Document 2jOgp4Y45QmR00Kpz89jK5D76

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-00048183 hctzimjcr *T u a iin '.fie electrical utility industry hen? l'C3s are usesl jn~ir.iv in two type? of equipment: transformers: con taining mixture! i ay karris j of PCBs ami PCBZs. uml cacacr.ors; containing onlv PCBs i/-). it :s .mely tnai mucn of the remammi PCBs "in use" ire oetne storm awaiting ihsnosaJ. 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 PCBs are heated and that PCDF* and PCDDs are formed when PCBZs are healed. It is therefore ixassible that large-scale formation uf PCDFs land PCDDsl from PCBs 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 colleagues have investigated the potential for PCDD and PCDF formation from PCBs and PC3Za by heating the latter two types of com pounds in sealed glass ampules in the presence of air and it different temperatures (13-17). Pyrolysis of PCBs Heiung PCBs (Aroclor 124S) in a sealed Pyrtx glass tube for 1 week showed that PCDFs were formed above aoout 27CTC 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 tetracniorooiphenyls, 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 temperatures above 330*C PCDFs decompose. It is noteworthy that 2.3.7,8-tetracnlorodibenzofuran at a level of ca. 30 ppm (parti per million! was confirmed in the products. Similarly, Buser and Rappe US) have studied the pyr olysis of 18 individual PCB isomen in the presence of nr and have demonstrated the formation of PCDFs via intramolecular cydixations [Eq. (1)] where m * varies from 4 to 8. Individual starting PCBs 'lUO ufi eachi were pvrulvzed ai m -enai-ate mun-umuouie*. The vieiiis of 1VDF* "ere in me r;unV uf U. uu lo several percent. Tne tncrmocnenucai eralion of tne PCDF- irurr. PCBs <*.- found tn four general reaction routes. The-e routes mciune n,N. of onhn C) / Eif. i -- l J. loss uf HCI m\ oiving a -f.j-cniurme snift at the oetizene nucleus lEu. i3)|. loss of on/,,, jar- (q. (4)| ami loss uf mthn H lEq. <5)1. The PClJl't noiained from the pyrnivsis uf '1.2 -peniucnmn,. bipnenyl show the lour reaction uutnwav* in a real >am- pie (Eqs. (til 1. The overall results obtained in tnis seneuf experiment.* are given in Table 1. - Cl, C! Cl Ciy cix^o r'-i,v r:) Cl, C! Cl H y Cl* U' (3) -HCI Cl* Cl H Cir Cl* Cir w Cl, H H Cly . ^^ Cl* 0 Clj (j Pyrolysis of PCBZs Buser (17) reported the pyrolyses of tri-. tetra- and pentacnlorubenzenes. which were earned out in sealed quarti mim-ampouies at liZfTC in the presence of air. The pyrolyzates of chlorobenzenes were analvzed di rectly: no cleanup was required. In the pyrolyied sam ples. chlorobenzenes were still the main component present. The <iecom(>osilion was higher for the lower chlorinated jpecies and was > 95' for the Lnchlorobenzenes. cat 90FJ- for the tetrachlorooenzene* and ca. Htt for peneachlorooenzene in the combined chiorooenzene pyroiyzate. Chlorooenzenes with a degree of cnlonnation higner than the comfKJunds used for pyroiysis were observed in'all pyrolviaies. e.g.. tetra- anti pentafrom trichlorobenzenes, penta- and hexi- from tetracrv lorooenzenes. and hexa- from