Document G5MRQYqrobv1oQYe6reyNLdNV

Brussels, Belgium February 22, 1967 DW Dr. R. Bmwt Rally St. Louis J.R. Buchanan, St teuii V >, . <1.*. Filar, Brussels P.V. Hardy, HCL --' ~ Eugene Hilda, St Louis Bear Dr. Kelly, I should like to refer to your letter dated the 10th of February and our telephone discussion of yesterday's data. 1 enclose a copy of BOren Jensen's original paper which in fact was presented in English - Dr. Jensen apologises for the typing etc. but this copy is taken from his original paper which has not yet been re-typed and tidied up. I asked our agent in Sweden to dig out the various pieces of information that you required and X attach a copy of his reply dated February 17th which X think fully covers the point raised in your letter. If there areany small points outstanding, please let me know and X vill try to get you further information. I am sanding the only aopy of Hr, Jensen's paper to you and therefore if any of the other recipients of this letter needs to have access, they can take a copy from yourself. Z would however emphasise the post script on page X of Ola Balm's letter in which he statea Mr. Jensen has consented to send us the full copy of his paper on the understanding that this is used only internally within the Monsanto organisation. LEXOLDMON000034 WATER_PCB-00035501 RISING & STRAND OP/ao aktiebolao TELErOM; 3461 93 TELESRAM; HENRI* TELEX; 1424 roTOmo 3*443 kanhoiro 73-64*1 Stockholm va February 17, 1Qo7 SVEAVAGEN 47 Mr. David Wood Monsanto Europe BRUSSELS J Belgium Pear David, re; AftOCLORS Reference is made to our telephone conversation ar.ci I have tried to dig out the information you asked for. Before going into any detail, however, I would like to refer to your letter to Mr. Soren Jensen , dated February 8. Mr. Jensen would be interested in samples of as many isomers as you can put at his disposal. The quantities cf course are very small indeed and he would need only about 10 mg of each. In theory you could put the lot behind a stamp and mail it to Mr. Sdren Jensen but in actual practice it is of course not as easy as that. Anyway, Mr. Jensen would be interested in both the lowchlorinated and the high-chlorinated types since this would help him to get a better picture of the metabolism. Now to the various points you raised. Enclosed you will find the original articles as published in "Dagens Nyheter" and "Svenska Dagbladet" on November 2;?, 'Jj6i. The people who organised the meeting wnere Mr. Jensen's paper was presented was a Committee - 190A &rs Natur- v&rdskemmitt& - operating under Statens Naturvet-hoitapl.. Fcrskningsr&d (The Swedish Natural Science Hesearcr* Council). The Committee (for Conservation of Natural Resources of 196^) is working under the chairmansnip of a Dr. B. Lundholm. .. The meeting was organised under the auspices of Naturv&rdskommittfen and was called apparently only In order to give Mr. Stiren Jensen an opportunity to publish his findings. The timing was made so as to coincide with a visit of Dr. A. Holden from Scotland. HONS 090516 LEXOLDMON000035 WATER PCB-00035502 *: i 3 t N G &. S T R A N O Mr. D. Wood - MCL Dr. Alan Holden - address fresh Water Flcheri.es Lciborai. cry, Pitlochry Pearcher, Scotland - is the coordinator for the twelve OECD countries, as far as the influence of biocides on Nature goes. Dr. Holden apparently is a specialist on such questions and particularly on fish. There is no intention that Dr. Holden, or the group of twelve OECD countries as such, should carry on any further investigations on the particular problem unearthed by Mr. Jensen. Any continuation will be carried on in Stockholm by Mr. Jensen or cooperating Swedish labora tories. The meeting of November 2J offered only one paper, i.e, that of Mr. Jensen. No decisions were made on any further action. The work done by Mr. Jensen was paid for by the abovementioned Committee for Conservation of Natural Resources. The further studies planned for on toxicology have not been started on yet since there is no money available. It is possible, however, that the same Committee of 196^ will be asked to subsidise even that work. If toxicological studies are to be made, these probably will be carried out at Karollnska Institutet, Division of Toxicology under Professor Bo Holmstedt. The full address of this institute is Kgl. Karollnska Institutet