THI S DOCUMEN TDOE S NO TCONTAI N CONFIDENTIA L BUSINES S INFORMATIO N (CB! )

RESEARC H 

### TSCA-HQ-2004-016 , RCRA-HQ-2004-0016 , TSCA-HQ-2005-500 1 SE P AFluorotelomer-Base d Produc t Characterizatio n Subject : MP I Researc h Technica l Progres s Repor t

Marc h 31,201 0 t o Apri l 23 , 201 0 1 Introductio n Thi s documen t present s th e progres s ofth e technica l wor k fo rcharacterizatio n offluoroteiomer base d product s an d correspondin g synthesize d o rpurifie d polymers i n suppor t o fth e Biodegradatio n Testin g Supplementa l Environmenta l Projec t ("Biodegradatio n SEP") . Thi s progres s repor

t i s prepare d pursuan t t o Characterizatio n Laborator yExhibi t A : Scop e o fWori< , Sectio n 4f . Thi s repor

t describe s th e technica l wori < peri'orme d u p t o th e wee k endin g Apri l 23 , 2010 . Th e followin g component s o fth e Wor k Pla n have bee n completed : Component s 1 , 2 , 3 , 5 an d 6 . 

### 2 Progres s Summar y Th e initiatio n o f technica l wor k bega n o n Marc h 31 , 2010 , afte racceptanc e o fth e MP I Researc h wor k pla n b ybot h EPAan d DuPont . Th e fluorotelome rproduct s wer e receive d fro m DuPon t an d th e commerciall yavailabl e standard s wer e ordere d an d receive d a t MP I Research . Th e invoice s are include d i n Appendi xD . MP I Researc h ha s obtaine d a quotatio n fro m Wellingto n Laboratorie s fo rsynthesi s ofth e thre e compound s (Wori < Pla n Componen t 4) . MP I Researc h i s waitin g fo rapprova l t o purchas e thes e standards . Th e quotatio n i s include d i n Appendi xE . Th e estimate d tim e ofsynthesi s i s si xweeks . Th e synthesi s wil l begi n upo n th e receip t ofth e MP I Researc h orde rb yWellingto n Laboratories . Th e technica l wori < consiste d o f metho d developmen t outline d i n Componen t 7 o fth e Wor k Plan . LC/MS/M S method s are bein g develope d fo rth e followin g analytes : 7- 3 Fluorotelome rAcid , 8- 2 Fluorotelome rsaturate d Acid , 8- 2 Fluorotelome runsaturate d Acid , Perfluorooctanoi cAcid , Perfluorononanoi cAcid , Perfluorodecanoi cAcid an d Perfluoroundecanoi cAcid . GC/M S method s ar e bein g develope d fo rth e followin g analytes : 6- 2 Fluorotelome rAlcohol , 8-2 Fluorotelome rAlcohol , 10- 2 Fluorotelome rAlcohol , 8- 2 Fluorotelome rEthene , 8- 2 Fluorotelome r Iodide , 10- 2 Fluorotelome rIodide , Perfluoroocty l Iodide , Perfluorodecy l Iodide , 8- 2 Fluorotelome r Acrylate , 7-2 Fluorotelome riso-ethano l an d PFOAtelome r8- 2 ester . MP I Researc

h 04/29/201 0 Technica l Progres s Repor t ^^^ ^ ^ °' ^ ^THI S DOCUMEN TDOE S NO TCONTAI N CONFIDENTIA L BUSINES S INFORMATIO N (CBI ) Th e tota l metho d developmen t tim e incurre d fo rth e perio d oftim e covere d b ythi s repor t wa s 2 2 hours . Th e associate d cos t fo rthi s metho d developmen t wor k i s $5,50 0 a s identifie d i n Componen t 7 of th e Wori < Plan . Th e cos t i s base d upo n th e dail yrat e of$2,000 . Th e cos t associate d wit h commerciall yavailabl e standard s that wer e purchase d durin g th e tim e perio d covere d b ythi s repor

t wa s $2,417.80 . Thi s cos t i s identifie d i n Componen t 3 ofth e Wori < Plan . Th e tota l cost s associate d wit h th e component s initiate d wit h respect t o thi s Progres s Repor t are $7,917.8 0 Th e associate d invoice s are presente d i n Appendi xD . 

