Document OzLNb3yvepKMR7RgoBbGNO38p
PHOTODEGRADATION (AQUEOUS)
TEST SUBSTANCE
Identity: NN--eEtfhyFlOpSeErflAulocroohoocltoarneFMs-u3lf4o2n2a.mid(o1e-tOhcatnaonle;sumlafoynaamlsiodeb,eNr-eeftehryrle-d to as 1.1,.2.2,3.3.4,4,5,5,6.6,1.7,8,88-heptadecafiuoro-N-(2-hydroxyethyl)-, CAS #1691-99-2)
Remarks:
Material is an off-white, waxy solid. The
*C labeled (220 dpmpg). Purity of the
test
test
substance
substance
used
is not
was
described. procedures
This and
bteessttinagvaiislacbulreenptrlayctbieceisn.g
repeated
using
current
The following summary is abbreviated due to the fact that a new study is pending.
METHOD
MFeetdehroadligRueigdisetleirne(Vfoollulmoewe4d3:,
NPor.oc1e3d2u-rMeo"nedsasyen,tiJaulllyy"10a,s
described in 1978) by the
the U.S.
Environmental Protection Agency.
TGyLpPe((YtIeNs)t:typNeo): Simulated sunlight
Year: 1981
LL3ii0gg0hhttnmSS.opueSrcpcteecr:turGmael(nneemnr)ea:rlgMEylaecxchtaorruiactcpFtu-etr4ia0tzBe~Ld3ff6lr0uoomnrem2s9ca0en-ndt60be0slsanecmnkt.iliaglhlty no output below
Intensity:
[Wavelength|Watts Radiated
[al _o- Tos 2520|
[G20- [13 40s0|
[aao-ss0
360-380
[e[12037 0] 0|
[ 380 --4 400 0-[26 30000|
[Boo- [036 40 00|
Spectrumof substance (max lambda, max epsilon and epsilon 205): Not determined.
Remarks field:
006446
w-aTteesrt/mmeethdainoulm/a(caeirt,ownaittrelre,
soil, other respectively
specify):
60/25/15
solution
of
-
-
DPousriattiivoen:Co3n1trdoalyss:
None
- Negative Controls: None
RESULTS
Concentration of Substance: 50 mg/L
Temperature Degradation
C: 22:2C %: 0% after
31
days
Rsteumdya.rkEsssfeinetlida:llNyothpehostaodmeegraanadlaytsiiosnorfestuhletstweestresuobbsttaainnceed wfoarsthdeet3e1c-tdeadyin this photolyzate sample (no photoproducts formed) as the 0-day sample. Radiocarbon assays at 0 and 31 days also indicate no significant amount of product was volatilzed during the study.
CONCLUSIONS
No photodegradation products were detected in this study using simulated
sunlight, indicating the test substance does not undergo photolysis.
Submitter: 3M Company, Environmental Laboratory, P.O. Box 33331, St. Paul,
Minnesota, 55133
DATA QUALITY
Rceulriraebnitlliytayv:aiKliaibmliespcrhorcaendkuirnegs,2.imPphrootovleydsiasnasltyutidcyalismbeetihnogdsr,epaenadtebdeusstipnrgactices
using a sample with characterized purity.
REFERENCES
3M Technical SUNLIGHT."
Report "FM J. W. Todd,
3P4ro2j2ecPtH9O7T76O7L5Y0S2I, SReSpTorUtDNYuUmSbIeNrG00S4I, MAUuLguAsTtE1D1,
1981
OTHER
Last changed: 5/18/00
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TECHNICAL REPO
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"AGRICULTURAL PRODUCTS PROJECT-LIFE SCIENCES SECTOR
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DECOMPOSTTY | photoproducts.
GAS-CHROMATOGRAPHY |
RPAHDOITOOTLRYASICSER
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||| sTTeeosryaaolrdtieacdthirooinnmaontfoogradaneptheaycq/tueredoaudsipohaosntotolopuartroidaounpchtyosfaFonnHd-3ab4yn2a2lgyassfiosrchb3ry1omdtaahtyiosn-
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REPORT $004
FN-3422 PAOTOLYSIS STUDY USING SIMULATED SUNLIGHT
INTRODUCTION
It is generally acknowledged that manufactured chemicals may find
their way into the environment in various degrees and means. Once in the environment they may be destroyed
by or
various chemically
altered by the action of sunlight (Crosby and Li, 1969). This study
investigated the possible photodegradation of FH-3422 in distilled
wwaastercoonnducetxepdosuersesetnotiaslilmyulaatsedrescuonmlmiegnhdted (bKyohltehre,En19v6i5r)o.nmenTthails study
Protection Agency (Federal Register).