Avd. Toxikologi Solnavagen 1 Stockholm 60. i Since no decision has been made on toxicological invest igations, obviously no information can be given as to the scope of the planned investigations. The LKB press release of January 10, 19uY mentioned tne research of twelve OECD countries. As was mentioned above, there is no question of any central investigations to be made under the auspices of the twelve countries. There is only the question of coordinated efforts by way of interchange of information. Enclosed you will find photo copies of the original paper of Mr, Sbren Jensen. We have taken this copy here and Mr. Jensen apologizes for the state of the paper which is his own typing. He has not yet had an oppor tunity to nave it properly retyped for publication. I nope the above answers your questions. Yours sincere iy, Er.c.. , , ;V. . itw ^ HONS 090517 LEXOLDMON000036 WATER PCB-00035503 ing *. strand Mr. D. Wood - MCL + H . .* Ok AA P.S. David:For the sake of good order, I would like to mention that Mr. Sdren Jensen has sent us these papers with the understanding that they are only for internal use within the Monsanto organisation. Ola. MONS 090518 LEXOLDMON000037 WATER PCB-00035504 o Ur Chairman, ladies and go*1ntlamon, ' In honor to our Brlttiah goet I will try to hold this lecture in English, As tho titlo of this loeture states, I an today going to tell about tbo diocovory of some hlthorto unobserved chlorinated hydrocarbons having up to eight chlorine in the molooule and found'in reolduo cnnlyoio. Iha chonlool none of polychlorlnotod bifenyle ( Xn the following oallod FOB). Io get fcnillar with FOB I will start with the ohoaietry and .toxloolbgi. Ohoroletry 'ni : EMFUpiT .'.i I '.wgptoih The main-oharaoterietio of FOB ie 1. Their very high stability* As on example they can be boiled with nitrin aold without being destroyed. 2* They aro netabollsed in living organiem. 3, if more than 4 chlorine arelpre^eent they are non infleasable. It is dear that theee threo characteristics does it easy to understand that when they havo entered the giving organisn.- the will have a low persistence . But it la difficult 'to explain how they find their way into the living organiem. . Ono thing seene to be elearr they don't ooae from agricultural use, but fron a technical one and most probable it domes to the nature via wastes that are tried to be burnt up, because then we have them, at .oneo in the air, btoauee of their non inflaaability. . ..loxlcologl HUNS 049048 S Tho FCB woro Intxoduoed in 1929 and no early as 1936 Jonoe and Alden reported that 23 out of 24 nen employed in manufacturing of ?CB sufferod from on mono fora eruption of the akin. Acne did not appear until 6 to 6 months after the material was first usod. In 1937 Drinker reported that rats sxpooed to chlorinated biphenyls in concentration of approxi mately 1 mg/a3 for 16 hours a day for 6 weeks chowdd damage of tbo livor. After that time tho alloTrod concentration of`PCS in air is 0,5 ng/a3. (For DDt the some value is 0.3 - 1 xog/a3). The soao authors finished tholr experiments in 1938, and related that these compounds have an lnjouriouo effect, manifested solely in the liver. Chlorinated bipohayloj p appeared to.be the moot lnjouriouo chlorinated compounds of (0.1 tested. LEXOLDMON000038 WATER PCB-00035505 Orenburg, Mayer and Smith 1939 reported that PC and polychlorinated naphtalcnoe are blamed for the death of three young workers, and that^* pregnant women and pereone who have at any time had any livor dlseasos nro particularly euspectible, t Wedol, Hollor and Benton gave 1942 animals PC including odminiotration by inhalation, ingostion and akin abeorbtion. Histological examination of tho viooera showed important toxic effect only in the skin and livor, and tho dogoneration effects in the liver are essentially the sane what ever was'tho method for the administration. Paribok (l955/ found as en occupational poison in the eleotrioal Industry, mixed totra and posts ehlorobiphenyl eauoos folliculitis, oomodo, pyodermia and other okia affections, and that its principal toxic effect is fatty degeneration of the liver. ' Miller (1944) injected 69 mg PCB (4 and 3 oblorine) subcontaneously In 32 guinoa pigs. Bight to ten days after injection, fat droplets wero noted in the liver cells, and after 16 days they were present in modcrato or very