109-92-2

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.

VINYL ETHYL ETHER(109-92-2) 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].

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

Carcinogen.

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.

Behavior in Fire: Explosive hazard

Colorless liquid. Extremely reactive, can be polymerized in liquid or vapor phase. Slightly soluble in water (0.9% by weight). Commercial material contains inhibitor to prevent premature polymerization. Often stored underground to minimize vapor losses.

Ethyl vinyl ether (EVE) can be prepared by reacting acetylene with absolute ethanol in the presence of an alkali catalyst. The most commonly used catalyst for vinylation is an alkali metal hydroxide or an alkali metal alkoxide.

In China, three processes for the manufacture of EVE using the acetylene route were used:
A continuous process with a homogeneous catalyst under high pressure. The advantages of this process are fast reaction rate and high conversion, but the disadvantages include the requirement of high standard equipment, large energy consumption, and easy safety issues.
A process with a solid catalyst (heterogeneous catalyst) under atmospheric pressure is relatively simple in product separation and refining compared with a process with a homogeneous catalyst under high pressure. However, it has the disadvantages of low output, the short service life of catalyst (about 110 h), and a high requirement on the specification of carrier lime.
A process with a homogeneous catalyst under atmospheric pressure has the advantages of high output and good safety but disadvantages of low conversion.
In the process with solid catalyst under atmospheric pressure, acetylene, and ethanol vapor were introduced into a fixed-bed reactor, and the vinylation reaction was carried out at a temperature as high as about 180 °C. EVE was produced with a concentration of about 70% in the outlet gas stream from the reactor. The fixed-bed reactor was charged with 4–5 mesh catalyst particles of potassium hydroxide supported on lime.

Ethyl vinyl ether is synthesized by bubbling Acetylene through Ethylalcohol in presence of Sodium ethoxide.

It usually contains polymerization inhibitors (usually amines, e.g. triethanolamine) which can be removed by fractional distillation. Redistil it from sodium. [Beilstein 1 IV 2049.] LACHRYMATORY.

The initial threshold screening level (ITSL) for Ethyl vinyl ether is 20 μg/m3 based on an annual averaging time.