EXPERIMENTAL
1. sample Materials
FM-3422 is l-octanesulfonamide, N-ethyl-1,1,2,2,3,3,4,4,5,5,
6,6,7,7,8,8,8
identified by
- heptadecafluoro-N-(2-hydroxyethyl)=. It is also
the Environmental Protection Agency (EPA) as CAS #:
1691-99-2.
cari --< hcanon
Tohtehemrajhoormolcoogmsp,onebnrtancihsedt-hcehasitnraiigshotme-rcshaianndCgotcheormpoiumnpdurbiuttiessommeay be present.
FM-3422 = We Aqueous Solution:
4cwor(k2i2n0gdpsno/lpugt)ioninwa2s800premlparoefd 6b0y/25d/i1s5sowlvaitnegr/m14e0thmagnoolf/aFcMe-t3o4n2i2t-rile mixture.
Fu-3422 Analytical Standard: obtained from Chemical Resources Division,
3 Co.
(St.
Paul,MN)
It is used to prepare the gas chromatographic calibration standards.
006449
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REPORT $004
2. Analysis Instruments/Materials/Concitions Ultrasonic Bath Model 8345-4 from Cole Parmer. Liquid Scintillation Counter (LSC) Beckman LS 8000. Rotary Evaporator Buchi Rotovapor R. Thin-Layer Chromatography (TLC) Plates MERCK Silica Gel 60 F-254, 0.25 mm thickness and 20 x 20 cm size 3st developing solvent-75/25 hexane/acetone. 2nd developing solvent-97.5/2.5 chloroform/methanol.
X-Ray Fila KODAK NS-2T, 8 x 10 inch size.
Photegraphic Print 4 x 5 Pilm Type 55 from Polaroid Corp.
Gas Chromatography Parameters: 2) Gas chromatograph Varian model 3700. Sample injection 5 pl of photolyzed solution via 10 p1 microsyringe.
Injection port Column
on column, 300C. 6 fr. glass 6% SP 2250 on GAS CHROM Q, 80/100 mesh.
Column temperature 155C.
Detector
Flame photometer operated with:
temperature
320C.
hydrogen flow
140 ml/min.
air #1 flow
80 ml/min.
air #2 flow
170 ml/min.
optical filter
sulphur-specific
"
006450
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-
Report #004
input range = 10
amps FS.
|
mode (linearized.) |
1
attenuation
x 256.
2) Except venereal for Figure 6 (impurities profile aorta analysis) where:
006451
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5. wo
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tine. The results are presented in Table II.
|
using a 100 pl microsyringe. The plate was developed two-
dimensionally, first with hexane/acetone (75/25) and then with
chloroform/methanol (97.5/2.5). It was
air dried and then
She ana 31 day pratotyzed samples vere directly ansiyeed rcipeien stants a 243s vere weed for sxeernel aeandard
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3. W. TCDD
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REPORT # 004
are presented in Figure 5 and the linear calibration plot in Figure 6.
Possible photoproducts were further investigated by reanalyzing the 0 and 3l-day photolyzed samples at greater detection sensitivity (x 16 attenuations) and over a wide temperature range (75 to 275C column temperature). The resulting chromatograms are presented in Figure 7.
DISCUSSION OF RESULTS
No photodegradation of FM-3422 was detected in this study. Neither TLC/radioautography (Figures 2 and 3) nor temperature-programmed gas chromatography (Figure 7) showed any components in the 3l-day sample which were not present in the 0-day initial sample. Gas chromatographic assay analysis of the samples showed FM3422 concentration of 49 pg/ml (49 ppm) in the 0-day sample and 44pg/ml (44PPr) in the 31-day sample (Table III).This 103 relative decrease was also substantiated by radiocarbon assay (Table II).