large numbers. Babbits and rats were also tested in this invosti- gation, as well as the PCB was adminietated both continously, subeuntin- ously or ingested in the food. In the feeding experiment Q guinea pigs received 2 doses of 69 mg of the chlorinated biphenyl 1 week apart. Death occurred in 11 to 29 days. Finally Mo Leughlin 1964 reported a method to test the chemical toxicity and teratogenic effect by injection Into the yolk sac of fertile eggs prior to lnoubatlon. PCB waa found between the eight compounds among 100 tested haring the highest order of toxicity. No hatch was found at a level of 25 mg ps egg. At a level of JO mg per egg, one ehiek hatched eut of 20 Injected eggs, but died 2 days later. Some embryos which were examined after they died, showed weak deformities (often a short upper brak) and growth retardation. Lead acetate resulted as an example in no hatch at a level of 1 mg per egg. Autopsy of the dead embyos have showed exten elve brain damage* Mercuric chloride showed no hatch even at a level of . 0,3 mg per egg. MQNS 049049 . As the analytical chemietry is a pronounced service science I have boen in contact with many scientists from other fields during the work with residue analysis, and X have always found this contact very stimulating for my own work. This co-operation often demands that we are talking the same scientific language. Because of this need X will today try to givo a lecture in low level analytical chemistry for biologists, illustrated by the residue analysis of polychlorinated biphenyls. The lecture will be divided in the following three eub-dlvieione: . LEXOLDMON000039 WATER_PCB-00035506 1. Chemistry of PCB and their tocicology. 2* Analytical methods for roeidue analyeis and proof of structures. 3* Behaviour of PCB in nature, dlfferenciee In metabolising xato of the PCB components, potenaation in on ecological oerie, con centration levele and examples of samples which have boon provod to con tain PCB* A residue analysis can be divided ini ' 1, Extraction of the poeticidee from the biological material, * followed by a careful cleanlng-up to tedce away interferring substances, most often fate* b 2* Identification onalysie by moan of gas chromatography. Thin- layer chromatography and maae Bpectroaetry. 3, Quantitative analysis. /. At on ecological laboratory in Blksmuaiet in Stockholm 1-2 g of a aamplo e la out out of the biological material and transferred into a weighed and oarefully cleaned teet tube, and stored at -20 until analysis. Smaller O samples have been ueed, min. 5 *g of body fat, and with dry materials such as hair, feathers, pins needles 100 mg are sufficient to reach the desired 10 ng/g level in residue analysis. In cases of water proofs 1 1. ie uBed for reaching the 10 pg/g* level* B.l(homog) In order to facilitate complete extraction of the fatty materials from the biological sample, the doulbe amount of finely powdered anhydrous ' magnesium sulphate ia added to the sampling tube, and the whole is'hooogenlecd with an intertable homogenlser. The resulting powder is transferred Into a special Soxhlet extraotor. After 4 hours of extraction the solvent ie evaporated, leaving the fat in a email weighed test tube at the bottom *8ox*-tube) of the extractor* This fat is dissolved in methylene chloride In such a way that 100 ul (0,1 ml} contain 20 mg of fat. The 100 ul solution is now transferred to a little object glass, 3 x 7 cm, covered with a silioagel layer 1 am thick, in order to fora a line 0,7 cm from one end of the elide* Inserting this thin-layer plate into a vessel the bottom of which is covered by a few mm of methylene chlorido, the solvent will be sucked up in the dry layer of silicagel, and at least reach the upper end of the plate. The fact is that the fat has a greater affinity to_ the powder on the plate than the chlorinated hydrocarbon have. - and we get a separation. The fat being more polar than the chlorinated (hydrocarbons will never go longer than 2 cm before thO HONS 049050 LEXOLDMON000040 WATER_PCB-00035507 ,1. / o |,,'7 JJ1UTX0H tuba 5 00 6 (i solvent roachos the upper part of the Blase. Tho front of the fat appoaro quito Yioiblo against a lamp, and with tho old of a razor bleda tho zone abovo tho fat is tranoferred to tho olutloa tubo and the ohlorinatod blooldoo absorbed on the powder eon now bo oluted by one ml of