Document qddeLBwY5qg4xO8Q8j6bbx8E5
3M General Offices
3M Center St. Paul, MN 55144-1000 612 733 1110
/4R2K0333
May 18, 2000
VIA EXPRESS MAIL
Dr. Charles Auer Director Chemical Control Division Office Of Pollution Prevention And Toxics United States Environmental Protection Agency 401 M Street, Southwest Room 403 East Tower (Mail Code 7405) Washington, D. C. 20460
Re: Inform ation On Perfluorooctane Sulfonates And Related Compounds
Dear Charlie:
Pursuant to our recent communications, 3M is enclosing additional information on perfluorooctane sulfonates and related compounds. The enclosed information supplements information submitted to you previously under cover of our April 21, 2000 and May 4, 2000 letters. Again, we are providing this information on a voluntary basis as part of our continuing discussions with EPA regarding fluorochemistry. Please note that some of this information qualifies as confidential business information (CBI); we also have enclosed a sanitized version of CBI documents.
The enclosed information covers perfluorooctane sulfonates and certain related compounds listed in Table 1 of the document entitled: "Sulfonated Perfluorochemicals In The Environment: Sources, Dispersion, Fate And Effects", at 12 (March 1, 2000). Specifically, the information covers the following chemicals:
=> Perfluorooctane sulfonates, including CAS numbers 1763-23-1 (acid); 29081 -569 (ammonium salt); 70225-14-8 (DEA salt); 2795-39-3 (potassium-salt); 2945772-5 (lithium salt).
=> Perfluorooctanesulfonyl fluoride
0S983
Charles Auer May 18, 2000 Page 2
=> Perfluorooctanesulfonamide
=> Perfluorooctane sulfonylamido (ethyl) acetate
=> Perfluorodecanesulfonate
=> Perfluorohexane sulfonate
=> N-ethyl perfluorooctanesulfonamide
=> N-methyl perfluorooctanesulfonamide
=> N-ethylperfluorooctane sulfonamidoethanol
=> N-methylperfluorooctane sulfonamidoethanol
=> N-ethylperfluorooctanesulfonamidoethyl acrylate
=> N-ethylperfluorooctanesulfonamidoethyl acrylate
=> N-ethylperfluorooctanesulfonamidoethyl methacrylate
=> N-methyl perfluorooctanesulfonamidoethyl acrylate
3M has provided you with information on perfluorooctane sulfonates previously under cover of our April 21, 2000 and May 4, 2000 letters. We are enclosing some additional information on perfluorooctane sulfonates located as part of our continuing file search. For each of the foregoing related compounds, the enclosed information includes the following:
=> Copies of post-1976 studies and certain other information relating to the following environmental science areas: (i) physical and chemical properties; (ii) environmental fate and transport; (ii) environmental monitoring; and (iv) ecotoxicity. For each study, 3M has prepared a summary in the HPV "robust summary" format. 3M already has provided you with a general executive summary addressing each of these areas under cover of our May 4, 2000 letter.
=> Copies of post-1976 studies and certain other information relating to the following health effects areas: (i) acute toxicity; (ii) genotoxicity; (in) repeated-dose toxicity; (iv) pharmacokinetics; (v) teratology; and (vi) medical surveillance and epidemiology. 3M has included a detailed index of this information subdivided by each compound.
005984
Charles Auer May 18, 2000 Page 3
=> Lists of all studies in progress and planned studies, along with study protocols or study plans, where available.
=> A bibliography of pre-1976 studies subdivided by each compound.
=> A bibliography of acute toxicity studies subdivided by each compound, except that we are providing copies of key acute studies (with reference to the HPV guidance).
=> A bibliography of published studies in 3M's possession.
=> An index of studies in 3M's possession believed to be in the FIFRA docket. Please note that this index has been submitted as CBI. 3M already has provided the Agency with a list of all fluorochemical-related submissions made by 3M to the TSCA Section 8(e) docket.
3M is continuing its file review and will supplement the enclosed information as appropriate. As you review this information, we ask that you bear several points in mind:
=> The enclosed information spans several boxes. We have organized the information in each box with labeled file folders and indices to aid EPA's review. To ensure that you and your staff are able to access the most pertinent information, we also are attaching to this letter the indices covering studies and other information.
=> Many of the studies refer to the test substance only by a 3M product identification number with a "T", "L" or "FC" prefix. Although analysis of the test substance has been included, where available, it is often not possible to determine from the study report itself the identity of the test substance. Thus, we have used the index to provide this information based on 3M's historical records keyed to the 3M product number to determine the composition of the test substance and have provided specific information on the index, such as percent composition, solvent context, salt form and purity grade. Please note that the term on the index "wide range" refers to a lower purity grade of the compound, and "narrow range" refers to a higher purity grade. Finally, it should be recognized that product formulations have evolved over the years, and thus, some of the test substances do not constitute current products.
