General Description
A clear colorless liquid. Flash point 15°F. May polymerize if contaminated or subjected to heat. If polymerization take place inside a container, the container may violently rupture. Vapors are heavier than air.
Reactivity Profile
VINYL ISOBUTYL ETHER(109-53-5) is a colorless, moderately toxic liquid, highly flammable. A very dangerous fire hazard when exposed to heat, flame or strong oxidizing agents. Highly explosive in the form of vapor when exposed to open flame or sparks.
Air & Water Reactions
Highly flammable. Less dense than water and very slightly soluble in water. Tends to form explosive peroxides when exposed to air. When ethers containing peroxides are heated (distilled) they can detonate [Lewis, 3rd ed., 1993, p. 728].
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 may cause pollution.
Fire Hazard
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. 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.
Chemical Properties
Colorless liquid. Very
slightly soluble in water; soluble in alcohol and
ether; easily polymerized.
Flammability and Explosibility
Flammable
Synthesis
There are two routes for production of IBVE: one uses acetylene as raw material, the other does not use acetylene as raw material. In industry, acetylene route is mainly used for the production of IBVE. IBVE is produced by vinylation of isobutanol with acetylene in the presence of a catalyst:
Commonly used catalysts for the acetylene process are alkali metal hydroxides (such as NaOH and KOH) and alkali metal alkoxides (such as sodium alkoxide and potassium alkoxide).
Properties and Applications
Isobutyl vinyl ether (IBVE) has a carbon–carbon double bond and is chemically active. It can react with a wide variety of substances to form various derivatives. IBVE is stable to alkalis but readily hydrolyzes to isobutanol and acetaldehyde under acidic conditions. Therefore, it is often stabilized by addition of a small amount of base such as triethanolamine.
Purification Methods
Wash the ether three times with equal volumes of aqueous 1% NaOH, dry with CaH2, reflux it with sodium for several hours, then fractionally distil it from sodium. [Beilstein 1 IV 2054.]
