2-Chloroethyl vinyl ether

106.55078

106.55

203-799-6

99O7V53TS1

8261

1992|1993

DTXSID0051570

Colorless liquid

2909199090

9.23000

1.38530

2-chloroethyl vinyl ether is a liquid. Insoluble in water. Sinks in water. Toxic.

1.0495 g/cm³ @ Temp: 20 °C

-70.3 °C

110 °C

61 °F

n20/D 1.438(lit.)

In water, 429 mg/l at 25 deg C

Ethers should not be stored near powerful oxidizers or in areas of high fire hazard. They should be kept cool and containers electrically grounded to avoid sparks. /Ethers/

26.8 mm Hg @ 20 deg C

3.7 (air= 1)

Dangerous; when heated or exposed to flame or sparks. Besides risk of explosion from air mixture of ether vapors, ethers tend to form peroxides upon standing. When ethers containing peroxides are heated they can detonate. /Ethers/

2-Chloroethyl vinyl ether is hydrolyzed to 2-chloroethanol and acetaldehyde.|Quite stable to NaOH solution; even dilute acids produce hydrolysis to acetaldehyde and ethylene chlorohydrin

Highly flammable. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Insoluble in water.

Ethers

Highly Flammable

2-CHLOROETHYL VINYL ETHER forms salts with strong acids and addition complexes with Lewis acids. May react violently with strong oxidizing agents. Typically stabilized against polyermizable by addition of triethanolamine.

III

3.2

UN 1992 3/PG 2

3

R11;R20/22;R36/37/38;R41

S26-S36-S45-S36/37-S16-S7-S37/39

KN6300000

F: Flammable;Xn: Harmful;

Quite stable to /sodium hydroxide/ solns. Even dilute acids produce hydrolysis to acetaldehyde and ethylene chlorohydrin [2-chloroethanol].

P210-P261-P301 + P310-P305 + P351 + P338

H225-H301-H315-H319-H335

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U042, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.

Can react vigorously with oxidizing materials. /Ethers/

Highly flammable. (NTP, 1992)|Flammable - 3rd degree, Reactive - 2nd degree

|Danger|H225 (92.68%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 42 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store it in a freezer. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: When working with this chemical, you should wear an impervious full-body suit equipped with an air line respirator or a self-contained breathing apparatus. RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that butyl rubber gloves may provide protection to contact with this compound. Butyl rubber over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)

DANGEROUS; SHOCK OR HEAT CAN CAUSE GASEOUS ETHERS TO ESCAPE FROM THEIR CONTAINERS. /ETHERS/|Moderate fire risk. Combustible.

Dangerous; when heated or exposed to flame or sparks. Besides risk of explosion from air mixture of ether vapors, ethers tend to form peroxides upon standing. When ethers containing peroxides are heated they can detonate. /Ethers/

To fight fire use foam, alcohol foam or dry chemical.|Water may be ineffective. /Use/ alcohol foam.

Only electrical equipment of explosion proof type (Group C classification) is permitted to be operated in ether areas. /Ethers/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Eye irritation has been reported following exposure to 2-chloroethyl vinyl ether.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 2 - Materials that readily undergo violent chemical changes at elevated temperatures and pressures.|W - No water: Materials that react violently or explosively with water.

The major hazards encountered in the use and handling of 2-chloroethyl vinyl ether stem from its toxicologic properties and flammability. Capable of producing eye irritation, exposure to this colorless liquid may occur from its use in the manufacture of anesthetics, sedatives, cellulose ethers, and acrylic elastomers. In activities and situations where over-exposure may occur, we ar a full-facepiece, self-contained breathing apparatus. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. 2-Chloroethyl vinyl ether can be ignited under almost all temperature conditions (flash point: 80 °F, open cup). When exposed to flame or sparks, 2-chloroethyl vinyl ether may explode. When left standing, 2-chloroethyl vinyl ether may form peroxides which upon heating may detonate. Also, upon heating to decomposition, this substance may emit highly toxic fumes of phosgene. For fires involving this substance, extinguish with dry chemical, CO2, alcohol foam, or standard foa m. Fight the fire from a safe distance. 2-Chloroethyl vinyl ether should be stored in electrically-grounded containers, away from heat, sources of ignition, sources of physical damage, and oxidizing materials. 2-Chloroethyl vinyl ether is a potential candidate for disposal by fluidized bed, rotary kiln, or liquid injection forms of incineration.

U042; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

U042; As stipulated in 40 CFR 261.33, when 2-chloroethyl vinyl ether, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

As reported in the USEPA Storet Database, 2-chloroethyl vinyl ether was detected in 1% of 1,291 samples with a median concn less than 5 ug/l(1). 2-Chloroethyl vinyl ether was not detected in Oak Ridge Gaseous Diffusion Plant wastewater (detection limit 10 ppb)(2).

As reported in the USEPA Storet Database, 2-chloroethyl vinyl ether was not detected in 339 samples(1). It was found in all six off site sediment samples near a manufacturing plant in Broadview, IL at concns less than 100 ug/kg(2).

