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Copyr'i *. 1973 I C E l 'i " r ; / r V Vol. 13 . No. 3 . December 1973 A M ibsidin ry of New England Nacdear A t'iu ilir U ci'io n n l h u h ortilory. !\tilinnal lir s r a r r li C .ininril o f Canntla. H a lifa x , A o rn S cu lia AM) I{ulgcr8u'crkcy Cuttrop-Hunxel, Germany Jn recent years there has been increasing concern about the possible harmful effects of organic compounds in the environment. An important class of pollutants are the polycyclic aromatic hydrocarbons (PAH) which have been shown to occur in air, water and food (see Table 1) via automobile and engine exhausts, the burning of fossil fuels, oil spills, food processing, tobacco smoking, and from natural sources. Moreover several PAH have been shown to possess carcinogenic (1-4) and mutagenic (5, 6 ) properties. This review is designed as an introduction to the general literature on PAI1 with particular emphasis on environmental analysis of these compounds. . \ l `\ l i : v I.AJ 1 ! Although several systems of nomenclature for polycyclic aromatic hydrocarbons have coexisted in the past (7, 8) the 1UPAC system (9) is becoming generally accepted now. Common names for the basic ring systems are retained (see Fig. 1 on page 2). For the construction of more highly condensed aromatic hydrocarbons the basic system is lettered (a, b, c, etc., (see Fig. 2 on page 3) and the "added" rings numbered in the fashion shown in Pig. 2. IN THIS ISSUE Article, Polycyclic Aromatic Hydrocarbons .......................... 1-11 Polynuclear Hydrocarbon Standards .................................. 12-13 Article, The Solubilities of Twenty-one Chlorobiphcnyls in Water ............ 14-10 Article, Progress Reports on PCB Isomers ............. 10-19 PCH Isomers, 99% P u re ............. 20 Polyurcthnn Foam Plug* PCI! and Pesticide Extraction 21 IVrclilorlnatlon Kits for Analysis of Polvchlnrinnted Aromatics ...... 21 Polychlorinated Diphenyl Mixtures, Dilrenzo-P-Dioxins and DiDenzoFurans ................. .... 22 Pesticide Standards 23-30 Precoated TLC Plates .. 30 Pesticide Solvents ............. 31 Pollution Standards, Catalog 32 JJ-:\t IONS A M ) R E A C T IV IT Y The standard reference books on the chemistry of polycyclic hydrocarbons are Clar's two volumes ( 10) and chemicoltcelmicnl aspects of diphenyl and the terphcnyls arc discussed in an encyclopedia article (11). The analysis of FAll Iras been reviewed ( 12). Most polycyclic hydrocarbons undergo the typical substitution reactions which nro known from the parent compound, benzene. In addition, many of the polycyclic hydro carbons show a tendency for addition re actions (cf. Fig. 3 on page 3) ("fixed double bonds"). NfcV 0 3 b d A 3 1 I T - I .( a u io m c i 11.1-< ? ? ?' 3' - . ' , ./' {' f ! : y! ff' ,i , ..im! ittm ilk ji of have <6) e 9 i .C c C/l *" systems. ", I cd >orMbtc \t<-' ? i H- '-i>. l; ; .> C. e *<55^ 6 7 Ir iph any I*n r cpi.l (c t efi* ( ( l i c e n e) C iI 43 Ftuoronlhcne II i? ' er Bent [o ] onlhrocen Dibent [oh] onlhioeent "J1it* reactivity oJ jrolycyclie hydrocarbons towards addition reactions can be (wplaiiicd and predicted qualitatively by O a r's * -sc.vtett theory (13. M ). A rjuantmn mechanical explanation of O ar's theory lias l>ccn given (15. 16). The stability oi polycyclic aromatic hydrocarbons depends on the structure as well as on the numlrcr of rings. 1lesalrcn/.woronenc (Fig. 4) for example is an extremely 2 NEV 0 3 6 8 4 4 i J i Bcnzo [a] pyrene in city air (meg/ 1000 m ') Los Angeles ..................................................................................... 5 London ........................................................................................................... 63 Bonn .............................................................................................................. 133 Benzo (a] pyrene in food (m eg/kg) Vegetables .......................................................................................... Smoked foods ....................................................................................... 10 1-10 Carcinogenic Polycyclic Hydrocarbons In waiter (m eg/m 3) G roundw ater................................................................................... Waste water .................................................................................. 1*10 100,000 Benzo [a] pyrene In cigarette smoke 1 meg in the smoke of 40 cigarettes Adapted from M. Zander, "Analysis of Polycyclic Aromatics" presented at the "Third Annual Symposium on Recent Advances in the Analytical Chemistry of Pollutants," Athens, Ga., May 1973. nophtho [ 2,1-a ] onthracsn* Fig. 2. Nomenclature for more highly condensed ring systems. Fig. 3. Examples for addition reactions occurring with PAH. Fig. 5. Heptacene ring system. F ig . 4 . Hexabenzcoronene ring system. stable hydrocarbon; even at 700CC neither decomposition nor melting takes place. Heptacene (Fig. 5) on the other hand, is extremely unstable with a reactivity that surpasses many free radiculs. The photochemical stability of a number of PAH has been investigated (17); the literature on the photodecomposition of the carcinogen benzo [a] pyrene is discussed in reference (18). 3 NfcV 0 3 6 d<s5 I'All occur n.iliir.ilK' in petroleum and arc also m uIL, i/ cu !\ living organisms stuli as highci )'>l.u11s. algae and niicmorgancn.s \ i I. IS. I!);. r Ml in' toimcd as p\ml\s)<. products at high Oinpciatmes {20-2?) and can. there fore. I< loiiiul in coal t.n. automobile exhaust. in emission hum hiill um: fossil furls I haeeo smoke. \ pai' l. studs ng p,nlisnla'v p . s c \cIK lit.mi m .it'ii 'i'ONJ concluded r-t enth !' nation-wide cinimssiiin o* l>rn /t< |a | p\s 11 * in tin l S . i,owi.t I i. -is f !..: and |v,-\< i *rn< lalinn. (>''* 1rs fimii i'.*fM"* I'timat" n- n ns ii. - m l,- . i: i 1 ' liii' I*' ini :iin*i v ' 11**% i .? Ai i. ; ;li * l `.\ll *s aim * i.r\ . . ; . * ... ** J l J' i:i *p.*i l :;*.I\ a. . ' )i< I. in-.i. n:i,r ir i iiliK. hi. 'Vi, o a: !;i eo.l ,i a:.! a;:- I**? and dtsiilhcd Hi rcfei'UiM IG<* >2 . In cans ul tin- direct iulaki in lainian mill 11 i . m uch v. .at. has bee., c a m e l .mi In dc\c lop analyliral methods and d rlrn n in r levels >1 )*lyc\clic aromatic hydrocailioiis in ikxIs (23, 33-I3). le vels arc highest in smoked Inods (occasionally values > Jl) ppm total polycyclic hydrocarbon arc observed), whereas levels in unsmoked loud pioduels are generally lower than 1 ppm. A large number of polycyclic aromatic (including Irenzo fa | pyrene) and licleroaro- m.itic hydrocarbons as well as related compounds have been identified in tobacco smoke (41-16). Polycyclic hydrocarlrons are also released into the environment from general oil pollution and the ever-increasing oil spills (47, 48). Analytical methods for the identification of hydrocarbon pollutants on seas and beaches are reviewed in reference (49). The uptake and cfled ol oil (including the polycyclic aromatic hydrocarbons) on marine life is of increasing concern (50-52). \\AI \sv., The extraction, separation (clean up) and analysis of I'A11 have been extensively investigated (53-56) and a review article on chromatographic procedures gives a useful comparison of the various methods (57). As is general for the analysis of any trace component, the need is felt (97) for nn extended collection of reference standards of polynuclear hydrocarbons and their alkyl and hydro derivatives. The later type of derivatives is of great importance since it is not ordinarily discovered by the conventional UV or fluorescence methods and is best identified