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AR036-O3& BIODEGRADATION TEST SUBSTANCE Identity: N-methylperfluorooctane sulfonamidoethanol; may also be referred to as N-MeFOSE Alcohol, FC-790, or FM-3925. (1Octanesulfonamide, N-methyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8heptadecafluoro-N-(2-hydroxyethyl)-, CAS # 24448-09-7) Remarks: Material is an off-white, waxy solid. Sample purity and lot number were not recorded. METHOD Method: COD/BOD study using 3M Environmental Laboratory standard protocols modeled after the Standard Methods for the Examination of Water and Wastewater, 14th Edition, American Public Health Association, 1976. Type: Potassium dichromate reflux COD and Aerobic BOD GLP: No Year completed: 1979 Contact time (units): See Remarks Inoculum: Not noted. Remarks: The laboratory was not able to generate useable data for BOD due to insufficient oxygen depletion. The COD was done in replicate. RESULTS COD: Analysis 1 = 170,000 mg/kg Analysis 2 = 156,000 mg/kg Average = 163,000 mg/kg BOD: A twenty-day biochemical oxygen demand (BOD) test with suspended substrate concentrations up to 1000 mg/L showed insufficient oxygen depletion in excess of the blanks to allow the calculation of BOD values. This result indicates that N-MeFOSE alcohol is not likely to degrade in a non-acclimated aerobic biological treatment system. Remarks: A 259 mg/L potassium hydrogen phthalate control, running concurrently with the same seed was found to have a BOD5 of 231. The mean BOD for this control substrate at this concentration is 208 mg/L. This indicates that the seed was active and acceptable for BOD studies. 006521 The fact that oxygen depletion rates during the first fourteen days in cultures containing N-MeFOSE alcohol closely followed those of the seeded controls suggests that the lack of degradation is not due to toxicity to heterotrophic microorganisms. DATA QUALITY Reliability: Klimisch ranking = 3. The purity of the test substance is not sufficiently characterized and the inoculum concentration is not described though the control indicates it was active. Study used individual weights that exceeded water solubility, thus the test substance was not solubilized and was not available to microbes. REFERENCES 3M Technical Reports: "Biodegradation Studies on FM 3925", E.A. Reiner, Project 9970012600 Premanufacturing Notice FC-790, Report No. 016, January 8,1979. "Chemical Oxygen Demand of FM 3925", E.A. Reiner, Project 9970012600 Premanufacturing Notice FC-790, Report No. 017, January 8,1979. OTHER Submitter: 3M Company, Environmental Laboratory, P.O. Box 33331, St. Paul, Minnesota, 55133 Last changed: 5/17/00 006522 3S3 Form 8747-11-A TECHNICAL REPORT SUMMARY Data 1/8/79 TO: TECHNICAL COMMUNICATIONS CENTER - 201-2CN (Important - If report is printed on both sides o f paper, send two copies to TCC.) Division E n v iro n m e n ta l L a b o ra to ry (EE & PC) Project P rem a n u factu rin g N o tic e FC-790 Report Title B io d e g r a d a t io n S t u d i e s on FM 3925 To V. Pothapragada Author(s) E . A. Reiner Notebook Reference None - See Environm ental Lab Request #4197 apt. Number 0535 Project Number 9970012600 Report Number ___ QU6_______________ Employee Number(i) 