### 3 Analysi s b yLC/MS/M S A n HP110 0 syste m interface d t o a n Applie d Biosystem s AP I 400 0 LC/MS/M S wa s use d fo rth e metho d developmen t work . Agradien t elutio n usin g a Zorbax ® SB-C18,2. 1 X 5 0 mm , 1.8|j m colum n wa s use d fo rseparatio n ofth e followin g analytes : 

### Analyte s 8- 2 Fluorotelome r

saturate dAci d 8- 2 Fluorotelome r

unsaturate dAci d 7- 3 Fluorotelome r

Aci d Perfluorooctanoi c Aci d Perfluorononanoi c Aci d Perfluorodecanoi c Aci d Perfluoroundecanoi c Aci d 

### lUPA C nam e Decanoi c acid , 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 - heptadecafluoro 2-decenoi c acid , 3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 - hexadecafluoro Decanoi c acid , 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 - pentadecafluoro Pentadecafluorooctanoi c aci d Perfluorononanoi c aci d Perfluorodecanoi c aci d Perfluoroundecanoi c aci d CAS # 27854-31- 5 70887-84- 2 812-70- 4 335-67- 1 375-95- 1 335-76- 2 2058-94- 8 Th e transition s fo rPerfluorooctanoi cAcid , Perfluorononanoi cAcid , Perfluorodecanoi c Acid , an d Perfluoroundecanoi cAci d wer e base d o n previou s work . Th e transition s fo r8- 2 Fluorotelome rsaturate d Acid , 8- 2 Fluorotelome runsaturate d Acid , an d 7- 3 Fluorotelome r Acid wer e determine d usin g flo winjection . A1 ng/m L methano l standar d containin g al l seve n analyte s wa s evaluate d fo rchromatographi cseparation . Th e 8- 2 Fluorotelome rsaturate d Acid wa s no t detecte d becaus e i t wa s determine d t o b e unstabl e i n methanol . Th e 8- 2 Fluorotelome rsaturate d Aci d degrade s t o th e 8- 2 Fluorotelome runsaturate d Acid . Stabilit ycondition s wil l b e furthe rinvestigate d an d wil l includ e solvent , temperature , an d th e effec t o flight . 

### 4 Analysi s b yGC/M S Th e analyse s wer e perfomne d o n a Hewlett-Packard GC/M S syste m wit h positiv e chemica l ionizatio n usin g heliu m can'ie rga s an d methan e reagen t gas . AHP-IM S colum n wa s use d fo r th e developmen t wor k

fo rth e followin g analytes :