LD50 Rat oral 250 mg/kg|LD50 Rabbit dermal 3.2 ml/kg.|LD50 Rabbit dermal 3354 mg/kg|LCLO Rat inhalation 250 ppm/4H

2-Chloroethyl vinyl ether's former production and use as a monomer for vinyl polymer synthesis, and as a copolymer(1) may have resulted in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a water solubility of 429 mg/l(2) and a regression-derived equation(3), indicates that 2-chloroethyl vinyl ether is expected to have moderate mobility in soil(SRC). Volatilization of 2-chloroethyl vinyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.8X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 26.8 mm Hg(4), and water solubility(2). The potential for volatilization of 2-chloroethyl vinyl ether from dry soil surfaces may exist(SRC) based upon its vapor pressure(4). As 2-chloroethyl vinyl ether is known to undergo general acid catalysis with an experimental rate constant of 0.168 l/mol-sec (7), hydrolysis in acidic soils would occur at a greater rate(SRC). The half-life for hydrolysis at pH 6 is 69 days; at pH 5, it is 6.9 days(SRC). Based on a studies in water, biodegradation of 2-chloroethyl vinyl ether may be possible in soil(SRC). In water, the theoretical biological oxygen demand for 2-chloroethyl vinyl ether was 76% and 52% (initial concn 5 and 10 mg/l, respectively) in seven days using settled domestic wastewater as a microbial inoculum(6,7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a water solubility of 429 mg/l(2) and a regression-derived equation(3), indicates that 2-chloroethyl vinyl ether is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.8X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 26.8 mm Hg(4), and water solubility, 429 mg/l(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.1 hrs and 4.1 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 20(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The rate constant for hydrolysis of 2-chloroethyl vinyl ether at a pH of 7 is 4.4X10-10 1/sec(4) which translates to a half-life of about 50 years(SRC). As 2-chloroethyl vinyl ether is known to undergo general acid catalysis with an experimental rate constant of 0.168 l/mol-sec (7), hydrolysis in acidic waters would occur at a greater rate(SRC). The half-life for hydrolysis at pH 6 is 69 days; at pH 5, it is 6.9 days(SRC). The theoretical biological oxygen demand for 2-chloroethyl vinyl ether was 76% and 52% (initial concn 5 and 10 mg/l, respectively) in seven days using settled domestic wastewater as a microbial inoculum(8,9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-chloroethyl vinyl ether, which has a vapor pressure of 26.8 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 2-chloroethyl vinyl ether is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-life for reaction with OH radicals in air is estimated to be 10.2 hrs(SRC), calculated from its rate constant of 3.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3); the half-life for reaction with ozone in air is estimated to be 1.3 days(SRC), calculated from its rate constant of 8.8X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 2-chloroethyl vinyl ether with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 2-chloroethyl vinyl ether with ozone has been estimated as 8.8X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.3 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). The experimental rate constant for acid catalyzed cleavage of 2-chloroethyl vinyl ether at 25 °C is 0.168 l/mol-sec(3). This translates to a half-life of 69 days at a pH of 6, and to a half-life of 6.9 days at pH of 5(SRC). The rate constant for hydrolysis of 2-chloroethyl vinyl ether at a pH of 7 is 4.4X10-10 1/sec(4). This value corresponds to a half-life of 50 years in neutral waters(SRC). In the laboratory, 2-chloroethyl vinyl ether was shown to disappear in autoclaved samples of a model aquifer system, suggesting that abiotic processes were involved(5). A laboratory rapid-infiltration microcosm study showed that 2-chloroethyl vinyl ether was removed from the influent stream(6,7). 2-Chloroethyl vinyl ether is not expected to directly photolyze due to the lack of absorption in the environmental portion of the UV spectrum (>290 nm)(SRC).

An estimated BCF of 20 was calculated for 2-chloroethyl vinyl ether(SRC), using a water solubility of 429 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of 2-chloroethyl vinyl ether is estimated as 160 (SRC), using a water solubility of 429 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-chloroethyl vinyl ether is expected to have moderate mobility in soil(SRC).

The Henry's Law constant for 2-chloroethyl vinyl ether is estimated as 8.8X10-3 atm-cu m/mole(SRC) derived from its vapor pressure, 26.8 mm Hg(1), and water solubility, 429 mg/l(2). This Henry's Law constant indicates that 2-chloroethyl vinyl ether is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 1.1 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 4.1 days(SRC). 2-Chloroethyl vinyl ether's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 2-chloroethyl vinyl ether from dry soil surfaces may exist(SRC) based upon a vapor pressure of 26.8 mm Hg(1).

