Document ppj787wqp4vkM16aLjggMBq4X

1 >-/7gf ' Roger J. Zipfel" <ZIPFEL@WWPS-A1 .EMAIL.DUPONT.COM > on 0 9 /1 4 /9 9 0 4 :5 4 :1 2 PM To: Roger J Zipfel/AE/DuPont cc: Subject: (C-8 BIODEGRADATION/14-Nov-19 9 6 )1 /DERS Perspective on Envirog Date: Thu, 14 Nov 1996 15:28:00 EDT From: "JOHN M. MIGLIORE" <MIGLIOJM0CSOC-A1.EMAIL.DUPONT.COM> Subject: 1/DERS Perspective on Envirogen and C8 biodegredation - FYI To: "Roger J. Zipfel" <ZIPFEL0wwps-al.email.dupont.com> MIME-version: 1.0 Content-type: MULTIPART/MIXED; BOUNDARY=nBoundary_(ID_SVrb9LBotNtgw9h2AxsOGw)" Delivery-date: Thu, 14 Nov 1996 16:07:00 EDT Posting-date: Thu, 14 Nov 1996 15:33:00 EDT Importance: normal Al-type: MAIL Roger, Attached is some information provided to me by DERS. I will be meeting with them on the 19th. Please let me know if you have any issues (i.e. future activities with 3M) that need discussed. Also, do you know of any studies where we identified the impurities in C8? Is there someone at 3M who can help us with this? Thanks, John r-'j 0^3 -- tn -GO VQ "ifT'J 33* r c mCD t*o no Date: Thu, 14 Nov 1996 13:31:00 EDT ' From: "DAVID E. ELLIS Ph.D." <ELLISDE@CS0C-A1.EMAIL.DUPONT.COM> Subject: RE: C-8 Meeting still on for 11/19? To: "JOHN M. MIGLIORE" <MIGLIOJM@CSOC-Al.EMAIL.DUPONT.C0M> Cc: "WILLIAM E. MANCINI" <MANCINWE@CSOC-Al.EMAIL.DUPONT.C0M>, "PHILIP A. PALMER" <PALMERPA@CS0C-A1.EMAIL.DUPONT.C0M> MIME-version: 1.0 Content-type: text/plain Posting-date: Thu, 14 Nov 1996 13:40:00 EDT Importance: normal Al-type: MAIL RJ7.014299 Gentlemen: EID937985 000040 I am forwarding a couple of E-mail notes to you so that you have a chance to think about them before our meeting. If we decide to look in the ponds for a degradation product it would be either a carboxylated C-8, or C-8's which have had carbons clipped off the end, one at a time. This would lead to C-7, C-6, C-5, etc. Do we know what impurities might be in neat C-8? This could be an factor in getting a good interpretion of any field analyses. I haven't yet heard back from Harry Gearhart about increased analytical sensitivity. Dave Date: Fri, 25 Oct 1996 13:40:00 EDT From: "J. Martin Odom" <ODOMJM@ESVAX-Al.EMAIL.DUPONT.COM> Subject: RE: C-8 Biodegradation To: "DAVID E. ELLIS Ph.D." <ELLISDE@CS0C-A1.EMAIL.DUPONT.COM> Cc: DALE S SCHULTZ <SCHULTDS@ESVAX-A1.EMAIL.DUPONT.COM> , "J. Martin ODOM" < O D O M J M 0 E S V A X - A 1 .E M A I L .D U P O N T .COM> MIME-version: 1.0 Content-type: TEXT/PLAIN; CHARSET=US-ASCII Posting-date: Fri, 25 Oct 1996 13:56:00 EDT Importance: normal Al-type: MAIL Dave, I have a final report from Envirogen entitled "Aerobic biodegradation study of TFA and C-8" dated June 1996. The report concluded a) that TFA was not degraded by the aerobic biochemistry investigated; b) the results on c-8 were inconclusive because the analytical method lacked sensitivity. The report summary concluded that further analytical development in needed before the question can be addressed. I think the sensitivity they had was somewhere around 10 ppm and above. I agree with that conclusion - if there were very low rates of breakdown we would never see biodegradation. However, it is also clear that if TFA doesn't degrade with the Envirogen microbes then it is extremely unlikely that C-8 will. Envirogen recommends that ANAEROBIC microbiology be tested with a more sensitive (GC/MS) method. It is not all clear to me why Envirogen thinks anaerobic would be more successful. Also AEROBIC microbilogy is Envirogen's strength- not anaerobic. My recommendation is to contract out an analytical effort (CRD analytical is looking to get more useful) to improve upon the HPLC EID937986 CO0041 KjZuhjoo method and then do an in-houBe study using site contaminated soil to look for breakdown products (intrinsic) as well as a lab demo of either aerobic or anaerobic biodegradation. Martin Date: Mon, 4 Nov 1996 14:30:00 EDT From: MARK H EMPTAGE <EMPTAGE@ESVAX-A1.EMAIL.DUPONT.COM> Subject: Biodegradation of C8 To: ODOMJM6MRGATE Cc: "David E. Ellis, Ph.D" <ELLISDE@CSOC-Al.EMAIL.DUPONT.COM> MIME-version: 1.0 Content-type: text/plain Posting-date: Mon, 4 Nov 1996 15:37:00 EDT Importance: normal Al-type: MAIL Martin, My rational for why TFA is not biodegradable should apply equally well to C8. The standard route (and I believe only route) for fatty acid degradation is activation of the carboxylate to a thioester of coenzyme A. The first step in this reaction is a nucleophilic attack of the alpha phosphate of ATP by the fatty acid carboxylate group. The fluorines of C8 will make the carboxylate a very weak nucleophile resulting in no or very little reaction. Even if you could make the thioester of C8, there is no place to go since the next reaction requires dehydrogenation of carbons 2 & 3. I don't think that C8 will be susceptible to biodegradation by this route. The only reasonable degradation route for TFA (and therefore C8 as well) in the environment is thermal decarboxylation (half-life = `1 million years at room temperature or *10 years at T=100C) or photo-decarboxylation (half-life = "1 year in O.OlmM free iron and sunlight at room temperature). Both high temperature and high free iron environments are extremely rare and should not have a significant impact on the degradation of C8. If the decarboxylation route (via radical chemistry) did take place with C8 then the expected products would be perfluoroheptane or perfluorotetradecane and 002 in anaerobic environments, or C7 and C02 in aerobic environments. If C8 could be degraded aerobically then so would C7, C6 etc. An expected degradation products profile from these reactions might then be C7, 06, C5, etc. C8 is not that far removed from Teflon. Has anyone looked at the degradation of Teflon in the environment? As you can read, from our experience with TFA I don't give much hope for any significant degradation of C8 (biological or chemical) in the environment. Mark RJZO14301 EKD937987 C^0042