=> We have included some additional studies on perfluorooctane sulfonates located as part of our continuing file review. As we have discussed, we plan to provide you with information on mixtures containing perfluorooctane sulfonates in the near future. Please be advised, however, that we already have provided you with studies and other information on aqueous and/or solvent solutions of
005985
Charles Auer May 18, 2000 Page 4
perfluorooctane sulfonates. As to the foregoing related compounds, the enclosed information likewise includes studies and certain other documents on both the compounds as well as on aqueous and/or solvent solutions of these compounds. We are not providing to you today, however, information on other types of mixtures containing these compounds and would like to discuss such information with you. => Consistent with the information previously provided on perfluorooctane sulfonates, 3M has not provided you with all analytical chemistry reports on these related compounds. Rather, we have enclosed certain analytical chemistry reports which may prove useful to EPA in interpreting certain studies; understanding the details of analytical chemistry methods; or verifying human and biomonitoring data. => We provided previously under cover of our April 28, 2000 letter to Oscar Hernandez a "Use And Exposure Information Profile" or "UEIP" for perfluorooctane sulfonates. Our present intention is to provide you with completed UEIP forms for these related compounds early next week. 3M needs additional time to clarify industrial hygiene and other release information to ensure that the data is accurate and placed in appropriate context. => The information on perfluorooctane sulfonates sent under cover of our May 4, 2000 letter included documents relating to ongoing mechanistic research by Dr. Ken Wallace of the University of Minnesota. Please note that this research also encompasses these related compounds. In addition, Dr. Marion Anders of the University of Rochester Medical Center is performing comparative metabolism research relating to perfluorooctane sulfonates and these related chemicals; there are not documents yet available relating to this research.
005986
Charles Auer May 18, 2000 Page 5
3M looks forward to discussing the enclosed information with you and other EPA staff. In the meantime, please do not hesitate to contact me with any questions.
Very truly yours
Enclosures
William A. Weppner, Ph.D Director of Environmental, Health, Safety And Regulatory Affairs Specialty Materials Markets 3M Bldg 236-1B-10 3M Center St. Paul, MN 55144 (651)733-6374 (phone) (651) 733-1958 (fax) E-mail: waweDDner(5).mmm.com
005987
Perfluorooctane sulfonylamido(ethyl)acetate = PFOSAA
Synonyms: FC-109, FC-109-X, FC-128, FC129, E2113, E2566-2, R1904
Physical/Chemical Properties Title
Laboratory or Author
Date Completed
Type
Environmental Fate and Transport Title
Tech. Report - Fate of Fluorochemicals in the Environmental (sic) (Warburg respirometer method for biodegradation of FC-128) Ready Biodegradability of FC-128 - BOD/COD
Laboratory or Author
Date Completed
Type
3M Env. Lab
8/12/76
Robust summary, technical report
3M Env. Lab
7/8/77
Robust summary, copies of data sheets
Tech report - Analysis for Fluorochemicals in Bluegill Fish
Ready biodegradability of FC-127 - BOD/COD
3M Env. Lab 3M Env. Lab
5/1/79 8/19/81
Robust summary, technical report
Robust summary, copies of data sheets
Ready biodegradability of FC-109-X - BOD/COD
Pace Laboratories, Minneapolis, MN
12/31/87
Robust summary, copy of computer results from archives
Summary Reports Title
Laboratory or Author
Date Completed
Type
Ecotoxicity Elements Title
Acute toxicity of FC-128 to fathead minnow Acute toxicity of FC-128 to fathead minnow Acute toxicity of FC-128 to fathead minnow Acute toxicity of FC-127 to fathead minnow Toxicity of FC-127 to activated sludge respiration
Laboratory or Author
Completion Date
Type
3M Env. Lab 3M Env. Lab 3M Env. Lab 3M Env. Lab 3M Env. Lab