pentachiorooenzene. These 4 i ic X 1 c f S V A 000943S WATER PCB-00048184 PCR C'J.UBl'TTtOS ,-LLgf chlorinated benzenes mutt have been formed in "'yorination process from lower chlorinated conge^Tbe formation of chlorobenzenes with a degree of jjjinirirm lower than the starting material utilized for frgaoiyva was not observed. In addition to chlorofftr-n** mass spectral analyses of the pyrolyzates re-Mied. the presence of other chlorinated compounds dadfinchtde PCDFs, PCDDv chloroohenola and in <Bt cases polychlorinated naphthalenes (mamiy hepta- and octachloro). polychlorinated styrenes fheota- and ocuehloro) and polychlonnated biphenyls (PCBs). Pol ychlorinated diphenyl ethers and polychlonnated biphenylenes were not observed. According to Buser, the thermochemical formation of PCDFs and PCDDs from chlorobenzenes is bimoiecular [Eqa. (7i|. The likelihootl of this formation is highly dependent on the concentration of chlorobenzenes in the reaction system. The author uses high concentrations HM iT twM I atesat dUuroeipftirra P)TalVU ui ur r 1 * *" d IQ umm &FZ-: j'.i.r-a-pcs T,t<'44'-Cr?CB PyroJvua m ur tr.uM.r-cvpcB UW 1la vnd U -- " tr.ir-cvPCB -- ** Pyridj-- 1* ur TSW* 1. MU oC errWru* W rent. Product!*) PCDF Viwd 0.1-11 PCDF tiTJ-TCDP a. 75 CX. n PCDF ir.W.S.i'-CVPCS 4.U\S.'-CVPCS Uhmt US* Aim 124| Pyroivuj ui ur In a, In N* PCDF 'IT.vrCDF uwini** Z.3,7.S-utnesiarodib<aWunB. 300 ppm 11U0 pom 7 3Dm R*m*rto PCDF ixjmn (ornwd accwdinf io pnjpoood metson motlUAOM Rgformot W) Formooo* ocroniinf to propQMd rooeuon moeftomom imoarum fonrutxw of 2.3.7.J.TCDF during Arooor pj-roiv-m t;;> Pur PCS iom*r* Hid r>ot rontxiA am* rtttrA** pear i;j) Prcrrnca at 0. i* ntgoMifr for th* formation of PCDF UJ) A 0009433 WATER PCB-00048185 ^(rTr/-'v OCR i> > \L- "*** * F#rmM ^ dibenrofurmns {f'CDFtl and **WrchJ#*rml*4 dil*nt4>--<4tusiru i^CDUtl from ihe prrotysw of thiofvMuim ( TC.-* PCDFf formed. nf'**mWt PCDLH fortno^i. n*'**my* Comvmmnd* Tnealor^. ------- - PmuchMtuO. *"*'____ CJVK. UU. I Trtn-CJ 400 <: <2 *0 Pma-Cl 1 IDO 3 <3 GOO Hx*-0 HrWJ-Cl 330 ISO <J UOO 30 ISO 5 *> Ooi-Cl <3 2U0 :ff) tsu Tein-Ci 30 <2 <2 W f'tnu-CI 20 5 <2 23) H.X.-CI HejK.j*C! Ocij-C <S <5 <5 UU <s <3 5 m 7<J S 'Ogt of Bu**f *TS rvacoMi w pcrformtd in the nM quru rrun^amoouict in iK prtMnci of ur. f200 TtrMi u* *ju*i tmounu of 1.2*3-. 1.2.4- &nd 1.3.3-menionK*m*n. *?00 M-f `-**1 unounu of 1X3.4-. 1X2.^ and !X4.3-<.eiricli*oroto*ni*fW. *200 *4 p*MMchkxvtomraMtm. '500 *4 local vrv& tqual amounu of all Lrv. Lrtr*- and poncaehioradvfWfwt (7 compound*!. in these experiments: the yields are expected to be sub stantially smaller if lower concentrations were used. The yields of PCDFs and PCDDs obtained as a result of pyrolytic decomposition of chlorobenzenes are re corded in Table Z A postulated mechanism for the thermochemicsl for mation of PCDFs and PCDDs from chlorobenzenes is given in Eq. (81. As stated earlier, all pyroiyzed samples contained chlorophenols. The degree of cjiionnation of these phenols was the same ind higher than the degree of chlorination of the chlorobenzene used: tri-, :etra ina pentachiorophenol were observed from