| Chemical Abstract Number (CAS #) |
110758
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| CASRN |
110-75-8 |
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| Synonyms | 2-Chloroethylvinyl ether |
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Ethene, (2-chloroethoxy)- | 2-Chloroethoxyethene |
| Analytical Methods |
EPA Method 601 |
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EPA Method 624 |
EPA Method 8010 |
EPA Method 8240 |
EPA Method 8260 |
| Molecular Formula | C4H7CLO |
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Link to the National Library of Medicine's Hazardous Substances
Database for more details
on this compound. |
| Use | Used in the manufacture of anesthetics, sedatives and cellulose ethers.
COPOLYMER OF 95% ETHYL ACRYLATE WITH 5% 2-CHLOROETHYL VINYL ETHER
/HAS BEEN USED TO PRODUCE ACRYLIC ELASTOMER
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| Apparent Color | Colorless liquid
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| Boiling Point | 109 DEG C @ 740 MM HG
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| Melting Point | -70.3 DEG C
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| Molecular Weight | 106.55
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| Density | 1.0495 @ 20 DEG C/4 DEG C
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| Sensitivity Data | Eye irritation has been reported following exposure to 2-chloroethyl vinyl ether.
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| Environmental Impact | 2-Chloroethyl vinyl ether is a synthetic organic chemical, designated as a priority pollutant
by the USEPA, and which is no longer produced in the United States. If released to soil,
2-chloroethyl vinyl ether would be expected to display high mobility. Volatilization from the soil
to the atmosphere may be an important fate process. Biodegradation in soil should occur, and
hydrolysis may be an important fate process in acidic soils or soils possessing acidic sites. If
released to water, hydrolysis at neutral pH should be expected to occur with a half-life of about
50 years; This value decreases to 6.9 days at pH= 5. Volatilization from water should be an
important fate process; the volatilization half-life for a model river can be estimated at 7 hours.
Direct photochemical degradation in water should not occur, nor should 2-chloroethyl vinyl ether
be expected to bioaccumulate in aquatic organisms. The half-life for the reaction with
photochemically produced hydroxyl radicals in the atmosphere can be estimated to be about 12
hours. The high reactivity of the double bond on this molecule makes it a candidate for reaction
with other radicals and oxidants which may be present in the atmosphere. The half-life for the
reaction with ozone in the atmosphere can be estimated at 1.3 days. Because of its water
solubility, rain washout should be considered as a likely fate process.
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| Environmental Fate | TERRESTRIAL FATE: If released to soil, the estimated values for Koc, 22-118(1,SRC),
suggest that 2-chloroethyl vinyl ether would readily leach through the soil(2,SRC). 2-Chloroethyl
vinyl ether is known to undergo hydrolysis by general acid catalysis , and thus hydrolysis in
moist, acidic soils may be a major fate process(4,SRC). It is also possible that hydrolysis may be
catalyzed by acidic sites in clay soils and on humic materials(4,SRC). Based on the estimated
vapor pressure, 30 torr at 25 deg C(5,SRC), and the Henry's Law constant, 2.5X10-4 atm
cu-m/mol at 25 deg C , volatilization from the soil may be an important fate process(4,SRC).
Biodegradation of 2-chloroethyl vinyl ether in soil can be an important fate process(5,6).
AQUATIC FATE: If released to water, the estimated Henry's Law constant for 2-chloroethyl
vinyl ether, 2.5X10-4 atm cu m/mol , suggests that volatilization from the water to the
atmosphere should be an important fate process. The estimated volatilization half-life for a model
river 1 m deep, flowing at 1 m/sec, and with a wind velocity of 3 m/sec is 7 hours(2,SRC). The
rate constant for hydrolysis of 2-chloroethyl vinyl ether at a pH of 7, 4.4X10-10 1/sec ,
translates to a half-life in neutral water of 50 years. As 2-chloroethyl vinyl ether is known to
undergo general acid catalysis with an experimental rate constant of 0.168 l/mol-sec ,
hydrolysis in acidic waters would occur at a greater rate. The half-life for hydrolysis at pH=
6 is 69 days; at pH of 5, it is 6.9 days. Direct photochemical degradation in water should
not be expected, however 2-chloroethyl vinyl ether should be considered as a candidate for
reaction with alklyperoxy radicals in humic waters. 2-Chloroethyl vinyl ether should not
adsorb to sediment or suspended organic material, and should not be expected to bioaccumulate
in aquatic organisms.
ATMOSPHERIC FATE: If released to the atmosphere, 2-chloroethyl vinyl ether would be
expected to undergo rapid degradation by photochemically produced hydroxy radicals; the
half-life can be estimated to be 7 hours(1,SRC). The high reactivity of the double bond of this
molecule suggests that the potential for atmospheric removal by the reaction with other
atmospheric radicals and oxidants may be an important fate process(2,SRC). The estimated
half-life for the reaction with ozone in the atmosphere is 1.3 days(3,SRC). The water solubility of
2-chloroethyl vinyl ether, 15,000 mg/l at 25 deg C , suggests that rain washout may be an
important pathway for atmospheric removal.
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| Drinking Water Impact | SURFACE WATER: US EPA Storet Data Base, 929 samples, 0.8% positive, median
concn less than 10 ug/L . 2-Chloroethyl vinyl ether was not detected in eighty-six samples from
fifty-one rainwater runoff catchments located throughout the USA (detection limits not given) .
GROUNDWATER: 2-Chloroethyl vinyl ether was detected in three of three wells on site at
Amphenol Products Division, Allied Corporation, Broadville IL, at concentrations less than 1
ug/l. Detected in eleven of eleven off site wells in concentrations ranging less than 1 ug/l to less
than 10 ug/l(1,2). Not found in 1174 community and 617 private wells throughout WI, early
1980's, detection limits ca 5 ug/l . Not detected in NJ coastal Plain Aquifer System .
EFFL: US EPA Storet Data Base, 1,291 samples, 1% positive, median concn less than 5 ug/l .
Not detected in Oak Ridge Gaseous Diffusion Plant wastewater (detection limit 10 ppb) .
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