and measured by MS. The alkyl derivatives arc in many instances more carcinogenic than the parent compound. The carcinogenic PAH benzo [a] pyrene has understandably been studied in some detail and a thorough comparison of the analytical methods used in the determination of this compound from air particulates lias been reported by Sawicki (58). Analysis of benzo [a] pyrene in cigarette smoke (59), air (60), bitumen and plants (61) mid water and other commodities (62) has recently been described. Thin layer and paper chromatography --TLC and paper chromatography lias been used successfully for the separation of polycyclic hvdrocarlxins (57, 63). Cellulose, .act viated cellulose and aluminum oxide (64) and silica arc the preferred layers. A mciliiiiidl-cthcr-wutcr (4:4:1) mixture (65) has been recommended for acetylatcd lelbilosc layers. A typical chromatogram employing this system is shown in Fig. 6. (66) 1apn i Iihiiii.ttngr.iphy on acdvlatcd paper lias Ihtii used for the chromatography of l.Ml with solvents similar to the ILC separation >n acctslatcd cellulose powder (67). l.leetimi acceptor reagents can lx- used to visualize l'AJl on paper and thin layer i liioniatogiains. I be Ilydroenlimns can be reinsert'd urn banged from the characteristi cally coloml clinigc transfer complexes (see section on mass spectrometry). The native fluoiesccnee or phosphorescence of PAM. however, oilers a much more sensitise method of detection (see section on luminescence spectroscopy). 4 NEV 0 3 6 8 4 6 -- Fron II ------ < 0.8 - (lT t t 0.6 E 4 - t>o- 0.4 - D @ M e o iT 0.2 ; Fig. 0. O rigin , x i t____L___I____1____t. - . 1 _ - t. 0.2 0.4 0.6 0.3 System l R f -- Two dimensional thin layer chromatogram. Layer: acetylated cellulose -- aluminum oxide, 1:2. Solvents: System I, n-hcxane, n-pentane, toluene (90:5:5). System II, methanol, ether, water 4:4:1: Compounds 1, dibenzo [a, e) pyrene; 2, dibenz [a, h] anthracene; 3, dibenz [a, c] anthracene; 4, perylene; 7, benzo [e] pyrene; 8, pyrene; 9, anthracene. Liquid chromatography - The behavior of 18 polycyclic hydrocarbons on two column materials (Durnpak OPN and 40% cellulose acetate) were investigated using an ultraviolet detector (68). Although neither system could resolve all components of the mixture, the method was shown to be of potential utility. A number of polynuclear nza-heterocyclic hydrocarbons were separated by high pressure liquid chromatography using Zipax packing impregnated with silver ions (69) and a chemically bonded phase (70). Polycyclic aromatic hydrocarbons were also separated by liquid chromato graphy using Corasil 1 impregnated with the complexing reagent 2, 4, 7-trinitrofluorenone (7 1 ). A number of column packings have been compared in the separation of polynuclear hydrocarbons in engine oils (72). Gas chromatography -- Ultraviolet absorption and luminescence analysis have dom inated the analysis of polycyclic hydrocarbons for some time, more recently gas chromatography has played an important role in the separation, detection and identifi cation of these compounds (57, 73-77). The use of capillary gas chromatography with its great resolution potential has markedly increased the analytical potential of this technique. Application of capillary G. C. have been reported in the analysis of polycyclic aromatic hydrocarbons and related compounds in anthracene oil (78), cigarette smoke (45, 79), air and car exhaust (80, 81), soot samples (75) as well as for quantitative determinations (82). Gouw et al. (83) have shown that PAH can be separated effectively on short capillary columns (10 m ). A typical capillary column chromatogram is shown in Fig. 7 (see Tuble 2). Ultraviolet spectroscopy - U.V. spectra of PAH show in the spectral range accessible by commercial instruments three electronic transitions which are differentiated by oscillator-strength polarisation and temperature dependency. The most intense bands in the U. V.-spectra of PAH nre the so-called p --or 'Bb-bands which show a molar extinction coefficient of ca. (10r ). The extinction coefficient for the para --or 'La-bands and the y --or `Lb*bnnds are ca. 104- 10r' and (10*- JO*) respectively. For analytical purposes, the para-bands are the most suitable. U. V. spectra are usually recorded in liquid solution at room temperature. It is some times advantageous, to measure the U. V. spectra in a solid matrix at low temperatures, frequently the bands are more intense and very narrow (84). 5 NV 0 3 6 0 ^ 7 No. und-s 1 Naphlb.dciK1 iJ A /uli in1 *1 I lijtiirisyl I .*. i I n . : ; 1.:;: .*nr ` . i * .* 1 `.. i t - 1-.. ..... Nit. Com puim us 2o.t CliiAvmt* 2"il> `J r.j !u i\ U no 2(: N'..;.!tili:!i*i-m*/'JVtr.i,:it* S' '<'](!:. 11-1; MV 1 `. . !"' '!/' | . J tl K!l ill'll.-, m* S'*!!* ! j ; j ib dn rj 1 . -U M a [.!) J |J.e!iaj>!bt'rije I t I-M cl](\]il.i;ii*.iilin . in* I `i tJ*M clli\l:uillir.ivc:io lfi 1`hinranllicuv J 7 1'jTC'llC- IS Jlli-H tn /.o [ii] fliiorcne I9a Jlll-b e n z o [b] fluurcnc J9 b T IM lcuzu M i kit ircne 2t> J -M elliylpyrene 21 3-Mct)tylpyrenc 22 Henzo | g, h, i] fluoranthene 23 Henzo [e] plicnanthrone 2*1 Itcnzo [a ] a n th ra c e n e 1 i : P>...... r> -..-v S - l . i 3 **i. ; !> :':*. l m i* 31 It 2'N1et bylclnil.iii!)u-eiif 3 5 D ilu ii/, [i, i] a n l'iin c e m* 3li.i JJihenz | a. c] anthracene 30b Dilrcnz [a, li] anthracene 37 Heuzoletra phene 38a Henzo (g ,h , I) pcrylenc 3bb Pivenc 39 A nlhantlircne JO D ib cn zo [a, e] p y ren e 41 Curoncnc 42 Dibcnzo [a, o] pyrene 43 Dibcnzo | a, i] pyrene 44 Dibenzo [n, h] pyrene (^uaiitilativc analysis of PAH by U. V. spectroscopy is possible after separation (r. g, bv TLC). Tor llu*. analysis in mixtures the qualitative composition most be known and a large number of key bands be measured. Mathematical treatment of data is usually done by computer (85). A collection of U. V. spectra including a large number of polycyclic compounds is available (80). Fig. 7. Clnonm Ingram nf a standard mixture of hydrocarbons. Glass capillary colum n co aled will) S lv o 2 . Linen) p ro g ram m e d te m p e ra tu re J 00-301 . ra te 1 .8 /in m . N um bers correspond to com pounds in T able 2. NEV 0 3 6 8 4 8 Fron H Fig. 8. Electronic spectra of phenanthrene. A. absorption (UV) spec* tram (cyclohexane); F, fluorescence spectrum (benzene); P, phosphore scence spectrum (ethanol, isopentane, ether, 2;5:5; 77K). !00 300 00 40) too Luminescence spectroscopy --The fluorescence qunntum yield for most PAH is relatively high to make fluorimetry a very sensitive and therefore widely used analytical method for these compounds. (For spectra of polycyclic hydrocarbons see (87). Fluorescence of individual members of a mixture can be observed when their absorption spectrn differ and selective excitation wavelengths ore used (88). Fluorescence spectra are usually recorded in solution at room temperature. Spectra obtained at low temperature in a suitable mnitrix ( n -alkanes, n -pentane to n -decane; cyclohexane)' frequently give very characteristic spectra showing many bands (ShpoVskiispeetra). An interesting new technique is the so-called "quenchofluorimetry" (89) of multicomponent mixtures. This method is based on the fact that the fluorescence of some compounds Is quenched more than of others if a "quencher" is added to the mixture. PAH with the fluoranthene ring system (89; quencher: nitromethane) and perylene (90; quencher; methyl iodide) for instance can be determined in complex PAH mixtures by this method. Phosphorescence spectra which are measured in solid solution at low temperatures usually show a higher selectivity than fluorescence spectra. Fig. 8 shows the U.V.