Document wgQ7MJRZr2VVBR6nwQ2njZdv4

AR226-3342 Bill Berti DuPont Central Research & Development Wilmington, Delaware USA Ths mif'Qcies a/seiencs" BiNing W a n g aDaryl Cobranchi aBarbara Larsen aBogden Szostek BMary Kaiser John Gannon Bob Buck gLisa Sulecki Pat Folsom aMark Starr aChien-Ping Kao gChristopher Bowers aVIadimir Capka OutSSne Background a Intermediates and Products Overview of E-fate studies Physical-Chemical Properties a Water solubility and Vapor Pressure ^ 6-2TBI, 8-2TBI, 6-2TBA, 8-2TBA B Measured vs. Predicted Values KCF^F^CHaCHsOH F(CF,CF^CH,CH,I n sa 3 or 4 E-Fate Testing: 8-2 TBA F(CF,CF^CH,CH^OH a Abiotic: Soil/Water Partitioning, Hydrolytic Stability a Biotic: Biotranformations Conclusions 1) Intermediates CF2=CF;, I (TFE) Ft.CFzCF;!),,! (Telomer A) n=2-8 F(CF2CF2),,CH;!CH;,E (Telomer B) Sates Products l SMifesteBMI^Malasaige Aaioaic - Phosphate, Carboxyiate, Sulfoaate Noaioaic Ethoxylste Betaine PCCF^CP^^CH^CH^OH (Telomer BA) Straight Chain Alkyi F(CF2CF2)nCH2CHpC(0)C(R)=CH2 Zonyl TM (R<:H) ; Zonyl TAN (R=H) 3)PoJSSBBig, Aci>'i.ic Ester ' A^iaide < Lirethane Urea Goal: Identify environmental transformations relevant to toxicity and chemical cycling ^Physical-chemical properties ^Aqueous stability Photolysis f 'Soil/water partitioning Respiration inhibition (toxicity) ^Aerobic transformations Anaerobic transformations a BacKground loterrnedlatea and Products in Overview of E~fate studies s Physical-Chemical Properties p^p ^ ^ ^ ^ ^ Water solubility and Vapor Pressure w^pcy '}CHCHI 6-2TBI, 8-2TBI, 6-2TBA, 8-2TBA B Measured vs. Predicted Values ^=^4 a E"Fate Testlna; 8-2 TBA FecFaCF^cH^cHaOH B Abiotic: SoiJAA^ater PartitlonInQ, Hydrolytic Stability M b-iQl'c; bilotranrofrnatlons f ' ' BSSii ?":. n ;'" I;; i i {": y"'- w \^^^ S^i^--.^^.^^ i ^ Demonstrate applicability of existing models for this class of compounds as Vapor pressure predictions are reliable on limited set of data (4 compounds) a Water solubility measurements vs. predictions need more study ss Examine other models bacNjgrxsuod s Intermediates and Products w Overview of E-fete studies Ph'i^^lr'ffl-r'hsirr'ii^p^ P!''^>n<K!;rflsSi!s; ? : ^- -f \.<' ;\^;:>.rf;- -,.^ ^ < ^- :; i i}\.^S.,.5 ^ ^ ^ ^-\..? ? ^/5-:.,,-\^ Wale?' solubiljly and Vapor Pressure FCCFzCiUCNaCHzOH FCCFaCF^^CH^CHaS ^ 6-2TBI, 8-2TB1. 6-2TBA, 8-2TBA a JVIeasured vs. Predicted Values n = 3 or 4 E-Fate Testing: 8-2 TBA FCCF^F^CH.CH^OH B Abiotic: Soil/Water Partitioning, Hydrolytic Stability Biotic: Biotranformations Conclusions Two materials m Keyport silt loam Sand 17%, Silt 62%, Clay21%,pH5.3,OM 4.0% m White Clay Creek sand . Sand 98%, Silt 2%, pH 7.2, OM 0.4% Mix for 15 m and 46 h, separate phases Extracted with hexane from solid and water phases, SPE to clean, analyzed At 15m Good recovery (>90% of expected) of 8-2 TBA from both soils Recovered primarily from solid phase, except for <4% in solution of White Clay a Poor recovery from control with no soil s Recovered from both solution and tube At46h B Poor recovery from both soils s White Clay <25% of expected s Keyport <75% of expected Improved recovery from control with no soil 62% vs. 45% after 15 m Losses due to volatilization, extraction inefficiencies, transformations??? (fiff Hydroiytic reactions are one of the most common means of non-biological degradation of substances in the environment. 150 pg8-2TBAL-1, sterile conditions pH 4, 7, 9 @ 50C pH1.2@37C Sealed glass vials with Alfoil liners 4 replicates at 0 and 5 days - Extracted with MTBE - Analyzed with GC/MS 8-2 TBA is hydrolytically (abiotically) stable <10% change in concentration after 5 days compared to day 0 .w Growth medium: OECD301D mineral medium without yeast extract Inoculum source: Municipal POTW, non-adapted Terminated early due to problems with killed controls "Ready Biodegradation" of 8-2 TBA JQ 700 0 rim < CQ 5> 5 0) c^ 00 8-2 TBA + Fresh Sludge -0- 8-2 TBA * Killed Sludge + 1 mM NaCN -y- 8-2 TBA + Killed Sludge 0 10 20 Days after the initiation Quick transformation in accelerated studies is Transformation products include FtCFaCF^CH^COOH F^F^CFsCHCOOH Mass balance <50% :a Other products/losses??? On-going studies to understand killed controls and incomplete recoveries 1) Intermediates CF2=CF2 (TFE) Telomer A Telomer BI Telomer BA I Zonyl TM (R-CH), Zonyl TAN (R=H) Sates Products > Anioaic ^hospha^.'arboxylate,, Slilfonate^^^ Nonionice^thoxyia^ Betaine Hydrolytic Stability Ready Biodegradability OECD 301B CO^ production Measurement F- endpoints "Parent compound L 'Products Measured vs. model values Telomer BA and BI a High confidence in vapor pressure measurements and model estimates a Low(er) confidence in water solubility estimates Need to assess alternative models 8-2 TBA a Hydrolytically stable Soil/water partitioning studies may indicate strong adsorption to soils Accelerated biodegradation studies show production of transformation products a Volatilization is of concern Need to develop and validate analytical methods in air /^Tr?