other. The concentration is sufficient for detection of tho chlorinated hydrocarbons down to tho 10-12 g levol. Tho noxt stop in tho analytical procedure concerns tho separation of tho difforont chlorinated hydrooarbons that tho samplo may contain. Ao a rattor of foot, this is a broublosome task. It is easy to estimate what is not prosont, but more difficult to say exactly one Is present. Ve ouffor from tho negative demonstration, as will be shorn later. . At first a fow words about the separation of the components preoont la the sample and their visualization. Tho ooparatlon ie aoooapllehod by mean of a gas chromatograph fitted to a dotoetor that transfers Its impulse to a recorder. o o \ I The system Is shortly .described: A spirally formod glass tube with an lnnor diameter of 2 am and about 2 m in length is filled up by a support, eovored with an thin layer of an oil. The tube is hoated in the chromatograph to about 200. Through the tube a stream of nitrogen contlnously follows. When about 10 ul (1/100 of 1 nl) of the purified sample la injected into the tube, the components of the sample will be evaporized and go forward through the column with the gas stream. As the constituents have different affinity to the column filling they will pass the column with different spood and it will take different time for then'to roach the detoctor at tho other end of tho glass tube. 1$ tho temperature and the nitrogen flow are held constant this time, tho retention time, has a epocificvaluc for a certain compound. Thle le true, but unfortunately it is also a fact that two components oan have tho'samo retention time. Thle la one of the bigger problems in gas ohromatographie analysis of unknown samples, ao will soon be obvious. To make it possible to estimato the retention time It Is necessary to vlsualies the chlorinated hydrocarbons. For that purpose mors or loss specific detoetors are used. The detector most often used In postlcldo analysis Is the so called eloctron capture detector, which can detect down to one picogram ( 10~ g of llndan). Unfortunately thiB detector ie not specific for chlorine, bu gives answer also for oxygencontalnlng compounds. The response here le muc*: lower but can be counterbalanced If the COBCOXW tration of the oxygen containing le much higher. HONS 049051 Tho principle for tho electron capture detector Is shortly: At the end of the gas chromatographic tube is placed a little tube con taining a foil of titanium tritido. This 1r an-rodlant. The o- LEXOLDMON000041 WATER PCB-00035508 t KJ O TJ O particles ora reacting with the nitrogen molecules coming from the column. Then we get + N2 -- e" + Mg. Over the detector we have a tenoion of 90 volt and by mean of the electrons wc will get a constant electrical curront over the detector. This standing current is transferred to a onv-mV rocordor aa a constant baseline. When now a chlorinated hydrocarbon loavso tho column this compound hoc high affinity to the olootrono and this moans thnt the amount of elootrons will diminish, and they will diminish proportionally to the amount of chlorine. The electrical curront will also diminish and this is noted ae a peak on the recorder. The area of tho peak will be proportional to the amount of eubstance in the sample. By moan of a standard injection it is now possible to compare the reten tion tlmo and the area of an unknown component with the retention time and area of the known standard. As said before thiB detector is not speci fic for chlrlne but anyhow very useful, because of its high sensitivity. The eyetom described hae, ae we have seen, two disadvantages: 1. Two difforont compounds can have the same retention time and be detected as ono psak. 2. A regiatrated peak doee not need to be chlorinated , because the 'detector ie not specific* If the sample is injected in two different columns with different chemical properties we have inoreased' the chance for a good separation. If two compounds have the same retention time on one column they may not have it on another. When a result seems doubtful, - if the compound being responsible for a certain peak contains chlorine or not - it is poseible to concentrate the sample and analyse,it on a less sensitive detector uoh ae the mlerocloumetrlc one, which la specific for chlorine. The oompound la burned in a furnace and teh generated chlorine