Document RJMa39RjeONQzx28O1ngyVMm7
Formation of Polychlorinated Dibenzofurans and Dioxins during Combustion, Electrical Equipment Fires and PCB Incineration
by Otto Hutzinger,** Ghulam Ghaus Choudhry,** Brock G. Chittim** and Les . Johnston**
"r .
Vn
I'MTthionnMt* dibm 0 dwmna (I'CDDt) a/W p4rchUirmA44 dibewxrWurm (l*CI)Fi arv lik#4v fnrmd
br Ihtrwutf irnthvtn o( t
ol primary prvfurtnrt. ihmrM ir*e o( th* enmouvnAi arr
kwmr. vha* Ifet naninf maiertaJ rvnim imir rmr or to reaction Mm for thoir formal ton. ki 11 (ht
cut vith chfotmphawata, cnltfaNwitw and ^veblnMiH bpfc*firii (|*C1UI. Lahnmiorr pymirvri
hr tnam
that I*CBt m* timiftesM rt*44s of 1`CDFa. in* ehloraOowtrfw* rr^t 6*Hh !`CDFi ar4
PCDDfc In o4it>*a. a rmnoty of other ehioroaromatk wwminM irv formed. Frwn thr*o nwniNnu
and frwa actidtwti iirmrinc i*CB Ana. it ia kmtii that l*Cl)Fi art Iht mm imoenani toiK eomoownta
n--naiad wit* KCDt.
Mm comwumai PCBi ctmiaia i*CI)Ft ki (h* iav pp raact. !*CL)F cowetniralkm dor not incrraa#
durmt nanmai aaarmima in oioetrteat ttaipwM. Aet>4ms thm and nfipNMM ifmttvtnf
ean tirt
PCDF
m am of it* to 10tt pm and hirher. CfTcdirt thermai ammelton n( PCM U aoaaibk in
madam inemaratioo tmm. pm idad hrrti irmatratum. firm air and uafftontt rmidanct time* art u*d.
tiad Aevrat for mmirmn umaarauart and rtiaanct time eirm bt rr*m. wna ftadslnek and mcintraior
emartetm rroolly iwAoawei dmn>cto tffioanrr. 171amis from EI*A-iicnsad mcineroioro u*#d for
PCB tatndM eomaia my rry im trrtia of l*CUL)a and PCUF&.
/introduction
The occurrence of polychlorinated dibento-p-dioxins 'CPCDDs) and polychlorinated dibenxofurans (PCDFs)
in effluents of municipal incinerators (1) has stimulated interest in the thermal formation of these compound* from different sources and by a variety of processes (7 11).
The presence of PCDDi and PCDFs in combustion effluent* can be attributed to several possibilities: (1) they could be trace components of the material to be burned snd do not undergo effective thermal destruc tion; (2) they could be produced dunnf the combustion and pyrolysis of chlorinated precursors like poiychlo-
Lioorstorv of Znwmummtt and Taxroor>ai Ottmutry. Uniray of Ajnauroam. The Netherlands.
|Wtlin(ua Enrireomnul Conauitanu. Inc. Cuelph. Ontario. Canada.
"M.1C Dillon Ltd.. WiUovdaio. Ontario. Canada. * Present address: Chair of EcotocKsl Chemistry and Geochemistry. UntTormy of Bayreuth. Poetises 3008. 3tyTTvti, Ccrmany. Addrvoa fw rtprint rvouoota. iPmont addrooc Ptstraoo Ranoarth Laboratory Dope of Sod Sonoa, UniTonrty of Manjuxu. Wljnupof, Canada.
rinated biphenyls (PC3s), chlorophenoLs. chlonnated phenoxyicids, polychlorinated diphenyl ethers (PCDPEs) and chlonnated phenoxy-2-phenois; (3) they could be formed as a consequence of a compiex array of pyrolytic processes involving chemically unrelated or ganic compounds, including anthropogenic chlonnated organic chemicals such as poiv (vinyl chlonde). or chionxarbons, anthropogenic nonchlonnated organic chem icals such ss polystyrene and inorganic cnlonne or naturally occurring organic chemicals like cellulose, lig nin. coal. etc., and inorganic chionne. i.c.. Cl" and HC1. Although data and theones in the literature suoport the theory ofde nave formation of PCDDs and PCDFs (i.e.. thermocnemicai synthesis from chemically unrelated precursors including naturally occurring suosunces). there is general agreement mat higher levels of PCDDs and PCDFs are likely produced by more direct thermal conversion processes involving poivcnloropnenois. polychlorobiphenyl (PC3s) and polychiorooenzenes
(PCBZs). It has been reported that of about 1.4 billion pounds
of PCBs produced in the U.S. between 1929 and 19T7, about *50 million pounds are still in use in some form. Approximately 25% of this is estimated to be associated
A 0009437
WATER PCB-SD0000029146
hctzimjcr *T u
a iin '.fie electrical utility industry hen? l'C3s are used jn~ir.iv in two type? of equipment: transformers: cun* ,:inir.f mixture! ia.*karris) of PCBs ami PCBZs. uml cacacr.ors; containing onlv PCBs i/-!.