-- fluorescence and phosphorescence speotrum of phenanlhrene. A comparison of U. V.-- fluorescence and phosphoresence spectroscopy is given in Table 3. For the analysis of PAH in the environment separation prior to analysis by U, V. or luminescence spectroscopy is necessary. The most commonly used combination is TLC fluorescence. Samples for quantitative analysis can either be eluted from the TLC plates or more elegantly determined by in sifw measurements (91). Mass spectrometry--Mass spectrometric analysis plays an important role in the Identification of polycyclic aromatic hydrocarbons (92-98) and this technique is particularly useful in combination with gns chromatography. The combined CC-MS TABLE 3 C o m p a ris o n ^ oX L:.V . flu o re s c e n c e a n d p h o s p h o re s c e n c e sp ectro sco p y Method Selectivity Sensitivity Reproducibility .V. Fluorescence Phosphorescence + ++ +++ + + 4-+ 444- + H --b excellent 4-4-j- average ++ ++ ++ 'Adapted from M. Zander, "Analysis of Polycyclic Aromatics" presented at the "third Annual Symposium on Recent Advances in the Analytical Chemistry of Pollutants," Athens, Co., May 1973 NEV 036849 : 69 * n 4* "*T3T Fig. 9. 70 eV mass spectmm of benzo [a] pyrene 9*cyanoinethylene-2, 4, 7-trinitroHuorene complex eluted from TLC at different sample tem peratures (as indicated); (a), benzo [a] pyrene (b).CNTNF. technique (97) has been used in studies in which the identity of the observed gas chromatographic peaks has been confirmed by the characteristic mass spectra of the components. PAH may be located on TLC plaites by the characteristic color they form with electron acceptor reagents. The complexes may be transferred directly to a mass spectrometer sample tube and individual spectra of the compounds be obtained by thermal dissociation and fractional sublimation in the ion source of a mass spectrometer (98). Mass spectra of benzo [a] pyrene and the complexing agent 9-dicyanomethylene2, 4. 7-trinitrofluorene obtained at different sample temperatures from the complex are shown In Fig. 9. The mass spectra of most polycyclic aromatic hydrocarbons exhibit several common fragmentation pathways; i.e.i 1) The molecular ion Is usually the most abundant ionic species and this greatly facilitates the determination of the molecular formula of the hydrocarbon. 2) In addition* the M +-1. M t *2 and M t -8 species are also relatively intense, 3) Methyl substituted aromatic hydrocarbons exhibit M f -15 ions, 4) Doubly-charged ions are observed for most of the aforementioned ionic species. These characteristics indicate that mass spectrometry does not readily distinguish between isomeric polycycolic aromatic hydrocarbons since very few fragment Ions are produced and the molecular ion tends to dominate the spectra. This characteristic can, however, be an advantage with the GC-MS technique since the separation of many isomeric hydrocarbons can readily be effected by gas chromatography and the resulting mass spectra gives confirmation of the GG assignments. Infrared spectra --IR spectra ore useful for identifying alkyl derivatives of naphtha lene. IR spectra, do not, however, have any advantages over U.V. spectra in the identification of unsubstituted FAH, but are very useful in the structure determination of new compounds (12). Surftur .v..:.!.';.. .>t-. Proton magnetic resonance spectroscopy can be used for the identification of PAH and their alkyl derivatives (12, 14). Experimental difficulties exist with the highly condensed systems because of their low solubility. 220 MHz Proton magnetic resonance spectrum of benzo [a] pyrene has recently been published (99) and C-13 NMR spectra of several simple condensed systems have been recorded (100). 1'!! V, * . It is now generally accepted (101) that to be carcinogenic, polycyclic aromatic hydrocarbons undergo metabolic activation. Epoxides (102, 103) may be involved and reaction with nucleic acid components (99, 103, 104) have been suggested. The 8 NEV 0 3 6 3 5 0 * - * * l' ! - I!.!i !\t V t I.- j,- . `j 'j j S tr . . * ;l*. . \\, :,! .<| -St-uUi* ..nmiatir liynn.:trlum<- (-15. JDS. ID:' >n ii..iuijn.ils and : ...' im.cish- > U i jit'ii lidi rlcriv alhvN. ( lUtputimis .ire ; ;in' *! VH 0 . I(*9. I |D) !j;i\ been simun : n'.cnnedsilev : . ):. juil.'i.* ..in! n.i i.itMi!,'-,:. ! I'AI l-ep- Nit!.*'* Ims ret* * hit i e.\lc:`W'el c 1 ` ' . 1 1 * 1 ' , . . r ., : .. > * i . .! '* . J , \ \ :!. * l - *. t. i.-.rii-. J!. \\ .. 1n 'if .'i- jj ,,it:! I'.i' '(`lifiii'sl; ' j | Annuali.- IJydmeal lions." KK-'iu. A.ii-'eliliiii). lilt*'). i. IVliluih. J... \V. I'laumi -.lini II. 1,, Falk, ''Chemical M utagens/' Academic I'leys, .Now York. 11)7b, jx 275. (>. Miller, lx (.*, anil J. A. 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Ftmtunges. Clirom:ilngraphta, 3, 5U7 (JU70). 9 NEV 0 3 6 8 5 1 Cl 2S. Romei). Jj. Cu.* - miti Wasscrfach. ] OS, Ji72 (1907). 30. Il- ( 'n;i1 Tur JIi'vi.imIi Assnriuliun, `T h e Ct;d Tnr Data Hook." 1033. 31. Ki libri. J).. A. larjlhr! and S. G igulrii. FnSol, Laide. S, 637 { 1035). JJ. 1 mg. K . ). tini 1. Migri t. l 'n il* c l:i. C lim i. Marvch. S, 9 J (UC>7 ; . 33. Criminer. e:.. Mrtul Kalile IO. 57S ili'OO). -i l. tan n ilir. I'. \. .uni I . Iliv/elli. Iti .hit- Iv.v. 0. 00 (1065). 3 r>. Ih m ani. J. W.. It. I !t ,;giie Jr.. 11. M. W],:u aliti li. li. Firy. Jr., J. Assoe. Oli. (.Iteli;. -IO. "05 t l'ifiii , ;!*. 1!... ..Ml. j. W.. 1:. 11. Wj,iU |>. K. J;n \ (.. .nul J-', W. TiinYr!!:I, (, Avmx\ 1. ( .linn. !a. M i i 1'!(.*() i. 3, 15-- 1 : !.. i : *:. A-.*. Hyp. JO-.-* ` !Vi. !*" . - . . i C . . i . J. 1 I y A i ' t i .i, ; ! ; i :, V. V.- I i.l ' ! '.. \ . I , i - *U:.\: r... : 11 . F ; r \ : * . . ! li - r.i/it*. |. A ;i. 1`a:;.: ( 17, 5-7 1 * 11. ! *1 D. 1- . II. 1>au:i. loiihie Ke\. 27, `9 (1909). u. ( A. Ililtiiiji.niil!. |. A.vstx\ Oil. Anal. Chem. 53, 631 (J972). JO. J'ii/ia. T.. li. ]J. White and J. \ \ \ Howard. J. Assoc. Oil. Anal. Chem. 50, (3 ( 1073). JJ. Wynder. 1*1. J... and D, 1loirinann, `Tobacco and Tobacco Smoke," Academic Press. New York, 1907. 15. Caruguo, .\. and S. Rossi, J. Gas ChiomaUig. 5, 103 (1907). JO. Xcnrulh, G*. li.. J'lunla Mcdicn, 22, 207 (1972), 47. Jioyland, 1). li. and U. \V. Tripp, Nature 230, 44 (1971), *JS. Rluincr, M. and J. Sass. Science, J70, 1120 (,1972). J9. Ad lard, K. H., J. Iitsl. Petroleum, 58, 63 (1952). 50. Nelson-Smith, A., Advan. Murine Diol. 8, 215 (1970). 51. Lit , 11. J'., H. Saucrhcbcr and A. A. liensra, Science, 177, 341 (1972). 52. Lee, R. 1\, R. Saucrhcbcr and C. IT. Dobbj^ Marine Biol. 17, 201 (1972) 53. Sawicki, E., Chemist-Analyst, 53, 24, 50 and 88 (1904). 54. Sawicki, 15., CUC CriUcal Rev. Anal, Cliein. 275 (1970). 55. Leillie, \ \ \ , "The Analysis of Air Pollutants," Ann Arbor-1 hunplncy Science Publishers, London, 1970, p. 253. 50. Dubois, L., Corkery, A. and Monkman, J. 1*, Ini. J. Air Poll. 2, 236 (1960). 57. Schaad, R. E., Chroma tog. Rev. 13, 61 (1970). 58. Sawicki, E., T, \Y. SUmley, W. C. Elbert, j. Meeker and S. McPherson, Atmosph. Environ. 1. 131 (1967). - 59. Davis, H. J., Anal. Chem. 40, 1583 (1968). 60. Strombcrg, L. E. nml G. Widmurk, J. Chromalog, 49, 340, (1970). 01. Scliamp, N. and F. van Wassenhove, J. Chromalog. 69, 421 (1972). 02. Sfddlql, 1, nml K. 11. Wagner, Chemospbere, 83, (1972). 03. Sawicki, C, R. and E. Sawicki, "Thin Layer Chromatography in Air Pollution Research" in Progcss in Thin Layer Chromatography and Related Methods, A. Xicdcrwiescr and G. Pataki (Editors) Vol. Ill, Ann Arbor Science Publishers, Ann Arbor, J972, p. 233. 