The cause of the 10% relative decrease in FM 3422 concentration during the 31 day photolysis is unknown. Possible loss through volatilization was investigated by analyzing the photolyzer vapor trap for radiocarbon but only a negligible amount was found 0.01%)
The most plausible explanation is the loss by precipitation in the photoreactor. The solubility of FM 3422 in the 60/25/15 watex/ methanol /acetonitrile photolysis solvent is apparently only marginal although initial studivs had indicated adequate solubility (and this in turn was 4 modification of a previous 70/30 water/methanol solvent which wes found inadequate). Also the 10 mi/minute air sweep through the photolyzer would preferentially volatilize the organic solvent
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REPORT 4 004
components and thereby would cause a decreasing solubility
SftourdyM3wa4s22comipnlettheed,remthaeinpihnogtoressacmtpolre wsaosluctlieoann.ed Abfutterthtehewashings
1
were not analyzed for radiocarbon content. Marginal solubiluty
Of FM 3422 in the photolyzate was further substantiated by the
tumbidity and white solids which formed when the collected samples
were refrigerated. Before analysis the samples were warmed to
35C and sonicated until the precipitate was resolublized. The
samples were then cooled to ambient temperature and analyzed.
A water/acetonitrile solvent system is recommended for any future
Phototysis studies on FM 3422. Methanol is a relatively poor solvent and its inclusion would be of dubious value.
|
REFERENCES
ii
Crosby, D.G. and Li, H. 1969. Herbicide Photodecomposition,
Chapter 12:321-363 in Degradation of Herbicides, Kearney,
P.C. and Kaufman, D.D. (ed), Marcel Dekker Inc. New York,
394 p.
Crosby, D.G. and Tang, C.S., J. Agric. Food Chem., 17, 1041 (1969).
Federal Register, Voluce 43. No. 132-Monday, July 10, 1978.
G-neral Electric Company, Lamp Division, Cleveland, OF 44112.
Koller, L.R. 1965. Ultraviolet Radiation, 2nd Bd. Wiley, New York. 312 p.
Submitted by:
lw.
3. W. Toi,
Sdeneidor
Research
Specialist
my
006454
J. W. Tomo
a
REPORT $004
Table I - Spectral Energy Distributicn for a GE PAOBL Black Light Bulb
wavelength 200 - 300 310 - 320 320 = 340
340 - 360
360 - 380
uates Radiated
0.00 0.235 1.420
19% acim tnteneiey
2.310 at about 360 va
380 ~ 400
400 - 500 500 - 600
1.680
2.300 0.300
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--
RepoRe 4 004
Table
II
-
Radiocarbon Function of
FIorurnaddiaitnioPnhotToilsyezed
Solution
as
a
SrianmepleinIDrarvaediation SiaisnatdeigoecaatsiboonnsMoibns.ervepsercent Recovery
0
10,984
(100.0)
1
3
10,822
10,340
98.5
55.6
7
10,958
0.8
1s
10,786
55.2
2
5,096
50.1
006456
-- BEST COPY AVAILABLE "
Sample Description
40
-
60
-
80
-
Peak Height pg/ml Conc. (ppm)
272 451 573
(40) (60) (80)
006457
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Figure 2 - P0h-oDtioygraFpMh 3o4f22TLPChoRtaodliyczaeudtoSgarmapplhe,.
-- ps2 --> .
H bs-1
p E2
ihe
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.
Lo
Reference Samples, 50 pg of FM 3422-14C, 10,984 DPM, not photolyzee.
|
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BM 3422
1-1 = Developing Solvent il, hexane/acetone 75/25. 15-2 = Developing Solvent #2, chloroform/methanol 97.5/2.5.
+ = origin (where samples were spotted)
006459
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Figure 3 - Photograph of TLC Radioautograph, 31 day FM 3422 Photolyzed Sample.
|
-- ps2 -->
ST
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DS-1
by
h
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| 10,984 DPM,
3
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+ = origin (where samples were spotted). DS-1 = Developing Solvent #1, hexane/acetone 75/25.
DS-2 = Developing Solvent #2, chloroform/methanol 97.5/2.5.
;
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Figure 4 = Quantitative Gas Chromatograms for
|
FM 3422 Photolyzed Samples
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