Methyl vinyl ether

0.777 at 32 °F (USCG, 1999) - Less dense than water; will float

0.7725 g/cu cm at 0 °C

Colorless, compressed gas or colorless liquid

Colorless, liquified gas

In water, 0.97 wt% /15,000 mg/L/ at 20 °C

Slightly soluble in water

Very soluble in ethanol, ether, acetone, benzene

Soluble in organic solvents; insoluble in glycerol, glycol

Soluble in oxygenated solvents

41.9 °F at 760 mmHg (USCG, 1999)

6 °C

-188 °F (USCG, 1999)

-122 °C

Danger

H220: Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P280, P377, P381, and P403 (click each P-code to see the statement)

Danger

H220 (100%): Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P280, P377, P381, P403, and P410+P403 (click each P-code to see the statement)

Chemical: Ethene, methoxy-

Regulation (EC) No 258/1997

Ethene, methoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethene, methoxy- 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: 25-09-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/13200

Ethene, methoxy-: Does not have an individual approval but may be used under an appropriate group standard

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: Containers may explode. Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999)

· EXTREMELY FLAMMABLE.

Inhalation causes intoxication, blurring of vision, headache, dizziness, excitation, loss of consciousness. Liquid or concentrated vapor irritates eyes and causes frostbite of skin. Aspiration of the liquid will cause chemical pneumonitis. (USCG, 1999)

· Vapors may cause dizziness or asphyxiation without warning, especially when in closed or confined areas.

VINYL METHYL ETHER reacts vigorously with oxidizing materials. Explosive in the form of vapor when exposed to heat, flame or strong oxidizing agents. Reacts, possibly explosively with halogens (bromine, chlorine) or hydrogen halides (hydrogen bromide, hydrogen chloride) [Baker, 1980, p. 487]. On contact with dilute acids or even mildly acidic solids (calcium chloride, ceramics) undergoes rapid, exothermic homopolymerization, which cannot be prevented by antioxidants. Must be stored in the presence of base [MVE Brochure, Billingham, ICI, 1962].

/GUIDE 116P GASES - FLAMMABLE (Unstable)/ Fire or Explosion: EXTREMELY FLAMMABLE. Will be easily ignited by heat, sparks or flames. Will form explosive mixtures with air. Silane (UN2203) will ignite spontaneously in air. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Vapors from liquefied gas are initially heavier than air and spread along ground. Vapors may travel to source of ignition and flash back. Cylinders exposed to fire may vent and release flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket. /Vinyl methyl ether, stabilized/

/GUIDE 116P GASES - FLAMMABLE (Unstable)/ Health: Vapors may cause dizziness or asphyxiation without warning. Some may be toxic if inhaled at high concentrations. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire may produce irritating and/or toxic gases. /Vinyl methyl ether, stabilized/

/GUIDE 116P GASES - FLAMMABLE (Unstable)/ 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 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind, uphill and/or upstream. Many gases are heavier than air and will spread along ground and collect in low or confined areas (sewers, basements, tanks). /Vinyl methyl ether, stabilized/

/GUIDE 116P GASES - FLAMMABLE (Unstable)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Vinyl methyl ether, stabilized/

For more DOT Emergency Guidelines (Complete) data for Vinyl methyl ether (8 total), please visit the HSDB record page.

· 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.

INHALATION: remove victim to fresh air; if breathing is difficult, administer oxygen; call physician.

General First Aid:

· Wear positive pressure self-contained breathing apparatus (SCBA).

200.0 [ppm]

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.