04. Sawicki, E., T. W . Stanley, W. C. Elbert, awl J. D. Pfaff, Anal. Cliem. 30, 497 (1904). 05. W ielam l. T li., C . L u b en , ami II. D o ten n u n n , E x ponent in 18. 432 (1 9 6 2 ). 00. Kolder. M., C.uldcr. 11. and ScInVsser. R., Z Anal. Cliem. 206, 430 (1964). 07. Wielaml. 'J'Ji., and W. Krucht, Angew. Chem. 69, 172 (1957). OS. J\e*. N. F. ami J.. Cmflnda, J. Ass. Olfic. Anal. Cliem. 55, 757 (1972). 09. Yivilecchiu, Jt., M. Tliiebaml ami H. W. Frci.J. Chrunmtog. Sei.TO. 411 (1972). 7(1. Ray, S. and R. W. Frei, J, Chromalog. 7J. 451 (1972). 7J. Larger, IJ. 1.., M. Marlin, j. Lohcuc and J. Gunchon, Anal. Chem. 45, 490 (1973). 10 NEV 036652 \ . t . :. < ' I. U. and K , I .p i. Environ. S ii. T u Inni'. 1. >2:: r. New ^ml., i liJii')1. s s - S.n-.iVki. I*... T. U, llauw r, u. T. \V. Stanley. l.itrr. J, Air Pollution 2. 253 (I960). s.iwii-U. K., T. W. Manley, u. \V. C. Elbert, Tahu ita J j. J-13*3 (1964). 9U. "/jit. Ut , M., / . tuul. Chon. 203, 19 {1973). i)l. S.iuicki. anti J. 1). IMafl, Anal, Chini. Acta 32, 52J (1965). 9~ M.ijc-r, J. H.. lVrry. . ami cadi*. M. J., J. Chrom., 48,326 (1U70). bJ- lam. 1!. ('.. 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Res, Commun. 43, 1010 (1971). inj G.t0VVr*P- L ' rtnd p *Sims*Bioclicm, J. 129, 4 IP, (1972). in* ^*1,Va^*erh lb and M, Calvin, Photoeliem. Phot ninni. 14, 641 (1971). Inn* \ ll*p ' A .,/. Naturici.st-li. 27b, 731 and 650 (1972). In- ^'^Itlnu-istcr, A., D. Tsai and X. D. Weiner, J. Pharm. Pharmacol. 01, 1065 (1972). < Johnson, M .|). am! Calvi. M.. Nature, 2 4 , 271 ( 1973). Wilhums, It. T., *'J)elmicatiiin Mediunisms" Chapman is Hall, Lnudon, ( 1959). ,l l! * D .lU \\f l v V i . .. . . . . . . . . . . . ,* . , i n n 1 - l i v n v (1972). JM J ,,IIS* P*. RiiH'hem. J. 130, 27 (1972). S',,,s* P*. Biocliem. J. 131, 405 (1973). 11 036853 NV h\i!' ,: Ji\ ; i***c 1\ , \ ' g /'l.ii/l.Ci \i t naphtlivnv uiulii.i* I.i : . .. * 1 J ' . : ! : Sl/IKlIJI/JII : . i-V Hi* *-** i . i in . !*>!/ Ci] . ''In.r.ii-:. -7. j.'- J o 1J'*is i>,. jV . S', i ;! i i, J-J'.' II.'I'lNU.iti. Ill 1.2- Hi 1;}ll lit - *.. `h fp!;-tvm' .Mi-Uvnz.u lb J carlinzn)f' Sn- 2. 3-Jlvil/tH`ill'll.lZ.l'lv HXIHUO HXlUHft 11X11031 HXJ1032 -- -- KX11033 -- 11X11000 11X11010 HCSOOl iix ijo n J`Ml 1012 HN1I013 UX11010 n x iio ir HXHOlS __ -- -- -- 11X11019 11X11020 r*c:sofi7 HCS070 11X1102J K \ 1101.1 11MI015 11X11022 -- J>iii70 Inj Dimr.iJitlmu* IW-iizo ig. li, ij lliitu'.iiiOii'm1. 2-Heii/tiIlimri,m* .j-llrii/.iiiliuifi iii' Hen/ p.h.i, ( pi), pvrylvm.* 1, 12-lieiizupvr> Ivne !J, JO Hi-jizoitlii-M.Mtllircm* Jlriizn Ini pyrene 3, -Mlcn/ipyrene ij, O.Hi'nz.oijiJimtlim.' Jii jizu Hi ijuinulfm* 1, l-liinuphthyl Jiiplieny] Carla)zoic Chrysene Cmunono 1, 2,3,4Dil>eii2anlhraccne 1,2,5,0bibcnzanthraccnc 1,2 7,8Dibriiznnthruccnc Dibenz In, t*l anthracene Dilwinz lu, h] anthracene Dihenz (n, j] anthracene 1, iS-Denzopcrylenc See llviizn lg, li,iJ I'erylenc Si r Triphciiylcnc 3 ,4-llvnziipyrcnc Sit. Denz.n La] pyrene Uvnzn Ifj quinoline ut ( i -Xnphlhoqmnolitic Set*5, (i-UvnzoqiunoHiiv Dinrnz. (a, cJ Anthracene 1>ibenz la, h] Anthracene Dihvuz la, jl anthracene See 1, Q, 3, 4-Ditwnxanllirnccnc Svv 1, 2 ,5 ,6-Dibcnzantliraccne See 1,2,7, 8-lXbenxnnthracene 2.3,5,6Ililieti/.fluunuitlienc 3, 4, 5, 61)ilu'iiziii-.irl>4i/.(>]e. 1)ilicirz.n.ji-cli(i\in I>i}rt-iiznliiraii 1. 2. -I. 5-1iiWir/.ipyrene I)i[ilirn> Ivllt'MllIilli* 1.2,6, 0IIjtiiii/peiitiKTiie !). lO-Diliyiliiiatilltiiiifin' | b, 15-1)ihyilni~M1-1Jiinilrno Sit TrnNVlu* il.2 a -r,2 V J Vliitin'itr 12 Mill. Purity oo;;. !W*; pi 1`iivc 7.n0/100mg 14.00/IUOihr 45.00/JOiiig 7.00/1 Mon* 10.00.H'me T.tHMOrai* ).;n:i >i : ; il.SC 7.00/JUOnn; !J.V,r 14.00/Wing 'M'fo 12.00/1(Klmg 13.00/1 (Wing ny/<- J7.00/J00mg yy% IO.OO/lOmg wr/o 10.(K)/10nifi m r/o lO.OO/lOing u s e 17.00/10(lni8 ou%> 10.00/lQQing 5% 10.00/100(118 W95t 7,(10/500mg m% 7.00/100n>g 09% 14.00/100mg use 18.00/lOmg lO.OO/lOmg 99% 7,00/lOmg 955b 12.00/Wing " 98% 14.00/Wmg 05% 8.00/lGiug 0!)% 15.00/50WK 0% 7.00/5lH)mg o se 17.00/1001118 (10% 7.00/1(K)iii8 00% 14.00/Wmg 00% 17.(m/100mg NEV 036854 J 'o ly m u lra r TT\I> o i-ar!jci" Si .'tjK lan ti I'ttnluct Aiin. P u rity Trice hMlHM Djiinh'im 11,2,3-cd-l', 2', IVriilanlhene J'-JwJ J'erylenu <j H% y.oo/ioorog I,M1024 3. (i*J)imrlhylpIicmti>lbrem! II.MIU25 0, Ifi-Oililn iiylunlJiiatme -- 1liplicivli-ncMillide See Diiien/.tilliioplK'iu* 09% 7.09/10ing 90% 7.00/UHJmj; liMtl* fi 1i.:;!tt.il.>(!i'itrfplu,n>lene MUM 1'll . av I, 2. -1. 5.Telriiinetli>]lit>nzene 90% 7.00/lOiyniji o.n% 7.00/1 IHhm* `-Il0.il I lie 00% 7.00/IOOiiiR . !:i.i;cik* XJK'jff lit xani-. t)^JU*n/vnt* Iiidi'tin J, 2,3-edJ pyrene See ii-1'In m lempyrriie 99%..,, 14.00/1 WhtiR 00% 7.00/lOthtig JAI KNJIlUJ HMI0J2 1IM1013 HM1014 HX11045 KX11040 9(3072 HX11U47 UM1048 9X11040 HX1I050 HXU051 HXH052 HXH0S3 HNH054 HXJI0S5 NH056 KXU057 KXH058 HX'HOSQ BCS030 HCSOoo HCSOOl ftXHoeo HXHOOl 2-Milli>I:mtlirneene .* yy% 8.00/1Wing *!NKlhylaiilhracvne " 99.99% 14.00/100mg .(-Mvlhjl Biphenyl * ' ,r*' .J-ThfHiUuhu'm' . I,S-MeUiylenephcnimOircne V% 99% lO.OO/lUOiiig 19.00/HMmg 2- MelhylIhujre J-Mvthylplicnnntliremj 05% 7.00/1 OOnrg m% 7.00/100mg 2*Methyl plifiianllm-ne 99% 7.00/lU0mg 3-Methyl phenanlhrem! Xaphlluiccnu See Tetraccne 95%. 7.00/I00m g Naphthalene fi -Xaphtluxiuinolma See 5, &-Ik-it<etK|iiim>line 99% "> 7.00/500m g (Miideeahydroehrysene . 95%, 14.00/I00nig I'cntaccfu! iViiilitnUtcne ) 98% See Diindeno U, 2, 3-cd-l', 2', 3'- 18.00/lQtng inu perylenc iVrylwMJ 99%, 14.00/100nig J'Jicnanlhrenc ` 99%, 7.00/100mg riivnuuthruncqulnene \ ,` * 95% 14.00/lW m g 9*Theny)anlliracene a-l'livn)lenepyrene' Iiidcnu 11,2,3-cdJ pyrene ; 93% 99% 14.00/1 oOmg. 7.00/10m g 2-rhcnylnuphtltaIene M'hunyltoluene . -J ' ' 4-Melhyl biphenyl 99% 19.00/lOOnig 99%, l'ittne 12.00/lOOing Tyrone 99% 7.00/100mg p-Quaterphenyl -.v ! 98% 14.00/lOmg in*Quini|ucphenyl , o-Tcrplicnyl iii-Terpcnyl p-Tcrphcnyl *t*\** : :.V * - 95% '99% 99% :99% 32.Q0/10mg 7.00/100m g 7,00/100m g 7.00/100m g 'lVlrncene Xaphtacene 99% 14.00/lOmg Tclradecabydrophenanittrone :% :05% 18.00/100rog 1.2.3.41 elrahydrofluoranthcno f^ . 99% lS.OO/lOOing 1.2.4. BluUnmelhylbcnzeno See Durcne [,-\'U0G3 Tvtnipheno 1. 2. 3. 4- Tetruphenylnuphtbnlenu See 1,2-Jlenzanlhrnccnc 07% 7.00/lOOmg tX'IKiOS ^MlOOO Triphenylene 'Irtplycenc 'l'i nsenu 9, 10-Bt`n?.p]nun111relie JJ, lO-o-Henzeno-9,lO-diliydroulithraerno JO, lS-Pilnilrn-SH-diindeno 11,2-n 1*. 2',-cl flutirene ut>% 05% 10.00/1 Oh.k 18.00/lQmg 14.00/100mg 13 NEV 036855 v i r . NvN i w w . n ie s o r r . ; v : v o \ i a w in y n a w 1*. K . W allno fcr, M . Koniger J)ayi')iM`lic Lundcsanslnh Ini' D o d cn k u ltu r and l 'fltin/,i'nb;Mi, Munchi'i), G n i u a n v iiml O. Hill/in per AllmLk- lit-yinii.il I ,.ilii ntitnry, National R c m \ ! u ,! i C'<>uiicil of ('mao.