Vinyl ether Chemical Properties

Melting point:

-101.1°C

Boiling point:

bp 28.4°

Density 

d2020 0.774; d420 0.773

refractive index 

nD20 1.3989

Water Solubility 

5.25g/L(37 ºC)

Dielectric constant

3.9（20℃）

EPA Substance Registry System

Ethene, 1,1'-oxybis- (109-93-3)

Safety Information

RIDADR 

1167

HazardClass 

3.1

PackingGroup 

I

Toxicity

LC50 (3 hr in air) in mice, rats (mg/l): 146.8, 386.5 (Molitor)

Vinyl ether Usage And Synthesis

Description

Divinyl ether is a mobile, colorless, inflammable liquid with a characteristic sweet odor, bp 28.4 ?C. Approximately 4 % ethanol is added as a stabilizer. Divinyl ether may contain 0.0077 % of a stabilizer, phenyl-α- naphthylamine, that produces a slightly reddish fluorescence.

Chemical Properties

Clear, colorless liquid with a characteristicodor; boils at 28.5°C (83°F); density 0.774[at 20°C (68°F)]; soluble in most organicsolvents, slightly soluble in water [0.53 g/dLat 37°C (98°F)].

Uses

Vinyl ether is used as an anesthetic and inorganic synthesis.

Uses

Copolymer with 3–5% polyvinyl chloride for plastic products such as clear plastic bottles; medicine (anesthetic, for brief operations only).

Definition

ChEBI: Vinyl ether is an ether.

Indications

Divinyl ether is used for minor surgery, obstetrics, dentistry, and inducing anesthesia. A certain degree of hepatotoxicity rules out long-term use. Hypersecretion has also been observed. Divinyl ether increases and decreases in tissue levels faster than diethyl ether.

General Description

A clear colorless liquid with a characteristic odor. Flash point below -22°F. Less dense than water. Autoignition temperature 680°F. Slightly soluble in water; miscible with alcohol, acetone, chloroform, and ether. Must be protected from light.Vapors heavier than air. Toxic by inhalation.

Air & Water Reactions

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

Reactivity Profile

Ethers, such as DIVINYL ETHER, can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert. Vinyl ether is miscible with alcohol, acetone, chloroform and ether and must be protected from light [Hawley].

Health Hazard

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 or dilution water may cause pollution.

Health Hazard

Vinyl ether exhibits low inhalation toxicity.Like ethyl ether, inhalation of its vapors pro duces an anesthetic effect. At concentrationsabove 5% (by volume in air), it can causeunconsciousness in humans. Exposure to a5.1% concentration of its vapor (in air) waslethal to mice.
Divinyl ether exhibited mutagenicity inmicrosomal assay and microbial mutationtests. There is no report on its carcinogenicityin animals or humans.

Fire Hazard

Highly flammable; flash point (closed cup) < -30°C (<-22°F); vapor density 2.4 (air = 1); the vapor is heavier than air and can travel a considerable distance to a source of igni tion and flash back; autoignition temperature 360°C (680°F); can be ignited by lightning or static electricity; fire-extinguishing agent: dry chemical, foam, or CO2; use a water spray to keep fire-exposed containers cool and to disperse the vapors
Vinyl ether forms explosive mixtures with air, with LEL and UEL values of 1.7% and 27% by volume of air, respectively. It forms unstable peroxides on long standing or in the presence of oxygen. These peroxides can explode spontaneously or when heated. It decomposes to acetaldehyde (toxic and highly flammable) when exposed to light.

Safety Profile

Mildly toxic by inhalation. Mutation data reported. Prolonged exposure causes liver injury. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. A severe explosion hazard in the form of vapor when exposed to heat or flame. Forms peroxides when exposed to air or oxygen. Hypergolic reaction with concentrated nitric acid. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. Used as an inhalation anesthetic. See also ETHERS.

Synthesis

Divinyl ether is prepared by the reaction of liquefied alkali hydroxide or sodium alkoxide on β,β_x0002_-dihalodiethyl ether or by pyrolysis of α,α_x0002_-dichlorodiethyl ether in the gas phase at 600 – 800 ?C in the presence of barium chloride catalyst .

storage

Vinyl ether is stored in a flammable-liquidsstorage room or cabinet separated from oxidizing and combustible materials. It shouldbe protected from physical damage andfrom static electricity or lightning. It isshipped in amber glass bottles or metaldrums.

Waste Disposal

Vinyl ether is mixed with an excess ofhigher-boiling solvent and burned in a chem ical incinerator equipped with an afterburnerand scrubber. Small amounts, free of peroxides, can be evaporated in a fume hood awayfrom a source of ignition.

Vinyl ether(109-93-3)Related Product Information

• Chelidonic acid monohydrate
• 2,6-Dimethyl-4H-pyran-4-one
• Ethyl maltol
• Maltol isobutyrate
• 4H-PYRAN-4-ONE
• 4-(DICYANOMETHYLENE)-2-METHYL-6-(4-DIMETHYLAMINOSTYRYL)-4H-PYRAN
• Maltol propionate
• 3-Hydroxy-2-methyl-4H-pyran-4-one
• Kojic acid
• ETHYL VINYL ETHER , STABILIZED WITH CA 0.1% N,N-DIETHYLANILINE
• n-Butyl vinyl ether, stabilized, 98%,Butyl Vinyl Ether (stabilized with KOH)
• ISOBUTYL VINYL ETHER-VINYL CHLORIDE COPOLYMER)
• Cyclohexanedimethanol divinyl ether
• Diethylene glycol divinyl ether
• maleic acid, methyl vinyl ether polymer, calcium sodium salt,Maleic acid monocalcium-monosodium salt/methyl vinyl ether copolymer
• TRI(ETHYLENE GLYCOL) DIVINYL ETHER
• tert-Butyl vinyl ether, stabilized, 98%
• poly(methyl vinyl ether-alt-maleic acid monoethyl ester) solution,Maleic acid monoethyl ester/methyl vinyl ether copolymer