
127
128
146
126
129
環境大気の異性体分布 (MCDD~ TrCDD)Isomer distribution of ambient air(MCDD-TrCDD)
Incineration ( f lyash)
Ambient air
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塩素漂白パターンの異性体分布 (MCDF~TrCDF)
0.000.100.200.300.400.500.600.70
1 3 2 4 13 17 14 18 16 12 24 37 27 23 28 26 34
00.050.1
0.150.2
0.250.3
0.350.4
137
138
136
168
134
124
147
178
148
123
139
127
146
167
247
128
126
248
246
237/
149
234/
238
347/
236
267
346
28-
23-
27-37-
2-
238-
128-
237-
1278-TCDF
2378-TCDF
238-TrCDF
237-TrCDF
128-TrCDF
37-DiCDF
27-DiCDF
23-DiCDF
28-DiCDF
Isomer distribution of bleaching process(MCDF-TrCDF)
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塩素漂白パターンの異性体分布 (MCDF~TrCDF)
0.000.100.200.300.400.500.600.70
1 3 2 4 13 17 14 18 16 12 24 37 27 23 28 26 34
00.050.1
0.150.2
0.250.3
0.350.4
137
138
136
168
134
124
147
178
148
123
139
127
146
167
247
128
126
248
246
237/
149
234/
238
347/
236
267
346
環境大気
0
0.05
0.1
0.15
0.2
0.25
0.3
1 3 2 4 13 17 14 18 1612
, 24 37 27 23
36, 2
8 2619
, 34 46 137
138
136
168
134
124,
147
178
148
123
139,
127
146
167
247
128
126
248
246
237,
149
234,
238
347,
236
267
129
346
環境大気の異性体分布 (MCDF~ TrCDF)
28-
27-
238-128-
237-2-
124-
24-
Isomer distribution of ambient air(MCDF-TrCDF)
Isomer distribution of bleaching process(MCDF-TrCDF)
Ambient air
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0
0. 5
1
1. 5
2
2. 5
1 3 2 4 13 17 14 18 16
12,
24 37 27 23
36,
28 26
19,
34 46 137
138
136
168,
134
124,
147 178
148
123
139,
127
, 14
6
167
247
128
126
248
246
237,
149
234,
238
347,
236 267
129
346
農薬 CNP 中の異性体分布 (MCDF~ TrCDF)
環境大気
0
0.05
0.1
0.15
0.2
0.25
0.3
1 3 2 4 13 17 14 18 1612
, 24 37 27 23
36, 2
8 2619
, 34 46 137
138
136
168
134
124,
147
178
148
123
139,
127
146
167
247
128
126
248
246
237,
149
234,
238
347,
236
267
129
346
環境大気の異性体分布 (MCDF~ TrCDF)
248- 246-
124-24-
24-
Isomer distribution of ambient air(MCDF-TrCDF)
Isomer distribution of pesticide CNP (MCDF-TrCDF)
pesticide CNP
Ambient air
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Detail is as follows
T.NAKANO and R.WEBEROrganohalogen compounds, (2000)
ISOMER SPECIFIC ANALYSIS OF MONO- TO TRICHLORINATED
DIBENZO-DIOXINS AND DIBENZOFURANS -
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TABLE II Resulting main PCDF fragments from the chlorophenols by pyrolysis at 400C
Fragment in resulting PCDF used Phenol by H-Elimination Phenol by Cl-Elimination
0 Phenol 2-C-Phenol
1 3- C-Phenol 2,3-C-Phenol
2 4- C-Phenol 2,4-C-Phenol
3 3- C-Phenol 2,5-C-Phenol
4 2- C-Phenol 2,6-C-Phenol
12 3,4- C-Phenol 2,3,4-C-Phenol
13 3,5- C-Phenol 2,3,5-C-Phenol
14 2,5- C-Phenol 2,3,6-C-Phenol
23 3,4- C-Phenol 2,4,5-C-Phenol