-.. Halifax, Nova Scotia, Cau-id.i l'Cli preparations consist oi complicated mixtures ol chlnn .biphenyls with dillerent chloiinc content anti their isomers. The comjwstlmn uf thesi" technical products lias only recently been established A knowledge of the solubilities of PCB components is necessary for experiments involving individual isomers and may also he useful for the evaluation of PCB distribution in natural waters. . Considerable .differences in the solubilities of chlorobuphenyls with different numbers of chlorination ns welt as positional isomers were indicated by change in the GC peak pattern of Aroelor 1254 re-extracted from aqueous solutions with hexane1 Solubilities of five mono-nnd dichlorobiphenyls also vary widely". We wish to present the results of our study on the solubilities of twenty-ono chloiobiphenyls in water. Most of the compounds investigated are majur components of commercial PCB preparations. Since water soluble humic substances were recently reported to act as carriers for lipopbylic compounds including pollutants0*10 the solubility of 4, 4'-dfchlurobipheuyl in aqueous extracts of humic acid was also measured. The solubility of this compound was also determined in the presence of different con centrations of Tween 80. Aroelor preparations have an Increased solubility in water in the presence of solubilizers11 and the presence of the biologically relatively inert Tween 80 (e.g. 2% Tween 80 in nutrient solution showed no measurable growth inhibition in n number of microorganisms ,a) may allow the use of higher concentrations of . chlorobiphenyl in many experiments. * EXPERIMENTAL Imtntmentatlon. Gas chromatography (GC) was carried out on a Varian 1800 instrument using' a ' glass column (5 ft. x 2 mm i.d.) packed .with 1.5% XE-60 on Anakrom Q operated at temperatures of 160-190C depending on the compound. Carrier gas was nitrogen at a flow rate of 30 ml/min. Injector and electron capture detector were kept at 220C. Chemicals. Chloroblphenyls (99% pure) were either Syntherized or obtained from Analaks Inc. (North Haven, Conn., U.S.A.). Humic acid was purchased from Aldrich Chcm. Co. (Milwaukee, Wise., U.S.A.). Methods. An example for the determination of the solubility of one' chlmobiphcnyl in water is given below. A hexane solution of the chlorobiphenyl (1 mg) was pipetted into a 300 ml Erlenmeyer flask and the" solvent evaporated to give a thin film of the compound. Water (100 ml) was added, the flask sealed with purnfilm and the mixture shaken at 30C for 10 days. After this time the aqueous suspension was allowed to equilibrate at 22-246C for 3 hr. Contact oi aqueous chlorobiphenyl solution with glass was kept to a minimum after this step because of the known adsorption effects'3. An aliquot (10 nil) was drawn using a syringe carrying a small filter compartment and Immediately 14 NEW 0 3 6 8 5 6 i titIt 'iN-A.inr (2 a 10 m l/. Thi! bcvanc extract w.n .w . :.;i..icrl lo 10 ml mul i.tt u ric iii)Vili`tl intn tlu* gas iluumutiigiapli, evaluation was In measuring llie peak height using calibration cmvc 1* kumvn unitamts of >!.*;>! slandanl in hexane. Sampling ami analyses wm - e.mieu mil in (luplcate. iv l tin* prillilciiis w ith adsorption anil lmv snhiluk:*. 1:n experim ents w ere ..... ;.i i:l\ r solubility ilata as absolute pliysfr.il e-r. bill were i1ended : - ..i!. *>>i- i .ivjwable a rte a e * ft: nneitts. . . 'i" e`i!: -bip'it ;.y>' in wulvi an : ,iMo 1. 'MUM. I Solubility of chlorobiphcnyls iu water Compound Solubility (mg) Monochlorobiphcnyls 2 -....................................... 6.0 3 -....................................... 3.35 4 -................................ :..... 1.20 Dichlorobiphcnyls , 2, 4. ................................. 1.40 2, 2 '-................................. 1.56 2, 4`- .................................. 1.90 4, 4 - ................................. o;o8 Trichlorobiphenyls 2, 4, 4'- ............... ;........... 0.085 3, 4, 2*- ............................ 0.075 Tetrnchlorobiphonyls 2, 2\ 5. 5*- ...................... 0.046 2, 3, 2\ 3'- ............... 0.037 2, 3, 2', 5'- ...................... 0.170 2, 4, 2 \ 4- ............. ;....... . 0.070 2, 4, 3', 4'- ...................... 0.055 2, 5, 3 \ 4*- .......;............ 0.041 3, 4 /3 ', 4'- ...................... 0.175 Pentachlorobiphenyls 2, 3, 4, 2\ 5'- ................ 0.021 2, 4, 5, 2*. 5 '- ................... 0.035 Hexiichlornhiphenyl 2, 2', 4, 4', 5, 5'- ............ 0.0088 Octachlorobipbenyl 2, 3, 4, 5, 2', 3', 4 \ 5'- .. 0,0068 IX'tfleliloi obiphcnyl 0.015 4, T-Dichlorobiphenvl ....... + Tween 10 0.17 ........... 6.2 + Tween 80 1% ............ 10.0 + Humic acid extract ..... 0.075 (ppm) . 5.8 3.6 1.17 1.40 .1.44 1.85 0.07 0.085 0.080 0.046 0.030 0,170 0.065 0.080 0.041 0.175 0.023 0.028 0.0088 0.0072 0.015 5.5 10.0 0.06 15 Q 36fl5^ We thank l)r. K in d for supplying data prior III publication. P.HAV. expresses his gratitude tu tin* "Deutsche Kurscliuiigsgeuiinschair' for linnncial support, Purl nl Ibis work as ca ril'd mit h ilf O. H. was on leave at the IIuM-risehe I.aiidesau'-lali. This author would like to thank the "Deutsche Akademisch)- AusUiuxchdicuts" lur die :n\iht<i).n to miany and linnncial aid. J. i *. S '.- a ::.; i i. W V hi |. (.d ittiin n lii'-'r. (id. J 7 i i 'jVI . : \\. A t \ McCall. J. Ass. Oflir. Anal t hem. .*i\ T-p: . 1'fTi!. ... .'hi. V Tmhso-.- K. Ogmi, M. A11iniur:i an t M. I[.iiii.u,.i. I nkimLa /.tssld (2, 'I i, lii'f l - : Client. Ahslr. 7-1. II(i2!M t I I . n I. A. C. Tas and H. 11. deVos. Environ. Sei. Tcclniol. 5, 1210 11971). 5. A. C. 'las* and H. J. C, Kleinpool. Hull, Environ. Contain. Toxicol. H, 32 (1972). 0. D. K. Willis and It. !'. Addison, J. Kish. lies. lid. Canada 29, 592 (1972). 7. V. 11. Freed, personal cmnimm cation (Some physical chemical properties of the polychlorinated biphenyls-Arocloi J25-1; manuscript). 8. it. C. Webb, PCI! Newsletter (1970). 9. G. Ogner and M. Selmit/er, Science 170, 317 (1970). 10. K. M alsuda and M. Schnitzer, Hull. E nviron. Camtarn. Toxicol. 0, 200 (1 9 7 1 ). J ). V. Zitko, Fish. lies. lid. Canada, Manuscript Report Series No. 1083 (1970). 12. II, J. Rellin. S. Lauror-Ucydcnrcfch and 1'. Wallnofer. Z. Lcbcusm. 'Unters. Forchung J35, 117 (1960). 13. M. L. Hatlnla, Dansk. Tidskr. Farm. 45, 259 (1971). V U O G U E SS H K rO U T S ON 1T.I5 ISO M EK S By: Michael Holgar Given the toxicity and persistence oi the widely dispersed polychlorinated biphenyls (PCH's) it seems logical that the U.S. Interdepartmental Taskforce on PCB's in their 181-page May 1972 Report (Cmn-7a*l0419) would include as part of llieir recommenda tion (page 18) the following additional studies, (italics arc ours): 1. Toxicologicnl c.txilnalinn of a select ilumber nf representative, purified PC if Isomers as well as purified trace contaminants such as the chlorinated dihenzofurans. 2. Definitive mammalian elaboration of the kinetics, absorption, distribution, meta bolism, and excretion of the technical PCBs ns well as a number of kcij isomers and the chlorinated dihenzofurans. 3. Elaboration of the sillreelhilar and intracellular actions of the technical PCHs as well as ti number of representative isomers and chlorinated dihenzofurans. J. More definitive epidemiological studies of the PCHs with lmtli more representative population sampling and standardization on the basis of lipid content of the tissues. In our list of biphenyls and 50 isomers of the 209 possible dilorobiphenyls we included a great number of the major components present in the commercial mixtures, l'or 1$ NEV 036858 instance, Willis and Addison1 report that the major components of Aroclor 1221 accounting for 92.3 weight per cent are biphenyl, 2-Cl, 4-C1, 2. 