5/18/74 6/29/74 8/26/77 7/24/81 8/14/81
Robust summary, copies of data sheets
Robust summary, copies of data sheets
Robust summary, copies of data sheets
Robust summary, copies of data sheets
Robust summary, copies of data sheets
005988
Ready Biodegradability: "Modified OECD Screening Test" for Fluorad FC-129
RCC, Itingen, Switzerland
Microbics Microtox Toxicity Test - FC-109-X
3M Env. Lab
Activated Sludge Respiration Inhibition - FC-109-
X 3M Env. Lab
ABC
Laboratory,
Acute Toxicity of E2566-2 to DaDhnia maana
Columbia, MO
ABC
Acute Toxicity of E2566-2 to Fathead Minnow
Laboratory,
(Pim ephales prom elas)
Columbia, MO
Pace
Laboratories,
Inc.,
Biodegradation (methylene blue active
Minneapolis,
substance)
MN
AScI
Corporation,
Acute Toxicity of R1904 to Daphnia magna
Duluth, MN
AScI
Growth Inhibition of R1904 for Green Alga
Corporation,
(Selenastrum capricornutum )
Duluth, MN
AScI
Acute Toxicity of R1904 to Fathead Minnow
Corporation,
(Pim ephales prom elas)
Duluth, MN
AScI
Corporation,
Microbics Microtox Toxicity Test - FC-129
Duluth, MN
AScI
Inhibition of R1904 for Activated Sludge
Corporation,
Respiration
Duluth, MN
AScI
Corporation,
R1904 BOD Report for 3M Company
Duluth, MN
9/19/84 10/15/87 10/30/87
Robust summary, memo about study reliability, final
report Robust summary, copies of
data sheets Robust summary, copies of
data sheets
1/9/88
Robust summary, final report
1/12/88
Robust summary, final report
2/15/89
Robust summary, computer report, copies of data sheets
6/17/97
Robust summary, final report
6/18/97
Robust summary, final report
6/27/97
Robust summary, final report
7/9/97
Robust summary, copies of data sheets
7/10/97
Robust summary, final report
Jul-97
Robust summary, final report
005989
N-MeFOSE Alcohol
Synonyms: FM 3925, L4528, L-4309, PPA-791, PPA790 (Me &Et FOSE mix) cc 796-10, FM 3974, cc 7963
Physical/Chemical Properties Title
Tech Report - Solubility of FM 3925
Laboratory or Author
3M Env. Lab
Date
Type
Completed
Robust summary, tech report,
excerpt from Tech report -
1/8/79, Analytical Methodology and
1/17/79 Support, 1/17/79
Environmental Fate and Transport Title
Laboratory Completion
or Author
Date
Type
Tech Report - Biodegradation Studies on FM 3925,
Tech Report - Chemical Oxygen Demand of FM 3925 3M Env Lab
Tech Report - Distribution coefficient of FM 3925 in n- 3M Env.
Octanol/Water
Lab
1/8/79, 1/8/79
1/10/79
Robust summary,2 technical reports Robust summary, technical report
Tech Report - Adsorption of FM-3925 on Soil
3M Env. Lab
3/22/79, Robust summary, critique from 5/19/93 S. Boyd (MSU), technical report
Tech Report - Bioaccumulation of Fluorochemicals in Tenn. River Fish, Tech. Report - Fluorochemicals in Tennessee River Fish, Ar No. 7238 - Determination of Fluorinated Alcohols in Fish Extracts
3M Env. Lab
5/22/79, Robust summary, critique from 12/28/79, J.W. Gillett (Cornell), 3 10/23/79 technical reports
Summary Reports
Title None
Laboratory Completion
or Author
Date
Type
Ecotoxicity Elements Title
Tech Report - Aquatic Toxicity Studies: FM 3925
Laboratory or Author
3M Env. Lab
Completion
Type
Date
Robust summaries for fish and
daphnia, copies of data sheets,
1/8/79 technical report
005990
Synonyms: FX-8
Physical/Chemical Properties Title
Water solubility estimate (screen)
Environmental Fate and Transport Title Environmental Aspects of POSF Reappraisal of POSF Environmental Fate Summary Reports Title None Ecotoxicity Elements Title
96-hour Toxicity to Fathead Minnow 7-Minute Exposure Activated Sludge Toxicity Test
POSF
Laboratory or Author
3M Env. Lab
Date Completed
Type
5/11/84, Robust summary, critique by 3/1/93 E. Tucker, lab worksheets
Laboratory or Author
3M Env. Lab
3M Env. Lab
Completion Date 9/1/83
12/15/83
Laboratory or Author
Completion Date
Type Technical report Technical report
Type
Laboratory or Author
3M Env. Lab
3M Env. Lab
Completion
Type
Date
Robust summary, data
4/6/84 sheets
Robust summary, data
5/10/84 sheets
005993.
