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Ethyl vinyl ether

Ethyl vinyl ether structure

Ethyl vinyl ether 

structure
  • CAS No:

    109-92-2

  • Formula:

    C4H8O

  • Chemical Name:

    Ethyl vinyl ether

  • Synonyms:

    Ethene,ethoxy-;Ether,ethyl vinyl;Ethoxyethene;Ethyl vinyl ether;EVE;Vinamar;Vinyl ethyl ether;1-Ethoxyethene;Ethoxyethylene;1-Ethoxyethylene;Ethyloxyethene;NSC 8405;[(Vinyl)oxy]ethane;[(Ethenyl)oxy]ethane;1-(Vinyloxy)ethane;A 15695-0F;A 15691-0F

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Vinyl ethyl ether appears as a clear colorless low-boiling liquid (35-36°C) with an ether-like odor. Flash point below -50°F. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a container, the container may rupture violently. Less dense than water and slightly soluble in water. Hence floats on water. Vapors are heavier than air.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Vinyl ethyl ether appears as a clear colorless low-boiling liquid (35-36°C) with an ether-like odor. Flash point below -50°F. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a container, the container may rupture violently. Less dense than water and slightly soluble in water. Hence floats on water. Vapors are heavier than air.

Ethyl vinyl ether Basic Attributes

72.10570

72.11

203-718-4

6235C9592H

1261

8405

1302

DTXSID3029609

Colorless liquid|Ether-like odor

2942000000

Characteristics

9.23000

1.16640

Vinyl ethyl ether appears as a clear colorless low-boiling liquid (35-36°C) with an ether-like odor. Flash point below -50°F. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a container, the container may rupture violently. Less dense than water and slightly soluble in water. Hence floats on water. Vapors are heavier than air.

0.8 g/cm3

-115 °C

36 °C

-45ºC

1.376-1.378

H2O: 7.8 g/L (25 ºC)

Refrigerator

581mmHg at 25°C

Relative vapour density (air = 1): 2.5

vol% in air: 1.38

A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials.|May polymerize exothermically if heated or contaminated. If polymerization takes place inside a container, the container may rupture violently.|Henry's Law constant = 6.3X10-3 atm-cu m/mole at 25 °C (estimated from vapor pressure and water solubility)|Hydroxyl radical reaction rate constant = 7.79X10-11 cu cm/molec-sec at 25 °C|Nitrate radical reaction rate constant = 1.40X10-12 cu cm/molec-sec at 25 °C|Ozone reaction rate constant = 2.0X10-16 cu cm/molec-sec at 25 °C

Highly flammable. Slightly soluble in water. Tends to form explosively unstable peroxides when exposed to oxygen.

Ethers

Highly Flammable

VINYL ETHYL ETHER is a very dangerous fire and explosion hazard when exposed to heat or flame. Undergoes autooxidation with formation of peroxides in the air. Can react vigorously with oxidizing materials. Undergoes explosive polymerization in contact with methanesulfonic acid [Eaton, P. E. et al., J. Org. Chem., 1972, 37, p. 1947].

Ethyl vinyl ether|D: Other compounds that may form peroxides|Kelly|Explosive polymerizations have occured. See Bretherick's and Eaton, P. E. et al. J. Org. Chem., 1972, 37, 1947|Eaton, P. E. et al. J. Org. Chem., 1972, 37, 1947

395 °F (USCG, 1999)|202 °C

-14.326 Btu/lb = -7959 cal/g = -333 X 10+5 J/kg

Lower: 1.7 percent by vol.; Upper: 28 percent by vol.

The vapour is heavier than air and may travel along the ground; distant ignition possible. As a result of flow, agitation, etc., electrostatic charges can be generated. Vapours are uninhibited and may polymerize in vents or flame arresters, causing blockage.

26.2 kJ/mol at 35.5 °C

Critical temperature: 475 K; critical pressure: 4.06 MPa

Safety Information

I

3

UN 1302

1

R12; R19; R36/37/38

S16-S23-S26-S3/7-S33-S36

KO0710000

F

Fireproof. Separated from strong oxidants and acids. Cool. Keep under inert gas. Store only if stabilized.

Stable. Highly flammable. Incompatible with strong oxidizing agents. May form peroxides in storage - check for their formation before use.

P210-P305 + P351 + P338-P370 + P378-P403 + P235

H225-H315-H319-H335

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.

Vapors may form explosive mixture with air.|... can react vigorously with oxidizing materials.

Vinyl ethyl ether is an indirect food additive for use only as a component of adhesives.

Toxikologische Bewertung. Heidelberg, Berufsgenossenschaft der chemischen Industrie 263 (2000)

Behavior in Fire: Explosive hazard (USCG, 1999)|Highly flammable. Vapour/air mixtures are explosive.|Flammable - 4th degree, Reactive - 2nd degree

|Danger|H225 (29.05%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 685 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 100 companies from 2 notifications to the ECHA C&L Inventory.|H224: Extremely flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P312, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 127P [Flammable Liquids (Water-Miscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). 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)

Excerpt from ERG Guide 127P [Flammable Liquids (Water-Miscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Full face mask, self-contained breathing apparatus, eye protection, and rubber gloves. (USCG, 1999)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing, flame retardant antistatic protective clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type AXBEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Flammable liquid

A very dangerous fire and explosion hazard when exposed to heat or flame.|Explosive limits , vol% in air: 1.7-28

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.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Avoid inhalation of vapor or mist. Use explosion-proof equipment. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.|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.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

/GUIDE 127P FLAMMABLE LIQUIDS (Water-Miscible)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Vinyl ethyl ether, stabilized/|/GUIDE 127P FLAMMABLE LIQUIDS (Water-Miscible)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution. /Vinyl ethyl ether, stabilized/|/GUIDE 127P FLAMMABLE LIQUIDS (Water-Miscible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind, uphill and/or upstream. Ventilate closed spaces before entering. /Vinyl ethyl ether, stabilized/|/GUIDE 127P FLAMMABLE LIQUIDS (Water-Miscible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Vinyl ethyl ether, stabilized/|For more DOT Emergency Guidelines (Complete) data for Vinyl ethyl ether (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. Vinyl ethyl ether, stabilized is included on the dangerous goods list.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. Vinyl ethyl ether, stabilized is included on the dangerous goods list.