24 2,4- C-Phenol 2,4,6-C-Phenol
34 2,3- C-Phenol 2,3,6-C-Phenol
123 3,4,5- C-Phenol 2,3,4,5-C-Phenol
124 2,4,5- C-Phenol 2,3,4,6-C-Phenol
134 2,3,5- C-Phenol 2,3,5,6-C-Phenol
234 2,3,4- C-Phenol 2,3,4,6-C-Phenol
1234 2,3,4,5- C-Phenol 2,3,4,5,6-C-Phenol
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TABLE III Sources of the PCDDs and PCDFs with 1 to 3 chlorines
No. Isomer CA registry Sources and puritynumber
MCDDs1 1 39227-53-7 (a)AccuStandard Inc., U.S.A. ; 100%(GC/MS)
(b) Pyrolysis(P+23-DiCP); 2 39227-54-8 (a)AccuStandard Inc., U.S.A. ; 100%(GC/MS)
(b)Cambridge Isotope Lab., USA; (c) Pyrolysis(P+24-DiCP);
DiCDDs1 12 Pyrolysis(2-CP+234-TrCP);2 13 Pyrolysis(2-CP+246-TrCP);3 14 Pyrolysis(2-CP+236-TrCP);
4 16 Pyrolysis(23-DiCP);5 17 Pyrolysis(23-DiCP+24-DiCP);6 18 Pyrolysis(23-DiCP+24-DiCP);
7 19 Pyrolysis(23-DiCP);
8 23 29446-15-9 (a)AccuStandard Inc., U.S.A. ; 100%(GC/MS)(b)Cambridge Isotope Lab., USA;
9 27 33857-26-0 (a)AccuStandard Inc., U.S.A. ; 100%(GC/MS)(b) Pyrolysis(24-DiCP)
10 28 38964-22-6 (a)Wellington Lab., U.S.A. ; > 98%(GC/MS)(b) Pyrolysis(24-DiCP)
TrCDDs1 123 54536-17-3 (a)AccuStandard Inc., U.S.A. ; 100%(GC/MS)
(b) Pyrolysis(2-CP+2345-TeCP)2 124 39227-58-2 (a)AccuStandard Inc., U.S.A. ; 100%(GC/MS)
(b)Copyrolysis(2356-TeCP+2-CP)3 126 Pyrolysis(23-DiCP+234-TrCP)4 127 Pyrolysis(24-DiCP+234-TrCP)5 128 Pyrolysis(24-DiCP+234-TrCP)6 129 Pyrolysis(23-DiCP+234-TrCP)7 136 Pyrolysis(23-DiCP+246-TrCP)8 137 67028-17-5 Pyrolysis(24-DiCP+246-TrCP) 9 138 Pyrolysis(24-DiCP+246-TrCP) 10 139 Pyrolysis(23-DiCP+246-TrCP)11 146 Pyrolysis(23-DiCP+236-TrCP)12 147 Pyrolysis(24-DiCP+236-TrCP)13 178 Pyrolysis(23-DiCP+245-TrCP)
14 237 33857-28-2 (a)AccuStandard Inc., U.S.A. ; 100%(GC/MS)(b) Cambridge Isotope Lab., USA;
(c)Pyrolysis(24-DiCP+245-TrCP) Acronyms a CDD = chlorinated dibenzo-p-dioxins ; CDF = chlorinated dibenzofurans ; CP = chlorophenols; M= mono; Di = di; Tr = tri;
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0
1000
2000
3000
4000
5000
6000
7000
24 25 23 26 35 34 235
246
245
234
236
345
2356
2346
2345 PCP
246-P/ 245-P =2
0
20
40
6080
100
120
140
24 25 23 26 35 34 235
246
245
234
236
345
2356
2346
2345 PCP
246-P/ 245-P =7
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02000400060008000100001200014000
2 1
DCDD 13
27, 23, 28
14, 17 18 16 12 19
TrCDD
137
138
136
124
139, 237 147
123
178
127
128
146
126
129
246-P/ 245-P =2
020004000600080001000012000140001600018000
2 1
DCDD 13
27, 23, 28
14, 17 18 16 12 19
TrCDD
137
138
136
124
139, 237 147
123
178
127
128
146
126
129
246-P/ 245-P =10
MCDD-TrCDD
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NMR 1,4,7-TrCDF
Authentic standard
H9
H6H8
H2 ; H3