it :s .ixelv tnai mucn of the remammi PCBs "in use" ire oeintr stored awaiting' tiisixisal. There are a numoer of different processes currently oeing used and/or tested for PCS destruction.
A* discussed, vinous researchers nave shown that PCDF* are formed wnen PCB. are heated and that PCDF* arid PCDDs are formed when PCBZs are healed.
It is therefore iwssible that large-scale formation uf PCDFs land PCDDsl from PCSs and askaret* cuidd occur. Fires involving electncaJ equipment or inefficient PC3 incineration mav give n* to conditions ideal for the formation of PCDFs and PCDDi.
Formation of PCDDs and PCDFs from PCBs and PCBZs in Laboratory Experiments
Buser, Rappe and colleague* have investigated the potential for PCDD and PCDF formation from PCBs and PC3Zs by heating the latter two type* of com pounds in sealed glass ampule* in the presence of air and it different temperature* (13-17).
Pyrolysi* of PCBs
Heating PCBs (Aroclor 124S) in a sealed Pyrtx giaaa tube for 1 week showed that PCDFs were formed above aoout Z7(TC and reached a maximum level at about 300*C (in oxygen). The product mixture contained di- and tnchlorodibenzofurans as ma;or components: the max imum yield of PCDFs in these experiments was 0.2^. Since major components of starting Aroclor 1248 were tetrachlorobiphenyis. it is apparent that one or two chlorine atoms were released in the reaction. The oxy gen atom m PCDF skeleton was assumed to originate from gaseous oxygen in the sealed tube. It was con cluded that temperatures above 270*C are necessary for the transformation, but at temperature* above 330*C PCDFs decompose. It is noteworthy that 2.3.7.8-tetracnlorodibensofuran at a level of ca. 80 ppm (parti per million! was confirmed in the products.
Similarly, Buser and Rappe (16) have studied the pyr olysis of 18 individual PCB isomen in the presence of air and have demarutnted the formation of PCDF* via intramolecular cydiaations [Eq. (1)] where m * varies from 4 to 8. Individual starting PCBs
lUl ufi eachi were p\-rulvzed at
m senai-ate him,-,.
mim-amoouie*. The yields r,f l'CDF* ere in in*. nun.,,
uf U. uu lo several percent. Tor inermoviienncai
eration of trie PCDF- from PCBs " w- found tn
four general reaction route*. These routes mciune h...
oionhn CllEif. :2)|. loss of HCI m\mvinr a 1.u-cniunne
snift at the oetizene nucleus lEu. 13) i. loss of mn,,, -r
(Eq. (4)| ami loss uf mthn H lEi|. ifiil. The ?'J!jk5
ooiained from the pyrnivsis uf '1.2 ,-l.j.j neniacnmn,.
bipnenyi show the lour reaction uulhwavs in a real >am-
pie (Eqs. (til 1. The overall results obtained in mis 'ene?
uf experiments are given in Table 1.
-
Cl, C! Cl Cty
cix^o
r'-'iV r:)
Cl, C! Cl 1
Cl* O'
-HCI Cl* Cl H Cir
Cl*
Cl, H H
Cly .