Methyl FOSEA
Physical/Chemical Properties Title
Study of Stability of MeFOSEA in Aqueous Buffers Using Gas Chromatography with Atomic Emission Detection
Laboratory or Author
3M Env. Lab
Date Completed
6/14/99
Type
Robust Summary and Technical Report
Environmental Fate and Transport Title
Determination of the Partition Coefficient (NOctanol/Water) of T-5969.4
Laboratory or Author
3M Env. Lab
Date Completed
11/9/94
Type
Robust Summary and Technical Report
005992
Ethyl FOSEA
Synonyms: FX-13, B1228, D-1
Physical/Chemical Properties Title
Laboratory or Author
Date Completed
Type
Determination of Physico-chemical Properties of Sample D-1
Mitsubishi Chemical Safety
Institute Ltd., Yokohama, Japan
2/14/96
Robust summary, final report
Environmental Fate and Transport Title
Ready biodegradability of FX-13 (BOD/COD)
Laboratory or Author
3M Env. Lab
Completion Date
4/26/84
Type
Robust summary, copies of data sheets
Ready Biodegradability Test of D-1
Mitsubishi Chemical Safety
Institute Ltd., Yokohama, Japan
10/31/95
Robust summary, final report
Mitsubishi
Chemical Safety
Bioaccumulation Study of Sample D-1 with Carp Institute Ltd.,
iCvDrinus carDio)
Yokohama, Japan
11/30/95
Robust summary, final report
Ecotoxicity Elements Title
Acute toxicity of FX-13 to fathead minnow
Laboratory or Author
3M Env. Lab
Completion Date
4/1/84
Type
Robust summary, copies of data sheets.
005993
Perfluorodecanesulfonate, Ammonium Salt (PFDS)
Synonyms: FC-120, FC-121, LR J2904
Physical/Chemical Properties Title
None Available
Laboratory or Date Author Completed
Type
Environmental Fate and Transport Title
Laboratory or Date Author Completed
Type
BOD/COD Testing Results FC-120 BOD/COD Testing Results FC-121-X
Pace Incorporated, Minneapolis, MN Pace Laboratories, Inc, Minneapolis, MN
Robust summary, lab 12/4/91 report
Robust summary, lab 11/3/87 report
Summary Reports Title
None available
Laboratory or Date Author Completed
Type
Ecotoxicity Elements Title Toxicity of FC-121-X to Microtox
Toxicity of FC-121-X to activated sludge
Acute Toxicitv of E2566-1 to Daphnia maana (FC-121 -XI
Laboratory or Completion
Author
Date
3M Env. Lab
1987
3M Env. Lab 10/30/87
ABC Laboratories, Columbia, MO
1/9/88
Type
Robust summary, test summary sheet
Robust summary, test summary sheet
Robust summary, final report
Acute Toxicitv of E2566-1 to Fathead Minnow (PimeDhales promelas)
ABC Laboratories, Columbia, MO
1/15/88
Robust summary, exerpts from final report
EnviroSyste
ms Division,
Resource
Static Acute Toxicity of FC-120 to the Fathead Minnow, Analysts, Inc.
Pim ephales promelas
Hampton, NH
March, 1992
Robust summary, final report
005994
Static Acute Toxicity of FC-120 to the Daphnid,
Daphnia magna
OECD Activated Sludge Respiration Inhibition Test #209 - Toxicity of FC-120
Microbios' Microtox Test - FC-120
EnviroSyste ms Division, Resource Analysts, Inc. Hampton, NH
3M Env. Lab
3M Env. Lab
Feb., 1992 3/9/92 4/20/92
Robust summary, final report Robust summary, data sheets Robust summary, data sheets
S99s
Attachments to Letter to C. Auer dated May 18,2000 Bibliography of Published Literature in 3M's Possession
1. POSF - Perfluorooctanesulfonyl fluoride
No literature located.
2. FOSA - Perfluorooctanesulfonamide
Arrendale, R.F., J.T. Stewart, R. Manning, and B. Vitayavirasuk. Determination of GX-071 and its major metabolite in rat blood by cold on-column injection capillary GC-ECD. Journal o f Agricultural and Food Chemistry i l (1989) 1130-1135. Cross, TJ., and R-G. Schnellmann. Mechanism of toxicity of a unique pesticide Nethylperfluorooctane sulfonamide (NEPFOS), and its metabolite perfluorooctane sulfonamide (PFOS) to isolated rabbit renal cortical mitochondria (RCM). Toxicologist 9 (1989) 224. Grossman, M.R. Tissue analysis o f afluorinated sulfonamide pesticide: An evaluation o f distribution, elimination, and potentialfo r bioaccumulation in orally exposed rats. MS Thesis, University of Georgia, Athens, 1990. Lofgren, C.S., W.A. Banks, R.K. Vander Meer, and D.F. Williams. Residual toxicity of some fluoroaliphatic sulfones to the red imported fire ant, Solenopsis invicra (Hymenoptera, Formicidae). Florida Entomologist 72 (1989) 140-146. Manning, R.O., J.V. Bruckner, M.E. Mispagel, and J.M. Bowen. Metabolism and disposition of Sulfluramid, a unique polyfluorinated insecticide, in the rat. Drug Metabolism and Disposition 19(1990) 205-211. Schnellmann, R.G., and R.O. Manning. Perfluorooctane sulfonamide: a structurally novel uncoupler of oxidative phosphorylation. Biochimica et Bicphysica Acta 1016 (1990) 344-348 Vander Meer, R-K., C.S. Lofgren, and D.F. Williams. Fluoroaliphatic sulfones: A new class of delayed-action insecticides for control of Solenopsis iniicta (Hymenoptera: Formicidae). Journal o f Economic Entomology 78 (1985) 1190-1197. Williams, D.F., C.S. Lofgren, and R-K. Vander Meer. The red imported fire ant, Solenopsis invicta: control with fluoroaliphatic sulfone bait toxicants. Journal o fAgricultural Entomology 4 (1987)41-47.