tnchioro beruenes. tetra- and pentachiorophenol from letrach- lorobenzenes. and pentachiorophenol also from pentachlorooenzene. These chlorophenols could possi bly sene a* reietion intermediates in the formation of PCDFs and PCDDs from chlorobenzenes. A reaction of chiorophenol with unreacted chlorobenzene could lead to polychlorinated diphenyl ethers, which are known to form PCDFs (and to a lesser extent PCDDs) upon pyroiysia. However. PCDEj were not actually observed in the samples analyzed here. Dimerization of chlorophen ols is a further route to PCDDs. According to Buser. the former condensation (path A) via PCDPEs may b^ preferred in these pyrolyses due to the initially mue: higher concentration of chlorobenzene present, but for a substantiation of these assumptions and to obtain i more detailed picture of the reactioni mvoived. further work will be required. r0H- CU a* C!m Cl*-, PCDPi PCDFs PCDDs f- "1 r f I iS) A 0009440 WATER PCB-00048186 nCB 0M8l'ST!0X Tbt 3. Fir** mvoinnr KC'B utiAr*4-AUr4 rimneil !.aCU" i L)1CClu** C,n. Oniano ' ,SMfflMr 19") unatrfround vault Cium Fault in nmin brwir rauaad "( *m*U C onaioons PCDF rVJI)-. fur-mad Awn* cu>e<l crac* n ^yot '4mi>*e* c**nian** irwformer ou*nmr* ex. sw ri. uf i>Kri ci. j ppm PCOF. Diitat; vom* vyoni#*i hr* :*ont ronuin*<i ei I" iu) imw I'TO* i ppm pror m PCB in -uoCJ ginrnmu>". S* York ifftn-iiarr 1963) of!Se EiectncaJ faiiur* in juucmnr tqujpowf* o-ckJa. Sow*" M*JTunK* m lAuru* l*l> *oneai > tnnlMmr tut** .itr*m*tv not firr: transformer njinuixl mtumr ol ifiO ini. of ixtarH Fir* 6rv*k**d: 10 PCB c*n*citor* tnvoJwd; som* exploded Suu< *amum artaiviad.' ChiormAtod bitincnvianf :.j.:.a-tcof u-rro Pl>m; local PCDF iPCBP*' iiMi ifior.ro local TG5-11UI mm: PCUPf MT.S-TCDD H 6-2.* 54 ppm mm: local PCDD? .V p|ll Wiu iMti analvtod: PCBP "d rhlonnaiod 2.3.T.&.TCDF 150 Bfirr. local PCDF* 1.1 iac m1 No TCDD* m~timf tPCrVn iMnoctwt PC3P ln-H cmitr lhan TCDF Inert <Jut io Total TCDF in TCP icmuomur* of fue in itmonad ciiwcnor IKf Sauvrt* fuel To nr" i". 1 ppm m intact capacitor 5o*(i EiocincaJ malfunction Fir? turtwi to other Wipe im vamotoa from PCPYi hnretod (March 19*21. auieh hr* tn c*prnoo:_2! contunod eapootor tauikiinf No PCBP* wer? Z - * "*"* "**"*'*. .... capet*' oauaw mineral oil MM capacitor ' ~ _ *ctflf7 PCBa: 12 PCII eapacitora ete opea Or fir? analttad HifB PCDF Wtert ware ontr found m imrnodaait nctaty o! net ret m due to "Imr' temperaturt of hra fir? Total PCDFi *> nrer 2.3.7.S-TCDF 100 rvf-nr No PCDD? riottettd ~TVr- tScpumPor 1WO -~-pZ*** noil r Tpinama in ueet Tiro dev? too* 500 tala: moltafl HMt capacnora irrrwrwj; tooed into 2U0 PCB/300 mineral cipoenar room oai Wipe toot lampte? in the capacitor roam rhoareri Inert e( l nmr TCDF No PCDD? detoctod PCPYi alao detected i.; 5 i lli.