This compound should be susceptible to removal from waste water by air stripping. /Bis(2-chloroethyl)ether/

Excerpt from ERG Guide 116 [Gases - Flammable (Unstable); polymerization hazard]:

Immediate precautionary measure

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a structure estimation method(2), indicates that vinyl methyl ether is expected to have very high mobility in soil(SRC). Volatilization of vinyl methyl ether from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 3.9X10-3 atm-cu m/mole(SRC) based upon its vapor pressure, 1316 mm Hg(3), and water solubility, 15,000 mg/L(4). Vinyl methyl ether is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not available(SRC, 2018).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a structure estimation method(2), indicates that vinyl methyl 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 3.9X10-3 atm-cu m/mole(SRC) derived from its vapor pressure, 1316 mm Hg(4), and water solubility, 15,000 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 hours and 3 days, respectively(SRC). Vinyl methyl ether is expected to undergo hydrolysis in the environment based on hydrolysis half-lives of 9.5 hours, 40 days and 10.9 years at pH 5, 6 and 9, respectively, in structurally similar butyl vinyl ether(6). According to a classification scheme(7), an estimated BCF of 3(SRC), from an estimated log Kow of 0.42(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data in water were not available(SRC, 2018).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vinyl methyl ether, which has a vapor pressure of 1316 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase vinyl methyl ether is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be 11 hours and 1.3 days(SRC), calculated from its respective rate constants of 3.35X10-11(3) and 8.8X10-16(4) cu cm/molecule-sec. Vinyl methyl ether does not absorb at wavelengths >290 nm(5) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: Vinyl methyl ether is a colorless compressed gas or colorless liquid. Copolymers are used in coatings and lacquers, as a modifier for alkyl, polystyrene and ionomer resins, and as a plasticizer for nitrocellulose and adhesives. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: Vinyl methyl ether does not produce inflammatory changes in either the skin or eyes of rabbits. Rats tolerate repeated inhalation of 2000 ppm. In two 28-day inhalation studies in rats restlessness, reduction in body weight gain and an increase in relative weight of the liver were observed at 25,000 ppm. In the male rats, an increase in prothrombin time and a reduction in total protein occured at higher concentrations. In the 28-day inhalation study, 1500 ppm was the no effect level for male rats and 3500 ppm for female rats. Methyl vinyl ether was not mutagenic on Salmonella typhimurium TA98, TA100, TA1535 and TA1537, and Escherichia` coli WP2 uvrA with or without metabolic activation. In the micronucleus test in mice, vinyl methyl ether did not produce a clastogenic effect following 5 exposures of 25,000 ppm.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of vinyl methyl ether can be estimated to be 5(SRC). According to a classification scheme(2), this estimated Koc value suggests that vinyl methyl ether is expected to have very high mobility in soil.

Vinyl methyl ether's production and use in copolymers for coatings and lacquers, in polystyrene and ionomer resins, in plasticizers for nitrocellulose, and in adhesives(1) may result in its release to the environment through various waste streams(SRC).

An estimated BCF of 3 was calculated in fish for vinyl methyl ether(SRC), using an estimated log Kow of 0.42(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

The Henry's Law constant for vinyl methyl ether is estimated as 3.9X10-3 atm-cu m/mole(SRC) derived from its vapor pressure, 1316 mm Hg(1), and water solubility, 15,000 mg/L(2). This Henry's Law constant indicates that vinyl methyl 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 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 days(SRC). Vinyl methyl ether's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Vinyl methyl ether is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

/LABORATORY ANIMALS: Acute Exposure/ Rats tolerate repeated inhalation of 2000 ppm (4.7 mg/L, 15 times 6 hours) without any symptoms and findings.

/LABORATORY ANIMALS: Acute Exposure/ According to earlier studies, vinyl methyl ether does not produce inflammatory changes in either the skin or eyes of rabbits.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In two 28-day inhalation studies with concentrations of 0, 500, 3500 and 25,000 ppm and 0,150, 500 and 1500 ppm (0, 1.19, 8.3 and 59.3 mg/L and 0, 0.36, 1.2 and 3.6 mg/L), restlessness, reduction in body weight gain and an increase in relative weight of the liver are observed at 25,000 ppm (59.3 mg/L). In the male rats, an increase in prothrombin time and a reduction in total protein occurs at higher concentrations. ... Following inhalation of 25,000 ppm (59.3 mg/L), atrophy in the region of the olfactory epithelium is observed on histological examination of the nasal mucosae. No other histopathological changes are observed. In the 28-day inhalation study, 1500 ppm (3.6 mg/L) is given as the no effect level for male rats and 3500 ppm (8.3 mg/L) for female rats.