47816 No. of Pages Including Covareheat C E rim iT v k a e i.u n i1T ^ ^ Open (Company Confidential) O Closed (Special Authorization) 3M CHEMICAL REGISTRY " New Chemical! Reported Ye* H No KEYWORDS: (Select terms from 3M Thesaurus. Suggest other applicable terms.) B iodegradation EE & PC D i v . Fluorochem ical D egradation BOD CURRENT OBJECTIVE: To e v a lu a t e th e s u s c e p t i b i l i t y o f FM 3925 t o b iod egrad ation . REPORT ABSTRACT: (200-250 words) This abstract information is distributed by the Technical Communications Center to alert 3M'ers to Company R&D. It Is Company confidential material. A tw e n ty -d a y b io c h e m ic a l oxygen demand (BOD) t e s t w ith su sp e n d e d s u b s t r a t e c o n c e n t r a t io n s up to 1000 mg/1 showed in s u f fic ie n t oxygen d e p le tio n in e x ce ss o f th e b la n k s t o a llo w th e c a l c u l a t i o n o f BOD v a l u e s . T h is r e s u l t i n d i c a t e s t h a t FM 3925 i s n o t l i k e l y t o d e g ra d e in a nonacclim ated b io lo g ic a l treatm ent system . FM 3422 h a s p r e v io u s ly been fou n d to be r s i s t e n t to b iod egrad atio n even in acclim ated a e ro b ic system s. Sin ce i t i s c h e m ic a lly s i m i l a r to FM 3422, FM 3925 i s p r o b a b ly also r s is te n t to biodegradation in acclim ated m icro b ial cu ltu re s. Information Liajspp i Initials: ^ i)) 006523 -2- BIODEGRADATION STUDIES ON FM 3925 In troduction P r e v io u s s t u d i e s on FM 3 4 22 , e t h y l f o s e a lc o h o l ( C g F - ,, , SO ,,N ( C^Hj-)CLH -OH ), have shown t h a t t h i s compound i s n o t m ea su rab ly d eg rad e d by e it h e r a cclim a te d or n o n acclim ated m ixed m ic ro b ia l c u ltu r e s ( 1 ,2 ) . T h e r e f o r e , i t ap p ea red u n l i k e l y t h a t th e FM 3925, m e th y l f o s e a l c o h o l ( C g F 17S0 2N(CH2 )C2H5O H ), b e c a u s e o f i t s c h e m ic a l s i m i l a r i t y , would be r e a a ily ^ d e g r a d a B le . The fo llo w in g work was co n d u cted to c h e c k t h e s u s c e p t i b i l i t y o f FM 3925 t o b i o d e g r a d a t io n . U lt im a t e B io c h e m ic a l O xygen Demand A tw e n ty -d a y b io c h e m ic a l oxygen demand (BOD) was co n d u cted on FM 3 9 2 5 .a c c o r d in g to th e s ta n d a r d E n v ir o n m e n ta l L a b o r a t o r y p r o t o c o l ( a t t a c h e d ) , e x c e p t t h a t FM 3925 was p la c e d in th e BOD b o t t l e s in s o l i d form and t h a t th e b o t t l e s c o n t a i n in g FM 3925 w ere c o n t in u o u s ly s t ir r e d fo r th e e n tir e in cu b a tio n p e r io d . S t ir r in g was done u sin g a Hach Model 2173 w ith m agnetic s t ir r in g b a r s . The seeded c o n tr o ls and r e fe r e n c e compounds were not s t i r r e d . The r e s u l t s o f t h i s s tu d y a re shown in TABLE 1 and a re p l o t t e d in F ig u r e 1 . No b io d e g r a d a t io n o f FM 3925 was o b s e r v a b le by t h i s m etho d . The method re q u ire s th a t th e d is so lv e d oxygen d e p le tio n in a t e s t c u ltu re exceed the oxygen d ep letion o f the seeded co n tro l by at l e a s t 2 m g/1. T h is d id n o t o c c u r . Thus th e BOD c a n n o t be c a l c u l a t e d . The BOD a