3. PFOSAA - Perfluorooctane sulfonylamido (ethyl) acetate
No literature located.
4. PFDS - Perfluorodecanesulfonate
No literature located.
5. PFHS - Perfluorohexanesulfonate
No literature located.
005996
Attachments to Letter to C. Auer dated May 18,2000 Bibliography of Published Literature in 3M's Possession
6. N-EtFOSA - N-ethyl perfluorooctanesulfonamide
Appel, A.G., and S.F. Abd-Elghafar. Toxicity, sublethal effects, and performance of Sulfluramid against the German cockroach (Dictyoptera: Blattellidae). Journal o fEconomic Entomology 83 (1990) 1409-1414.
Appel, A.G. Laboratory and field performance of consumer bait products for German cockroach (Dictyoptera: Blattellidae) control. Journal o fEconomic Entomology 83 (1990) 153-159.
Arrendale, R.F., J.T. Stewart, R. Manning, and B. Vitayavirasuk. Determination of GX-071 and its major metabolite in rat blood by cold on-column injection capillary GC-ECD. Journal o f Agricultural and Food Chemistry 37 (1989) 1130-1135.
Cross, T.J., and R-G. Schnellmann. Mechanism of toxicity of a unique pesticide Nethylperfluorooctane sulfonamide (NEPFOS), and its metabolite perfluorooctane sulfonamide (PFOS) to isolated rabbit renal cortical mitochondria (RCM). Toxicologist 9 (1989) 224.
Forschler, B.T., and Evans, G.M. Perimeter treatment strategy using containerized to manage Argentine ants, Linepithema humile (Mayr) (Hymenoptera: Formicidae) (abstract). J Entomol. Sci. 29 (1994) 264-267.
Grossman, M.R., Mispagel, M.E., and Bowen, J.M. Distribution and tissue elimination in rats during and after prolonged dietary exposure to a highly fluorinated sulfonamide pesticide. Journal o fAgric. Food Chem. 40 (1992) 2505-2509.
Grossman, M.R. Tissue analysis o f afluorinated sulfonamide pesticide: An evaluation o f distribution, elimination, andpotentialfo r bioaccumulation in orally exposed rats. MS Thesis, University of Georgia, Athens, 1990.
Lofgren, C.S., W.A. Banks, R.K. Vander Meer, and D.F. Williams. Residual toxicity of some fluoroaliphatic sulfones to the red imported fire ant, Solenopsis invicra (Hymenoptera, Formicidae). Florida Entomologist 72 (1989) 140-146.
Manning, R.O., J.V. Bruckner, M.E. Mispagel, and J.M. Bowen. Metabolism and disposition of Sulfluramid, a unique polyfluorinated insecticide, in the rat. Drug Metabolism and Disposition 19(1990) 205-211
Nabbefeld, DJ. An Investigation of the Effects of Fluorochemicals on Liver Fatty Acid-Binding Protein. A thesis submitted to the Graduate School of the University of Minnesota, April 1998.
Reid, B.L., G.W. Bennett, and SJ. Barcay. Topical and oral toxicity of Sulfluramid, a delayedaction insecticide, against the German cockroach (Dictyoptera: Blattellidae). Journal o f Economic Entomology 83 (1990) 148-152.
Schal, C. Sulfluramid resistance and vapor toxicity in field-collected German cockroaches (Dictyoptera: Blattellidae) (abstract). J. Medical Entomology 29(2) (1992) 207-215.
Schnellmann, R.G., and R.O. Manning. Perfluorooctane sulfonamide: a structurally novel uncoupler of oxidative phosphorylation. Biochimica et Bicphysica Acta 1016 (1990) 344-348
Schnellmann, R-G. The cellular effects of a unique pesticide Sulfluramid (Nethylperfluorooctane sulfonamide) on rabbit renal proximal tubules. Toxicology in Vitro 4 (1990) 71-74.
