Document x92DL9KQXzpDo7n5Q6jJEVY0

fR 226~36i{ HYDROLYSIS (ALKALINE) TEST SUBSTANCE________________________________ Identity: N-ethylperfluorooctane sulfonamidoethanol; may also be referred to as N-EtFOSE Alcohol or FM-3422. (1-Octanesulfonamide, N-ethyl1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-N-(2-hydroxyethyl)-, CAS #1691-99-2) Remarks: Material is an off-white, waxy solid of uncharacterized purity. METHOD_________________________________________________________ Method/guideline followed: Procedure developed by 3M Type (test type): Alkaline potassium hydroxide solution exposure GLP (Y/N): No Year: 1977 or before Remarks field: - Test medium (air, water, soil, other - specify): 20% alcoholic potassium hyrdoxide. - Duration: 24 hours - Positive Controls: None - Negative Controls: None RESULTS_________________________________________________ Concentration of Substance: 362 mg/L Temperature C: 50C Degradation %: 92% after 24 hours Remarks field: IR and NMR studies confirmed that the N-EtFOSE Alcohol was broken down to perfluorooctane sulfonate under these conditions. CONCLUSIONS___________ ___________________________________ Under the conditions of this test, N-EtFOSE alcohol partially degrades to form perfluorooctane sulfonate. Submitter: 3M Company, Environmental Laboratory, P.O. Box 33331, St. Paul, Minnesota, 55133 DATA QUALITY___________________________ ________________________ Reliability: Klimisch ranking 2. Purity of the test substance was not characterized. 006466 REFERENCES 3M Technical Report "Analytical Methodology on FM 3422." A. Mendel, Fate of Fluorochemicals, Page 11, Project 9970612643, November 15,1977 OTHER_________________________________________________________ Last changed: 5/18/00 006467 3>.STMD.7>,,a technical report summary TECHNICAL COMMUNICATIONS CENTER - 201-2CN D ite 11/ 15/77 (Im portant - I f report is prin ted on both sides o f paper, send two copies to TCC.) Division Project Report till* To Au m orts) N otebook Rafaranca Environmental Laboratory (EE PC) Fate o f Fluorochemicals A n a ly tic a l Methodology on FM 3422 0 . L. Bacon A. Mendel c c n iD iT v k i s e c u r it y D Op#n {Com pany C o n fid e n tia l) Cj . C lo itd (Special A u th o riz a tio n ) KEYWORDS: (Salect tarm s fro m 3 M Thesaurus. Suggest o th e r applicable term s.) C U R R E N T O B JE C TIV E: 3M C H E M IC A L w R E G IS TR Y ^ bept. Numbar 0222 ProJ#ct N u m b ff 9970612643 Sapor Numbar E m ployee Num ber(s) 43939 No. o f Pages In c lu d in g b o v e n h e e t 13 N ew Chem icals R e p o rte d Yee 0 No HE $ P C -D iv . Fluorochem ical A n a ly tica l Progress Report ,,t \ R E PO R T A B S T R A C T : (2 00-2 50 w ords) T h is abstract in fo rm a tio n it d istrib u te d by the T echnical C om m unications Center to a le rt 3M*ers to C om pany R & O . It is C om p any c o n fid e n tia l m a terial. ' 'V 1 fJ J In fo tm a tio n U iauon In .i.a it > 0064G8 -11- Revised 12/27/77 ALKALINE HYDROLYSIS OF FM 3422 The s t a b i l i t y or i n s t a b i l i t y o f FM 3422 toward base was ap paren tly stu d ie d sev eral years ago under aqueous c o n d itio n s. Because th is m ateria l steam d i s t i l l s and because o f i t s lack o f w ater s o l u b i l i t y , the s t a b i l i t y o f FM 3422 toward base in alco h o l was stu d ied in the p resen t work as fo llo w s : S ix samples each o f a 25 ml s o lu tio n o f 362 ppm o f FM 3422 in 20% a lc o h o lic potassium hydroxide was kept in a 50 o i l bath fo r varyin g le n g th s o f tim e. A sample was taken a f t e r 0 .5 - , 1 - , 7- and 24- h r s . , and n e u tr a liz e d w ith concentrated n it r ic acid to the phenolphthalein in d ica to r end p o in t; th is allow s p r e c ip ita tio n o f potassium n it r a t e and minimizes w ater which tends to in t e r fe r e w ith the EC/GC a n a ly s e s . GC a n a ly s is o f th e a lc o h o l s o lu tio n gave the r e s u lts in TABLE V. TABLE V HYDROLYSIS STUDIES OF'FM 3422 Time (in h r s .) 0 0.5 1 7 24 3422 (in ppm) 362 380 362 256 28 A s ix t h sample was allowed to remain in the o i l b ath fo r 50 hrs/50 C . I t was n e u tr a liz e d as above and f i l t e r e d to remove s o l id s . The f i l t r a t e was concen tr a te d to dryness and the resid u e was analyzed by TLC, and IR and NMR (Req. C46749). A comparison o f the R f value o f the resid u e with th a t o f a u th en tic FC-95 showed they were the same. IR and NMR s tu d ie s confirm ed th a t th e FM 3422 was broken down to FC-95 under these c o n d itio n s . GAS CHROMATOGRAPHY OF PERFLUOROOCTANE SULFONAMIDE AND FC-128 (41947-48) The re te n tio n time o f FM 3422 was 2 .8 m inutes isotherm al a t 160 u sin g the co n d itio n s described e a r l i e r . To determ ine whether the above sulfonam ide and i;C-128 posed as an in te rfe re n c e to FM 3422, d ilu t e s o lu tio n s ( in methanol) were made fo r th ese two m a te r ia ls . The sulfonam ide co u ld be chromatographed is o th erm ally a t 200 (about 3 .3 minutes r e te n tio n ) w h ile .FC-128 co u ld not be chromatographed. T h erefore, there is no in te rfe re n c e problem. THIN-LAYER CHROMATOGRAPHY STUDIES OF FM 3422 R ad io lab eled FM 3422 (5) was examined by TLC fo r p u r it y . About ten micrograms o f sample was spotted on a p la te which was then developed in e th y l a c e ta te . The p la t e was exposed to an X -ra y j|'ilm fo r about one week and the film was developed. I t revealed th at the FM 3422- C had th ree im p u r itie s , two components o f g r e a te r R f and one component rem aining a t the o r i g i n . A c c o r d in g ly , the e n t ir e r a d io a c tiv e m a te r ia l, n e a rly 1.7 g , was column chromatographed on s i l i c a g e l by chloroform e lu t io n . About fo rty 15 ml fr a c tio n s were c o lle c te d and m onitored by T L C -a u t^ radiography. Pure m ateria l was combined fo r fu tu r e s t u d ie s . Impure FM 3422- C . was combined and rechromatographed as above u n t il e s s e n t ia lly a l l o f the m a te ria l was rendered pure (6). 006469