Document 85LDOQNvqKDJkaxRKKb5oLeNd

r,".r I U. M . r Ir.u- I "KHMU \... . I'm.' ! 1 .. ' c. -I.... . I ill ( 11 K'C ).M.\ ] ( >< , K ,\ ] '1 [ |( ,\.\l) I' I Of.(;(i I(`.\ ], AST ICC IS 01I'M.Will nUIN.Vi Kl) MI I'l I K.\ Y l.S LAW K i M \: I ISilKL.lN .Wilt ii.tl I ii ./I'lr/r / I: n ! i r(,it v*Vjr>HT.\. In^h.'i r{,`i t<j' IU #.'//<, i'uhln /Itiiith .Nih'in' i:/ I > f'tirhtu ul rj Ihtiftl,. I thtiiiiu'H tiiu! Il7//ffr, /fV>'; tn r i< / rirjuy//' i'tui'., X.C. -JJ"') (U.S.A.) ` (Uuuis i-'l 3lh. ii; i) Vu\ ] I. \ i s l. lulu; I 111 t l' Ml . .................................................................................................. -jll II. ! .I'ljK'CtN ......................................................................................... .... \\J I! L I o \ if. ,i'| 'i. (s.............................. . . . . ....................................................... j5 t IV. (.'.`liinm . 11 u l linn l.tvcr Jn'miMitM^r:i|>hy ul |ul ych lurmu t utl biphenyls......................... j ^ < V.(,.i> 1 h|ii111 'lire>:n.ii;jr iphe . , . .................................................................................35c; VI (hi- Ii.juul . lir.Mn,iiij^t'.nh\-'iu:is^ spriAru-'Ciipy....................................................................400 VII Xn.ily-v^ nl 1'IiIomm,tin! iKiphlluileMix am) dibinzofnrans................................................... 418 \ 111. bn nwn.i rv........................................................................................................................................ ^ j3 K.'lri rui vn ... ....................................................................................................................................12 \ I. IN I KOhlTl K.N I)i-']m11 tin.- fart that polychlorinated biphenyls (1'CIVs) 11avi` been available nmiulrici:itK 1m lorry vi-iir\ it is only within the last five years that they Have been re. ngui/cd In Hr of environmental concern. . l'olvi lilnriiiated blphfinls arc produced Hy a rornpai a.ivel V small number uf manufacturers, marketed under a number of commercial trade names, r.;'., Aroclor, ('lopln'ii ami I'lirum lnr, and are represented as "a series of inert, elremiealle rcsis- tanl, fire-retarding plastiei/ers compatible with a .vide varietv of resins, varnishes, waxes and paints; tliev varv from mobile, oilv liquids to white crystals and hard transparent resins"'. The series of Aroelors (Monsanto) arc marketed under various numbers ami consist of mixtures of chlorinated biphenyls ami terphenvis. The first tun dibits iepre~ent the moleenl.ir tvpo: ['--chlorinated biphenvls; 25 "and 44-- bli nds of chlonnaterl Inphertvls and chlorinated terphen. Is (75% Hiphettyl and Go0,), bipliem I, respei'11\el.); 54 --chlorinated tcrphcnvls. The last two dibits give the weight pcrrci 11 of chlorine, r.:; , Aroclor 124.: is a chlorinated biphenvl containing 42% chlo rine. The viscosity of the 1'TII's increases in direct proportion to the chlorine con tent Horn verv lltiid liquids to viscous products and solids. In the t ornineiri.il process lor IT 11 manufacture, luplienvls are rliloi mated w ith a 11 Iivdnnt 1 chlorine with either iron filings or leri ir chloride as the eat.ilvsl, the byproduct is hydrogen chloride and J. Clirumuliifir . ns (ii)7Jl H5 41(1 027047 STLCOPCB4011009 STLCOPCB4011010 : >- pr\ by process. (A typical ITT; v.,m; !' i a.a,1 ..'.a t .c.-;.h1. e bi; v ' ?>la< -pccrr--<>;>;< . :i:c pro'-'-ri--. f i :A .d:'.::' e 'M at'.; :> r c . live . on: , a.ing -i \ , i 11 r.r. uPt,:. .ic .-.min riir.g '' i.i.'r An :--r ;. : 1: ' c:;.i:u . :_i.t '';.:u;io;n,l' : ;; ,,n. -i.f(uric rl.b.i m- li;:. " : rv.r,'.;;.; ; t; r . .e;' . '. J r,: '. .. ::b f >;r ' o;-,:ammg <n -n:.. :r. mg rive ' r:! li'e .'out 1'-me - hi- r- \ 1 no nnmi.i1 erode tarn o: '! I','. -- . V, -t:-rr! a >!;; i:b. most rce:.;iv w;s r-tiiiv.t.ii at ;eo uni'ioi: <nn<i- The ;!v nv.i a: jvOiT'i* that .he IV 1J7 fio-ir;.!<;o industrial -ii- .u- i vi'. iithermal >t::>i.<t, tnoir tr:rt;resisf.if'.re to both. m ull': ami ba-i vales ami . ao,'. u;' i: ;::.a;vc r'l.i-n-ir.iU n:n! their ^ri:<,,.g bierruoss. I nr . .-.T-ie in v...t.T ba: pos$is.> a ! w tin: tv: vapor orcssrire. Ti.tir ioi!in^ pongs ran;* zji-'' for Art !r 1221 to 4:5 for Anulnr rao-S. A!l are stable to j'-r ' i OSH 02 7048 i 1 Am.;or \ \ 1 :i \ . .iC-.M'.. \ : n '-,r 'iI > .[-.III j \:. ...r , \ . ; . Si *_*i >r 7 ''.1 -1lo 1111r*>\ . '!;ij'n: r: :..i !.).- .. ..;i<[ Jv. u:'i - 1 .1 i ;i 1 11 > 1;! . 111 1 ;' m ^ 1.1 1 r.;i' iv ,i-i> ( Ii'u<t t- vr I ;; ' .M t [i.-in W..: :v; *; i.\!.i t\> m r*--1 -t wr cjii.Jili' . . f '.1; ...lil r. .mi >1 ..n- .11 11 rr 1 1 '.i'll! " 1 ' r' '' : n I li r, / 11: ! ,1.,; 11:< ' ,M, ; fi 4 | U'-'.iiAi hit; AVI UH); OViCU i ' \r\\\ J-*/ ^ at 15.' a i ;l ! n vr A: r' r,. ;i 1>a . !,~t at m-"; -110; ! prr-o;;.- - I ii'p:.;. 1 iv:..tioo ! Tii... .orA.'^t ;o-' >t i1! K'n 0 r.'lat'. ti to tortr oi'-. trjral p.r,p..ro, _ L-ool.int i: 1 1 ^ it; tmnsfornvr^ and it>>r-. <_ 11ii r u--.'a of I'i f',\ on i:l<- i; 1.pr - :;;.:n oi;;r.n and lor ) r:i ii I 1 inoiiition of cl c: t r i r a I 'Airing. f v;:ni rii!..ridi: and \v .Ivan'r fr?";!-. as phi-.; u in wire aid (.tide rimonc;-. and in adlants ior |)iu>r>.-'i ent fiXUtres. Ikvau-=e of tlieir tiicrmal stahilitv and lit" re.'inltuu-.; ;,e PC P.'s al'o find appiicatmil in lii^h-pre'-surc Iiydratiln. lluitls, iioat tran-for agr-nts. n.-.c.'.ine tool 1 uttiiig nils, spciiali/ed lidirn-ants and gasket sealers. Mi-eeliancnns a ias'lade: formulations in epoxv paints, resins and riilorin.v.ed rubber, priutou -sits, waxes, synliielie adliesi.es, textile dves. protective matings for wood, metal md concrete', as sealers in water-proofing compounds .and puttv. and in carbonless icprodtHng pap. r. PCIi's have been incorporated into pesticide formulations, especially witli such nsecticides .