005997
Attachments to Letter to C. Auer dated May 18,2000 Bibliography of Published Literature in 3M's Possession
Smith, L.M., Appel, A.G. Toxicity, repellence, and effects of starvation compared among brown cockroaches (Dictyoptera: Blattidae) (abstract). J. Econ. Entomol. 89(2) (1996) 402-410. Stump, DG; Nemec, MD; Holson, JF; Piccarillo, VJ; Mares, JT. Study of the Effects of Sulfuramid on Pre- and Post natal Development, Maturation and Fertility in the Rabbit. Toxicology (1997) 357. Su, N.-Y., and R.H. Scheffrahn. Laboratory evaluation of two slow-acting toxicants against Formosan and eastern subterranean termites. Journal o fEconomic Entomology 84 (1991) 170175. Su, N.-Y., and R.H. Scheffrahn. Toxicity and lethal time of N-ethylperfluorooctanesulfonamide against two subterranean termite species Isoptera Rhinotermitidae. Florida Entomologist 71 (1988) 73-78. Su, N.-Y., Tokoro, M., and R.H. Scheffrahn. Estimating oral toxicity of slow-acting toxicants against subterranean termites (Isoptera Rhinotermitidae) (abstract). J. Economic Entomology 87 (1994)398-401. U.S. EPA Office of Pesticides and Toxic Substances. Pesticide fact sheet number 205: Sulfluramid. Washington, DC 1989. United States Air Force, Tyndal AFB, Florida. Environmentally Acceptable Live Fire Training Facility. 5 pages. Vander Meer, R-K., C.S. Lofgren, and D.F. Williams. Control o f Solenopsis invicta with delayed-action fluorinated toxicants. Pesticide Science 17 (1986) 449-455. Vander Meer, R-K., C.S. Lofgren, and D.F. Williams. Fluoroaliphatic sulfones: A new class of delayed-action insecticides for control of Solenopsis iniicta (Hymenoptera: Formicidae). Journal o f Economic Entomology 78 (1985) 1190-1197. Williams, D.F., C.S. Lofgren, and R-K. Vander Meer. The red imported fire ant, Solenopsis invicta: control with fluoroaliphatic sulfone bait toxicants. Journal o fAgricultural Entomology 4 (1987)41-47.
7. N-MeFOSA - N-methyl perfluorooctanesulfonamide
No literature located.
8. N-EtFOSE alcohol - N-ethyl perfluorooctane sulfonamidoethanol
Nabbefeld, DJ. An Investigation of the Effects of Fluorochemicals on Liver Fatty Acid-Binding Protein. A thesis submitted to the Graduate School of the University of Minnesota, April 1998.
9. N-MeFOSE alcohol - N-methyl perfluorooctane sulfonamidoethanol
No literature located.
005998
Attachments to Letter to C. Auer dated May 18,2000 Bibliography of Published Literature in 3M's Possession
10. N-EtFOSEA - N-ethyl perfluorooctane sulfonamidoethyl acrylate
No literature located.
11. N-EtFOSEMA - N-ethylperfluorooctane sulfonamidoethyl methacrylate
No literature located.
12. N-MeFOSEA - N-methylperfluorooctane sulfonamidoethyl acrylate
Lawson, R.G., Jurs, P.C. Cluster analysis of acrylates to guide sampling for toxicity testing (abstract). J. Chem. Inf. Comput. Sci. 30 (1990) 137-144. Lawson, R.G., Jurs, P.C. Cluster analysis of acrylates to guide sampling for toxicity testing (erratum). J. Chem. Inf. Comput. Sci. 31 (1991) 361.