t e a ch tim e i s t h e r e f o r e c o n s id e r e d to be l e s s th a n 2000 mg o f o xygen p e r k g o f t h i s compound. A 259 mg/1 p o ta s siu m hyd rogen p h t h a la t e c o n t r o l run c o n c u r r e n t ly w ith th e same s e e d was fo u n d to h a v e a BOD,- o f 2 3 1 . The mean BOD fo r t h is co n tro l su b stra te at th is co n cen tratio n is 208 mg/1. T his i n d i c a t e s t h a t th e s e e d was an a c t i v e a c c e p t a b le s e e d f o r BOD stu d ies. The f a c t th a t the t e s t s u b s tra te d id n ot degrade to a d e te c ta b le le v e l in t h is study s u g g e sts th a t th ese compounds would not degrade s ig n if ic a n t ly in a nonacclim ated w aste treatm ent system . Whether o r not m icro b ia l p o p u latio n s can acclim a te to degrade, th is compound can n o t be d eterm in ed from t h i s s tu d y . How ever, s in c e FM 3925 i s s t r u c t u r a l l y v e r y s i m i l a r t o FM 3422, w h ich h a s been shown n o t t o d eg ra d e in a c c lim a t e d c u l t u r e s , we a n t i c i p a t e t h a t FM 3925 w i l l r e s i s t d e g r a d a tio n by even a c c lim a t e d m ic r o b ia l c u l t u r e s . The f a c t th a t oxygen d e p le tio n r a te s (F ig u re 1) d u rin g th e f i r s t fo u r t e e n d a y s in c u l t u r e s c o n t a i n in g FM 3925 c l o s e l y f o llo w e d th o s e o f th e seeded c o n tr o ls su g g e sts th a t la c k o f d eg rad a tio n i s not due to t o x ic it y to h e te ro tro p h ic m icroorganism s. 006524 Figure 1: Oxygen C oncentration o f C u ltu re B o t t l e s D u r in g U lt im a t e BOD S tu d y o f FM 3925 L in e Key Average Seeded Control A A 10 mg/1 FM 3925 e - -------- & 100 mg/1 FM 3925 ft................- p D is s o lv e d Oxygen C o n ce n tratio n (mg/1) ccnn Time (D ays) io in 006526 D e s c r ip tio n and C o n c e n tra tio n Day 3 Seed ed C o n tr o l #1 See d ed C o n t r o l #2 See d ed C o n t r o l #3 Seed ed C o n tr o l #4 8 .9 8 .9 8 .9 8 .9 Avg. Seeded C on trol 8 .9 FM 3925: 10 mg/1 32 mg/1 100 mg/1 560 mg/1 1000 mg/1 8 .4 8 .7 8 .5 8 .7 8 .7 Potassium hydrogen ph th alate: 2 .6 mg/1 4 .3 mg/1 6 .1 mg/1 7 .8 mg/1 6 .5 5 .0 3 .3 1 .7 TABLE 1 ULTIMATE BOD DATA FOR FM 3925 Day 5 8 .7 8 .9 8 .8 8 .9 8 .8 D issolved 0,, Concentration Day 7 Day 10 8.4 8 .3 8.6 8 .5 8 .5 8 .4 8.6 8 .5 8.5 8 .4 Day 14 7 .8 7 .9 7 .7 8 .1 7 .9 8 .3 7 .9 7 .7 7 .4 8 .3 8 .0 7 .7 7.4 8 .3 7 .7 7 .7 7 .5 8 .4 8 .1 8 .0 7 .6 8 .5 8 .1 8 .1 7 .7 -- -- -- -- --- - Day 20 6 .1 6 .3 6 .2 6 .1 6 .2 6 .7 7 .0 7 .0 7 .4 Lost - - -5R eferen ces: (1) R ein er, E . A ., B iodegradation S tu d ie s o f Flu o ro carb on s, 3M T e c h n ic a l R e p o rt 8/12/76. (2) R e in e r, E . A. , B iodegradation STudies o f F lu o r o c a r b o n s -II, 3M T e c h n ic a l R e p o rt 1/9/78. EAR/cen 006527 i gm iHBnMNT " .Form 6 7 47 -1 1-A TECHNICAL REPORT SUMMARY Date 1/8/79 TO: TECHNICAL COMMUNICATIONS CENTER - 201-2CN (Im portant -- I f report sprin ted on both sides o f paper, send two copies to TCC .) D ivisio n E n v iro n m e n ta l L a b o ra to ry (EE & PC) ^ Project Report Title P re m a n u fa ctu rin g N o tic e FC-790 C h e m ic a l O x y g e n Demand o f FM 3925 To V. Pothapragada