Document nvX5qGxz095v9JnY2e6jLwQX

AR226-3344 ) Biotransformation of the Fluorotelomer 8-2 Telomer B Alcohol Ning Wang, Patrick Folsom, Bogdan Szostek, Vladimir Capka, Barbara Larsen, William Berti, John Gannon, Robert Buck The mirades o f science 1 8-2 Telomer B Alcohol: C8F17CH2CH2OH (8-2 TBA; CAS# 678-39-7) A key raw material used in the manufacture of sales products May be a transformation product of fluorotelomerbased sales products Is it biodegradable? Under what conditions? What are the major transformation products? What are the likely biotransformation pathways? What are the stable/ultimate transformation products? UK The miracles o f science'" : , Outline Physical - Chemical Properties Ready Biodegradability (Modified OECD 301 D Closed Bottle Test) Accelerated biotransformation in acclimated bacterial culture Conclusions The miracles o f scienceTM . 3 TKe Physical Properties - "Difficult _______ to Test Substance"_______ Low solubility: ~ 150 jutg L-l Vapor Pressure : 3 Pa at 21C Adsorption to surfaces Closed experimental system with thefewest compartments (closed glass serum bottles) was used to conduct the tests. HE The miracles o f science" : , 4 A GC/MS Chromatogram of 8-2 TBA Used in the Test assoin* 2GQCOOO 3J itiim fM ifi W The miracles o f scienceTM C6Fi3CHXH,OH ~ 0.04% sI J 8-2 TBA (99.2%) C7F15CF=CHCHzOH ( 0.8%) > l-S.it fs. as. ' _ J Aerobic Ready Biodegradation: C8F17CH2CH2OH (Modified OECD 30ID Closed Bottle Test) Method Experimental method'. Modified OECD 301D Closed bottle test Experim ental System'. Closed bottles (35 mL of test substance solution in 60-mL glass serum bottles) Inoculum'. Fresh sludge from Municipal POTW (Non-acclimated) Experim ental Duration'. 0-28 days at room temperature. A nalysis: GC/MS for 8-2 TBA parent and fluoride selective electrode- for fluoride ion. mm : The miracles o f science* .. j mmm Aerobic Ready Biodegradation: C8F17CH2CH2OH (Modified OECD 301D Closed Bottle Test) The 8-2 TBA is not readily Biodegradable. mm The miracles o f scienceTM : . 7 _. Aerobic Ready Biodegradation: C8F17CH2CH2OH (Modified OECD 301D Closed Bottle Test) No defluorination occurred during the test. Activated sludge filtrate + 8-2 TBA saturated mineral medium - 0 ~ Killed sludge filtrate + 8-2 TBA saturated mineral medium HE The miracles o f scienceTM 0 5 10 15 20 25 Days after the initiation : - 30 Accelerated Biodegradation: C8F17CH2CH2OH Method Experimental method: Modified OECD 302 (Inherent Biodegradability) test with 0.1% yeast extract as additional carbon source Experimental System: Closed bottles (30 mL of test substance solution in 120-mL bottles) Inoculum: From industrial waste water treatment facility and the inoculum has been grown (adapted) with 50 mg/L of 8-2 Telomer B alcohol prior to the test Experimental Duration: 0-28 days at room temperature Analysis: GC/MS for 8-2 TBA parent, fluoride selective electrode for fluoride ion, and LC/MS/MS for fluorinated acid metabolites (transformation products) The miracles o f science" : ' H f> fl Accelerated Biodegradation: C8F17CH2CH2OH The 8-2 TBA has been rapidly Biotransformed underfavorable conditions. Adapted bacterial culture + 8-2 TBA Killed bacterial culture + 2 mM NaCN + 8-2 TBA IB The miracles o f science 0 0 5 10 15 20 25 30 Days after the initiation of the experiment 10 #. il Accelerated Biodegradation: C8F17CH2CH2OH .Significant defluorination occurred during the test Adapted bacterial culture + 8-2 TBA Killed bacterial culture + 2 mM NaCN + 8-2 TBA HE The miracles o f science m. w w Accelerated Biodegradation: C8F17CH2CH2OH (LC / MS / MS Analysis) Estimated metabolite concentrations Day 0 Day 28 % of Total Mass (PPb) F(CF2)8CH2COOH (8-2 acid) 0.0 20 ~ 2% F(CF2)7CF=CHCOOH (8-2 unsaturated acid) 0.0 147 > 10% F(CF2)7COOH (PFOA) 0.0 12 <2% F(CF2)5COOH (PFHA) 0.08 4.3 ~ 0.4% The miracles o f science" mmm Potential Biotransformation Route (Products Investigated in Accelerated Test) F(CF2)8CH2CH2OH I F(CF2)8CH2COOH I F(CF2)7CF=CHCOOH X-------- - F(CF2)8COOH Not Formed MajFoorrPmreodduct f (c f 2)7c o o h F(CF,),COOH Hi The miracles o f science Afploordoromdkdieetuidodcntfsboaurlmttorawrayenidhrseeafonvnrteimofitebadetieonn 13 Summary C8F17CH2CH2OH, 8-2 TBA, is not readily biodegradable. Under accelerated conditions, 8-2 TBA is being rapidly transformed to fluorinated acids and other unidentified transformation products. F(CF2)7CF=CHCOOH is the major identifiable metabolite. Although PFOA is one of the identifiable metabolites, it accounted for < 2% of mass balance. PFOA apparently may be further metabolized to form PFF1A and may not be an ultimate (stable) metabolite under the accelerated conditions. HR : The miracles o f science* . a