2'*C1X, 2, 4'-Cla (all available from Analabs stock). From Sissons and WeltiV list of the major com ponents of the more important Aroclor 1254 (we list more than half). Methods have been developed* to recover PCB's present in wtisie and river water and to increase detectability by perchlorinating the samples sensitizing them to electron-capture detection by gas chromatography4. We have made the tools available (polyurethane foam plugs and perchlorfnation kits). Assembled below is data of melting points taken of our pure isomers and taken from the literature. This list reveals interesting features of configuration/phystcal property corelation. MELTING PO IN TS O F POLYCHLORINATED BIPHENYLS Chlorine Position Mono 2-C1 3-Cl 4-C1 Di % 3-Cla 2, 4-Clj 2, 5-Cla 2, 6-Clj 3, 4-Cls 3, 5-Cl3 2, 2*-Cly 3, 3'-CIa 4, 4'-Cl2 2, 3'-Cl2 % 4'-Cl3 3, 4'-C)i Tri 2, a, a , 2, 3, 3-Clg 2, 3, 6,-Clj 2, 4, 5-Cl, 2, 4, 0-CI, 2, 3, 2'-CI3 % 3, 4'-Cl3 2, 4, 4'-Cla 2, 5, 2'CIa 2, 5, 3'-Cla 2, 5, 4'-Cl1 3, 4, 2'-Clg * 3*.4, 4'-CI3 3, 5, 2'-Ci3 3, 5, 4'-Cla Melting Points 32.0*32.5C oa 75.5*77.0C Oil (Lit. 27.7-28.2C) Oil (Lit. 24-25C) Oil (Lit. 22-23C) 34-35C 47-48 C Oil (Lit. 31-32C) 60-61C 25-26C 148-149 C Lit. Oil 42.5-43.5C Lit. Oil 101-102 C Lit. 41C 5B-60C 76-78c'C 62.0-63.5C Lit, 28-29C Lit. 73C 57.0-57.5G 43-44C 40.0-40.5 C 03.5-64.5C 0O.O-6O.5C Lit. 87-88C Lit. 58C Lit. 88C 17 NEV 036359 i ) J f; \ ? mi 4; I7* P 0 11.V1 o r j ' C L Y a i L O U ^ A T E i ) B IP H E N Y L S C ift'J'l.L,1 /'l.-M, fiJH Trtro 2, 3, 4, S-C]4 2, 3, 5 0*C14 2, 3, 4, 4'*CI4 2, 4. 5, 4'-Cl4 2, 3, 2' 3'-Cl4 2, 3, 2' S'-C14 2, 4, 2r 4'-Cl 2, 4, 2' 5'-CI4 2, 4, 3' 4'-Cl4 2, 5, 2' 5*-CI4 2, 5, 3* 4*.C14 2, 0, 2'. 0'-Cl4 3, 4, 3', 4'-CI4 3, S, 3', S'-CI4 Penta 2, 3, 4, 5, 0.-C1, 2, 3, 4, 5, 4'-Cl5 2, 3, 4f 2', S'-Clj 2, 3, 4, 3* 4'-C11 2. 3, 0, 2' S'-CI, 2, 4, 5, 2' 3'-Cls 2, 4, 5, 2' 5*-Cl3 2, 4, 5, 3' 4'-Cl5 Hexa 2, 3, 4, 5, 8, 2'-Cl<j 2, 3, 4, 5. 0, 3'-Cl 2, 3, 4, 5. 0, 4'-Cl 2, 3, 4, 5, 2' 4'-Cl0 2, 3, 4, 5, 2' 5'*CI0 2, 3, 5, 6, 2* S'-Clt, 2, 3, 4, 2' 3' 4'-Cln 2, 3, 4, 2' 4' S'-Cl,, 2, 3, 5, 2' 3' 5'-Cl,t 2, 3, 6, 2' 3' 0'-CItl* 2, 3. 0, 2' 4' 5'*C),t 2, 4, 5, 2' 4' 5'-Cln 2. 4; 5, 2* 4' 0'-Cl,, 2, 4, 8, 2' 4' 8'-CIr 3, 4, 5, 3', 4* S'-Cla ./fi/in; / 'lin i.v 91.5-92.5C 77.0-77.5C Lit. 141-142C Ut. 125C 119.5-121.5C 40.5*47.0C 41-42C 04-60C 127-128C 88-87C 104-107C 190-200C (sublimes) 132-184C Lit. 104C 123-125C Ut. 98*99CC 1J1.5-H3.0C Lit. 101-105C 97-98 C 81-82C 70.5-77.5C Lit. 105-107C Lit. 134-137C Lit. 97-100C Lit. 16O-105C Lit. 77-78C 89-91 G 100-101C 155-8C 78.5-80.0 C Lit. 128-129C U5-I17G Lit. Oil 102-104C Lit. Oil 113.5-114.5C Lit. 108 18 v NEV 036860 $\ 1 M E L 'IT '.' ; P l . V f U P PO .'.Vt L-.. \ . n .l Chlorine Position Hepta 2, 3, 4, 5, 6, 2' 5'-Cl7 2, 3, 4, 5, 6, 3', 4'-Cl, ` 2, 3, 4, 5. 2'. 3*. 4'-Clj 2, 3, 4, 5, 2' 3' 8'-ClT 2, 3, 4, 5, 2' 4' 5'*C1T 2, 3, 4, 5, 2' 4' 6'-C1t 2, 3, 4, 5, 3' 4' 5'-Cl, Ocia 2, 3, 4, 5, 2' 3' 4' 5'-Cl8 2, 3, 4, 6, 2' 3' 4' 0'-Cl8 2, 3, 5, 0, 2' 3' 5' 0*-Cls Nona 2, 3, 4, 5, 0, 2' 3' 4' 5'-Clu Deea 2, 3, 4, 5, 0, 2' 3' 4' 5* '-CI Melting Points 147-150C Lit. 110-118C Lit. 134.5-135.5WC Lit. 130.5-130.7C Lit. 109-110C Lit. 152-153C Lit. 162-163C 158*159C Lit. 132C 101-102C 204.5-206.5C 300-310C (sublimes) All melting Points token on n Fischer-Johns melting point stage. 1. D, E. WilUs and R. F. Addison, J. Fish. Res. Board Canada, 29, No. 4, 592-595 (1972) 2. D. Sessons and D. Welti, J. Chromatography, 60, 15-32 (1971) 3. H. D. Gesser, A. Chow, F. C. Davis, j. F. Uthe and J. Reinke, Anal. Lett., 4, 883-6 (1971) 4. V. Zitko, O. Hutzinger and S. Safe, Bull. Environ. Contnm. Toxicol. 6, 160 (1971) 19 NEV 036861 1 99% Pure PCB Isom ers For clarity we have kept the position numbering separate (or each ring. For Chemical Abstracts nomenclature transpose numbers listing lowest number first. RCS-001 Biphenyl.................................................................................. *7.00/500mg RCS-002 2-Chlorobiphenyl.................................................................... 7.00/100mg RCS-003 3-ChlorobiphenyI.................................................................... 7.00/100mg KCS-004 4-ChIorobiphenyl .................................................................... 7,00/100mg KCS-005 2 ,2'-Dichlorobiphenyl.......... .................................................. 18.00/100mg KCS-008 3 ,3'-Diohloroblphenyl............................................................. 18.00/100mg RCS-007 4 ,4'-Dich1oroblphenyl ............................................................ 18.00/100mg RCS-008 2, 4'-DichIorabiphenyl ............................................................ 32.00/50mg RCS-009 2 ,3*Dlchlorobiphenyl ............................................................ 14.00/100mg RCS-010 2 ,4-Diohlorobiphenyl ............................................................ 14.00/1OOmg RCS-01I 2 ,5-Dichlorobiphenyl ............................................................ 14.00/100mg RCS-012 2, 6-DiohlorobIphenyl ............................................................ 14.00/1OOmg RCS-013 3, 4-Dichlorobiphenyl ............................................................. 14.00/10Omg RCS-014 3 ,5-Dichlorobiphenyl ............................................................ 14.00/100mg RCS-015 2 ,4 ,4'-Trichlorobiphenyl ...................................................... 26,00/20mg RCS-052 2,4,3', 4'-Tetrachlorobiphenyl................................................ 32.00/20mg RCS-018 2 ,5 ,2'-Trichlorobiphenyl ....................................................... 28.00/50mg RCS-017 2,5,3'-Trichlorobiphenyl ........................................................ 28.00/50mg RCS-018 2, 5 ,4'-Trichlorobiphenyl ....................................................... 28.00/5Omg RCS-019 3, 4,2*-Trichlorobiphenyl ........................................................ 28.00/50mg RCS-020 2 ,3 ,4-Tricblorobiphenyl ....................................................... 26.00/50mg RCS-021 2 ,3 ,6-Trichlorobiphenyl........................................................ 36.00/50mg RCS-022 2,4, 5-Triohlorobiphenyl........................................................ 22.00/100mg RCS-023 2 ,4 ,0-Trichlorobiphenyl......................................................... 20.00/lOOmg RCS-024 2, 3 ,2 ', 3'-Tetrachlorobphenyl .................. ............................ 28,00/100mg RCS-025 2 ,4 ,2 ', 4'-Tetrachlorobiphenyl ............................................... 28.00/100mg RCS-028 2,5,2', 5'-Tetrachlorobiphenyl ............................................... 28.00/100mg RCS-027 2 ,6 ,2 ', 0'-Tetrnchlorobiphenyl ............................................... 28.00/100mg RCS-028 3,4,3', 4'-Tetrachlorobiphenyl ............................................... 28.00/100mg RCS-029 2 ,3,2', 5-TetrnchlorobiphenyI ............................................. 3S.0O/50mg RCS-030 2, 4,2', 5'*Tetrachlorobiphemyl............................................... 22.00/20mg RCS-031 2.5,3', 4*-Tetrachlorobiphenyl ............................................... 35.00/50mg RCS-032 2 ,3 ,4 ,5,-Tetrachlorobiphenyl ............................................... 20.00/50mg RCS-033 2 ,3 ,5 ,6-Tetrachlorobiphenyl ................................................. 20.00/50mg RCS-034 2 ,3 ,4 ,2\ 5'-Pentnchlorobiphenyl............................................. 25.00/20mg RCS-033 2 ,3 ,0 ,2 ', 5*-Pentachlorobiphenyl ........................................... 22.00/10mg RCS-030 2 ,4 ,5 ,2\`3'*Fentnchlorobiphenyl........................................... 22.00/10mg RCS-038* 2, 4 ,5 ,2 ', 5'-Pentachlorobiphenyl ........................................... 35,00/50tng RCS-039 2 ,3 .4 ,5 ,6-Pentachorobphenyl........................... ................. 28.00/lOOmg RCS-040 2 ,3 ,4 ,2 \ 3\ 4'-Hexach!orobiphenyl ..................... ................. 32.00/20mg RCS-041 2,3,4, 2', 4', 5'-Hexachlorobiphenyl ....................................... 28.00/lmg RCS-042 2 ,3 ,8 ,2\ 3', 0-Hexochlorobiphenyl ...................................... 36.00/20mg RCS-043 2 ,4 ,5 ,2\ 4*, S'-Hexnchlorobiphenyl ....................................... 36.00/lOOmg RCS-044 2,4 ,0 ,2 ', 4', 8'-Hexachlorobiphenyl ....................................... 