Ethyl vinyl ether

log Kow = 1.04

1.04

1.04

0.7589 at 68 °F (USCG, 1999) - Less dense than water; will float

0.7589 at 20 °C

Relative density (water = 1): 0.8

0.754 @25 °C

Colorless liquid

Ether-like odor

In water, 7800 mg/L at 25 °C

In water, 10000 mg/L at 37 °C

Slightly soluble in carbon tetrachloride; soluble in ethanol; miscible in ether

Solubility in water, g/l at 15 °C: 8.3 (slightly soluble)

less than -50 °F (USCG, 1999)

< -50 °F (< -46 °C) /closed cup/

96 °F at 760 mmHg (USCG, 1999)

35.5 °C

36 °C

35.6 °C @760 [mm Hg]

Hazardous decomposition products formed under fire conditions. - Carbon oxides

When heated to decomposition it emits acrid smoke and irritating fumes.

-175 °F (USCG, 1999)

-115.8 °C

-115 °C

-115 °C

Danger

H225 (29%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 710 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H224: Extremely flammable liquid and vapor [Danger Flammable liquids]

Chemical: Ethene, ethoxy-

Ethene, ethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethene, ethoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24588

Vinamar: HSNO Approval: HSR004474 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Behavior in Fire: Explosive hazard (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Vapour/air mixtures are explosive.

INHALATION OR INGESTION: Excitement followed by unconsciousness and respiratory paralysis. CNS depression. EYES: May cause irritation and transient injury to cornea. SKIN: Prolonged contact can cause tissue defatting and dehydration leading to dermatitis. (USCG, 1999)

· Inhalation or contact with material may irritate or burn skin and eyes.

A mild skin irritant; Causes general anesthesia in inhalation lethal-concentration studies of mice; [RTECS] May polymerize on heating or contamination and form unstable peroxides on exposure to oxygen; [CAMEO] May cause CNS depression; [ICSC] A skin and eye irritant that may cause transient corneal injury; May cause reddening of skin if spilled and allowed to remain on clothes; Inhalation can cause CNS depression; High vapor concentrations may cause mild smarting of eyes and respiratory system; May cause liver injury; [CHRIS] Stabilized with 0.1% potassium hydroxide; May form explosive peroxides; A skin and strong eye irritant; Inhalation may cause unconsciousness and respiratory paralysis; May cause liver injury; [Sigma-Aldrich MSDS] Vinyl ethyl ether, stabilized (UN1302) has warning of explosive polymerization; [ERG 2016] See Butyl vinyl ether.

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:

Use foam, dry powder, carbon dioxide, water. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Refer immediately for medical attention.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Call a doctor.

General First Aid:

Alcohol Foam.

Water May be Ineffective.

To fight fire, use alcohol foam, foam, CO2, dry chemical.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Further information: Use water spray to cool unopened containers.

ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Evacuate danger area! Consult an expert! Remove all ignition sources. Ventilation. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Wash away remainder with plenty of water. Then store and dispose of according to local regulations.

Alkyl ether-degrading Rhodococcus sp. strain DEE5151, isolated from activated sewage sludge, has an activity for the oxidation of a variety of alkyl ethers, aralkyl ethers and dibenzyl ether. The whole cell activity for diethyl ether oxidation was effectively inhibited by 2,3-dihydrofurane, ethyl vinyl ether and glutaraldehyde. Glutaraldehyde of less than 30 uM inhibited the activity by a competitive manner with the inhibition constant, K(I) of 7.07+/-1.36 uM. The inhibition type became mixed at higher glutaraldehyde concentrations >30 uM, probably due to the inactivation of the cell activity by the Schiff-base formation. Structurally analogous ethyl vinyl ether inhibited the diethyl ether oxidation activity in a mixed manner with decreasing the apparent maximum oxidation rate, v(max)(app), and increasing the apparent Michaelis-Menten constant, K(M)(app). The mixed type inhibition by ethyl vinyl ether seemed to be introduced not only by the structure similarity with diethyl ether, but also by the reactivity of the vinyl ether with cellular components in the whole cell system.

1. In rats, surgically anesthetized with Urethane, an increase in the depth of anesthesia upon administration of ethyl carbamate (Urethane), pentobarbitone sodium (Nembutal), thiopentone sodium (Intraval), althesin, ketamine, trichloroethylene, halothane, methoxyflurane, diethyl ether, ethyl-vinyl ether, cyclopropane, enflurane or chloroform resulted in a dose-dependent increase in the latency, the decrease in the amplitudes of the initial positive and negative components of the short latency cortical response to electrical stimuli applied to the forepaw. 2. The same changes were seen when starting from initially unanesthetized rats and anesthetizing them with Urethane. 3. With all the inhalational agents used, these changes lasted for as long as the administration except with nitrous oxide where the changes in the cortical response were transient. 4. The tranquilizing agents diazepam, chlordiazepoxide, and haloperidol showed no such action. Chloral hydrate and chlorpromazine, on the other hand, produced moderate changes in the evoked cortical response similar to those seen with the other anesthetic agents used.