titrated directly. MONS 049052 As is seen from the two last mentioned possibilities it is anyhow possible to get a rather high degree of certainty in residue analysis, but it is _ a rather tiae-oonsumeing work.When using this method just described, we very often found that many chromatograms from residue analysis of most carefully purified samples still contain a large number of peaks, llapy of these have retention times that do not agree with any known chlorinated pesticides, or their metabolites. This chromatogram con serve as an example. It was obtained by residue analysis of a sea-eagle found deed In the archipelago of Stockholm. In the range of the known peaks, there are do many unidentified that there also must be an obvious rick of the known penko to bo covered by unknown ones. If thlfl remark in fftnnrt + T*n*. +h* ,*gr>nv',f+ o n*f wnnw . LEXOLDMON000042 WATER PCB-00035509 titabivo ana/;, As must be brought Into quese-\, iinn.. In the present investi gation it is shown that nost of the unknown peak of chromatograms at rooiduo analysis of chlorinated pesticides are due to polychlorinated biphenyls. X will show a chromatogram of human fat analysed on a so called S? 96 column, the nost often used type in pesticide analyses. Early retention times were in agreement with DIB, DDTop and DDTpp. Hoxt slide shows the same sample analysed on a QP-1 column. Now the former 2 DDT peake have ' divided into 4 peaks,and two of them are sllll in agreement with DD2pp and op., tho two new wore unknown. logically, those unknown components were at first thought to be metabolites of the insecticides. Against that spoke that neigther treatment nor conoontratod sulfuric acid in other. This treatment made it rather cure that the compounds did not contain oxygen. In Sv/odon residues of organic mor oury have boen investigated rather intensively in the Swedish fauna. As those compounds give very high responses to the electron capture doteo- tor it was also Investigated if the unknown peaks could have a mercuric origin. It was found that the water-ecologioal series had high residues of both mercury (Weotermark,Johnelo) and the unknown ones, when the same indivi duals were analysed. Anyhow, the pheasant suffering most from mercury poisoning only contained low levels of electron capturing compounds and thece belonged ' ` to the normal insectisldes. Therefore the unknown could hardly be mercu rial. or metabolites of them. M0NS 04905J As the eagle sample giving the chromatogram shown in fig. 10, could be estimated to contain DDT and DDE up to 13 g/kg in extractable fat, the amount of unknown compounds also were suggested to be in the same range, and tehn sufficiently high to do a run on the combined gas chromatograph mass spectrometer. Xf this could be done successfully it would be possible to get very important informations about the chemical nature of the unknown, for ex. the mclekular weight numbers of chlorine etc. This method is up to now the method giving the highest degree of certainty in the low level analytical chemistry, amounts of 100 ng substance being enough. As this method for identification of totally unknown residues surely will be very important in the future (when f.ex. a biologist has found that fishes in a river die) it roaybpossible by mean of this method to find out exactly what compounds are responsible for the death. For this reason, I will go into come details with this method. In the actual ease we took the extract from 20 mg eagle and concentrated LEXOLDMON000043 WATER PCB-00035510  (y U it as much as possible and made an injection on the gas chromatograph o combined with the maso spectrometer. The result wob the chromatogram ehown on the next slido. Every time the recorder showed that u compound is loaving the oolumn, the effluent is led to the mass epectromotor. Now juet a few words about the mass spec. '* The molecules leaving the column are bonded with electrons at K. Vo b&vo How got the molocule positive charged, but with the same maoo ao before. " This 11+ is aceolorated in a vacuum and will than gat a kinetic onergi. whero is the speed. Next comes the magnetic field that . trioe to bend the direction of the molecule. This will bt big for a small molecule and lees for o If we have a sieve in the other end we can direotly .read the molecular weight. Added to this parent