13. PFOS - Additional references on Perfluorooctane sulfonate
PFOS Schnellmann, R-G. The cellular effects of a unique pesticide Sulfluramid (Nethylperfluorooctane sulfonamide) on rabbit renal proximal tubules. Toxicology in Vitro 4 (1990) 71-74. PFOSH Derbel, M., Hosokawa, M., Satoh, T. Differences in the induction of carboxylesterase RL4 in rat liver microsomes by various perfluorinated fatty acids, metabolically inert derivatives of fatty acids (abstract). Biological & Pharmaceutical Bulletin 19(5) (1996) 765-767. Haughom, B., and O. Spydevold. The Mechanism Underlying the Hypolipemic Effect of Perfluorooctanoic Acid (PFOA), Perfluorooctane Sulphonic Acid (PFOSA) and Clofibric Acid. Biochim. Biophys. Acta. 1128[1] (1992) 65-72. Henwood, S.M., McKee-Pesik, P., Costello, A.C., Osimitz, T.G. Developmental toxicity study with lithium perfluorooctane sulfonate in rabbits (abstract). Teratology 49(5) (1994) 398. Costello, A.C., Henwood, S.M., Osimitz, T.G. Developmental toxicity study with lithium perfluorooctane sulfonate in rabbits (abstract). Toxicologist 14(1) (1994) 161. Hato, M., and Shinoda, K. Solubility and critical micelle concentrations of fluorinated surfactants in water (abstract). Nippon Kagaku Zasshi 91(1) (1970) 27-31. He, M., and Fu, X. Kinetics and linear free energy relationship of superacid POSA (perfluorooctane sulfonic acid) catalyzed esterification (abstract). Wuli Huaxue Xuebao 6(6) (1990) 739-742. Hosokawa, M., and T. Satoh. Differences in the induction of carboxylesterase isozymes in rat liver microsomes by perfluorinated fatty acids. Xenobiorica 23 (1993) 1125-1133. Ikeda, T., K. Fukuda, 1. Mori, M. Enomoto, T. Komai, and T. Suga. Induction of cytochrome P450 and peroxisome proliferation in rat liver by perfluorinated octane sulphonic acid (PFOS/
005999
Attachments to Letter to C. Auer dated May 18,2000 Bibliography of Published Literature in 3M's Possession
Peroxisomes in Biology and Medicine. H.D. Fahimi and H. Sies, Eds., Berlin: Springer-Verlag, 1987, 304-308.
Kozuka, H., Yamada, J., Horie, S., Watanabe, T., Suga, T., Ikeda, T. Characteristics of induction of peroxisomal fatty acid oxidation-related enzymes in rat liver by drugs: relationships between structure and inducing activity (abstract). Biochem. Pharmacol. 41(4) (1991) 617-623.
Lyon, P.A., Tomer, K.B., Gross, M.L. Fast atom bombardment and tandem mass spectrometry for characterizing fluoroalkanesulfonates. Anal. Chem. 57(14) (1985) 2984-2989.
Remde, A., and Debus, R. Biodegradability of fluorinated surfactants under aerobic and anaerobic conditions (abstract). Chemosphere 32(8) (1996) 1563-1574.
Sohlenius-, A.K., A.M. Eriksson, C. Hogstrom, M. Kimland, J.W. Depierre. Perfluorooctane sulfonic acid is a potent inducer of peroxisomal fatty acid B-oxidation and other activities known to be affected by peroxisome proliferators in mouse liver. Pharmacology and Toxicology 72 (1993) 90.
PFOS.K salt
Brown, R.B. The Treatment and Disposal of Aqueous Film Forming Foam. Masters Thesis in Public Health Engineering, University of New South Wales, Australia, 1986.
Cavalli, L., A. Gellera, and A. Landone. Las removal and biodegradation in a wastewater treatment plant. Environmental Toxicology and Chemistry 12 (1993) 1777-1788.
Chan, D.B., and E.S.K. Chian. Economics of membrane treatment of wastewaters containing firefighting foam. Environmental Progress 5 No. 2, May 1986, 104-109.
Chan, D.B. Disposal of wastewater containing aqueous film forming foam (AFFF). TM No. M54-78-06, Civil Engineering Laboratory, Naval Construction Battalion Center, Port Hueneme, Calif. 93043, April 1978, 19 pgs.
Chan, D.B. Disposal of wastewater containing aqueous film forming foam (AFFF) - by physico chemical processes. TM No. M-54-79-19, Civil Engineering Laboratory, Naval Construction Battalion Center, Port Hueneme, Calif. 93043, Sept. 1979, 21 pgs.
Chan, D.B. Toxic substance: Disposal of wastewater containing aqueous film forming foam (AFFF) - A summary of progress to date on development of all AFFF treatment processes. TM No. M-54-80- 10, Civil Engineering Laboratory, Naval Construction Battalion Center, Port Hueneme, Calif. 93043, August, 1980, 6 pgs.
Chian, E.S.K., T.-P. Wu, and R.W. Rowland. Membrane treatment of aqueous film forming foam (AFFF) wastes for recovery of its active ingredients. Georgia Institute of Technology for U.S. Navy Civil Engineering Laboratory, Port Hueneme, CA 93043, Oct. 1980, 10 pgs.
Darwin, R. L., R. E. Ottman, E. C. Norman, J. E. Gott, and C.P. Hanauska. Foam and the Environment: A Delicate Balance. National Fire Protection Association Journal, May/ June 1995, 67-73.
DiMaio, L. R., and R. F. Lange. Effect of Water Quality on Fire Fighting Foams. Plant. Operations Progress 3 (1984) 42-46.