-t!) [-? Formation of PCDDs and PCDFs in [ Electrical Equipment__ | PCB Traniformer and Capacitor Fires i There h*vt been few documented inadenu of fires . involving PCB-filled electrical equipment CJ-ZS). This ' is likely to be due to the fact that PCBa are fire resiatant, j ' although it is ponibie that many aueh Area go unreporud. | in North America, to our knowledge, only two aueh | tnddenu have been reported and are reasonably well I documented (see Table 3) U3). Both were transformer i fires caused by electrical malfunction. In Scandinavia, since 1977, there have been seven [ iueh fires (five in Sweden, two in Finland). Ail of these j involved capacitors and all but one waa caused by an | electrical malfunction. j These fires were characterized by the release of large j unounti of oily black soot with very little fire. Where i the fire involved a transformer containing PCBa and i i i 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 (PCBPsl and pyrenes (PCPYs) have also been found to be formed in some of these fires. PCDF and PCDD contamination of the surrounding environment wai 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, as shown in Table 4 123-27). However, there haa 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-00048187 rfL'TZlSGCfl 7 ,-iL. TftM 4. PCDFi in Aj-oetor. Clopfttfi Ph*noclor. * PCDFi 3Dm PCB Axocior U4 ' 19691 Ajtjciot 12S4 i19691 Ajtjqor 12*4 119701 Axooor 12S0 11959) Ajvaor 1260 iloc AJC3) ^reeior 1016 (1972) OooMti A-60 PSanoonr DP-6 Cl i;;.. Total 0.5 1 0 ') 3 :.o 0.1 0.2 1.4 L.7 0.2 0.4 0 9 i5 0.1 0.4 0.5 1.0 0/2 0 3 0 3 ND ND ND 0.3 - U 5.0 12 3.1 0.7 10.0 2.9 13.6 "D*i* oTiti it il. iZJ), Ra*di :tf) and Bowa aL 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 aakarela 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 this 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. non. in 1970 the possibilities of usinz nig*,. for the fiisDosal of ?C3i was put forward manufacturer of these compounds in \0C. Monsanto iSince mat lime. ieveP4| investigated anu<or are using mgn it-,. ,,v< cesses. In 1970, Monsanto reported :ha; ire destroyed at sOO*C 'with a transit t:ra* ; at 1CXXTC with a transit time of 2 sec. ?ra' portedlv destroyed in a muitioie near-.n'3r!,,`s> erator equipped with an after ourner at oOr^? contact time of 0.1 sec 199.9^ efQciencvi n,:* chlorinated hydrocarbons, including PCBs, /" * in a rotary cement kiln i99.98^ destruction*^ (Jl). PCB* were destroyed in a laooratorv ^ stage, 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 wu^m cinented in the Gulf of Mexico using the ship Vuianas (OCS. Rotterdam). A minimum1 fame temperature of 1200*C was maintains ^ idence tune of 1 sec (J7). PCBa were ignited i^V by atomizing with oxygen at the up of an burner giving a Qame temperature ov*. * (99.99999^1 destrucuon reported) (J.S). ' The Energy Systems Group of Rockwell ;a tional recently (1981) developed a PCB destine* (incinerator) which feature* a Quid-bed chamber followed by a catalytic afterburner. ature* in both unita do not exceed 695*C (99.995* struction efficiency reported) (JS). Two bt^ incineration uniu, one In Arkansas (ENSCO r, Systems) and one in Texas (Rollins Envcrx Seme**) have been licensed by the U.S. Envusr Protection Agency (EPA) for de*trucuon (fJJftj of these system* use combustion temperatures p than 1200*C and report PCB destruction eifiae excess of 99.9999^. Several other similar mam units have been tested and are