-ts I)U\T. Imdane4 ', chlnrdai'.e, aldrin. dieldria and toxaplienc to sup press tin ir vaporization and lienee extend tlieir "kill-lile" rfnd have also becii shown :a increase the in-i'ctn idal properties of DUT'', . Table t lists a number of uses of the Arnclor polychlorinated biphcnvls and the material and percentages with which tliev are combined tl. ECOl.or.ICAL ASPF.C.TS The hist identiTH alion nf polychlorinated biphenyls in regard to ecology teas by Jensi:.\:, who identified PC IVs in the I indies of ^oo pike taken from dilieient parts nf Sweden, in other fish anil in eagle feathers collected in 1044. PC IVs along with DDE rr,I dicli|.)ro-a,2-lns(/'-cliloniplien\l)-etli,ine] are now reported to be the ir.n-.l abundant of the chlorinated aromatic pollutants in the glob.il rcusi'-tem8. Extracts if sea eagle;, pike and salmon* as well as in British"' and Canadian10'12 wildlife con tained Pt.TVs, and in the former instance it uas tound that in bird'' liver and eggs the PCB re-idues were greater than the organorlilorine pesticide residues. I'Ll!'s bare also been found in lisli, mussels and birds from the River Rhine and The Nether lands coastal aria.-2 and in marine animals and wildlife in Sweden, England and the lt.S.A.2"-,1-i;l. Polychlorinated biphenyls have also been found in human adipose ti"Ucu, samples of I m man milk '' anil in foods (margarine, vegetable oils and par! ii mini I. tisi1,;). Es'..mti;illy, the same tvpe of rcsidm; pattern is becoming apparent for the poly chlorinated biplirinls that lias been .'omul for the pcr'i'trnl organnehlorine msm |i cities "I l.e IT II s arc extremely 'table, ehemn ally fa! '.dable anil lieme pi r'l't1 nt in the en \ iionn.ent. I 1 ie lonr p<i"iblr pallea .i\ s lax u Ini Ii IT II ' ( mid be dop. T'.-.I in the env ironment no lode' (a) be* ails- ol then lunner-ni' nuwiufa. turmg appli cation' ami gma r:d lm lines', pi IV' eimld hi' llii'li. ii a' waste' into liver-, lakt'. etc., to pollute li'li ami other wildlife; (b) v ia uidii'lrial smoke, m , xli.ui't In.111 .111- yrtift i ngun '. U11 1 tn ra I u u amt ci .nil ui't ion ot IT I' -f 1 aitauiing pi odu. I', and I. ,u long ni pi \ -(1 ,-t r p0.1; 1 pla' t c . I p-. [' in u .1 -1. < li 'p- .'.11 iir,.s, h ) via ie.-' - I e i' 1.11 I m 11 iatious to euh.mce kill iile (d.'. iib.d ahowi. and (d) v 1., du.it Co;:'........ ... . ..1 Rixl' and f-o..t-i 111]. through leakage *>f heat transfer llunl' Inf. .1 mat a .ii re h.r iv e to t lie bn .h .gu a I dr. . mip< .'U1..11 ol the I't R - i' 'Caul and / < >' < ' ' 1 11 *- ii' I \)'d I. i \i HX'w | >. | \ | .1 ,-| |, |.V | '(. / 1' (]-, ..f ' I < )> n-j 1 . M I ll<-,l ]\|" K.rl K.iblul m . I.. .1 v Im i. ,l.n> ('< ( I. ,<* m.; d.,ii\ f>a U| l * > l- Hu -ii t Its ( K.xt V> ami i j' i1 id HI lilt I lilt I 11.( V V (.M C 1 ' \n>.l,iv) Jv.it '" ] p HI. m <|[' t ;i"i p ) ni in diet r`" l> p in m iIn i OmUn 'UiA]' 11 't, |, \.UU ^ |,t !- mu,,I, ,.ltl t rnlr.il i I > "pin , ! .tI iu-, i . i > ""ti <1 Mi ,i I. i . i;: i .,fs ( el K m\ i >1 Ji r. 11 \ ,i I in- L'l.ilruK , | I i v, nl . jiin,l 'li- tj v. P |. in |, u ,[,r. s 1 Hi. if., i .1 { } .. u. ii- h I IH' IlN), 1 i ' ;! > HUlilIn r nl' ) I \ .i 111 lc- "|. f) IJ i -.m I \ Inj'f 1-..M . <-1;i J (lu (1 tint in:; i ,\ j.. i 111 n-fi t I IK I l .1 M 1! I i\ i i ;h{ , l fUTt im n.,i .me. a it It im u .i' in;; <- Mhi iii' i. `iiU'ii t. A id- clui t i in"... i -* j: j 1 ii at.>. - j l'w al V p p m, Nn i iii.i t N'n died I nl.ii v . I .uni nn -UK 11 1' d Kn:,:i.Iu||v mmual . ' Oamm^d I' ' `i :i> /::/ m ti n:i / n/. n- r.m Xu n.-t ei 1 h v Slight 11 yrl i upmciirilm nt llv.ll '1 Cl' .Hi 1 i n !;l lU-W.., . i r 11 h 11. Il ( I ll I l| M I | l(l<ll <1 II I uil.myi| l, \d I i II,r U. . Ilu I n 11 , m I la di mul .|i> p p in. in 11M l tor t \\ nek's l \ _l',.. At ut l<t j (. liietu-i) V .1 r K/tlv de-CS (34",. < 1. Ari'i lui) p.u |) p m. in dint lnr tm d.iN *' tCl-] Hcll^alc^e iinch Chicken .No cl>;iiif,'L..- noted No uct^lil changes Contrt'loti.ilar necro>is> (quU. I ami 1); lit er uu^lit increased from 2.70 (j/itin K Hi x 31 n/ 100 u (epd. j); laity (IngeiuTatiiMi 1'J 1 11 l > S ill /1AU p.p.m,, extensive hemot 1 banc, and cnlat cement at ^oo p p in. Weight was v.40: of brain weiftlil tor contrtds and 3j 5u for tlmse d\ in from l't'll p(ivomn'' l ubular dilatatiun (cpds. I and 2); rare tt 11It eptl. 3 LllI.Kdk.ll lluUl III pericatdial sac at U\o higher conceittration Sliedit u nif;ht increase, a few showed 1 u| it id in pericardial sac 1 - 1 l ........ .. enlargement nt adi'emd trad siuaU spleen at low tun ecoUuUons. .U higher com.i'u l rat ions pale cream colon d pancreas, adrenals heniorrha "ic H s ilt upei leardiutn Common w ith cpds. 1 and 2. rare with C|hI j. Increased |u/r J >1) ( 1 a. Spleen small with reduction of red pulp and atrophy ul u liite pulp (e pds. 1 ami 2}, 7.|>iien decreased Irom 0.140 100 " t" 0. I 3b '^/ 1 uo ^ p pil \) * I 'In 1 u it'll n 1 >1 `0 (cpil 1), ( Inpheii At in (cpil. j) a nd \ rtuirir 12O0 (c[xl. 3) were used f idler e 11 tial c Heels noted under cpd. n urn bers. \ l( clue ki 1 `ji 11 nn t ]uk t am! j \> n Inn no da v n. only t 5mortality on cjkI. 3. - DSW 027049 '.r< a i ll it a m ' .-II-J.M H .I'. a ; a s i -i c ~, STLCOPCB4011011 a \m * i.h ; n.ii \! A''ri i r- 1 *! M it n> -'j::,*'-'-:-- :17:!. it they !ik-!\ o- w me,- th.u. [ `I > ('1 11. em. ;i: ['. l'f I > - -."Is 11\-` rri 'W. i. cv r,: ! " ` w -* u t i a : >;na t . ri:: i: - v. - i , pic. sjrai am, i eu,a; rii.. r.i-'t'Ti -5: - J*r p r .f :)<r i a.!; ,i: > t. m. r: n - aTO ci pa > I ! <;* i* ! ii: a_,';iin a\ a. i.p tin.- i* - M ! i.i in A.; i n uo. t J i. 1 >:, ; i r i of the IT`M > iirc L'cneru:!v r.i tin* p p S.