/GENOTOXICITY/ ... Mutagenicity tests of 14 compounds and 1,3-butadiene on S. typhimurium TA98, TA100, TA1535 and TA1537, and E. coli WP2 uvrA were also examined by the developed gas exposure method. 1,3-Butadiene, propyne (methyl acetylene), monochlorodifluoromethane, ethylchloride, diborane and silane were mutagenic. 1-Butene, 2-butene, 2-methylpropene, methyl vinyl ether, trichlorofluoromethane, dichlorodifluoromethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, 1,1-difluoroethane and phosphine were not mutagenic on S. typhimurium TA98, TA100, TA1535 and TA1537, and E. coli WP2 uvrA with or without metabolic activation. These results were compatible with a previous report, and this developed method has the advantage that it can be tested easily and safely for combustible and self-combustible substances such as 1,3-butadiene and silane.

/GENOTOXICITY/ In the micronucleus test in mice, vinyl methyl ether did not produce a clastogenic effect following inhalation of 25,000 ppm (59.3 mg/L) 5 times.

The rate constant for the vapor-phase reaction of vinyl methyl ether with photochemically-produced hydroxyl radicals has been reported as 3.35X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of vinyl methyl ether with ozone has been estimated as 8.7X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). This corresponds to an atmospheric half-life of about 1.3 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(3). Vinyl methyl ether may undergo hydrolysis in the environment based on hydrolysis half-lives of 9.5 hours, 40 days and 10.9 years at pH 5, 7 and 9, respectively, for structurally similar butyl vinyl ether(4). Vinyl methyl ether does not absorb at wavelengths >290 nm(5) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

According to the 2016 TSCA Inventory Update Reporting data, 2 reporting facilities estimate the number of persons reasonably likely to be exposed in the manufacturing, processing, or use of vinyl methyl ether in the United States may be as low as 25-49 workers up to the range of 100-499 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).

NIOSH (NOHS Survey 1972-1974) has statistically estimated that 23,702 workers are exposed to vinyl methyl ether in the USA(1).

Vinyl methyl ether's production and use in copolymers for coatings and lacquers, in polystyrene and ionomer resins, in plasticizers for nitrocellulose, and in adhesives may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 1316 mm Hg at 25 °C indicates vinyl methyl ether will exist solely as a gas in the atmosphere. Gas-phase vinyl methyl ether will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone; the half-lives for these reactions in air are estimated to be 11 hours and 1.3 days, respectively. Vinyl methyl ether does not absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, vinyl methyl ether is expected to have very high mobility based upon an estimated Koc of 5. Volatilization from moist soil surfaces is expected based upon an estimated Henry's Law constant of 3.9X10-3 atm-cu m/mole. Vinyl methyl ether is expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data in soil or water were not available. If released into water, vinyl methyl ether is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 2 hours and 3 days, respectively. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is expected based on hydrolysis half-lives of 9.5 hours, 40 days and 10.9 years at pH 5, 6 and 9, respectively, for structurally similar butyl vinyl ether. Occupational exposure to vinyl methyl ether may occur through inhalation and dermal contact with this compound at workplaces where vinyl methyl ether is produced or used. (SRC)

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/

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/

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/

Vinyl methyl ether

1

10000

Flammable chemical that can be released at a facility.

Used to make polymers or modify polymers for coatings, lacquers, and resins; [Hawley]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Copolymers used in coatings and lacquers; modifier for alkyl, polystyrene and ionomer resins; plasticizer for nitrocellulose and adhesives

2023: 25,000,000 - <75,000,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1974) 4.5-6.8X10+9 G (VINYL ETHER CONSUMPTION)

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

Catalytic reaction of acetylene and methanol.

In a catalytic oxidation process developed by ICI for the production of methyl vinyl ether, ethylene is reacted with methanol in the presence of palladium chloride complexes or palladium metal. It is not known whether this process has been developed on an industrial scale.

Methanol + acetylene (ethynylation).

All Other Basic Organic Chemical Manufacturing

Ethene, methoxy-: ACTIVE