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Hylton, T.D., and J.F. Walker. Environmental studies in support of the live fire training facilities project. Prepared for the US Air Force under Interagency Agreement DOE 1489-1489-A1 by Oak Ridge National Laboratory, Aug. 1989, 55 pgs.
Johnson, J.D., S.J. Gibson, and R.E. Ober. Cholestyramine-enhanced fecal elimination of Carbon-14 in rats after administration of ammonium perfluorooctanoate or potassium perfluorooctanesulfonate. Fundamental and Applied Toxicology 4 (1984) 972-976.
Kroop, R.H., and J.E. Martin. Treatability of aqueous film-forming foams used for fire fighting. Technical Report No. AFWL-TR-73-279, Air Force Weapons Laboratory (DEE), Kirtland AFB, New Mexico, 87117, Feb. 1974, 94 pgs. Available from NTIS, order no. AD-755 336.
Landon-Amold, S., and D.B. Chan. Application of rotating biological contactor (RBC) process for treatment of wastewater containing a firefighting agent (AFFF), undated report, / 7 pgs.
Landon-Amold, S.E. Microbial treatability of aqueous film forming foam (AFFF) with a chemostat and a rotating biological contactor. Ph.D. Dissertation, University of Oklahoma, Norman, Okla. 1982. (University Microfilms International, 300 N. Zeeb Road, Ann Arbor, Mich. 48106, 800-521-0600, Order No. 8302452).
McKay, J.C., and B. Mason. Improved fire training facility plan. The Military Engineer 523 August 1988, 457-8.
Mueller, J.A., E.W. Poth, and W.W. Melvin. REHL(K) 67-14 Biological treatment of fire fighting foam waste. Regional Environmental Health Laboratory (AFLC), USAF, Kelly AFB, TX, 78241, Sept. 1967, 38 pgs.
O'Brien, A. F. Treatment of Aqueous Film Forming Foam (AFFF) Wastewater at Andrews Air Force Base, Maryland. Masters Thesis, University of Maryland, College Park, Maryland, December 1, 1994.
Saam, R-D., P.A. Rakowski, and G.M. Aydlett. Treatability of firefighting school wastewaters: U.S. Navy Compliance with POTW pretreatment requirements. Presented at the 34th Annual Purdue Industrial Waste Conference, undated, 40 pgs.
Salazar, S. M. Toxicity of Aqueous Film Forming Foams to Marine Organisms: Literature Review and Biological Assessment. Naval Ocean Systems Center, San Diego, California, Technical Document 825, July 1985.
Shinoda, K., and T. Nomura. Miscibility of fluorocarbon and hydrocarbon surfactants in micelles and liquid mixtures. Basic studies of oil repellent and fire extinguishing agents. Journal o f Physical Chemistry 84 (1980) 365-369.
Ventullo, R. M. Biodegradation of Aqueous Film Forming Foam Component in Laboratory Scale Microcosms. Department of Biology, University of Dayton, Dayton, OH. November 30, 1986 - November 30, 1987, 34 pages.
PFOS.Li salt
Costello, Henwood, and Osimitz, "Developmental Toxicity Study with Lithium Perfluorooctane Sulfonate in Rabbits" (abstract)
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Attachments to Letter to C. Auer dated May 18,2000 Bibliography of Published Literature in 3M's Possession EPA, "New Pesticide Fact Sheet: Lithium Perfluorooctane Sulfonate (LPOS)" (abstract) Henwood, Costello and Osimitz, "Developmental Toxicity Study with Lithium Perfluorooctane Sulfonate in Rats" (abstract) Matsuki, H., N. Ikeda, M. Aratono, S. Kaneshina, and K. Motomura. Study on the miscibility of lithium tetradecyl sulfate and lithium perfluorooctane sulfonate in the adsorbed film micelle. Journal o f Colloid and Interface Science 154 (1992) 454-460. Shinoda, K., M. Kobayashi, and N. Yamaguchi. Effect of "iceberg" formation of water on the enthalpy and entropy of solution of paraffin chain compounds: The effect of temperature on the critical micelle concentration of lithium perfluorooctanesulfonate. Journal O fPhysical Chemistry 91 (1987) 5292-5294. Tamori., K.,- K. Kihara, H. Sanda, K. Esumi, K. Meguro, C. Thunig, and H. Hoffmann. Phase behavior and dynamic properties in mixed systems of anionic and cationic surfactants: lithium perfluorooctanesulfonate/diethanolheptadecafluoro-2-undecanolmethylammonium chloride (DEFUMAQ and lithium dodecyl sulfate/DEFUMAC aqueous mixtures. Colloid and Polymer Science 270 (1992) 883-893.
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