Document BRVbDEn1oM1VGpppx8rqvZNo4

= --- SERVER WIAPR-9 PH 2:25 ARA2-G 1266 EE TRP Telomer Research Program A, asco Ig == Clariant 31 March 2003 Telomer Process Diagram for US EPA - OPPT DaKIN Pw i Contains no TSCA CBI 3 I re) TetraCflFuorCoFet,hylene F(CF,F),1 F(TCeFl.oGmFe,r) 8CRl,odGiHd,e1 Tel"oBumielrdiInngtBelromcekdsi"ate FTCeFl.omFe)r,BCOHl-efHin, F(TCeFl,oCmFe,r)8,CAHl,cCoHh,o0lH uAcsreydla1tecMreoantoemFeirniishtehdePmraosdutcctsommon raw material FICTeFl.oCrFme)r,CAcHr,yClHa,te0GM(o0n)oCmHe=rCH, 4 FiJnAiLsGhnedd * mAcatnuuaflacptruorciengss and Spraamcetiacneys vary by PFOAis not used or added in these processes + Generally, these processes are closed and PFOA creation aenxdp/eocrteedmitsosbieonast are very low levels ro = Telomerization was initially developed free-radical polymerization of ethylene. by the The DuPont process Company in was defined the as 1940's for reacting a telogen, with two or more ethylenically The product was called a telomer. unsaturated molecules, called taxogens. = Telomers containing fluorine were telomerization of tetrafluoroethylene developed (a taxogen) in 1949-1950. Commercial with pentafiuroethyl iodide (a telogen) was developed by the DuPont Company in 1961. = pSetrafrltuionrgoamlaktye!riiaodlisdef.orOftetlhoemevrariboaussedperfflluuoorroocalhkeymliciaoldsidaerseusteetdraifnituhoerettehlyolmeenerizaantdioan processes, produces a pentafluorethyl iodide is mixture of straight chain the most important one. The telomerization (linear), even-carbon-numbered perfluoroalky iodides differing in their overall average 3 (or 8 total carbons). carbon chain length where n will vary from 2-6 and CF + nCF, => CF(CF) [or FCF) s LO rer = pInersfulubosreoqalukeynltetrheya!citoidoindsesp,erafllcuoohroolasl,kaycriyoldaitdeess oarremegtehnaecrraylllayttersa,nsrefsopremcetdiveeiltyher to CFCF)I+CHCH, => * CFSCFICHCH! => * CoFi(CF.CHCHOH => CF(C,F,),CH,CH,I CFy(C,F,),CH,CH,0H C,Fy(C,F,),CH,CH,0COCR=CH, (R=H,CH,) Allthese fluorinated intermediates the fluorinated portion into the final are used as "basic product used in the building blocks* formulation to incorporate = Tlihnekabgaessictobauivladriinegtbyloofcoklsiagroemelriinckeodr either by acrylic, ester, polymeric hydrocarbon ether, or urethane backbones 6 LO re = The majority polyacrylics of telomer-based fluorochemicals or polyurethanes) for treatment are of used in polymeric form (e.g surfaces and materials to provide oil, soil, tain, and water resistance to carpets [high molecular weight (MW) polymers] fabrics and upholstery (high MW polymers) leather (high MW polymers) paper and packaging (phosphate esters or high MW polymers) = wSimtahllheyrdraomphoiulnitcspoorftitohnesatboovcreeamteentfilouonreodsubrafsaicctanbtuisldwihnigchblaorceksuasreedceoimtbheirneads specialty additives in such applications as coating and cleaning formulations, metal treatment, or as a component in fire extinguishing foam concentrates. . 7 e References = For a description of the processes used for Telomer products see: "Textile Finishes and Fluorosurfactants," N. S. Rao and B. E. Baker in "Organofiuorine Chemistry," R. E. Banks, B. E. Smart and J. C. Tatlow, Eds., Plenum, 1994, p. 321-338. "Fluorinated Surfactants and Repellents", E. Kissa, Second Edition, Marcel Dekker, Inc., New York, 2001. e Communication Process = TRP member companies will meet with EPA individually to describe their US Telomer manufacturing processes and exposure / release information = Initial discussions by April 2008 EE -- g