^
Cl* 0
(3)
Ciy (4)
Cly (j
Pyrolysis of PCBZs
Buser (17) reported the pyrolyses of tri-. tetra- and penuchlorobenieties. which were earned out in sealed quarti mint-ampoules at liZfTC in the presence of air. The pyrolyiates of chlorobenzenes were analvzed di rectly: no cleanup was required. In the pyrolyxed sampie*, chlorobenzenes were still the mam component present. The decom(>osilion was higher for the lower chlorinated specie* and was > So1* for the Lnchloroben2ene*. ca. 90** for the tetrachlorooenzene* and ca. 50dfc for pentachlorooenzene in the combined chlorooenzene pyroiyzate. Chlorooenzenes with a degree of cnlonnation higner thin the com(>oundj used for pyroiysu were observed in'all pyrolvzaies. e.g.. tetra- and pentafrom trichlorobenzenes, penu- and hex*- from teiracnlorooenienes. and hexa- from pentachiorooemene. These
-4 i
ic
u *
r
-c r
S
v
A 000943S
WATER PCB-SD0000029147
PCR C'JMBI'STIOX
chlorinated benzenes mutt have been formed in , formation process from lower chlorinated conge^Tbe formation of chlorobenzenes with a degree of jjjnpaoon lower than the starting material utilized for ^Bolyst* wu not observed. In addition to chlorocrrr*** mass spectral analyses of the pyrolyzaus reaaled- the presence of other chlorinated compounds rtedfinchtde PCDFs, PCDDv chloroohenols and in bseases polychlorinated naphthalenes (mainly hepta-
and octachloro). polychlorinated styrenes (heota- and octachloro) and polychlorinated biphenyls (PCBs). Pol ychlorinated diphenyl ethers and polychlorinated biphenylenes were not observed.
According to Buser, the thermochemical formation of PCDFs and PCDDs from chlorobenzenes is bimoiecular [Eqa. (Til. The likelihood of this formation is hiphiy dependent on the concentration of chlorobenzenes in the reaction system. The author uses high concentrations
HM iT
| Umi eUersapMnrla f ' * *" nd
1 rt UMI
r*T8rM Pyudtiu ia ur
-Mx-a-PCB S, i, 4' '-CS*- PC5
tr.u\.ra-PCB tmd* 12U vnd u C- "
trjr-a-PCB
Pyrotvua m ur PyrWyua la ur
1. RaaalU of pyraiyut of PCH*.
Product!*) PCDr
Viwd 0.1-11
PCDF diTJ-TCDP
a. T* cx. n
pcdf
tr,t.<-.5.S--CV?CB iUr.IJ'-CVPCS tnaar 12S4
** 1341
Pyrwvuj ui ur In 0, In S\
PCDF
UTJ-TCDr iini Z.3.7.Vumesiarodib<aahinB.
300 ppm 11(10 pom
3 aDm
Ramarto
PCDF ixjmari (ormad xcrardinv to pro pood metson mttfUAOM
Reformat u)
formsoon oeroniinc to prapoood meuon mocftonunt
imooruM formoixm of
2.3.T.J.TCDF riunnf Arodor pymyiu
t;;>
?MP PCS iom*r* dk< r>ot rontxin tm* rmrcLiM PCDF
US)
of 0- i wmurr (or th formoocm of l*CDF
UJ)
4 0009433
WATER PCB-SD0000029148
nr-czT
tfCTZt>GR i. i -\L.
"*** * F#rmM
^
dibenrofurm** {f'CDFti and 9*WrchJ/*rmi*d dit*nu>--uiuT>ru il'CDUsl from ihe prro4TH of thiofvMuim ( TC.-*
Comvmmnd*
Thehl*wni'**` THmfci.auOaiiM''** PwiuehtotuO.nM"*'____
------- -
PCDFf formed. nfumpto
PCDL3 fortno^i. nt'Mmux
Trtn-CJ
400 <: <2 30
Pms-Cl
1 IDO 5
<3
GOO
Hx*-G HrWJ-Cl
iiO
im
<J UOO
b6 iso
5 400
Oci*-Cl
<3 2l
:ff) 60
Tein-Ci
30 <2 <2
f'tnu-CI
20 5
<2 ru
H.X.-CI
<s
WU
<s
3)
HrjHj*C!
<5 n <3 7l>
Ocij-C
<5 3o 5 s
DiU of Buf U~l *TS rracuon *v pcrformod in the *aM quru rrun^omoouict in ih prtMncs of ur.
f200 TtrMi *hJi oQiui tmounu of 1.2*3-. 1.2.4- &nd 1.3.3-menionK*m*n.
*200 M-f '-**1
*qu*i amoonu of Z.2J.+-. I.2-2.^ ond 1.2.4.3-<.eiricli*oroq*ni*fw.
*200 *4 ptHjehkrfTfbonion*.