The effects of ten inhalational anesthetic agents on drug metabolism were studied in rats. Male Sprague Dawley-rats were exposed to below anesthetic concentrations of the test agents 7 hours a day for 1 to 7 days, or up to 15 days when nitrous-oxide was used. A single intraperitoneal injection of 125 milligrams per kilogram (mg/kg) hexobarbital, a sleep inducer, was given 20 to 22 hours after the last exposure to the anesthetic, and sleeping time was determined. Some animals were given an intraperitoneal injection of 50 mg/kg SKF-525-A, an inhibitor of hepatic microsomal enzyme activity, 30 minutes before the hexobarbital injection. Liver homogenates prepared from some rats pretreated with diethyl-ether or halothane were incubated with hexobarbital and assayed for O-demethylase activity and aniline-hydroxylase activity. Hexobarbital sleeping time was significantly reduced after a single 7 hour exposure to diethyl-ether, isopropyl-ether, fluroxene, enflurane, and Forane. Two exposures to halothane and ethyl-vinyl-ether were required to cause a significant reduction in sleeping time. Chloroform caused an increase in sleeping time after one exposure, no change with two or four exposures, and a decrease after five or more exposures. Nitrous-oxide and cyclopropane had no effect on hexobarbital sleeping time. SKF-525-A blocked the decrease in sleeping time caused by diethyl-ether and halothane. The rate of hydroxylation of hexobarbital and aniline by rat liver homogenates was increased by pretreatment with either diethyl-ether or halothane, but demethylase activity was increased only by diethyl-ether pretreatment. The authors conclude that exposure to inhalation anesthetics can enhance the ability of rats to metabolize drugs. ...

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that vinyl ethyl ether is expected to have very high mobility in soil(SRC). Volatilization of vinyl ethyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 515 mm Hg(3), and water solubility, 7800 mg/L(4). Vinyl ethyl ether is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. A 100% degradation using activated sludge in the OECD Guideline 302B (Inherent biodegradability: Zahn-Wellens/EMPA) test(4) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that vinyl ethyl ether is not 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 6.3X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 515 mm Hg(4), and water solubility, 7800 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.6 hours and 3.4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 2(SRC), from its log Kow of 1.04(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 100% degradation using activated sludge in the OECD Guideline 302B (Inherent biodegradability: Zahn-Wellens/EMPA) test(5) suggests that biodegradation is an important environmental fate process in water(SRC). Vinyl ethyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Vinyl ethyl ether is an olefin and olefins react with photooxidants in natural waters (such as hydroxyl, peroxy and singlet oxygen) exposed to sunlight with a half-life on the order of 25 days(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vinyl ethyl ether, which has a vapor pressure of 515 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase vinyl ethyl ether is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 hours(SRC), calculated from its rate constant of 7.79X10-11 cu cm/molecule-sec at 25 °C(3). Vapor-phase vinyl ethyl ether is also degraded in the atmosphere by reaction with ozone and nitrate radicals(SRC); the half-lives for these reactions in air is estimated to be 1.4 and 0.6 hours(SRC), calculated from respective rate constants of 2.0X10-16 and 1.40X10-12 cu cm/molecule-sec at 25 °C(3). Vinyl ethyl ether does not absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: Vinyl ethyl ether is a flammable liquid. It is used in proteomics research and organic synthesis. It was studied as an anesthetic agent in the 1950s. HUMAN STUDIES: Vinyl ethyl ether was studied in clinical trials to investigate whether it was suitable as an anesthetic. Some patients participating in these studies suffered complications (generalized convulsions due to hypercarbia and respiratory and circulatory depression as well as respiratory and cardiac arrest), which were attributed to overdosage. The degree of muscle relaxation obtained with this type of anesthesia was considered to be inadequate. Liver function tests conducted after several hours of anesthesia showed that hepatic function was not affected. Urinalyses, blood counts and electrocardiograms obtained after anesthesia revealed slight, reversible changes in some cases. There is a report of one case of transient damage to the human cornea, which was reversible after 48 hr. ANIMAL STUDIES: In rabbits, it caused only very mild irritation to the skin and eye. On acute oral administration, dermal application and inhalation exposure, vinyl ethyl ether was found to be of low toxicity. A rapid induction of CNS depression and rapid recovery from narcosis was noted with monkeys, dogs, rats. The clinical signs of intoxication were characterized by the CNS depressant effect of the substance. In the Salmonella/microsome assay, vinyl ethyl ether was found to test negative both with and without metabolic activation. In the sister chromatid exchange assay in Chinese hamster ovary cells, the chemical caused a significant increase in sister chromatid exchange rate.

Cough. Incoordination. Dizziness. Drowsiness. Headache. Wheezing. Unconsciousness.

Redness. Dry skin.

Redness.

Aspiration hazard! Headache. Nausea.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of vinyl ethyl ether can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that vinyl ethyl ether is expected to have very high mobility in soil.

/HUMAN EXPOSURE STUDIES/ ... /CNS depression/ was also studied in one human subject. The induction period was 60 seconds, duration of light anesthesia was 6 minutes. Recovery was rapid and uneventful. Blood pressure and pulse were not altered. The subject stated that the vapors did not irritate the upper respiratory tract.