Author(s) E . A. R ein er Notebook Reference None - See E nviron m en tal Lab Request Dept. Number 0535 Project Number 9970012600 Report Number 017 Em ployee Number(s) 47816 No. of Pages Including Coversheet # 4 1 9 7 ____________________________ SECU RITY Open (Company Confidential) D Closed (Special Authorization) 3M CHEM ICAL ^ REGISTRY w New Chemicals Reported q Yes |jg No KEYW ORDS: (Select terms from 3M Thesaurus. Suggest other v applicable terms.) Ch'ernie a l O xygen Demand (COD) CURRENT OBJECTIVE: To d e t e r m in e t h e e x t e n t t o w h ic h FM 3925 i s o x i d i z e d b y r e flu x in g in th e p resen ce o f potassiu m dichrom ate under stro n gly a c id ic co n d itio n s. D egrad ation F lu o ro chem ical EE & P C -D iv . REPORT ABSTRACT: (200-250 words) This abstract inform ation is distributed by the Technical Communications Center 1 alert 3M'ers to Company R&D. It is Company confidential material. T h e c h e m i c a l o x y g e n dem and (COD) o f FM 3925 w as d e t e r m in e d acco rd in g to th e 3M Environm ental L a b o ra to ry 's stan d ard p r o to c o l w hich i s m odeled a f t e r th e S ta n d a rd M ethods p r o c e d u r e . T h e COD was d e te r m in e d t o b e 1 6 3 ,0 0 0 m g / k g . T h i s i s 35% o f t h e t o t a l t h e o r e t i c a l o x y g e n dem and ( a s s u m in g N i s n o t o x i d i z e d ) a n d 71% o f t h e o x y g e n dem and c a lc u la te d assum ing th a t o n ly the n o n flu o rin a te d p o rtio n o f the m olecu le is degraded. Inform ationn Liaison \ Initials: 006529 -2 - CHEMICAL OXYGEN DEMAND OF FM 3925 T h e c h e m ic a l o x y g e n dem and o f FM 3925 w as c a l c u l a t e d a c c o r d i n g to the stan d ard p ro toco ls o f th e E nvironm ental L ab o ratory (a tta c h e d ). These p r o to c o ls are m odeled a f t e r th e p ro ced u re d e s c rib e d in S tan d ard Methods (1) . The r e s u l t s o f two r e p l i c a t e a n a ly s e s a re shown in TABLE 1 . TABLE 1 COD o f FM 3925 A n alysis 1 A n alysis 2 Average 170.000 mg/kg 156.000 mg/kg 163.000 mg/kg >y T h is COD i s 35% o f t h e t o t a l t h e o r e t i c a l o x y g e n dem and a s s u m in g c o m p le t e o x i d a t i o n t o F , C O g , S O , N H ,,, an d H ,, 0 . I t i s 71% o f th e oxygen demand c a lc u la t e d assu m in g t h a t o n ly th e n o n flu o r in a t e d p o rtio n o f the m olecule is degraded as in the fo llo w in g r e a c tio n : C 8F 17S 0 2N (C H 3 ) C 2H4 OH + 4 2"^ C 8F 17S 0 2NH2 + 3 c 0 2 + 3 H2 0 (MW 5 5 7) R eference : (1) Stan d ard M ethods' fo r th e E xam in atio n o f W ater and W astew ater, 14th E d itio n , Am erican P u b lic H e a lth A s s o c ia tio n , 1976. EAR/cen Attachm ent 006530 3M ENVIRONMENTAL. LABORATORY CHEM ICAL OXYGEN DEMAND PROTOCOL (Used p r io r to Jan u ary 4 , 1979) EAR 1/4/79 C h e m ica l oxygen demand i s d e te rm in e d by a m o d ific a t io n o f th e method d e s c rib e d in Stan d ard M ethods fo r th e E xam in a tio n o f W ater and W astew ater, Am erican P u b lic H e a lth A s s o c a tio n , p . 