SURFACE WATER: 2-Chloroethyl vinyl ether was detected in 0.8% of 929 samples from the US EPA Storet Data Base with a median concn less than 10 ug/l(1). 2-Chloroethyl vinyl ether was not detected in eighty-six samples from fifty-one rainwater runoff catchments located throughout the US (detection limits not given)(2).|GROUNDWATER: 2-Chloroethyl vinyl ether was detected in three wells on a manufacuring site located in Broadville, IL at concns less than 1 ug/l(1,2). 2-Chloroethyl vinyl ether was detected in eleven off-site wells in concns ranging less than 1 ug/l to less than 10 ug/l(1,2). However, it was not found in 1,174 community and 617 private wells throughout WI in the early 1980's (detection limits ca. 5 ug/l)(3). 2-Chloroethyl vinyl ether was not detected in a NJ coastal Plain Aquifer System(4).

2-Chloroethyl vinyl ether is no longer produced in the USA(1). NIOSH (NOHS Survey 1972-1974) has statistically estimated that 23,221 workers were exposed to 2-chloroethyl vinyl ether in the past(2). Occupational exposure to 2-chloroethyl vinyl ether may have occurred through inhalation and dermal contact with this compound at workplaces where 2-chloroethyl vinyl ether is produced or used(SRC).

ACUTE/CHRONIC HAZARDS: Dangerous when exposed to heat, flame, or oxidizers. Moderately toxic by ingestion and inhalation. DO NOT INDUCE VOMITING. Volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the exposed person is convulsing or unconscious, you should not attempt first aid. Transport immediately to a hospital emergency room or poison control center. If the victim is conscious, administer large volumes of liquid then immediately induce vomiting. Transport at once to a medical facility. (NTP, 1992)

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Provide a low-stimulus environment. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Treat frostbite by rapid rewarming ... . /Ethers and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethers and related compounds/

/HUMAN EXPOSURE STUDIES/ Eye irritation has been reported following exposure to 2-chloroethyl vinyl ether.

RESEARCH GRADE: 99%

Ethene, (2-chloroethoxy)-: ACTIVE

Method: EPA-EAD 624 Purgeable Organic Compounds via GC/MS; Analyte: 2-chloroethyl vinyl ether; Matrix: water; Detection Level: not reported.|Method: EPA-EAD 1624, Revision B, Volatile Organic Compounds by Isotope Dilution GC/MS; Analyte: 2-chloroethyl vinyl ether; Matrix: water; Detection Level: 10 ug/L.|EPA Method 8010: Halogenated Volatile Organics. For the analysis of solid waste, a representative sample (solid or liquid) is collected in a standard 40 ml glass screw-cap vial equipped with a Teflon-faced silicone septum. Sample agitation, as well as contamination of the sample with air, must be avoided. Two vials are filled per sample location, then placed in separate plastic bags for shipment and storage. Samples may be analyzed by direct injection or purge-and-trap using gas chromatography, with detection achieved with a halogen-specific detector. A temperature program is used in the gas chromatograph to separate the organic compounds. Column 1 is an 8 ft by 0.1 in ID stainless steel or glass column packed with 1% SP-1000 on Carbopack-B 60/80 mesh or equivalent. Column 2 is a 6 ft by 0.1 in ID stainless steel or glass column packed with chemically bonded n-octane on Porasil-C 100/120 mesh (Durapak) or equivalent. Under the prescribed conditions, 2-chloroethyl vinyl ether has a detection limit of 0.13 ug/l, an average recovery range of four measurements of 4.5-35.5 ug/l, and a limit for the standard deviation of 8.3 ug/l.|EPA Method 8240: Gas Chromatography/Mass Spectrometry for Volatile Organics. Method 8240 can be used to quantify most volatile organic compounds that have boiling points below 200 °C and that are insoluble or slightly soluble in water, including the title compound. Volatile water-soluble compounds can be included in this analytical technique, however, for the more soluble compounds, quantitation limits are approximately ten times higher because of poor purging efficiency. The method is also limited to compounds that elute as sharp peaks from a gas chromatograph column packed with graphitized carbon lightly coated with a carbowax (6 ft by 0.1 in ID glass, packed with 1% SP-1000 on Carbopack-B (60/80 mesh) or equivalant). This gas chromatography/mass spectrometry method is based on a purge-and-trap procedure. The practical quantitation limit for Method 8240 for an individual compound is approximately 5 ug/kg (wet weight) for wastes and 5 ug/l for ground water. Practical quantitation limits will be proportionately higher for sample extracts and samples that require dilution or reduced sample size to avoid saturation of the detector. A representative sample (solid or liquid) is collected in a standard 40 ml glass screw-cap vial equipped with a Teflon-faced silicone septum. Sample agitation, as well as contamination of the sample with air, must be avoided. Two vials are filled per sample location, then placed in separate plastic bags for shipment and storage. Under the prescribed conditions, 2-chloroethyl vinyl ether has an average recovery range for four samples of detected-50.4 ug/l with a limit for the standard deviation of 25.9 ug/l and a retention time of 18.6 min.|For more Analytic Laboratory Methods (Complete) data for 2-CHLOROETHYL VINYL ETHER (8 total), please visit the HSDB record page.

Fire Hazards -> Flammable - 3rd degree, Reactive - 2nd degree