` run^r in tin- environment. th-ir hien hj>i 1 So.umhtv result- in their accumulation in f.ittv (iv"'' o{ lower ani'caM and in,inn'.1 life.) Me'ause of toe vcrv low aqueous vnubiiitv of the PCM's when thev are rli- choreal into a river or lake, they will accumulate on the sediment in r,'iat;. c,v concentration and rpchssnlve verv slowlv. III. TOMCOI.OUICAI. ASPI-CTS Compared to the chlorinated Indrocarbor. peMi'ide-, (lie to\iroii**\ .f the polychlorinated biphenyls remains rather poorlv known. The svMemw Mia ts in humane and deaths resulting from exposure to Hie UCM's and polvt hlorinat* d naph thalenr was described hv C,Rn.i-.xnr.Ru <7 iii.1* and tie chlonMcnce'en effects reporf- d by Schwartz and co-unrkersll,"'n. Joxrs and Auh n22 and Vox Wi-oni. </ ,// 21. Sax2' rcpoitcd the toxicity of IT'M's to man as moderate to high, opei'i.ilh' when inhaled as vapors. .Animal experiments with rats and Lpnnea-pip'- I a\e di-nui that ingestion of PCU nuw "ivc rise to liver injure2*-2'*. Oral adinmidration *t chlorobipiienyis resulted in enlargement of the liver and vacuolar or faffv degener ation of liver cells. 13 i:nnj:tt ct al21 have prrviouslv shown that rhlorinat-'d hi|dn;nvl ii,'-ulied in liver changes markedh' different from th-we caused hv other well known toxi-' agents such as eari)on tctraehloride and chloroform poisoning and thought that tins tvpe of injury- was persistent "ith slow reroverw The cherts mi mouse and mmih'v hwr of lor.o-tcTii; oral achnini^tration nt chlomhiphem Is (15 m^alav *r more) have hern re ported h\ Xlsiiizt Ml'-S. One PCM has ham diown to produce chick hedropa icardial edema ami *\\ th depression pmjiortlonal tn dietarv levels O00 and .400 p p in.) of the (o.\i'\uit-:' n>. These elian,"rs were accompanied hv such pathological Ounces ns: eulirc'*,d li-um*r rhacic kidnev. eular^rd adrenal ^!and. >snali spleen, civnm-enlured jsim rr.e, cierni.t tit is. fie Ira t her ini; and I ransjcn t change- m blood ^lueosc, i n-iii'-] Inn ami hr m.i r< >0 it levels. M\ dro)rrii ardium and ai>douiinal edema have also Ix-cu ohserved in J.ip.i nesc (piail" altei I'CM in^cstmn. Toxic and teratogenic effects of IT Ms in 1 hi* k emhrcos have nN<> hern reported hv .MeI,.u eH1 l x it u/11. Ate.d'*p<>u-l\ with tie* eldonuate<l hv di'mxirhou pe-ti' ide-'. the uiM-t unp-ct uit efJeets .ire ioiu; r.m^e Mihh-tiial ellerts. I In- patholo-ir changes m vaiioii- oiy.mA are siunmari/cd in l.iiu'e j. iilnstr.itiii^ sonic interesting ihifereiurs hefwecn ina.iimaK and hud'' I or exauijilr, the nm^t 'trikin^ limhu^" m mainmaU are .ill. rate mi-' f> t.'ir liver, vv i-riea- llmd m the pen* aidi.J sn'. kidmW damage and reduced spl,-,-u .,ir toned in hmi' "1 in fo\|. i t \ 11I rlvA, u Aroi |ii|s m leniis ut oial I.I VM hat--) and "km Ml i) (rahhitNj w Miirmiari/.ed m I able j 05w 027050 STLCOPCB4011012 ' I I -1 ..11 .......... t lu" .ir( h ir lli' \in. ru .in (1 >', I >n o "iiml / i 1,. * s i.s 1 017 : 1, s 1 'l.N I ' OSW 0 2 7 0 5 1 STLCOPCB4011013 ; i: * wi it-* -..ii as. i - >i l'< 1'. ,n ' i i'i \.m< 7. iv- I h.e - 11 i> >r ; ! . t I<, J I )ct * T :; i i;i.i f i- >n of 19 !C- ;ui- i . i .! i .ill- - a i r.i* r< ''.uni-h:.. > > ^ wit: e - a t > r<.--;n I m r- e. a !. r > \ ; - .\r.' >i - i 2s J and I ;*m ,,mi of -,v*Tal 1 Uormated \'-Aif id*> r a *; ^: i; i: !r in ;'i \ :on(i and s'* to t" '* .. ti\r 1 v. T!;c ch-vI '[ \\at r -or.t-'r.t ! .-iii- a'a-i -mi - In ,n *: u l -r ' >:i r a r i-'i i ii .\r>" ifir ij'io I /1 > i ;tiiu an.iiot;^ <>. r. in I I. I1.' >;i;ai;n inar'^i:* of -a p:\ rn r a -.; of |*i j', :r`:a po mI1. .(K-- v.atli cv; r*'f{r.' io ;:*v <( cc, utioa pait' ra vva^ l11a;av<l wuh '-ili' i'- a^a.I Cota,lining 3 '., .v.ia'r A p >..ir urnt w.i'. r'pur*.'I !r tlic compli tc vI 11i>n ol 1)1)1 ami -PDF.. \\in:n tli` dtar cot;t'Mit ua- V'j A ^cini'ptantJtati'. r datcrnu.iation of prjVs ui >ampl'.^ b\' TL(. v. a< 1 lv M m.hL`un ci ui.if> ('U'.annp bv l-.uxanc -acct^mlrdt: p;u Mtior.iiu; and I io .>il column rhromatu^raph v was performed cm ^amp!^ be for-' nxiflati^'c trea;mr:ui: ) convert DDK to DCIU' (4,4-dield<ir<d)en;.oplirin>ne). then the 1`M', (oinj *n*-ut- 0.P'- DOE ere determined scmi|uamitntivolv (witii a lower limit ot <cnsitivitv nf o 2 uu) by Lf with no prior separation front chlorinated pcMicido pMjuircd. TLC >cparati`*n ;\, \ ;. n - * - ' * . a ~ ,m art :v..*.rd CimCd column tcehnwmc winch :as acconijili-hed on silver nitrate ineorporated Aluminum Oxide 0 plat> developed r:< -1 h : ,n \! i [) h and 1 'l. i ' with the hr-* eminm p o ml ofK-hcxam . :p .j otii 50;, nenj'.eno in bexar.e. The were detc ted a '.pray consisting of 5 ml a:;.1, hi j i,l< r : *i \i>; . i)l)l> and with the -ero;;d elution y 4\' cxpoM.re to germicidal Ki c;\ x t .* /. - eh i led a a: un' j--r i .iani.j: compound" int hid my I) I) If and P('I: ;Y li^lit. The Rr values of Aroclor mixtures ciiromatoi^raphed by tins TLC s\ <tem r; ..CtivapV: ch.:';--;? eoh,;;;;n- n-any /then dirhj;; v! -a C x.u.r iiin and cndrii: with k/' `.miu: 6 .o pa;; l;n.,n f)l H iir.t, ;* ;u.:doys and other common : : mi- Hi- A L l' KS MR AkocLOK MIXTA RFS AND rKSTICILX'S ON As'\C ); i NCOM CO K AT i.\) 'id-.. - :*.y vt k m:; n.;,mp;iv on <\',u ic acicl-Cii;o u;i . OxiDF. G PL ATI'S l.'kl\ ia,OI'Fa> WITH 5% UliNZr.Nt IN HKXA.Nt .Mr.r. IVJ; t reported by .\k'.,ov x '' ;t!: t'"' hr"; Irartmn fj^n mI of ivtro|( ~nni f'uu nd vt.'nr, -Ua; imd.j.-.-. i.rj<ua !i[, r. iu. p ..u '* a' ppoxidi*. di'ddi'U'i. enfh in. )|)[` 0. I d ) i . p,f.' 10'1 aa.d J-. : !))[ v 11! 1 tla,- 'vund ir; I'timi (2no nil of acet<i: 1111 li-- li Is Ry ualtic n 0r 0 9.1 O to z: 3-0 3-0 r/ !25 1 ; jhn 1 V.` Dm: DMT 0 0.1 0.01 0 94 o.> \ O NS 0 ro 0 0 F>1 > 11 -j'oxi, 1" II< hl.T ,,A ui Ki PieMitn .. 4S in nr 0. n> ALLMlW'i STLCOPCB4011014 :n 1. . :n 1 >1 > 1 . ; i are lifted in I'aMr i> lb" 2illii^trate" a chromatogram ol a j^du an eu" '.unple eon tain ui" 1 '\idi/.rd ''.unpli--' a<\\ el! a-' Ann lor 1 23 4 and |n,"ti< ule >land at d v I In* \i ma-r limit ui` detection of PC ft bv tfu^ *IT.C pri.rrdure 1^ o 2//". Aradvlieal d.ita ot prlaan r"" .ind Mi^dr liwr sinipK-s an- shown m lable y. P(f 11 u .0 d> U'l n:nit'd l)\ I CC .u id 1) I) If data were nl ta i;ied hv tin- ( J.( p;. < .'d 11; r - ,| Ri iem.i ,( // M Tlie CCp. !)DIf ratio was approximat-dv 1,0 e\r. [t tor toe pi-fir.m H`"in ( .ini-ama AiOKH ii \ \ 11 111 km i|^(tl j 11 'Co, 11 ed iluimniim o\id'' with bipli 1/. ,(;;d c'!'::, /'!;?{.pn- {2:,r') `'liriit s \-^| r j J of ! lir 'r 1 >.i fa I) 'u , p./*` 1 d M and /'./>' j )i) I". 