/HUMAN EXPOSURE STUDIES/ In the 1950s, ethoxyethene was studied in clinical trials to investigate whether it was suitable as an anesthetic. Some patients participating in these studies suffered complications (generalized convulsions due to hypercarbia and respiratory and circulatory depression as well as respiratory and cardiac arrest), which were attributed to overdosage. The degree of muscle relaxation obtained with this type of anesthesia was considered to be inadequate. Liver function tests conducted after several hours of anesthesia showed that hepatic function was not affected. Urinalyses, blood counts and electrocardiograms obtained after anesthesia revealed slight, reversible changes in some cases.

/HUMAN EXPOSURE STUDIES/ The pharmacological effects were studied in 29 patients, aged 14 to 58 years (7 males, 22 females). Gynecological and orthopedic cases prevailed. Ethyl vinyl ether (EVE) was used in combination with other common anesthetics. In brief, findings were as follows: Liver function was unchanged in 58% of the patients. Bromsulphthalein excretion was observed in some cases. In two of these, large doses up to 110 mL EVE had been used. Urinalysis: no changes were noted in 68% of the patients. Six patients (20%) showed findings (traces of acetone (n=6), increased sugar (n=2), traces of albumin (n=3) which had returned to normal on day 5 post treatment. Blood: no changes in 82% of the patients; the remainder showed slight leucocytosis. ECG: no change in 48% of the patients. Tachycardia, auricular and ventricular premature contractions were all seen. Mild myocardial depression was noted in 5 cases (17%). Nausea, vomiting: was seen in 10 out of 29 patients. Salivation: was quite severe at times; was treatable with atropine.

/CASE REPORTS/ There is a report of one case of transient damage to the human cornea, which was reversible after 48 hr.

/OTHER TOXICITY INFORMATION/ A rapid induction of /CNS depression/ and rapid recovery from narcosis was noted with monkeys, dogs, rats, and man. Compared with diethylether approximately 50% less the quantity was required.

Vinyl ethyl ether's production and use in copolymerizations and as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). Vinyl ethyl ether is released to air in emissions from turbine engines(2). Vinyl ethers are released to the atmosphere entirely from anthropogenic sources(3).

AEROBIC: Using OECD Guideline 302B (Inherent biodegradability: Zahn-Wellens/EMPA Test) with an activated, non-adapted industrial sludge inoculum, vinyl ethyl ether, at 400 mg/L, reached 100% degradation (DOC removal) after 5 days of incubation. Using OECD Guideline 310 (Ready Biodegradability - CO2 in Sealed Vessels, Headspace Test) with a domestic activated sludge, the analog isobutyl vinyl ether, at 27.7 mg/L, reached 60-70% after 28 days of incubation(1); the interpretation of the test result was readily biodegradable, but failing the 10-day window(1).

An estimated BCF of 2 was calculated in fish for vinyl ethyl ether(SRC), using a log Kow of 1.04(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).

Vinyl ethyl ether

1

10000

Flammable chemical that can be released at a facility.

Used to make large scale chemicals, polymers, and resins, and as a laboratory reagent; [ExPub: ECHA REACH Registrations]

Copolymerization, intermediate.

A useful vinyl ether for proteomics research and organic synthesis.

Vinyl ethers are mainly used for the production of homo- and copolymers, in the adhesives and varnish industries. /Vinyl ethers/

MEDICATION /Former Use/

2022: 50,000 - <250,000 lb

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Ethyl vinyl ether:

Reaction of acetylene with ethanol.

In industry, vinyl ethers are produced in autoclaves (stirred or not stirred), in reaction towers (tube reactor), bubble columns, or loop reactors. The catalyst, normally potassium alcoholate, is in most cases prepared before the reaction. Therefore, solid KOH or KOH solution is added to the alcohol. Excess water can be removed batchwise in a stirred vessel or continuously by distillation in carbon steel apparatus. The acetylene-if not consumed in the reaction-can be recycled into the reactor and supplemented by pure acetylene (fresh gas). /Vinyl ethers/

CH3CH(O(14)CH2CH3)2 and CH2CHO(14)CH2CH3 have been synthesized from CH3CHO and CH3(14)CH2OH. The synthesized vinyl ethyl ether (b.p. 35.5 deg) is accompanied by diethyl ether (b.p. 34.6 deg) and other impurities. A satisfactory separation has been made by gas chromatography in a 2 m dimethylsulfolane column followed by a 3 m squalane column on Celite. In this way, 0.5 mL of CH3(14)CH2OCHCH2 of 99.4% chemical purity and 98.3% radiochemical purity has been obtained; the position of the C-14 has been checked by hydrolysis in acid medium. The ether was pyrolyzed in a high vacuum apparatus by the static method. The amounts and specific activities of products were determined in a gas chromatograph connected to a flow ionization chamber with vibrating reed electrometer. Results obtained around 450 °C seem to prove that vinyl ethyl ether decomposes mainly (78%) by a rearrangement process forming an hexagonal activated complex.

All Other Basic Organic Chemical Manufacturing

Ethene, ethoxy-: ACTIVE