'500 *4 loud vn& equal amounu of all Lrv. Lrtr*- and ptmjchlofetiaw> (7 rompoundal
in these experiments: the yields are expected to be sub stantially smaller i/ lower concentrations were used. The yields of PCDFs and PCDDa obtained as a result of pyrolytic decomposition of chlorobenzenes are re corded In Table Z
A postulated mechanism for the thermochemical for mation of PCDFs and PCDDs from chlorobenzenes is given in Eq. (81. As stated earlier, ail pyrolyzed samples contained chlorophenoia. The degree of chionnation of these phenois was the same ind higher than the degree of chlorination of the chlorobenzene used: tri-, tetra ina pentachiorophenoi were observed from tnchioro beruenes. tetra- and pentachiorophenoi from leu-ach-
lorobenzenes. and pentachlorophenol also from pentachlorooenzene. These chlorophenoia could possi
bly serve as reietion intermediates in the formation of PCDFs and PCDDs from chlorobenzenes. A reaction of chiorophenol with unreacted chlorobenzene could lead to polychlorinated dionenvl ethers, which are known to form PCDFs (and to a lesser extent PCDDs) upon pyroiysis. However. PCDEj were not actually observed in the samples analyzed here. Dimerization of chlorophenols is a further route to PCDDs. According to Buser. the former condensation (path A) via PCDPEs may b-1 preferred in these pyrolyses due to the initially mue: higher concentration of chlorobenzene present, but for a substantiation of these assumptions and to obtain a more detailed picture of the reactioni involved, further work will be required.
PCDFs
f- -it
r0H-
cj ct*., PCOPs
CU
f i
PCDDs
iS)
A 0009440
WATER PCB-SD0000029149
I.jClUon i L)1CClu**
C,n. Ontarw
' ,SMfflMr 19")
unatrfround vault
Cium
r*uJt in nmin
brwir nuMrt
"( .*m*U
C onaioons
PCDF. rVJI)-. furmm
Arcing cau>e<l crue* n
^yot '4mi>*e* r**ntam^t
transformer ou*mngex. rai. uf i>Kri
ci. j ppm PCOF.
suiitat; vome vporii#<
hr*
:*ont rumainett ea I" iu) imw I'TO* i ppm pror m
PCB in -uoCJ
3inf,,,mu*v N^_Vort Eiectncai faiiur* in
(ffpruarr 190)
juucmnr
of!Se* miudmg
tqujpowf*
ckliotm. S**dan lAuguat 19SU
Malfunction m tteemesi svnm
innMwvmr tut**
.itr*m*tv Sot firr:
Swot amum anaivtnf.' Chinrmatrri biunrnvietir
transformer njinuixl releasing ol 100 fii.
2.j.:.f-tcdf 122:0 ppm; local PCDF
lPCPP*> aiMI .irirctrd touJ
of axtarH
TG3-21I9I mm:
PCBPf
Mt.a-TCDD I' 6-2.* 54 ppm
inw: total PCDLrt
Fire 6*v*kned:
2U Dion Wip* iMti tnalvted:
PCBP "rt rh)onrvatd
10 PCB canentor* *ert involved; some
exploded
2.:.:.s.tcdf iso nf-nr. total PCDF*
1.1 it* m* No PCDD*
|mth* )PCrVi iMaoctart PC3P Inert rmiar than
I'CDF Inert <Jut 10
Total PCDF in PCD
tamueriiur* of fue
in ttmortod eiiwcnor [*? Sauvrt* nr*)
To nr** v. 1 ppm m
intact apecnor
Sfcgebe, 5den (Mrcfl 19821.
...' noaotor battere
,, . ia maul \mUMrt.
_ *esflf7
ElactncaJ malfunction cauaort An in mineral oil MM cipaeuor
Fir? ivmi to othor
"'ip* ir*t Mmptaf (rent PCPYi rtotoetod
npacnon: 21 ranmnod eipacstar building
No PCBP* were
PCBa: 12 PCB
anaiywl
ilnoettd duo to "Imr1
capnenort vara Orooen
HifB PCDr Inert
trmportturt of hit
09m or fir*
*trf ontr found m
umnadjat* nenatv of
fir?