11 *tiii A rot lor r234 and 121" 11 "' \ er, l lr- ab> > \`e A r-" |. ,r . and l >1 >(1 w eii' not r,^. .J \ ,-i 1 W 0 O oO Q <o a 09i jopojv so 'rV> u0 Ootco* LQoJ Q rTl: o L0 o & <? DO UooJ aQ Uoral a of -- -- s------------ 'if'OIOuO jQQ I7.'i .ii'OOjv 0J o * <? o. ! K`? I " :j - DSW 027053 STLCOPCB4011015 \- :i) ------------------ -- >. i of r':i o: I- 1 l,iT j.,,: t:f>i>I .aiini.'e-c :i~ j * T^ flinier.M'Mi.TI scpiration of I'OVs vlatc*.! from a fi -.h simple' l>v the silicic ncrJ colnmn <-.i.vr.\tmn c.f Armour a'so iK:RKr`;'. : cspeetivi. Iv (both Aokttcd from fish sample bv the sihne acid column scpar.it'.mi of : IXMOl'K AND bl'KKr.4'*'). i Arnclors [254 an< 1 rsbo are the two of "rentes/ intcreoi in ne^ti- ide woik be- :avise their r(.C peaks elute in the same general region as the DDT anahg> ami chm- ualogmph on manv TLC systems at approximately the same Ry value as />./>'-DDL. The synthesis and TLC of twenty-three c.hlorohiphcnvh has bee:', de^enDd bv rip rziNm.iv cl nlA* .All chlorobi phenyls prepared were homogeneous on silica ge; thm i>jr l.'u: !;u :. the i'dlT ,;uiio,,v \ri, 11:c PLl'i .tri;i!u^N r-4 * * ------- -- `V-, ' fc-J ------ --p <: e- iQ\* Sr < . f . , . f, .v 5(iinp|i' tont.iinm^ I1' ua 0O 2 *v ?2 CY < SdiC'C COd Col S'ss eiuote Arococ 1254 DOT catalogs p,o'-DCE O,0 -OCT P,D' - OCT AP'-TOE Keithane Flip 15 Two-dimensional separation of kclUiane. p.p' 00~i. o.p'OOl and p.p -DDK i-'ol.t ted from I'e. b s hi a fish sample In the siiicic acid column separation of Armour a no IU'Rkk1'. i.-.ver riiroin.itograisis dcv<:!>|<cfl in heptane and pave one peak when chroiiiat'iprapln-d on a 4% SC-30 column . ; Table 3 lists the names, structural formulas, starting material sources, method o! p'uriheation, mcltinp points and Ry values ol the individual chlorobiphem Is. V. GAS-Ll|ll-'tD CHKOMATOGKAI'KV 1 ! "ri**3 (Jjscovery ^in t!'s e'!\,rririniejit was not 2,'f~iirTipr::rl,,`f.l until i^[*fi ; DSW 027054 J Chrninati'gr . 6.S )4^-|-'6 STLCOPCB4011016 f \ 1 . i\ \ \\n \|. r- ;'a jcM'irnl.V.4'1-3 .4 - 5.3'-5'- ,*`'tn>lni ut^'i i ;ru ( s-Mf rcc'*-r : />' f r>.-. - -------- Mi r f i) 4.j' niciU>*:o-4mtro li; > 11 n v 11 * 2 - Ammo. i. 4 '-`hcliU'mluphrn vl 2. j ' I 'icMoro- or 2. | lOfl^licn/cnc1'' Mil )l( n<j ('ll . CtOH ji-j 3. 4,3'.4'-Tct.r.i.minnliiplu m I (VI) nr 3. )*-Pirlilortjljcn/.iilinc (Vl'.li TL< . r.tf-14 arp 3.5.3'.5'-Tctrn- cnlorohoiu.ulinc^ TLC. McOH. hex.me 57-.^ 4< 173 l'>) 55 5^ Ai 03 SW 0<J 7055 5. j',6'* i5 j/> I >i. Iilnroanilinr (() i ,f- Oichluroiniioiicnicm: Col . litOH a> Ix.nzrnr ({V) I 4,3, 1.5- Ielravililuro.uwlme Col.. Me* HI . Of 4' 3.5.ft' it.irhii.i iphtn \ 1 ; J.4.5.'*- Uchli.ru 'iphcnv I-, 4 V1' Cl 0 Vj/ )y_ Cl 0 2.). s.'1-Ti t r.ichlomnit r- lirii/oK' (11 1 j <1 *lc l r*ir 1:1'T. i.l II111 IH.` I'll., hl*\.lMc /`I r~` \ Cl 0 /V-CI v /r JYul.u hi* >r him 11 tilic n/'iic (II I Yu (.a hlum.tmiiMc ol . \K( )| ( 0c Cl c . ,, 1 r.1. Ilium- ~\jr i ( 11 / n|i 1 ir " *-r i. | h 1 rn 11! 1 if. Cl 0 IimIoIk-II/i i 1 11 1 ..1 N:' 1 M 1 ' 1 ' * * fC 1 - I 5 5 STLCOPCB4011017 'lu in n - > DSW 027056 STLCOPCB4011018 ll'< ` -.ih k STLCOPCB4011019 t fd vl'l l ri'.att/.umr. j:iiWos pr. dv.'-.^ m-.m'.v ydrnoido;; i; 11 i. v.uh ' fr > r ? c 7 r v t r; 11.. n i;r-: - Tins j. > i.r-t i: for I)I>T. DDD and thcur i- > 11.0rs a> wci 1 ,iv;. ar.i; !::!;.' auntie. ' ' - Tvi'i'-;i! GLC separation PC!'*. pcstirido and n mixture of rhe two j shown in Fit;. iS. Tlx two n*'"t rnmir.oniy -l;;; : ^54 a.'"i l2<;o. Certain difference* are exhibited in their C,LC pattern* that .:an !- iscJ to distinguish one from tiic other (Fig. 19). Aroelor i2f), with a liielicr rli;-*r.; or.tuitt. shows about seventeen major peaks, on ari SK-jn/pb-i column compared o eleven v.itii Aroclor 1254. Another major difference is the peak height ratio ol teaks 10 ard 13. e... f).i ratio is approxiuiateie 9.3 and r o foe Arodors 1232 anil ibo, rc'ivi.tivclv. i . i'i". 20 illustrates GI.C chromatograms of a number of Ar.iclnr mixtures d' ter timed on SK-Jo/QF-t columns. The more highle chlorinated biphcnvls (Aroclois 254 and 1260) are easily detected while the compounds of the lower chiorm.ited nixturcs, c.g., Aroc'.ors I22r, 1232 and 1242 and the liiglior-mnleeuinr-weigi.t mix Jj-I____ I .1-^^.. 3J ji-s; .. \ v, :> i.r rijluiini { , D I'( i! 1 .,s <n i` Ilf'S .: - i;; I -.puKi If . , - !HM. 5 -2 ,;i. . tin' iiir/r ..i.m.vs :r<* min.l'e; if,-; ti.cf.n!i; of utiti'iii is vincls'.r.^rf! ) {<. uif :;:;\;;irc .hkI .\n:lr i~54 Other OLt > 1; U "N ^ 3 (o) lb) (c) O U) z: o \. ... ; . ......... _ A r. -t. ,ur 12 5 ( ;[.c fobritai m,i|cr ;n ; . iy ,'ui i r.,1 ol AroAor i :'`o . >t.- c;.' c fit-j i.i-ij;;.: w th^-r; ,i\ Aroc'.i'f i -Fit,' jo, C'iI.C prohh.5 ol `hr more popular An>.liir mixtures under nf rmal .Tn.tlilic.il condiintnx : \ 1; pv.ik n 11 in be 1 :> cor re-.pond tu those ol .Arcxlcr i 2 5^ {ai 5 nfi of \rvf.ior 1 j i 1 (b] 5 m; of Arodc r ! ' (', (*;) <, ng t.f A roc lor 1 i .j 2 . (*:j 5 of A roc ior 1 - 5 . l'.`) 5 of A rot; lor 1 260 , (I | 5 nn ol Ann lor s.t'ii 01 A.' L'af.trr.crrrs as m Fi^ 17 J C hrtiut />/ , bfi (10 7 2' ^ STLCOPCB4011021 STLCOPCB4011022 I ibi 1/ i i i o CO s: o rvj o a o I ! 3 t it \ TA:'i \ i ' \ i 'i: n 1> 1 *. > \. a**;-, r ; ^ * >. 1 ; . Jr i V i A. k ?i:t'a f k s t a. i i'iis' ' rrti s n THHKt p; 1 i-1 R K.s T f -LC roLv `IN'- (1- f KLii Kc'-u-f.-: i 5i>., r, >; n r i.- \ *1 r \tr ic `. PC Li - nnb'cfii'T'il );} a 1 ru i rf>i:\ .`"1 L C v i *'-n ' l.'if Ci./.\T if. 1 :i *'i 1 KUi pen u! /: PC it Kl.R 7*C ):' i.j: l.-ti * -3 1-7 * l .01 I on : S i :. s r 3 5n 3 Vs 3 7' 1.70 \ ;.(jS i,j- 5 > 7.10 7.1 r ^; i 07 j-o I 3.O') 5 U<* ^37 -'r'1 2.1)7 3 "3 5 oh 503 f>. 5O i.; 1 34 > 33 2 jn 10 2.()2 2 1)1) 2.07 : 'jn j.r,o 3 no -lO, 4 "j 5 L ' 5 <1 ?, 7 i M r> I H K N M \\ s 5 `O ''3 6 10 20 25 rrmu'.f'j : -1 < '1 p `i: \ i. r ? ;, o < ; ;> f:i .. .--i'ci.t ' i; :< ii ''ll i'\ i* r f.-1u.*l*-` ;V : (fi (\.~'. ; > p i;. '-I-' r j 1 : : 1' ........ * *' *' n ' ` 1' : ` ; : r ............t ........................... ........u : a. :: . ,.i . . .. . ; ; . i ;r n :I <.f It IS |i|r ;>,i i ,u ion . M pvt >> . >. r..i Vii Pin An c'.or i p >' 1 ;V. . i;': 5 : . i,.' I'. : - 11 i... j; i * ; |> ;mii ' i >iU . ;or , : .i ; i;-; : i . r * 1.1 1 s >i IJ. >:. r im n: i it nt;t k * 0;iH''.r;ii i .no. J u.'int: i% arotouc in hexane .is developin'; solvent. Spots rorn^pixidini: to die IT I> s J are found at Ry value'; between G.-S atul r.o. whereas the cumnumly (>eru-rin^ or ] grumehSome pesticide^ and their metabolites produce ^pnts of loiecr Ry values. J A similar reparation can also be shown with reversed-phas.: papor rliromato- ; grapliys\ whereby the unknown com;>>un(ls (1TB>i have ^'cry n .i-'ii lower Ry values compared with the chlorinated pesticides and their metabolites. HoLnr.N nn Maksotn10 reported that seals and porpoises in Scotland mid i > -r *' I 1 :' T'1 1 - i' : 1 ;M. i M , I ^ j - . p ;U 1 )I )T. JM .1 1 -i- l5i- 'i'.ii " ( i' ;'.:!I !.< S\ I! riui." "a- niv;i''iivil in !u ' : -o f >;.i! .1 i ,i ;v-: . : ' .: i'. t; ir \ :i r- < c:. ; ;;; ^ .'i-.i (<. r : ; i:\ :, i - i ha;n;v,mt n-! i! m i: u* ;. - - hid * k- 'tr ' p - .11 X ;. -i " I . ''O-. . :.i- . t'r. i I)::.'( culiijniis. ;-i r . * 3' - r< < w (in I I <r tin* | n-.; k - 1 ' J; f 1 1 . .i 4 ii' r11 . r r:< n r\ f r.i< f ' ii .i .." 1 ;' i: 1 *' . - ^ '' : ' : :' !11 : /' I m *i m: "orn :.. -:u 'm' `,X j- _>< .l o . :::. : ; ;'i ifi * .i .im! iitu-; ra'. > 11.-' ^ ` : i- - ' : ' ' ! ' i > ..k X-,i.i m. !. ii \ in kr-'.r- v- l < : : i. ; ! *, ` 11 \ A .: ; .! r i i . y. ! : i ' 1 : i i : * :i> . I.!.i ;i j ^; 11 i,;; 11 -: n: \ . .' .' i ; * \. ; .........: : ,: : . I i i !,. m, j i.,;i. i (a) cO Wv'cnivjn tiTi.' ' n- n) .*3 t s.. j\ , i - ii. |, 11.! i ' i' mi.. 11. j r.i m i' . \i i ,, i ..i ki a n l l. i STLCOPCB4011023 llll r*(i {' \ nni. rc n o n ra ( p / m ) Q Q t I m in r \ riiut.'r- i tisr N f.rti! nrc 't i tr r m ir .n l c a rn i\'n ra !s o f a c o m p le x ni<>ii o f tood chain-* in the '-on The d n o rm c co n te n t o f <?.\trart> n f o th e r b ird s nnd lid i was d e te rm in e d u itu i.r 'C t: c. I.) c. a c i 0 C> ~ -H 'o n C 0 vn /) a C-C d ii \r\ ->4 c t c C O ---- c eccddccd HH o f7 ? U~> co 6c 0 O i-- -M < I f-* vn C C \r, - o -H <SI u*\ - C T. - c c -- H -U deco n -n e* ccc OSW 0 2 7 0 6 2 STLCOPCB4011024 ; '! ' STLCOPCB4011025 I M I I 1/ 'I I `i1111 ii I '..... . II l V ' ' 1 1 IMI 1 -1. \ V 1 ' 1-1 VI.1. >H- \ i m; i . 1 IV 1 l li'V! Si. V. VIM' I'll i \ \1V ' i < .... , i Vv h ,! : ., 1 /' 1 .A/ r v .Am rI , 1 U /jJ,l --------------- '< .1 1 ' ({' i h, \j . 1 V- l , < .1 1 1 *> I7 i l 2 i .S i - \ P' 5 l s <.: i 1 >{ ; 11 .< c i j M, I'1 .'I i JH 1V 11 il i S l<M \\\,!. , t. n . . tr> ' i , i- 1 `i {. '1 ' ! .' \ ' ' t | S. i m i r) I' i ' - 1.11 \ti <<]11.11 i "{ li'.'i 'i'll' h<'M m <orl!' I M.-I * .1: r I \ "I ^; u M i \ j........ . t" 5 |. i> I. Aim l'i ' CM .ill I I 1< .1 . ' I ' I - ll MiSIn.. ,iin' p> i k ill v-'.i iUn : i, i m .i, cuntr*'! :mui,i!ils iimcT i-n. Ji_d M';ni(iciu.ll\ -r-Ml' i !* jll tr-sl-; (; < .<!} I:*it tli.il i>l ............ !* h (/' '.In* - I'WU.i 16 v i m i s u- \umi.uk i .* % | in |)|'ni , iv i i ivKit;mi . in spot l.U'Osp.d to i p.p.b. or i mis niFMiCAJ. (i;.\ri( samim.k consist ni ni msm;i ^ i um I hill M lui.il mi\ ul Aimlm m p.ircmln -.cs. ) ! . . Ill' .\ llin/li > l ! l/.I IM , S' mnhrr nf (I<tys a) j!n. ........ .. \ .1111 t -ilU 1 K .IT t l n it Mu-, k \\ 1m,].Ii-h () J ' - .. - > 1 (IV 1 | O MO <) VI ( 'I N1)' ' l- ' 'I i.j (., :) (I. 1 (,l 1)1> ( (- Jl 5 f> (o 1' } J.f) I' J-nt 1 ! (1 >1 ('5> (? "1 7 .*6* --------------- -- ----------------- 3<>* ----------------------- (r i) i-' ') !i o i' i n> o .s ( 5) 75 0 ll- '-I l .s (l 51 7- f J f> 1 ul M.6 (j < -v) *> (n-o) (c> o (i <>) VO.O I'M u> I' 7 "! i; o (()<<!.u) n Ij 71 40.0 CM") I JO ' -MOO ( 1 -`0 0) 7) (-M "1 .17 <> (1 1170) 1J.O (5 [l) ^0 O (S: 0) I 7-0 (1 "1 lOJO (Sf, 0) 7 .ii (lO.o) {0.0 C.5.5J "1 Ki 4<> u (7.-o) f y0 c si *\ 0 <7- "i 05 U5 ") j7 0 (IQS | 0) N Jfi 5/' - ----------------........... ................... ------------ --- -- . . 7" ..-- . . 7.ll (5-n * j (1 (.) (75 f>) 1 li.O c 7) /.j ,, (Sj.u) 60 C*5 "1 Jj.O i -11- ") 5 -5 n-7) JO.u (71 ") ?* ( 1 O) 5- 0 {00 u) (1-1 ") l> Cl [-usl.nl 5" (4-0 - I-0 C'5 "1 0\ (o-.1l jS 0 (.H 0) 3-4 (.H 11) lJ 0 ( l J 7.1 "1 33 (.151 1O 05 "J 33 ii <,) 1 7 .) I.W") .1 3 i-N ") 03 (1 \m 34 (1 l > 1 1 i ! p' ol - M .'J 1; 1 '>] j5 ! 4" O) 01 (i l-N(' O) 5 -> U'i 1 j i !</': .- j <1 i 1S -0 (5 7 '' (-M : ... * ] 1m- IIMC tl-MlU S .lll.llv 'ml 1'rom ccuilrol sjv.il OlllliHIlLl I nu k-tccl.iMo .\roclor n.M (<-" 1 to <. 1,0 1' p .ui. cU-pv luluv.-, on S.lllij'llc o Mi M"l ll ll cU-.l r 'i ..I..I Uin r in;t .1 ms ill nij-1* . s.iill}>).* appruMin.ituly j i.;. of t. ( 11 a muu ut <>c lllllM'!('. d 1 nil. [ U>MU N .U'l *v l > /I'll nil ll.IV s , M.r.- ^..111 .Inl.liT l 11" ni. i.'un.nl 0 <) (v< j). sill - 5 !? M. rc-l ol iiiusclf ^ 5 ( J l '!. .uni skin [ J 1 QSW 027064 STLCOPCB4011026 I I 9 *> 8 6r!M3 c:Y 9___ar> 0 fcKjO C -c ' -5 _X. DSW 027065 .3 STLCOPCB4011027 STLCOPCB4011028 ! .1 i ; 'll 'v ; r \\ 11 - :n I.( .u'i "f i' 111, 11. ; . re-;' **j J i. i. . chfnine p< : .1 pesticide- : :n in food ana'. c:in< \; m(,;c j. ii \ \ ; .v^r. i - * )i PC lv s rnin^'es l ) i S p.f.u[ i l . i':^. 3 i dv;m 1- c.;- * in- -mu - Hi a ".i.'i'i'i" i11*ri`;i ^ .mi;* (/' r>' [>n K i- d- In > -m.it riiis,i.i: k. ! V'., I>* -1 : " * Hi;;'''., :.; d i% p et <; r . -i s - [ s l'\ r- \ n:i \\ Fie ',i C.i- < iironi.i 0 grains pirfo: r.n J |>ir Liu- sr <( (`Civ mu I clilorinat- `I ; -OkiI-s in .1 s.n n*. ^ it* u( U.Ulic r-|iM-lc mUi-il ;i > internal -tan-c.r*!', l">r i eni.in!-. <f Ki-s _*<-> .iml \. i. (.i f >*i11 < \ 11 .-,r i ; f! 0 c <T r.n t uf \ rr.1 11. he - \ 1`clirc in i<|-> t > m V .- \ir-iwt of \fi.v li. 1 e .iX .;( i i-\ni.i!..nn (,i) \lr;iel /f area I. I '-; ar.d carbon t.ctr!11*ri<io-ireati'lI rats. Hexane extracts of tissues were amdvzed bv Gf.C-clectr-in capture anaivsis on a Vartan A<?r<iirapli Model (>ooD chronuito- grnpli tilted with a coiled -| ft. x ijj in. O.l). column ront-iiiiiiu' 4"\, ^F.