32.00/50mg RCS-045 2 ,3 .4 ,5 . 2'. S'-Hcxnchlorobiphenyl ....................................... 28.00/10mg RCS-040 2, 3, 5, 6. 2', 5'*Hexachlorobiphenyl ....................................... 28.00/10mg RCS-047 2 ,3 .4 .5 , 0, 2', 5'-Heptachlorobiphenyl ................................ 30.00/lOmg RCS-048 2,3 ,4 ,5 , 2\ 3', 4', 5'*Octachlorobiphenyl ............................... 26.00/20mg RCS-049 2,3.5,0,1*, 3\ 5*. 0`-Octaohlirobipheityl ............................... 20.OO/2Omg RCS-050 2 ,3 ,4 ,5 ,0 , 2', 3', 4', 5'-Nonachlorobiphenyl ......................... 38.00/10mg RCS-051 2 ,3 ,4 ,5,0,2', 3\ 4', 5*, 6'-Decachlorobiphenyl ..................... 7.00/100mg Diicount on tingle order of any 3 PCBV10% 10 PCB'f-13% BihltogropliT on PCD Literature nvnllnbk- on rcrjuctl. 20 NEV 036862 POLYURETHAINE-I'OAM PLUGS For complete extraction of pesticides and PCB's from environmental water samples (for instance --river water). References: 1. The extraction and recovery of polychlorinated biphenyls (PCB) using porous polyurethane foam. H. D. Gesser, A. Chow, F. C. Davis, J. F. Uthe, and J. Reinke. Anal. Lett., 4, 883-6 (1971). 2. Extraction of organochlorine pesticides from water by porous polyurethane. J. F. Uthe, J. Reinke and H. Gesser, Environmental Letters, 3, 117-135 (1972). Written procedure for extraction of pesticides and PCB's from water samples will be supplied with each order or on request. Polyurethane-foam plugs (22mm x 38mm) RCS-083 ..................... Untreated ........................................................ $10.00/50 RCS-084 ......................Washed ............................................................ 12.00/12 RCS-085 ......................Treated with 0.5% DC-200 ............................. 12.00/12 Chromatographic Tubes (20mm ID, 400mm long) RCS-088 ......................Tube without fritted disc ............................... $13.00/2 tubes KCS-087 ......................Tube with fritted disc ................................... 11,00/eaeh References: Perchlorination Kits for Analysis of Polychlorinated Aromatics 1. Analysis of chlorinated aromatic hydrocarbons by exhaustive chlorination: Qualitative and structural aspects of the perchloto derivatives of biphenyl, naphthalene, terphenyl, dibenzofuran, dibenzodioxin and DDE. O. Hutzlngcr, S. Safe, and V. Zitko. International Journal of Environmental Analytical Chemistiy, 2, 95 (1972). 2. Column chromatographic separation of polychlorinated biphenyls from chlori nated hydrocarbon pesticides, and subsequent gas chromatographic quanti tation in terms of derivatives. O. W, Berg, P. L. Diosady and G. A. V. Rees Bulletin of Environmental Contamination and Toxicology, 7, #6, 338*347, (1072). 3. Screening method for the detection of chlrwodibenzo-p*dioxins In the presence of chlorobiphenyls, chloronaphthalenes, and chlorodibenzofurans. D. T. Wil liams and B. J. Blanchfield, JAOAC. 55, 93-5 (1972), RCS079...................... Perchlorination reagents Aj andA* ................................ $10.00 For PCB's, PCDD's, PCF's, and p,p'-DDE (in equal volumes). RCS080...................... Perchlorination reagent B ................................................. 6.00 For PCB, PCT and p,p'-DDE RCS081...................... Perchlorination reagent C .............................................. 6.00 For PCN'j RCSQ82...................... Perchlorination kit (Alt A, B, C) ................... 16.00 Detailed perchlorination procedures will be supplied on request and with each order. 21 NEV 036863 K( *stn;(; .................... 'Ch-K h i f*'1each f i Arr.^-lo:- Jir, 1-;S. 3.v;. . . t.Otl/kil .0 0 / t .J u t Number oi Chi::: in**.*............. ---------- 1------ -1 " T--------] L j* 4 1 e --7 8 Tr of Chlorine ......................... 21.85 36.40 40.00 53.38 59.07 63.6 67.2 70.3 Referente: Behavior of ch)c>:inaled naphthalenes in analytical methods for orgnnochlorinalcd pesticides and pulvchlorinaled biphenyls. J. A. Annom and J. A. Burke, JAOAC, 54, 175-7 (1971). KCS053-- l-Cldorodihcnzo-p-dioxin,.............................. 20/50 mg KCS054 ...2-Ch lorodiiu-uzo-p-dioxin........................................ 20/50 mg HCS067 . Diben/n-p-dioxi ......................................................................... $15.00/50 mg HCS055 .-2, 3-Dichlorndihcii/o-p-dioxin...................................................................25/50 mg KCS06S.. 2, V-Dichlorndibcnzo-p-dioxhi...................................................... 25.00/50 mg 1CSG69 ..1 ,2 ,3 , 4 ,6, 7, 8, 9-OeUuhlorodibenzo-p-dioxin.......................... 20.00/50 mg HCS050 " ], 2, 4-TricliiormHbcnzo-p-dioxin...................... 25/50 mg HCS057---1, 2, 3, 4-Tctrndilormlibenzo-p-dioxin.................................................. 25/50 mg References: 1. Tiin-laycr cliromatographic .separation of two ohlorodibenzo-p-dioxins from somo polychlorinated biphenyls and organochlorme pesticides. D. T. Williams and B. J. Blanchfield, JAOAC, 54, 1429-31 (1971). 2. Determination of polyohlorodibenzo-p-dioxms in chlorophenols and lipids. D. Firestone, Paper presented at the 162nd National ACS Meeting, Pesticide Div., Sept. 12*17,1971. V'J'.< PCM,Y( '.I M.(J P JNATF.D ItfP.K N /O K U K A N S RCS070 ..................Dibenzofuran....................................................... $ 7.00/500 mg KCS058................... 3, 6-Dichlorodibcnzoiuran.............................................30/20 mg RCS073 .................. 1,2,3,4,5,6,7,8-Octachlorodibenzofuran................ 15.00/50 mg Reference: Identification and toxicological evaluation of chlorinated dilrenzxifuran and chlorinated naphthalene in two commercial polychlorfnntcd biphenyls. J. G, Vos, J. 11. Koeinan, II. L. van dcr Maas, M. C. Ten Nocvcr dc Brauw and 1\. 11. dc Vos, Food Cosmct. Toxicol., 8, 625-633 (1970). RCS077 .................. Hcxachluroplicne [212'-MclhylenebiS' (3,4,6-tiicIiloiophenoI)] ...................................... $ 5.00/1 mg RCS078 ..................Perd donnalcd p.p-D D E...................................... 20.00/50 mg 22 NEV 036864 ! 'i !,: l C i l i l . . - ' TIic* Jisi oi pesth'iilo sliimlaids t)inl follows i** possibly tbr most c.vUmivr ifnnpil.tlinii offend. I'or your cniivenfem-e wo have ills lisletl tin* f^nniiytn* .nul a cross r*ltuu-. for iliffncnl tnide iMUtcs. If lire |K*slkid(` you not'd in nnl listed. ploasi* iittjiiirc. i Ws.itl.iMi .i1m>fn .solu tion eomeiiUuliuns ol .) In 1000 PPM in powers of 1UJ. r.fJk I.... \.1 i ii.s*.ti'-.r-'. t ' hN't'V, 1' .(.til -IiMM--'iV s11i:1*1..A.kirl-iJ ILMliWi tonii}m- KM1WJ Aun'lrsnr,kill. --- hsiwn IIItSMIWDOifJt * AAmfiiilllminkV*,Irtlt. m--i-n-o-r AutmU- - ,__ A1,1111,1IK* IlMWJ * Aturiui* HMDOJ Alritrini',U\h* ItsnJH) AsJili11 nsma Arii'filnnniH)i)) hmwis nsiwa HMWO* .AtItbirmlirtIntij.ittWtruiiiNnrln'ivi-lktla nsmi ---- lIIUVLiiiunmmddm1) HMD ll.iyfttin .usiwa HrW*>l AjisMrVoUwl aIHtlml-Oln-intwe!l*r riMta p -Hi: --nsiwi _ y9.ninm:: ttsiws lhtsi|Ud}l -W-S.I--Wa6-- lHlrfhltrsninililt usher iii,,it}).......... .. 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KS-5s? lt l l f l l l 5 l ! p s*4S-55 o J55ErJgfSR;, I i f s a d 3 2 w ^ < < i o c u I H n s u n u s i i i 1i j l l l l i ? l | ^ l II i I l i l i II l ! l ! l l ! ! ! ! ! l l ! 1 8.3 i O vO CO V OrO > OJ z r<*M* i i 1 i fc f1Iu ! frt f | ! II f [ I &-v #> \\ SantJjrltv s2 ~ 3 J iI 2g 2s 3> P I l J fl I V 'X ii Ii 13 U *9 S 5s 3 3 f 31 e e s S3S g2 s? ? a n s ip ! W H U --rj ^ t 5 I i S ? ! a g-3 9 s l i? VaCoMa C"p3l s3 g S5O r f 4 IIy3- o7 ptipM E a*.a l5al&sl If ? f rFi ri*lr 1 siy E sS-f * Kr 1 i? < i i s c t r 6 x* ? Srel'entittfiiuioplwml M =r I = - ^ ?Va-srs5S-. [ li 00 ? ? f ? Z-I i wg* fr* i l fl. T&1! 