molecule M+ we will also get addition in formations, because of ths fact that M+ may not be sthblo, a port of them will be broken down before they reach the sieve in the other end. ?.ex. U DKf U jjjjj _ cc, Haas spectrograms from ths different unknown peaks In the eaglo sample as shown. Tho mass numbers equal to the molecular weights of the unknowns could bs read to 426,392, 336, 324. Astonishingly, ths molecular diffe rences wsre constantly 34 mass units. This difference shows a femilerity in origin of the unknown. Now the fact is that chlorine ezsiote as a mixture of two Isotopes with atom weights 33 and 37 in proportion 73:25. If the molecule has one chlorine, this will give two molecule petke, one for Cljj and one for Clj^. If there are two chlorine wo have the poooibility . of one with only Clj,., one with both 01^^ and 37 and one with 2 Cl^ end therofore MONS 049054 LEXOLDMON000044 WATER PCB-00035511 She relation of the peaks found on the different naae epee worst Hoi ocular weight ' ' 324 358 392 426 Ohlorlne content 5 6 76 An explanation of the familiarity of the oompounds oan he given if one eubetwice is built from the former by substituting a hydrogen with ohlorine RH M+ + 01, RC1 HC1 M++ 34 Thon it is poeeib) to calculate the molecular weight of the parent hydrocarbon PHC. - K - x HC1 + x Mjj , where H la the molecular weight of the conponont having x chlorine atoms. ?.ex. for m 426 and 8 Cl we will get . 426 - 280 + 6 m 154 and equal with the other molekylo. Iho moot probable formula with carbon and hydrogen giving thin molecular weight is C12 H10 and *thie can only be satisfied when the porent-hydro- earbon is blphonyl, and the unknown being polychlorinated biphenyls. This explanation was later fully verified by injection of a synthetic IBC on the mass epee, Furthermore extensive gas chromatographic investigations provod that the ISC standard gave peaks with the same retention time as the unknown * peaks from the sea eagle. With the method just described I suppose that we have a new possibility to study the residues in the air because the pine needles can allwaye bo We have had great difficult; in Quantifying the ?CB, but when getting a little more time it will be possible. We have done a few calculations on a few species, and I suppose they are right within a factor 2. We have found the residue to be from It has been ay statement here to-day to present this method for studies Of defiling of the nature, and with this method a new typo of doflliag agents has been found to be present In nature, and a few experiment have shown where they may be found. How this method is going to be used in the firct hadn to estimate how the situation is In nature as a whole, and in the other hand to find the leaks throug which they find its way to nature. Soem maybe are prcaont here today to get news about the leaka, and to them X want to o&y cone back in a year* MOWS 049055 LEXOLDMON000045 WATER PCB-00035512 So much I think I can coy again that the PCB hardly can coma from agriculture. Aa suppoft for thia suggeotion 1 can say that we have found PCB In eagle feathers from Rikarauseot from 1944, where hardly any chlorinated poatioidea were used in agricultrue. One more thing that Z find important to eay is that in contrast to the mercury problem this does not aeon to bo a pure Swedish problem, 1 have just studied chromatograms tcdcon from London air, and they cloorly contain PCB, and dr. Holdon hun told me that ho also find them in hie fishsomplee* But finally in waiting at more results Itshould like to point$$e morething. It is proved that PCI eomos to neturo, no dont know now where they are uood, but they are very persistant to chemicals and to fire. I think the poieon jury should try to state that a content of PCB shall always be found in an open declara tion. O HONS 049056 / LEXOLDMON000046 WATER PCB-00035513 ............................... '. co LMiHurt o4 tuseJ idJet and PC3. -frorn e^yfc JamfU 2. Some som^/e A'Htr f?/* ^ irdiea ., Only 'PC& JUfnain. &* PC3- * ndard- Column'' QFl 6% on ejasdircrn ? too-n<> meih C *hofcccf, (sJi m e nh'fod. t3o. C*v* in O, t2 ^v / ' . * - CQr*it*,y&s !$ C m/set ip. lo bo ml/min- bd, fCD. LEXOLDMON000047 WATER PCB-00035514 8506+0 SNOW O o cP * * SQ, O* 3 *s. I 3 7n*n, $ S5 5* .1 5 * M <3 N ?! * N N >6 o. 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