-^o aiul h'\', OI' -1 (>a si, - ;oo nielli W. The r ii l r- i.cin !l"W rat-; u as ijo ml. min until column and iniech.ui temperatures -d luj' and 22=)'. respective]v Kesidues were found in all tissues nnalvzcd (blood. hear:, kidney, brain, liver and fuU. witii t!u; s^n 1 test concentration :U tlie ;at. 1 he ( Id I'd pattern of the res idues was diffcivnl front the standaid mixture administered. indicating tliat a.K components were not metabolized at the same rate i lie her rc-id iu Acre found in the carh-in tetradilondc-trcated rats. Aroelor r25a i endues in the bram. liver, -(d*n. blood, testes, heart, kiunev and fat wore reduced by ()'), $4. So. 70, 7b, 70, nj and 3 $",'., (u) .,! ii i. \ i: i 11 * \ \ Ti I-' ` ll (. m.n,jies I V.. ; .1 . 1 027067 (.in :\ J!-i in ! .! i ! \ v 1 . i i I!,'.'. > : : \ '! l 10 STLCOPCB4011029 ,\A'\ I,lie ; ' t ill 11*>r n i .*: \ t STLCOPCB4011030 \\p STLCOPCB4011031 IMtjJM 111.Ml v j.,||u II ' flMJ*|I* - ) MjWI ' J ),| }n |Mi IIII . STLCOPCB4011032 k ' : i;> < ! I r r I ; u ; i 1 . 1 - ; .1 . - r - ' `l >r n ii.N : n r--- >( A r - i. - |" r : J .i;n l STLCOPCB4011033 OSW 0 2 7 0 7 1 j* . * i ;s U IU , i o ; liiiil.iiit". i o, iil'lrin . : n MIM in | iom t u /ii i i i i ' l Jin. '' 11.it n mc in STLCOPCB4011034 DSW 027072 |u a lluiv rate of 60 tul/mtn. D.C. voltage in the electron capture detector iva-. '15 Y tt.rf meter sensitivity was t x to * Solutions of rhlor,!>;>!`t iMpheisyU in j'v J Chri'inaiOf^'' . { i <) 7 i) 3 I ^ " 4 ^ STLCOPCB4011035 STLCOPCB4011036 .nr. ^c .O ~ - U J i J i j j*. ... i(, STLCOPCB4011037 r i; ; \n::< _\>.i > o . i..;t' m \ . i. . >i 1 'i' [^ 6 S T `*2 :5 C ;Y TC ' .I . :r.. -,v :d : a So .-V t i tr.ui energy v\ i;! i ' ; . V I'dm: :.t m:. i-m e, . ::: v..i, ; onA [ ! i r " : . i': - -1 :..... ' ' r \ c r * I .c r;i j. ; : ,, ' :i; o m i \ m.i yi ; I ' i; n <: i` - .! iiiiin.n; 11-* \ .-'I" :>v ;i!' f.'i;r;*''i i i.f !i;i:i im'ui {.V i ''; ?(''> j;i - r.:- *::::.! Mipr: v-*!u;v:' ' u,v u>ol I. r t i u p. i ,i- is A- S..v; ; A .V a ; S 1- a;ul y\, r^p-cti- W\ : . r. i * ;n _*i t 1 * ; . iv. : ( a \ ! A. !) n- i{lr:n;;i* ! ;v -. n- : v i :'; i.. :;: ` i; -> j v i . r i- v: I'.'iM, i n v !r i i n* ini 11\ i.! n if 1 1. i: 1 i. i . ,.;i1 - r- ' (i\. m.i - - r-'ii :c r\ u i i > i n . : ., ;t! . i :, : i:. i1 ' ; A1 i i i *: i j i. S. A11 mi: m mu;; r f t . i. i . m!..;- ;. ; u:'. rr - - if i ;_-i. ;i - ir v, v.. ;jM Io in ! ': . i:. i i ;;ir< I'h' r; M-i'.tU'i .i-t:/ .-. c i ' >i; . i* - : i; ; w!'ii ;.. t! \ :.i i: ;* . 1 >i . .il - ; :r. tin: ;.ri i ;< m ,i ;-il t !:! :.; v..-rr!.y . ';:f- j'.'-'.ra Ui.Ti1 i`.- iiv : i;- : - n t i i-s r- >n: the imici t ii i: , 11; 1 t! : : : ' ) .JL______ I i. 5-- Mtri:in mI ,i I.i. j>'1.[i.Iil'>rnliij'li.m I ti.ninl in st ni'i.irit Aroi.l-.r i .`'in cr.' O t iitti-ii'i- diuilily rli.irurd lVa"ini'nt^ wttliiu tlir 1ra nl` tnn^t m'11 1'i'i; com; 'I I k'.-, yr ;unl yj -Iimw iumn s] i lr.i nliimm-rl frr n tridihirnliiyiicin l i,nnir-i in Aroclnr mu! i lic|>t.v`li|.iinl>i|>!n-n\-| I'umi.r in .\rm |.ir r'r>u. ri^|>ci'ti\ .-l\. Tim-, in tlie cIir.iin:itior1! - i*1 lay... mid |M-nkn I ;iin 1 j u itc -Inm :i t,n In* tr!: md;I..r. ybipl a n Vi -; ;ii'.il<s ; Ii. lu'Mudiii i.-nl 11;>(11 ii\ l< ; po.ik- ;mcl o - ( i:r-pt.i1.>11 I i;.i i ii \ I. P'.'.'ik-i 1J5 nod ."4. . tin liln i>I>ipIn-ii\ 1-,; (Irak.-, 15 and id. inmr.i ITir"l'r1\i',ii\i-; and peak 17. dom liliiriiliipli' in I. I in- 111a,-; -pectra nt tin: i'iini|:iiiii'iu> of adipi'-e tissua of -ainple e.Ntr.iot ,\ (!dg. 40) rcvcnlcr! tluit peak, a, b, r. and d were poll chlorinated biphoniT* irlcntic.il with 1 lni,e obUuind rc--pcctivclv for |>cak^ d, 7, 0 and i 1 of Ann-or tj=,4 'l ie 47k The ni.isj spectrum of peak d fan isomer of hccnchinrohij-li'.-r.vl u-.oi v.t 34s) ts shown in i'ig. 54. [lie mass spectra of components nf ;idi|Xisc tissue If (I ic 30) slir-u.sd that peaks a through j were- identical to those obtained fur peaks 7 and 0-17 in the Am lOO- SO so- so 'CO '50 200 250 ICO 3 SO n/e i t Njh.iHifit <i| .1 lit \.tt. Uinp'l II | ilirn \ I t mi (.tun-| m liMin.ui .i'llpi>i tivsip -.imjti. ' >. ( 1 ~ i'ti V r '"i' I i. * -t.i ix i.i: I (1:^ f S) In .h!' Ii t i"i i, /\/>' 1 >1 'I ,, .1 m 1 /',/s' I) I ) i . 1 v 1, - I, ut : t a ,a La rU di.m 11,*v,- 1 n< >unlrr-t I m -.ini} - Iv A. wvj .11 - - t *. !,: nn (I 1 ti I fils ; (i< hi * t i-'-i i*- 11.1; >K A -a l1111. I * ; i:.M- it i-n 1! 11 1 i ) >t. 1 ; III 11111 j !> 1 >< -l i> i> It 11 -It I'll s 111 I.......|. ! n 'in I-'* : l l II!. 1 -- - j n]i\ W.l , tji's, f|l 11 In. I ill I M 1 \ 't \ I ' I 1 \ I ' .in* I tin *f '1 iir.;)Un a .in 1I t - >!, 111 - : 1-; j 11. 11.1) 1- in r . W I *' l - .1- .i n 11.1, 1 ::-i ,11.11, 1 1 11 ("in.! 1.:;; ,111, : 1^ /1 |) (1 | .11:1! A1 A ' I M M' ,. 1 111 -- ! 1 u n l -ni- A11 i , 1.1111- A i 111 '1 1 t -i ii -11 M. ! 1 v ' '' 1 11 r 111 11 *1 1; m \\, - 11-1 -i i * ' it 111 -i l iv \ 1 .1 11.. 111, 11 11 /, 1 * 111,. 11, OSW 0 2 7 0 7 6 STLCOPCB4011038 :r'- .l- 'iji' iD A tj .if m W '/ i ') ) ! < STLCOPCB4011039 rcl'r.t!*n tirii- OSW 0 2 7 0 7 8 STLCOPCB4011040 '),\n ' .'i ' V > -II. i ( I K II w. I, ll..- . N- I ..... .1- I .....! "i 1111 i , > a I . . ( Im.'III ' ' ` "<l I , l<: t t --M mi i: v r- /v h \ i:. i 11 - i: . . r(A ( in- !" : :r. i- . ' ... ' i..... I !., Iv r \ (i r . i i- ' .\i ii 1 ; s . * . ,. *rh. ) | ! an.' ! ; It,-,- ...V, . ./.,! I ' -I I h > 1 \ ' \ I i :i . m'.i> S.inil. u l im.-i Si I II , ): , I I i ~ -1. i ,111.1 I- . | KM: J v; l.| In'd i.iMf. f.m.-.d.-M II'. I ' and . ' 1 HA IV'! 1 N It .|l I , I I ;f ;. I 'Ill-in III. -t I) I 'll A I I " ll!