awaiting aoprwi EPA (Jl). Dstruction/lncinratlon of PC8s: PCDD/PCDF Formation Technologic* for PCB Destruction A number of processes are currently being evaluated or. in some case*, are already in use for the destruction of PCB* or PCB containing waste* (Jl). These ineiude: incineration, including conventional mcineration (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 coat, is high-temperature mcuiera- PCDFs and PCDD* Formed During Lb Scale PCB Incineration There is very little data on the levels of PCDFi PCDDs emitted from large-scaie PCB inonenaa The Rodin* ard ENSCO inenerstors have btai for such emission, and "small amount*" were rtn in the inanerarion products. The levels were sua the "additional cancer nsk" was considered to * tremeiy low (Jl). . PCB* were test burned in a rotary cement c Norway and the products and emissions army PCDFs and PCDD* (22). None couid be found i of the samples. It la quite probable that the temperatures * these incinerators (i.e., > 1200*C) comoieteiy '* the PCB* and any PCDFs or PCDDs that ire A 000944^ WATER PCB-00048188 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 3ibmjo- r..-- Lumtaooo* to tha Current Analytical Teeftmoua*. Ni~ Rjeaerea Counol at fiimu (NRCC). Pupl. 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, PuM. 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- nOML. Pcrpaon Praia. Oxford. 1982. Hviumpr. 0.. Frai. R- W.. Manas. E.. snd Rafjtani. G. (Eds.) , moronud Dwnns ud Related Compounds. Chamospnan. Spa-j. tout. No. VS. 1982. Psnpaaai Praas. Oxford. 1982. pp. 125- 1^04. A. and Tuekar. R_ (Eds.). Humu ud Environmental from Chiormated Dianna sad Raiatad Compounds. Planum Nr* York. 1982. 1 imdurr G. G.. Keith. L H.. ud Rappa. C. (Eds.). Qdon-jud Dianna ud DCbaRandPraas is tb* local EaTtronmam. Ass ire* Samoa PubL. Asa Arbor. MI. 1982. 1 Mudhary. G. G.. Keeth L- H.. ud Rappa. C. (Eds.). Chieri.jut Dianas ud Dibssudmas is tha Total Effnroaoanc. II. i*a Area Snaps PppL. Ass Arbor. 3i praas. v*e*. G. Tha parsacant PCB proedam. Environ. So. Taehnol. . -*-000 (1982). H-viu- X.. Nuafsw J.. ud Rapp*. C. PoinPlormaud diban- luraa formation from PCB nuxuiras by boa! ud oxygen. BuiL uni Contam. Toneoi. 19: 68&-870 (1973). Uvr H. R.. Boaanardt. H. P . Rapp*. C.. ud Lindahl. R. unification of polynniartnstad dibenxnfuran laoman m Ity un PCB pyroiy***. Cbamoaonars 7: *19 *29 (1978). h--f, H. R,. BrnansriW. H. P.. ud Rapps. C. Formation at .>nuormat*d dihmsodarsns from tha pyrolyia at PCB*. CKo--wn 7: 10P-11J (1973). Hi'rr H. R.. ud Rappa. C. Formation at polyohlennatad <iininhirsn* from tha pyrolysia at individual PCB isomars. Cba- at* fl: 157-174 (19791. Ki*rr, H. R. Formation at paiychioratad dibansofursns and 1 ("daonna from tha pyrelyu at eaiorooanaanaa. Cbatnoavv lli-U* (1979). s N DiQeoi ud WdUnyton Lnnnaunantal Ccamihant* lne. --dasnaa for Prrvanuon at PCDF Concasunotien from Elaetneal wtk Ftm. Pr^r%d for EPS. EanimuBom Ciamu. 1 19. Mmiitrv of :h Environment. Ciaaajl News rfieu^ No Envi* ronnwntai Health Hataro From Truaformer Fire Feoniar*' 'l '.973. JO. 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