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

# MP ! 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 ! Researc h Technica l Progres s Repor t

l\/la y22,201 0 t o Jun e 25,201 0 1 Introductio n * ' Thi s documen t present s th e progres s o f th e technica l wor k fo rcharacterizatio n o f fluoroteiomer base d product s an d correspondin g synthesize d o rpurifie d polymers i n suppor t o f th 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 f Wori< , Sectio n 4f . Thi s repor

t desaibe s th e technica l wori < performe d fro m May22 , 201 0 u p t o th e wee k endin g Jun e 25 , 2010 . Th e followin g component s o f th e Wori < Pla n hav e bee n completed : Component s 1 , 2 , 3 , 5 an d 6 . 

### 2 Progres s Summar y Th e technica l wor k

consiste d o f metho d developmen t outline d i n Componen t 7 of th e Wori < Plan . LC/MS/M S method s ar e 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 , 1.0- 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 ! Researc h ha s bee n infomrie d that th e followin g non-commerciall yavailabl e standard s tha t require synthesi s ar e n o longe rrequire d fo rthi s project : 2- H perfluorooctanoi cacid , 7- 3 fluorotelome runsaturate d aci d an d 7- 3 fluorotelome runsaturate d amide . Componen t 4 o f th e Wori < Pla n wil l not b e executed . Th e tota l metho d developmen t tim e incurre d fo rth e perio d o f tim e covere d b ythi s repor t wa s not tabulate d a

t th e tim e o f thi s submission . I t wil l b e include d i n th e nex t Technica l Progres s Report .

MP I Researc h 06/30/201 0 Technica l Progres s Repor t ^^^ ^ * ' ^ ' *THI S DOCUMEN TDOE S NO TCONTAI N CONFIDENTIA L BUSINES S INFORMATIO N (CBI ) 

### 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 . Th e chromatographi ccondition s fo rth e followin g analyte s wer e investigated : Analvte s 8- 2 Fluorotelome rsaturate d Aci d 8- 2 Fluorotelome runsaturate d Aci d

7- 3 Fluorotelome rAci d Perfluorooctanoi cAci d Perfluorononanoi cAci d Perfluorodecanoi cAci d Perfluoroundecanoi cAci d lUPA C nam e Decanoi c acid,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10, 1 0,10-heptadecafluoro 2-decenoi c acid,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10 , 10-hexadecafluoro acid,4,4,5,5,6,6,7,7,8,8,9,9,10,10,1 0 -pentadecafluoro Pentadecafiuoroctanoi caci d Perfluorononanoi caci d Perfluorodecanoi caci d Perfluoroundecanoi caci d 

### CAS # 27854-31- 5 70887-84- 2 812-70 ^ 335-67- 1 375-95- 1 335-76- 2 2058-94- 8 Tw o chromatographi csystem s wer e developed . A n isocrati csyste m fo r8- 2 fluorotelome r saturate d aci d an d a gradien t syste m fo ral l th e othe rcompounds . Bot h system s utiliz e th e sam e colum n an d mobil e phas e whic h allow s fo ra smoot h transitio n betwee n th e tw o chromatographi csystems . Qualitycontro l sample s wer e prepare d i n Methyl-t-buty l ethe r(MTBE ) t o simulat e samples . Bot h nitroge n evaporatio n (n-evap ) an d dilutio n technique s wer e investigated . Lo w recoverie s wer e obtaine d wit h th e nitroge n evaporatio n techniqu e an d thi s wa s mos t likel ydu e t o th e volatilit yo f th e compounds . Sampl e dilutio n produce d acceptabl e an d reproducibl e results . Th e solubilit yo f MTB E an d th e effect s o n th e chromatographi c condition s wer e als o investigated . 

### 4 Analysi s b yGC/M S Th e analyse s wer e performe d o n a Hewlett-Packard GC/M S syste m wit h positiv e chemica l ionizatio n usin g heliu m carrie rga s an d methan e reagen t gas . AHP- 1 M S colum n wa s use d fo r th e developmen t wor k

fo rth e followin g analytes : Analvte s 6- 2 Fluorotelome rAlcoho l 8- 2 Fluorotelome rAlcoho l 10- 2 Fluorotelome rAlcoho l 8- 2 Fluorotelome rEthen e lUPA C nam e 1 H, 1 H,2H,2H-perfluorooctan-1-o l 1H,1H,2H,2H-perfluorodecan-1-o l 1 H, 1 H,2H,2H-perfluorododecan-1-o l 1 H, 1 H,2H-perfluoro-1-decen e 

### CAS # 647-42- 7 678-39- 7 865-86- 1 21652-58 ^ MP I Researc h 06/30/201 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 ) 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 PFO Atelome r8- 2 este r 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 2043-53- 0 2043-54- 1 507-63- 1 423-62- 1 27905-45- 9 24015-83- 6 Not Availabl e 10- 2 Fluorotelome rAlcoho l an d 8- 2 Fluorotelome rIodid e co-elute . Altemativ e instmmen t condition s wer e explore d an d bette rresolutio n betwee n thes e tw o analyte s wa s achieved . Th e secondar

yion s fo r8- 2 Fluorotelome rethen e exhibite d wea k intensityunde rth e PC I mode . Alternativ e ionizatio n mode . Negativ e Chemica l Ionization , wa s explored . Th e intensitie s o f th e secondar yion s ar e muc h bette runde rNC I condition . Th e ion s monitore d unde rNC I are 406 , 38 6 an d 426 . Th e pea k

of 8- 2 Fluorotelome rethen e i s broa d an d un-symmetric . ADB-62 4 colum n (30 m x 0.25m m x1.40pm ) wa s use d an d resulte d i n muc h bette rpea k shape . Du e t o th e compatibilityo f PFO Atelomer e 8- 2 este rwit h othe ranalytes , i t wa s prepare d byitsel f at th e followin g concentrations : 10 . 20 , 50 , 100 , 50 0 an d lOOOng/m L an d analyze d unde rPC I condition . Alinea rcalibratio n curv e wa s generated . I t wa s sho wthat th e curv e i s linea rfro m 1 0 ng/m L t o 50 0 ng/mL. . 

### 5 Attachment s 5. 1 Appendi xA : 5. 2 Appendi xB : 5. 3 Appendi xC : Ra wDat a (LC/MS/MS ) Ra wDat a (GC/MS ) Certificate s o f Analysi s 

### 6 Signature s I certifyunde rpenaltyo f lawthat I hav e examine d an d a m familia rwit h th e infomriatio n submitte d i n thi s documen t an d al l attachment s an d that thi s documen t an d it s attachment s wer e prepare d eithe rb ym 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 infomnatio n containe d therein . I furthe rcertify , base d o n m ypersona l knowledg e o ro n m yinquir yo f thos e individual s immediatel yresponsibl e fo robtainin g th e infomriation , that th e informatio n i s true , accurat e an d complete . I a m awar e that ther e are significan t penaltie s fo rsubmittin g fals e information , includin g

IVIP I Researc h 06/30/201 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 ) th e possibilityo f fine s an d imprisonmen t fo rknowingl yan d willfull ysubmittin g a materiall yfals e statement . 

# &Mi^ ^ Xian g (Robert ) Zhu , Stud yDirecto r Dat e

rviP I Researc h 06/30/201 0 Technica l Progres s Repor t PAG E 4 O F 4