550554, (1976). Procedure M o d ificatio n s The r e flu x ap p aratu s d if f e r s from th a t d e s c rib e d in S tan d ard M ethods in th a t 500 ml rou n d -b ottom ed b o ilin g f la s k s w ith g ro u n d g la s s 24/40 neck are used in p la c e o f com parable g ro u n d -g la ss Erlenm eyer f la s k s . In a d d itio n , e le c t r i c h e a tin g m a n tle s , w hich are cap ab le o f ad eq u ately b o ilin g th e co n te n ts o f th e r e flu x fla s k s , are used in p la ce o f a hot p la te . The s i l v e r s u l f a t e c a t a l y s t i s added d i r e c t l y t o e a c h COD f l a s k p rio r to r e flu x in g the sa m p le -su lfu ric, acid -d ich ro m ate m ix tu re . The f e r r o u s ammonium s u l f a t e t i t r a n t i s s t a n d a r d iz e d a g a i n s t t h e b la n k . I t is assumed th a t no dich rom ate is red u ced in th e b la n k d u rin g th e r e flu x p ro ced u re. Sam ple S iz e and R eagen t Q u a n tity and N o r m a litie s Sam ple s iz e i s 50 m l. The re a g e n t q u a n t it ie s and n o r m a lit ie s are th o se p r e s c r ib e d fo r t h is sam ple s iz e in T a b le 5 0 8:1 o f th e 14th E d itio n o f Stan d ard M ethods, e x ce p t th a t A g-SO . i s added in 0 .1 2 g q u a n titie s and i s n ot d is s o lv e d in th e c o n c e n tra te d s u lfu r ic acid reagen t. P r o c e d u r e f o r Low COD S a m p le s The a l t e r n a t e S ta n d a r d M eth od s COD p r o c e d u r e f o r low -C O D s a m p le s i s u s e d when COD v a lu e s o f 50 mg/1 o r l e s s h a v e t o b e d e t e r m in e d . In t h is p roced u re th e sam ple s iz e and re a g e n t q u a n t it ie s rem ain th e sam e, but th e n o r m a litie s o f th e dich rom ate and fe rro u s ammonium s u l f a t e s o l u t i o n s a r e r e d u c e d t o 0 .0 2 5 N an d 0 .0 1 N , re sp e ctiv e ly . 006531 EAR 1/4/79 3M ENVIRONMENTAL LABORATORY CHEM ICAL OXYGEN DEMAND PROTOCOL C h em ical oxygen demand i s d eterm in ed a c c o rd in g to th e m ethod d e s c rib e d in S tan d ard M ethods fo r th e E xam in ation o f W ater and W astew ater, Am erican P u b lic H e a lth A s s o c ia tio n , p . 550-554, 976) Procedure M o d ificatio n s The r e flu x ap p a ratu s d i f f e r s from th a t d e scrib e d in Stan d ard M ethods in th a t 500 ml round-bottom ed b o ilin g fla s k s w ith grou n d g la s s 24/40 neck a re u sed in p la c e o f com parable g ro u n d -g la s s E rlen m eyer f la s k s . In a d d it io n , e l e c t r i c h e a tin g m a n tle s , w hich are cap ab le o f ad eq u ately b o ilin g th e co n ten ts o f th e r e flu x fla s k s , are used in p la ce o f a hot p la te . Sam ple S iz e and R eagen t Q u a n tity and N o r m a litie s Sam ple s iz e s o f 50 ml a re u sed w ith th e re a g e n t q u a n t it ie s and n o r m a litie s g iv e n in Stan d ard M ethods, T able 5 0 8:1 . P r o c e d u r e f o r Low COD S a m p le s The a l t e r n a t e S t a n d a r d M e th o d s COD p r o c e d u r e f o r low COD s a m p le s i s u s e d when COD v a l u e s o f 50 mg/1 o r l e s s h a v e t o be d e t e r m in e d . In t h is p ro ced u re th e sam ple s iz e and re a g e n t q u a n t it ie s rem ain th e sam e, bu t th e n o r m a litie s o f th e dichrom ate and fe r r o u s ammonium s u l f a t e s o l u t i o n a r e r e d u c e d t o 0 .0 2 5 N and 0 .0 1 N ,. re sp e ctiv e ly . 006532