* M ! .'III. ( l('|>1 n it Aim Hi -fid * ( |! -*5' ! \) -r> Cl 1 ( I) i . I ; -d ' {>) .1 'l (;) l'l I 11 I 1 '1 TAHI.I-; 32 MASS N UM IH- I? S IKH NUMItK HS Of C IM.O If IN Iv ATOMS I'KR MOl.F.CfLF. (IN I'A K K N T M KSl;S) 01 I'l-AKS Willi R L L A It V L` R L TKNTION TIM i m<iv ^ i.oo) (vi i-r.aks iuv.ru rnvN 1.00 (|<| l. I I , I. I ' . L \\h l h 1 he r ion of T > l "* 1-1 a 11 o mi i ("Minds idem Hied are con forma ble to I'CH'-v 4- =~ At the given rc-Unitum lime a peak is pn- -i. n l m the c r. r or. ^ gram. lor In: lhe:- inturination, e I al'h 1 r. Snnif'hni* a red 7 yf'f of u}*u[<le K, 1.01 ''7 1-2J [..}> i-57 / .60 /a/.' - -7 f,7 J -* JM 1 Konch (/riiTi5Ciii rti/j.'ns) tola! DDK boilv extracts 19*17, njotf 3 111 (V 33 (ft) 353 (<.) 333 (&) 3`H |7) 153 (i.) .)<)7 (7) yr. (7) .cl--1?) ..ii 1;. - 4- .l`>- (71 J^-t (5) r1 Groundling {(ivbio gaOio) total -1- +4 4- + 4- 14 -t- i- body extracts 190N 7 Mussel (t.\f vtilns eihi'.is) 190S 4- .v- A 4' -1- 1 4 r h ) Sami cel (.-J m m>n{ylcs luntiolalus) 1- I- 4 } r i -h \ 1 l 3 Sandwich tern (>/-mm s.uui- i n>i-: vu fuu d t i-ssnc am l v/g 3'f> (4) 353 (c.) 353 (ft) '3 33 (..) v>7 (7) 3ft-' (7) 30' i;j (n- f?n tracts ions. loon + 3M (55 JJ| (3> 3 f-'.idi-r (Sinnn(eria mnlh.. I >i d-: tixme and enu extracts lodO, 3',J (ll 3.3-3 3.33 (") .133 (") Cl.. (7) 3')-' (7) 3')-' (7) >.) ' i 7; t d. 1 1 nyny 11 I'hemh.h.r Dl'n A t in 1 il< n' t 7ho 3 -t (5) 3 5s (') 3 3 s (") 35-3 ((.) 353 (1.) 3-1 (3) lv^ (!', .1 -1 ^ ') 3 3' (>' f'-J 3.1- ! 7' i.-j 3|3 (.4 r> ^ " " f- (n t- tn (7) .W.' Cl 10 J i i to. , . ; | d. ' t : ' t loj'lii'ii Ado 15s (<) 333 ("1 {) li-s !') .; ' (;i >'' ft 3" (;) nj.: (7) 3'- `. * i- ; c , . * DSW 027079 STLCOPCB4011041 IC-6 ll ii :'IT in ;1.,- i ,.!) ,iii iti.-iit ill' : -:i of : i;'"!.i 1' 1.1 MS i- ,.i;: i' i i. 1 . 11 .n c. ` I / i1 ^ ; i 111'- !; i.mi n .jivn :S.r', u..i"i- j4n . . .>f 35 :ni '..in, rl i.,:v s(i..* ' 5.5 V.Y in.! : - r;I . 1 i>v Ml .in w ... I _____ I ...... J~ i ,;.i ; ui,'c, . -it"*- * \: ,-k.I,*V1M I- "f. DSW 027080 01m--L ,0) 20 40 60 I. X. 60 MO o m/e 60 00 300 ?0 40 50 00 *X >ia.-'S s;c':l:ur.i of peak i {['i^ <>\r, b. ami d). ciMpirr;.i `>n. 'CO | j eo-j GO1! 40 b0 Ii20 i 'o ii255 l >I.| 0'.00 20 40 60 80 200 20 <*o 60 8C 300 20 40 60 80 400 m/e T;^'. f-. spectrum of' p.-nk 1 (['i^v '^v.. b. .and di. cmp*ncnl formula C,2Hp. - ico- 30 6G 40- no i 20- 0: '50 I ,e- I 255 |j | L-^-. 4-^-1' 1 100 20 40 60 ec 200 20 40 60 60 3CO 20 40 60 80 400 m/e l i2-dj. Mass spectrum of peak j (Fj^s. empirical formula C,Jlt< *]100 8=1 ecj I40 20 j'P -50 ollrvJrJx 'X 20 4C 60 60 200 20 40 60 50 300 20 40 60 60 4CO m/e -Ii;. Mn> , sjH c tr u j;i of pi-aK ^ i Fi-i boa an.! * _ empirical lot mu la C,,l i/ I , J( . b.s i|<; ) 11 s -1 STLCOPCB4011042 STLCOPCB4011043 1 i 4.:c i <\. j.'-i re _ . j 0 uv O'-- <1 CO ; c.irrcuL ciumiciioem j:*s 00 DSW 027081 ,.11 'Ai'iii * \ni> j.i<\. \ -- i*i- I*< \\\ 60 60-1 ! J 177 22CC-;!VT79 II - ICC 20 *0 50 '?4 a**! i- ao 200 20 40 50 60 300 20 *0 60 m/e 60 4CO ;riir Co. M.is- >;>cciriir.i of p;.:k o * I ` r u: > oo.i -uni c,. cii';<iri< n; !"im<ii.i 1 60 60 -j i 4CH sol'09 f US 'B-> 1 T !OX^i----ll---rA- .Jr *-L- ICC 20 AD 60 M 200 X' *0 60 m/e l:Ji.1 j5H;|!, eO 3CC 20 40 6C 30*00 ci^, 70. ^jircifKiM of p-;ik 10 (I* i" -i. (*0.1, b. mid l), c111p1nc.1l forniwl.i Cj.fl,1 100 00 601 J0] 353 j ! *i*w 'V j-a sli-XjCCJ._*_ 100 20 40 60 00 300 20 aO 60 m/e >8, 1 ' 3Sal) 90 300 2) <0 60 60 aoo F'.'-l 71. 'jk v.`.;r,;u m p.-.d. I t (lie nnr sj54.ll! pM.il i-'U cum'iil chrr>vn.\l"\;r.i*n m-; vl-. for Aroci'T i-ii. I IX' /'in- I 11 j 7. cmjiinc.il lnnmt!,i I, f, 100 j 1 00-j 6C-i a1 I *77 _L _. U>00 20 40 fcO^aO^Wx) 40 60 *-) >00 20 40 63 60 4 03 f 12 7i \l , f I -- vr. I I I I c~ V. < ? < I| CO o n* o <A Q ! I; I <> e Or> '------------_- ~*-5 t i i' -1 rv3 rvj ko. o- <1 A) ic ti m *n DC T 1 O rw 3O 3 t 2 I a [ 14 - -i I> i ! 1 LV * l I *- ; 4 -11' rj STLCOPCB4011044 r iS U ;r O C (< j f f// DSW 0 2 7 0 8 3 if* m is. tr T. C Z ? A D >n ''"I -t i *n iv C 'A I s lA| -- _ / c > r* X -r u-, 7? ^ vr -- m r -T --s l<*. o - ^x Is-/-. -- -- U~1 -C C 'n c r >n I I s C- I s - s -o e -o c r* c* c* - c c- Is T tV -I -- vo ^n n v* tn * in ^ C / 'r. : A c C C C* 'i n n fi n fi N i n 'i r* 'i * r< pi p pi -- u- C I'/. C ri m *n >~i **t > iv-i I ' - -/ r. - o -^ STLCOPCB4011045 OSW 027084 i STLCOPCB4011046 ( y ir iri! in ' > jmi *.| j ; t/</ m i I i! r ii p u ` j] t ] | V in ! ! i Co:'. < \ " ' ' -;; I ! l : ;" . A : i . I '* i - . - . ' . 1 I : i.; . p , l , : ^ p . ;i. I I , - "U ,i \; | n I ; o ; ; -t. . . > n.' >.: : . -.tr'i.ri r;.: '`i;i i 7 pi * r iri*Jn;r i |i*.i t; rt -;n . v. I '< r utr l .-mu .;] ,i; i- ,tc : ; r. >ii ::n; in , m j ; ; ;i ., ;, ,1 ji h r ; v .; ,,:i ;s\-. 1 I - . - :: i . ::i I, --av-' . . 3 r:;. < 'i'! vn< n'!< :r !>!*() .,.4 .a ti I. J, to\i,-it\- <>(' ii;i~ ' i .- - 1 m. icon: ! ':0 ,-ri .':.t :i . m. r. . i t:.: frirt!* r. -.1 a tht-d p. me >.map m: a A w :i`* me Iinleil tci r.i . ;,d .' m ; nra C mail w i m; a ti ;>v ma " -;<`i :u lr11' and inn i ori >i.j] e,u ; i> A ii'.i-i'. fn the r ; >. i :i . :< r.i; >; \- . ino; i-.il) of tin- !' i \ ;r ,\Ni> ur h n> i'i < 7' or ivr.A 4- I r \ ii*-i rct` \ ; ;-">n :n;\ \ \ : i r,\..L : m \ s=; > <* i; t p.< mi r r i c i \ i v < -i pr : is ?i<\ p(a* A'1. R'l.ifur /cttH'Inr.* *.//T<: h t/u.i A'' nf (nl>rn,' (if--m 5 *< ;ti td'ulitv '! / .'Hi, . I J ;o 3 4 U C! 1 2 * .5s \ 1 11 > i'll 3 35s j ri. y>- (; c;, 4 - -1- IT CS` ya t? 11: 5 i 4 y,f, [7 r Si T. t r,-i lil'i.' i; I >' M n 11*. \.u !iicr.ui.ipl.ih.ilchP I Ir \:u.o!orihip!,.ravi l Sr;Lu hl< --nit;; i!ii :i \ i i'f ;izn|ur;m (lc:Ua ` 'cpi.'tc)'-lf)rr,ri:v|>lit!i.i!^ rjc a U-`U iiLm;h r lnt(."l to dicifliiu : oo, ^ M.i's r.wnil'-M I),jm -l on ( ) - ^ wore aualw.rd In' 1 .[.(. eniolovm" a \'arlan* Aenicr.n.ili cliroii'..'!tiir;ro|'li with clei'tfn rapture detection. The .alt. v t;S lit. Pyuw ylaa^ column iw hlUu with I0",, I)( -ioo on ,Sn - too n 11. <11 (las-( hrnin O tuul oi O'ra t'rl at 2o<> ' with :mr''^cn as carrier fta- at 50 nil 'min. M.'i'S spi'ctrnnu'trt' was 11 ta lrkntilV 1 nuipmtnils pres ent in the polar Iraction dictli\'I mhcr-licxanr) irnm (lie r.'lumn frartin;::.tton of PCB's. i-'or this purpose a CH ^ mass sp< ctronietrr rVarinn MAT) was com !.