3 r lf ilif i i i f H ? 1.3 f frH l* ' 5!5X O S ^ I2?J* Cf a c f f l | P.C "Ilr f U s l * ? I I f1 U 2 S ?S I 1 1 s2 m < * p. 3v Syp. 3ta I l i Il 1 IUo a a oo ssss Ci 11 1 n *S 11 fC a n1 S s 1 il 0 CA 11 a 1 >0 M e 1 m1 i a s8?5 33a Mf 10 * 181I 5 11 a ** I sr s9 3 IIf- 1 I Cf: jh*.""y k*J c L'J ; V. V* V. PESTICIDE STA.UMK Celato| # riattati OSTO Sdtwdan RSF173 Sdirodwi, ireh. RSP170 t Stvln HSP171 KitTM RSP17I Stive*, ledi. BSP039 lifnntsh _____ IISF174 nSP175 yp Spergun Strabane *-- - Sutf*43de RSP170 Sulfotlde --------- SnUuxyl --------- Suntftkkm -- -- -- S)tar ------- Sytem RSP1T7 3,4,5 T>tdd RSP178 2,4, 3T*edd --------- TCI>S --------- TDEmta -------- li, p>TDB ---------p.p'TUE HSP188 Tedio iu pit -- nsnss a, a. 4,* Tetrrcfloropbenol Trtradlfon Tlitavt ESPI TItimH,lMbL R5P040 * Tendati -- Tlikmlida Thbplwl --------- Thtupho* HSFM1 Tuwpheo* nsroia Trtddfon EISPtOO RSP181 nsrios RSrW Iridilo* idtennedune 2,4.5 Triihkroplierul 2.4,0 Tricb, kiriphenol TrilMon 5pni>ftp(n OMPA h itn Stftin brinijrl Friupwp Cootup Ste r^retldavi CliWnfl Str Sul/oxid Snlluiyl Stilirecide SccSutfoxlde 5w PVnitrolhhm Sor Demeton Set Sdtradan Sre Tedimi Sm DDD-mli StrObplWD' Ser p. p'-DDU llnphn / Ttlredlfun TCD5 Str Trdioq Unni* Endoratfan / Mah* / Ser Zlnopbtt Sor Phalten Sw Parathion ITieaitdtlc llnmatoe Ttigon Cltlnruphol Diptera Dyta Nejuvwt IHptefet Qihtroplcdn Aiiptlalte Ptnvntoll CarimplimnlttIna Tnpm --------- Undcn - -- - . Vapor nsPIQl Vari RM W Warforin Str Trtchkirfon Sm Bypw Sre DMiImvm Ctmmafcne Adite anttkol Orfaunrtli)ipprup(iiip]MtriunnIr OllaaiethyfpymplmipUiMiidHe lA'aplithyl N-mrlhpl caHumalr l- ( l,l, ITHtIilunpiHMir ) pniphinc Add 2*(2,4, -VTridiloTVphentnr) piup* hatteAdd 3-dilnro~l,8-bii (elitifatino ) trUdne Trliadtkn>-p4ietitu(|tUtianr Terpene jwlydilorinatei I, S.Mr(lirWcdlitp.|-(2.((x-tyl nitdnyl) propri) fattene * A .1. w .sn W* w* WJ% W J* Tedi. M* Pilori W* Film 11.00/1 H.OO/k ii.aviooma I0.0u/100n>t 6.10/U ll.KI/lWntf 6.00/ I6.0U/I 12,00/1 2,4,3-Tridikmjp|irin)'wrettc Acid 2.4, S.THeblurpphcnmt'acntfo Acid UVA Trek lA.OO/lUOms .ut/s p-CMoropWn>l 2.4, Vliidilunn phceyl mlione 2,3,4.0 TetradtluTupItcmd O.ODlrthjr13.( brillilo) mrtkrl pbosphorodllhloate 0 ,0 [Hrthyl S-{rthy1lliti>) iMthyl pSinphonidllNuutr 0,7, S,0,10, m-Hilavl>Viro.|, 3,3a, 0,0, Ondtrwlirdn^, U-mrltuitu 2,4,3faitodktiatlilrpin a^ixide OH* W* Wt0 * 01* 06* Pufjdilunitakd rompiarar O, O Dmirtliyl {Mtrdttixyi, i, 2-ttW cblwortJtrD plwiphonatc Tedi. OH* lO.tD/j 12.00/lOOinf 10.0(1/1 eoo/n 23.im/l(XknB 17.00/b 12.00/g TridilatanltTiNurtliane 3,4.3 TrRhlnrnpItetad 2,4,6 Trtchfaiptieiml S-[I p.CItltinriHimyl) thfcil mt-ikil) 0 ,0 dietliy) plwjplnim. Uttlihate Methjrl bollilarvanole 3-1a '.4ti-limyHn*vW-llyilrmy iwrauutn OB* 12.00/m 00* 10.00/HKkn.9 0* in.no/mTiir 3* lo.on/a 211* Troll. I2.1W/ tiino/iuuuie NV 0 3 6 8 7 1 29 I'liSTUilUl-: STAiNDAJSDS BSFIM BSP[09 asriw aspisT Predict Zectna Zfctnn. tech. Zlmti Zinopho* nsFiss RSF100 Zytnw Zytron. itch. Spnonpa DtthtM'tfoC Ftntatt Tlttanluln Cynrt Ncnuft m ir* Active Ingredient <-dimethyl amtruO, 3-iylyl-M.Mrlhyl cnilitmta 4-dinicthyl andno-3, .?-*>Jyl-N*MMhyl Indiamate Zinctthyknt UidltUtmftMBwl O. O-Dtethyt-O-i-pyririnyl pho*pturfotMoat Q*(1. t-DtchkmTphcnyl)-OmttUyl tor propyl pbmpbnnmldolhioala 0.(C. 4-Dtehlsnphenyl).0*(Mlh)il (mipnipyj plMvphawiaJiMjdtftla %A.(. W* T5 wr*> Tnb. rte* 19.00/1 9.00/g 80.00/* lfl.UD/IWko* li.OO/IOOni .TO/* PRECOATED TLC PLATES from ANALABS Analabs TLC plates ore of precision quality. They are precoated using procedures developed by leading chromatographic Investigators. The prescored 20 x 20 cm plate can be snapped in sections for two 10 x 20 cm, or four 5 x 20 cm plates. Scoring on the uncoated side makes snapping the plates easy. A clear edge on the plate allows <the plate to be grasped without disturbing the coating. Separation information can be marked In this area. ORDERING INFORMATION 20 x 20 cm PRECOATED PLATES 250/* thick. 25 PLATES/BOX NUMBER CATALOG TLC PLATE TYPE PRESCORED PRICE UNSCORED PRICE 5 x 20 cm 10x20 cm 20 x 20 cm TLP-001 TLP-002 TLP-003 TLP-004 TLP-005 TLP-008 TLP-007 TLP-008 Anasil G Anasil GF (254) Anasil H Anasil HF (254) Silica Gel G Silica Gel GF (254) Microcrystalline Cellulose (Avlcel) Microcrystalline Cellulose, F (254) (Avlcel) $30 $30 $30 $30 $30 $30 $31 $31 $20 . $20 $28 $20 $20 $20 $27 $27 $22 $22 $22 $22 $22 $22 $23 $23 Analabs precoated plates are guaranteed to arrive at your laboratory in condition for immediate use. Any plates that arrive damaged will be replaced at no cost to you and no troublesome paperwork. NEV 0 3 6 6 7 2 30 CEPP 147 I'ESTICIDECRADE SOLVENTS - Pesticidegrnde Solvents tire certified to contain no interfering substance greater than that equivalent to 10 parts per trillion of a chlorinated pesticide. Catalog # Solvent SSP001 5SP002 SSPUU3 SSP004 'SSP005 SSF006 SSP007 SSPOOS SSP009 SSP010 SSP011 SSP012 SSP013 SSPOU SSP015 sspoie SSP017 SSP018 SSP010 SS Acetone, Presticldgrade Water ............................................. . 0.059 max. Acetonitrile, Pesticldegrade W ater............................................... . 0.05% max. Benzene, Pesticldegrade W ater..................................... ......... . 0.03% mux. 2-Butanone, Pesticldegrade W ater........................ !..................... . 0.05% max. Butyl Alcohol, Pesticldegrade W ater............................................... . 0.05% max. iso-Butyl Alcohol, Pesticldegrade W ater............................................... . 0.05% max. Cnrbon Tetrachloride, Pesticldegrade W ater........................ ...................... . 0,02% max. Chloroform, Pesticldegrade W ater............................................... . 0.02% max. Cyclohexane, Pesticidegrade W ater............................................... . 0,02% max. Dichloromethane, Pesticldegrade W ater................................................0,02% max. N, N-Dimethylformumide, Pesticldegrade W ater............................................... . 0.05% max. p-DIoxnne, Pesticldegrade W ater............................................... . 0.05% max. Ether, Pesticldegrade W ater............................................... . 0.05% max. Ethyl Acetate, Pesticldegrade W ater............................................... . 0.05% max. Ethyl Alcohol, Pesticldegrade Completely Denatured W ater........................... ................... . 0.05% max. Heptane, Pesticldegrade W ater............................................... . 0.03% max. Hexane, Pesticldegrade W ater............................................... . 0.02% max. Methanol, Pesticldegrade W ater............................................... . 0.05% max. Methylsulfoxlde, Pesticidegrade W aMi1 . 0.05% max. SS SS Si S: Unit Price 1 Liter $14.00 1 Liter 15.00 1 Liter 12.00 1 Liter 13.00 1 Liter 12.00 1 Liter 15.00 1 Liter 16.00 1 Liter 17.00 1 Liter 16.00 1 Liter 16.00 1 Liter 19.00 1 Liter 17.00 1 Liter 12.00 1 Liter 13.00 1 Liter X Liter 1 Liter 1 Later 1 Liter 12.00 13.00 12.00 11.00 21.00 t NEV 0 3 6 8 7 3 Aj'jMOUMCJS Jo/ ',9 7 A ?OUU7JON CH2AUCA1 J jt" \ J .V / " \ j \ . T I jJ J ^ Contains: PCT's PCB's PCN's Dioxins Pesticides Dibenzo Furans Polynuclear Hydrocarbons Send In your name and address for a copy of our Pol lution Control Catalog. This catalog will only be sent on request. Available Febru- 80 Republic Drtv, North Haven. Connecticut 06473 Telephone: (303) 388-6463 Telex: 064516 i PAID I North Haven, Conn I Permit No. 20 Nev 03687^