MP I Researc h 04/29/201 0 Technica l Progres s Repor t PAG E 2 O F 4THI S DOCUMEN TDOE S NO TCONTAI N CONFIDENTIA L BUSINES S INFORMATIO N (CBI ) Analyte s 6- 2 Fluorotelome rAlcoho l 8- 2 Fluorotelome rAlcoho l 10- 2 Fluorotelome rAlcoho l 8- 2 Fluorotelome rEthen e 8-2 Fluorotelome rIodid e 10- 2 Fluorotelome rIodid e Perfluoroocty l Iodid e Perfluorodecy l Iodid e 8-2 Fluorotelome rAcrylat e 7- 2 Fluorotelome riso-ethano l PFOAtelome r8- 2 este r lUPA C nam e 1H,1H,2H,2H-perfluorooctan-1-o l 1H,1H,2H,2H-perfluorodecan-1-o l 1H,1H,2H,2H-perfluorododecan-1-o l 1H , 1 H,2H-perfluoro- 1 -decen e 1H,1H,2H,2H-perfluorodecy l iodid e 1H,1H,2H,2H-perfluorododecy l iodid e Perfluoroocty l Iodid e Perfluorodecy l Iodid e 2-propenoi cacid , 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 - heptadecafluorodecy l este r 2-nonanol , 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9 - pentadecafluoro Octanoi cacid , pentadecafluoro 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 - heptadecafluorodecy l este r CAS # 647-42- 7 678-39- 7 865-86- 1 21652-58 ^ 2043-53- 0 2043-54- 1 507-63- 1 423-62- 1 27905^5- 9 24015-83- 6 Not Availabl e Al l analytes , wit h th e exceptio n o f6- 2 Fluorotelome ralcoho l an d 7- 2 Fluorotelome riso-ethanol , wer e prepare d i n methy l tert-buty l ethe r(MTBE ) at concentration s rangin g fro m approximatel y 10 0 pg/m L t o 200 0 |jg/m L fro m neat standards . 6- 2 Fluorotelome ralcoho l an d 7- 2 Fluorotelome r iso-ethano l wer e purchase d a s 5 0 ^ig/m L solution s i n methanol . Thes e standard solution s were analyze d b

yPCI/GC/M S i n th e sca n mod e t o detemnin e th e appropriat e ion s t o b e monitore d fo r eac h analyte . Not al l analyte s produce d dominan t molecula rions . Alternat e instnjmen t condition s wil l b e investigated . Fo reac h analyte , a 1 |jg/m L solutio n wa s investigate d usin g singl e io n monitoring . A n interferenc e signa l wa s detecte d i n th e solvent , methy l tert-butylethe r(MTBE ) fo rth e 8- 2 fluorotelome rethene . Highe rpurit ysolven t wil l b e investigated . Th e molecula rio n fo rPFOAtelome r8- 2 este r(M W = 860 ) coul d not b e observe d becaus e th e uppe rmas s rang e fo rth e instmmen t i s 800 . MP I Researc h i s investigatin g whethe ra firmwar e solutio n exist s fo rth e instmmen t limitation . Otherwise , a lowe rmolecula rweigh t fragmen t mus t b e used . 5 Attachment s 5. 1 Appendi xA : 5. 2 Appendi xB : 5. 3 Appendi xC : 5. 4 Appendi xD : 5. 5 Appendi xE : Ra wDat a (LC/MS/MS ) Ra wDat a (GC/MS ) Certificate s o f Analysi s Invoice s Quotation s

MP I Researc h 04/29/201 0 Technica l Progres s Repor t PAG E 3 O F 4THI S DOCUMEN TDOE S NO TCONTAI N CONFIDENTIA L BUSINES S INFORMATIO N (CBI )

•VH;^ - I certif yunde rpenaltyo f lawtha t I have examine d an d a m familia rwit h th e infonnatio n submitte d i n thi s documen t an d al l attachment s an d tha t thi s documen t an d its attachment s wer e prepare d eithe rbym e personall yo runde rm ydirectio n fo rsupervisio n i n a manne rdesigne d t o ensur e tha t qualifie d an d knowledgeabl e personne l propert ygathe ran d presen t th e informatio n containe d therein . I furthe rcertify , base d o n m ypersona l knowledg e o ro n m yinquir yo fthos e individual s immediatel yresponsibl e fo robtainin g th e infonnation , tha t th e informatio n i s tme , accurat e an d complete . I a m awar e that ther e ar e significan t penaltie s fo rsubmittin g fals e infonnation , includin g th e possibilityo f fine s an d imprisonmen t fo rknowingl yan d willfull ysubmittin g a materiall yfals e statement . 

# '/Af/^^/ ^ Xian g (Robert ) Zhu , Stud yDirecto rDat e

MP I Researc h 04/29/201 0 Technica l Progres s Repor t '^'^^ ^ '^''"^' ^