<l to a Vat ian .Ant o"ra ph t \ ;x` .A550U oven, u itli a 5 ft ' t /o in. IT res plass r 1 >U; 11 in 1; I lei \ with to",, iX'-jon on So- too mesh fuis-Chrom O. Tin: design of tin: intrriai e !>v;uv.-n 1!ic almw "as rhnunatoprapli n;i<l the inns; sp.cttroineter has been ril;d in.' Tiinnoi vi i; hi: r,K.u \v ,\n:j Hi:t,sNi-:ii!"`. |-iipl:-rrsnlution mass spectra were taken on a donble-h" us .'prrtrouisier t\ | e SM (Vartan MAT) Exact mass measurements "ere made In' the peak-inatcliin" metiiod aiai 11 n-;isi::imtents were also made Irom spectra wlm ;i uric rerordeii on photographic plates [iroeesscd lie a Vnriuu MAT on a l.eit/ iimiparator SAMi. Ouantitative f.LC information was obtained via uiuroioulona trie analwis of the third polar i-Tonsil column fractious usin" a Dohnnann nueincouloinoter cca-tled to a Microtek Model MTi-u gas clir-niatoitrapli wuli a 6 It X t't in .phi's column eont.iinini; the same 10% DC-200 columns packing dc-i ribed above. T lie STLCOPCB4011047 DSW 027085 To M......... , n I,. . .a I. 11 I.a.r .. I1U1 ii/.-ru, .1,1 ini..' N,, |.|,I .............. . ll'im lln U.u U I r.., . l`ri.-s i-i i ! 111 1.1 11 \i-i uni rin If *r I'l'h (] << ik ( m I-1: ,"'i u tility , i i mi -'jii ;i I . li- li ilm liiu ;tnd t< * \u ir \ m l! .i' i l i \ ' i(r ,1 i<>ii f i i n n ^ !i |11->rm, (< <I [ k- it l-- a i h I ^u 1 (ii i i11 STLCOPCB4011048 STLCOPCB4011049 V| N i i y. ; ; 4. . - /. -! ( i .w V VV f. W IISMV a;, j r^-T-x ; (. -r. . :7 ; iv :-;s 1. 1. 'i - k l1 1". I's'lfv, A !jrA isr F J i ;*i I 'A ,'lii 1 r *\f (, O Pf; nv ( H [1: r . C nf ,sn ,1 i3 i< ni F4I' 'v.', 1 (Sj ^ "sV `.il*.. |lni r,;i i \t \; r \ > j M %S . J u a n n 11 ? OlC**' T 1. 1Vfc'uv. i F * r1 nc^ \ M' i' I;, I ;i KI ' `' ' ' ' 1 '' ` . ` 1L j ,s- A ' -''U V \ < 1 1 i' T p,i ' N 11. ,\ rita 'ib*)' i.i J -iv !>>!. -n i.-r'iui F--it' cl . 5 [ |-x; l ' s ' :-.'* N . ' ! V .:i., r` 1 : (; o 7 j I'. ^' 1 ' ; in >`"*5 : \ ' v- >i .'no j i 'nr 1 ; ii to ' * ' 1 ' ; Li' 7. ,Y. V ;<) 1 '.s > ^ v K x:' i; " ^ ' . :< -Vi:-.. / Hvtf . 11 {10 lO; y, jt " w* ' I': -\ i M,.f / ii-'i-KU \in ' f* a, F \ ^ K\ F ' 1 :. \ 11 i'r'rx'i'x. i (,1 A. V l-^; ,V<t:-sm ^ :n 7^ 63 A iii't'.'F am; I\ Makai*i .. j fur it-`n C./'r(ni: To u nt . i (I *i'i; 37 r jt (<<*'*>' 4-l,s ^ [) j jl x.Nx'N. p. U pARPtb'i. 1. ' Lowe. \ j 'An sos. ] a>u P D. Wilson;. Bud Ei -1-..-rt C'-nt im 7< . b . n; 11 114 6j P A Mills. J. F f-.ifv avo A J ^ss .Iff. CHr . *>*>3> 1^2 C6 P (vr>rn.i{ t<:;;iti*>in.r.iUo in ref f> j 67 l) ] IUn4*n a.no A J Wjlvo-m Prutc M-m; J . 1 (n70) \ OS J KP!L. L. I' i'R:_c7xH <M' 5 M S* l AO II.Ir.in C' >il,vn Toxir-.i'.b Co T W. PVK Is. j ( i. <' asp A I. W'lLx'is. |b, n,,d t-neir.m. C',tila--n. Tjusv/ , 3 A vm- 1; - \L'K.\ .( 0 > >:/>! . A.ph l-l . IJ n')yf,. m:: 171. ' A, \\ \ !" v \M. J. ^N7-S'. (X,... Wri,*. 51 |i-,,r ;o S I'l.FSTP \N|I. A Symsr.PI.N ssu J iv\H'>L. .Vn7..r.' t\I (IQ71I 4^*7 71 G es t !> a.m*K Nonf v .-!{/<./' . 'si a"<(. 24 {io;o> toy*. / Wji> 'in.'.t, 2nd I '1 . Roithiv \ ork, * ! s * ` * ' . Ir:'. v' A : l `> s f t r. j. !>:,{ HZ'-.rr ^ . ' i.v A'. V.. : V. n , n , y ! n>i r ./ .. r.`,. :: ijr,- .1 ' |<) (1 j ;: ,.Hj . ,,-o j 19JM >;. i i 7: K NsiRFv am' Wksi^o. At fa CL"r Srnitd . |ki*>5) it>i) 73 M F. Ko\acs /. .lu .He*' Cii--a , -,o 74 D L. G\st, VV F. J 1'ntLLirs ano P l. V illf.sf.i ve, (lull. . 6 `.10:11 i<->i 75 J A n>. M:. ANH W Mot.sss'auk / .L>i Op:' .In-tl Ch ft F.m;'on Contain (iV^'i _<4 7 7otu.>;, ' r j l '-O i* 1*1 /;. .7i-v 5<i. ji 293 -(/ M K \tsl 77 T K*)jriA. II J'vki-moto ,sso S M m3 Jnp j 1/ M'<1 . 23 [f/t'i 4 tj *' ` 1 1 > r- -: AS' /, M) (iAI.LO. t . 4 i ( !' 1- >> Jf j s' 'f. ; .^r. \'i ) Vf.r^t.tt. M iv. Mni.iar ami O (i s;-' ..' 5 r. : v. .%'.*> \ i> i\i .>. c>ic*-. s,>c. .v>-*. Xt-* > / _. 1 ' . - i- J *sn S \*i' Muiwv. F/nifdi r j. - f J ; is *.M 'i > >. i > 1 .7 / ' * I'h.11 nitii n! . 17 ( nr7*)j *<yi 7I L. C. .VUvjiLLL. }. ,<s; Oinc Ax*. (.'/< . 4o p*>37; '>00 );9 K 1<. Takpant ano J OG TaIIO'-. Saint'. :t<> (1 ><.'<) 725 yty S Jknst.n. A JtP\t;.Ov. U_ Lance anO lx ll [LalmoRk. /-`i AfGr'jo/C 5.1. [:AO Trcnn.tai Cnnf. fit AZoiiiri* Pni/itthm. If.-mr, Ok </-/?, /'*7< [ 51 P Alt ling an () S j 1. nv \ . f Hfl/, ('imr , 4: J 1 5^ 52 T. T. Sa MMlOT. R W KisKHKO' OII a> r Curss, RuU llnnren Contain. T'iitf `1, t> ( 10711 > ' ' ' ';:i' <* `Mi./ 7 :* ,* cv >,f i./!/< "f1/ /f;y>fc,nv<:.v or 'iroc,>"' s, Jnnr M5"S3 R. I. Stavlfy a\o )l T i.rl'A\'o\ fm . J Ass. OUc. A uni. Chan . 4.3 {ki'n-,1 VN-' ' ' r . j. .-i^r l-c.,- U . i I *),' o) 1IO*. smt. :i f> , v*5 ..V A V ; . ; I v | 'AMI.. .V j. 2 .'5 : 1OT1V. r.-t J '' '. 11 I. < -r- \|. J I'111 u ip'. .M L.C(.aok ann D J. Clf.oi. hull J* 4 V. fjTKo. Ruli Lnr:r n r"tc!/. 5 (10701 :79 Sj H. W1:1 nc.\stk,%. W D. Koss. J. M Sc'ilabf.r inu (i G. Wmellfr. Anal fiofl:) jo 1 S'j N. L. C*K`.;onv, ] Chint 5 c fU). (in^vj 203 S 7 F. M Emfrv \ s i) f. VJ (iASf.R. 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J r n. .C.,. ft; 1.^45! . y,l r..; . 4 xi ,\M) { T k^'N.\t>}l trH r.iinr^H C''lta>n r*r<ro/ . 4 41 '|F*n i J li . * '*'1* ^ r 4, . 1 Iw ;* V. / i'> 1. /i.*i. ft,i!i , \n rjt? . j. <"-.? .nmit^r (irj-r, 1 in,'. I-..-,nr.. Cnutom 11 ^177 jioriV i \ork. [O'jo. f> 295. 95 S. W\ Fip 1.lma\ and T. I. Habrv. / Ass Ofti Anal C'Af" . 5l (,07:) 490 S. P. Markky. An id Chi'in . 42 (in;o) yin 9? FiSUcut' .`lit*lytu.al Manual, i-.w-l auslDriu \<|nit;iiNlr.itign. W.tshmL'.'n, 94 M C I iinnowt# deHr \ i;w ano C ftm s>m 4*jo' Cii . 229 {1007 )21. 99 D l; Flick, R G O'Plll am* V' A O'Ilo?, P-"tr.''*' .''ci 42 (i' 3' i4r* ooU H v I f ,\c. F. Anal. Chan.. 16 (1904) 750 Sn-CI. Ill 5< (. 'A1 .kk, is- f'rlUridr Conf Lnuitrudcd Rf 'idit'S tu //- L,,% :( 5: * v i -1 I'F .1 ' K; 1. isa s ;i 11 S * 'lco :t. fin'd F.miran. C<inlat Tot tcol , 4 ` ' f*-)' S'* ! r *. a s A 1 .ii 1 (l :!. 1: ' ,, - \ s<)6 2 V i t i I loi B M .\ii;Lit*KN, /. Chnjmatnpr ' [irjftN} s5# i2 0. Ul'T71ng*:r, W. ]). Jamieson and V. 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