Total PCDF* *> nrnr 2.3.7.S.TCDF
r^` c
100 nrnr No PCDD* dottettd
(Srpumfear 1980 ^Tiual nail
r iptnann in at**) 'mitt; mattan ttoM toned into cipnetar room
Tiro dart too* 500 npnonort inverted: 200 PCB/300 mineral
oai
Wipe im aamptea in tha eapacnar roam *nored Inert of J nrnr TCDF
No PCDDo detected
PCPYi UM detected
i.; 5 i
UJ.JJ 1
Formation of PCDDs and PCDFs in Electrical Equipment__
PCB Transformer and Capacitor Fires
There h*vt been few documented inadenu of fires involving PCB-filled electrical equipment (fJ-Zl). Thia is likely to be due to the fact that PCBa are fire resistant, although it is possible that many aueh Area go unreporud.
in North America, to our knowledge, only two auch inbdenu have been reported and are reasonably well documented faee Table 3) U3). Both were transformer fires caused by electrical malfunction.
In Scandinavia, since 1977, there have been seven ueh fires (five in Sweden, two in Finland). Ail of these involved capacitors and ail but one was caused by an electrical malfunction.
These fires were characterized by the release of large imounti of oily black soot with very little fire. Where the fire involved a transformer containing PCBa and
PCBZa. PCDFs and PCDDs were detected: where ca pacitors were involved. PCDFs and no PCDDs were found. In addition to PCDFs and PCDDs. chlorinated biphcnvlenes (PCBPs) and pyrenes (PCPYs) have also been found to be formed in some of these fires.
PCDF and PCDD contamination of the surrounding environment waa almost entirely due to movement of the soot formed during the fire.
Five of these fires, their cause and the resultant con tamination. are summarized briefly in Table 3.
Other Factors Leading to PCDF and PCDD Formation in Electrical Equipment
PCDFs have been found as contaminants in virtually all commercial PCB mixtures, both North American and European, aa shown in Table 4 123-27). However, there has been very little effort to determine if these levels increase during the operation of PCB-filled electrical equipment and, if they do, what factors are respoiuioie.
A 0009441
WATER PCB-SD0000029150
rfL'TZlSGCfl T At.
TftM 4. PCDFi in Aj-oetar. Clopftifi
Ph*noclor. *
PCDFi 3Dm
PCB
Axocior 1*46 ' 19691 Asaci&r 12S4 ; 19691 Aroaor 12S4 11JT01 Arocwr 12S0 119S) Ajvaor 1260 iloc AJC3) Armor 1016 (1972) OooMa A-60 Phmooaf DP-6
Cl i;;., cl Total
0.5
1 0 ') 3
:.o
0.1 0.2 1.4 L.7
0.2 0.4 0 9 i 5
0.1 0.4 0.5
1.0
0.'2 0 3 0 3 0.3
ND ND ND
-
1.4 5.0 12 3.4
O.T 10.0 2.9 13.6
"D*i* oTiti it il. IZJ), Rases :tf) and Bowa ai. u'H.
It has ben found that transformer askareis are con taminated with PCDFs and that their levels increased with the tune in service of the transformer US). Levels of TCDF in these Quids reached a maximum of approx imately 5 ppm. This study, however, was earned out in 1978 and used analytical techniques that have since been outdated. In addition, the authors found that it was very difficult to obtain sampies from various trans formers so that one variable (e.g., size. age. volume) could be unequivocally isolated. Since that time it has been reported US), although using a limited number of samples, that askareis that have been in use in electrical equipment do not contain higher levels of PCDFs rel ative to the unused Quids. In retrospect, it was consid ered that the normal operating temperatures in such equipment were not high enough for PCDF formation.
There is also a possibility that 'abnormal' operation of a transformer or capacitor may create conditions (e.g., arcing, overheating) that may lead to the formation of PCDFs (and PCDDs). Again thia n an area where much more research is required.
The Electric Power Research Institute has recently (February 1983) initiated a project to study the for mation of PCDFs and PCDDs in electrical equipment under normal and abnormal conditions (JO). This project has not as yet been completed.
tion. in 1970 the possibilities of usinc nig*,.
for the fiisDosal of ?C3s was put forward
manufacturer of these compounds in N'o-. '1. Monsanto i./.M. Since tr.at time, ieveP4|
investigated anu<or are using mgn terno' 'v< cesses. In 1970. Monsanto reported that
ire destroyed at aOO*C with a transit t;rrie : at ICXXTC with a transit time of 2 sec. ?r-j
portedlv destroyed in a muitioie near-.n T'.*'1
erator equipped with an after ouimer at oOr^?
contact time of 0.1 sec i?9.9* efficiencvi n,:*
chlorinated hydrocarbons, including PCBs, * in a rotary cement kiln i99.98* destruction^
(Jl). PCB* were destroyed in a iaooratorv ^ stags, quartz furnace at 1000*C (99.995^
PCBa were, again, incinerated in a rotarv
temperature of approximately U00*C iSS.goqi1
ciency) (JS). Organochlonne chemical
cinerated in the Gulf of Mexico using the
ship Vuicanas (OCS. Rotterdam). A minimum
fame temperature of 1200*C was maintained
idence time of 1 sec (JT). PCB* were ignited
by atomizing with oxygen at the tip of an
burner giving a fame temperature over *
(99.99999* destruction reported) (J.S).