...Ethoxyethene causes no or only very mild irritation to the skin and eye.|A skin irritant.

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.

Fireproof. Separated from strong oxidants and acids. See Chemical Dangers. Cool. Keep under inert gas. Store only if stabilized.

A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

The substance is mildly irritating to the eyes and respiratory tract. The substance may cause effects on the central nervous system. This may result in unconsciousness and narcosis. If swallowed the substance may cause vomiting and could result in aspiration pneumonitis.

The substance defats the skin, which may cause dryness or cracking. Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the liver and kidneys. This may result in organ disturbances.

NO open flames, NO sparks and NO smoking. See Chemical Dangers. Closed system, ventilation, explosion-proof electrical equipment and lighting. Prevent build-up of electrostatic charges (e.g., by grounding). Do NOT use compressed air for filling, discharging, or handling. Use non-sparking handtools.

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety goggles or eye protection in combination with breathing protection.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 4 - Materials that rapidly or completely vaporize at atmospheric pressure and normal ambient temperature or that are readily dispersed in air and burn readily.| 2 - Materials that readily undergo violent chemical changes at elevated temperatures and pressures.|W - No water: Materials that react violently or explosively with water.

Vinyl ethyl ether has been detected in emissions from turbine engines(1).

Toxicity

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.

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. ...

LD50 Rabbit dermal > 15000 mg/kg bw|LD50 Rat oral 6153 mg/kg bw|LC50 Rat inhalation > 21200 mg/cu m/4 hr

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).

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).

The rate constant for the vapor-phase reaction of vinyl ethyl ether with photochemically-produced hydroxyl radicals has been measured as 7.79X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). The rate constant for the vapor-phase reaction of vinyl ethyl ether with ozone has been measured as 2.0X10-16 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 1.4 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). The rate constant for the vapor-phase reaction of vinyl ethyl ether with atmospheric nitrate radicals is 1.40X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of approximately 0.6 hours at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(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). 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(5). Vinyl ethyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(6).

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).

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.

The Henry's Law constant for vinyl ethyl ether is estimated as 6.3X10-3 atm-cu m/mole(SRC) derived from its vapor pressure, 515 mm Hg(1), and water solubility, 7800(2). This Henry's Law constant indicates that vinyl ethyl 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 2.6 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 3.4 days(SRC). Vinyl ethyl ether's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Vinyl ethyl ether is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure.

According to the 2016 TSCA Inventory Update Reporting data, 3 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of vinyl ethyl ether in the United States may be as low as <10 workers and as high as <10 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|Occupational exposure to vinyl ethyl ether may occur through inhalation and dermal contact with this compound at workplaces where vinyl ethyl ether is produced or used(SRC). Vinyl ethyl ether was used as an anaesthetic drug for general and thoracic surgery(1) which exposed patients via inhalation. Use of vinyl ethyl ether as an inhaled narcotic in the 1950s has been reported(2).

Drug Information

/EXPL THER/ Ethyl vinyl ether is a useful anesthetic drug in all ages and for all operative procedures not requiring muscle relaxation or the use of the cautery. 2. It is an adequate and safe analgesic agent by the open drop technique or as an adjunct to nitrous oxide and ethylene. 3. It can be employed /in/ the non-rebreathing, semi-closed, or closed carbon dioxide absorption techniques. 4. Its advantages are rapid induction, emergence, and shift of level of anesthesia. 5. Its disadvantages are hypotension in the deeper planes of anaesthesia and lack of reliability of muscle relaxation. 6. It has proven to be a satisfactory agent for thoracic procedures if one is very careful to prevent the hypotension which may develop. /Former Use/|/EXPL THER/ 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.

There is evidence for rapid absorption after inhalation

In vitro studies with ethyl vinyl ether suggested that vinyl ethers may undergo microsomal oxidation to unstable epoxides, however, no mutagenic activity was found.

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)

Call a doctor. INHALATION: Remove from contaminated area and administer artificial respiration and oxygen if necessary. EYES: Flush with copious amounts of water. SKIN: Wash with copious amounts of water. INGESTION: Gastric lavage and saline cathartics. (USCG, 1999)


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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Ethers and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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 is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethers and related compounds/

/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.

ethyl vinyl ether

The substance can be absorbed into the body by inhalation of its vapour.

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


Redness. Dry skin.


Redness.

Ethyl vinyl ether Use and Manufacturing

Methods of Manufacturing

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.

Uses

Monomer for tackifying adhesives.


Intermediates

Production

100,000 - 500,000 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:

Technical

Pesticide, fertilizer, and other agricultural chemical manufacturing|Ethene, ethoxy-: ACTIVE|Ethene, ethoxy-, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).

Vinyl ethers are preferably analyzed by standard GLC methods. They may also be determined quantitatively by addition of iodine to the double bond of the vinyl group in the presence of methanol (Siggia's method). /Vinyl ethers/

Fire Hazards -> Flammable - 4th degree, Reactive - 2nd degree

Computed Properties

Molecular Weight:72.11
XLogP3:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:72.057514874
Monoisotopic Mass:72.057514874
Topological Polar Surface Area:9.2
Heavy Atom Count:5
Complexity:24.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Downstream Products

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