'
The Energy Systems Group of Rockwell ;a
tionii recently (1981) developed a PCB destiw
(incinerator) which features a Quid-bed
chamber followed by a cataiytic afterburner.
atures in both units do not exceed 695*C (99.995*
struction efficiency reported) (JS). Two cobt^
inanerarion units, one in Arkansas (ENSCO t,
Systems) and one in Texas (Rollins Envmx^
Services) have been licensed by the U.S. Envm^
Protection Agency (EPA) for destrucuon (fJJftj
of these systems use combustion temperatures p
than 1200*C and report PCB destruction efSoea
excesa of 99.9999*. Several other similar mean
units have been tested and are awaiting aoprwi
EPA (SI).
Dstruction/lncinratlon of PC8s: PCDD/PCDF Formation
Technologic* for PCB Destruction
A number of processes are currently being evaluated or. m some esses, are already in use for the destruction of PCBs or PCB containing wastes (J!). These include: incineration, including conventional mnnemion (high temperature oxidation) and "novel" incineration (i.e., molten salt, oxygen incinerators, diesel engine incin erators): chemical processes such as dechlorination, photolysis and wet-chemical oxidation; and. biological processes (e.g.. bacterial degradation).
By far. one of the most promising, on the basis of both efficiency and cost, is high-temperature incinera
PCDFs and PCDDs Formed During Lb Scale PCB Incineration
There is very little data on the levels of PCDFi
PCDDs emitted from large-scaie PCB inonenaa
The Rodini aui ENSCO inenemors have beeu
for such emisaion. and "small amounts" were rtn
in the inanerarion products. The levels were sue
the "additional cancer nsk" was considered to a
tremeiy low (j;j.
.
PCB* were test burned in a rotary cement c
Norway and the products and emissions anuv
PCDFs and PCDDs (22). None couid be fount t
of the samples.
It is quite probable that the temperatures x
these incinerators (i.e., > 1200*C) comoieteiy '*
the PCBa and any PCDFs or PCDDs that ire
A 000944^
WATER PCB-SD0000029151
PCB C0MBCST10S
REFERENCES
. ^ Vermeuiao. P I__and Huuufer. 0. Chiorooibanxo-ouo cniorodibenxofuru* Lt :r*c component* of rty un
'' .,jr pi of jom* municipal incinaretore in :ne Netntnuaa.
~ | 6: 1-56 ' ifii ( ly ( ` '.
. tnnouwer. J. A... OU*. K.. and Hutnnrer. 0- Chlorinated y-^tnnm me related compounds lq irannur lAutna
1 f^nceonef* r SOI-422 [19801. \ x. P.. Tiaman. T. 0.. and Drydan. F. E. Dwnni. U.3.
Protection Armey, Cincinnati. 1980, ,,,iraniotfUl Secretariat of NRCC. Poiycnlonnatad Dibatap.
r..-- Lumtaooo* to tha Current Analytical Teeftmoua*. Ni~ Rjeaerea Counol at fiimu (NRCC). Publ. No. 18678.
Canada. 1981. ,,,.ji*imaf *1 Secretariat of NRCC. Polychlorinated Dibenao' >u* Cntan* for tbasr Effect* oo Mu ud am Environment. 1~ ---i ? u rn Causal of Canada, Publ. No. 18674. Oam
, 1*1.
leudhry. 6. "d HutsDfsr. 0. Mechanist* Aaoertl at the F ormaoon at Haiopenstad Orjatuc Compounds Indud-
,x paycuormated Dib*njo-p-Diaxin*. Cordon ud Breach. New
1 ,m. 1983. Hv-anfar. 0.. Fro. R. W.. Mama. E.. uid Porrtnani F. (Eds.). , .jonmud Dwnn* ud Related Compounds: Impact on tha n-
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___
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A 0009443
WATER PCB-SD0000029152