Ethyl vinyl ether is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the chemical formula CH₃CH₂OCH=CH₂. It is the simplest

enol ether In organic chemistry an enol ether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Important enol ethers include ...

that is liquid at room temperature. It is used as a synthetic building block and a

monomer In chemistry, a monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification Mo ...

Preparation and reactions

Ethyl vinyl ether is made by reaction of

acetylene Acetylene (systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure ...

and

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

in presence of a base. The alkene portion of the molecule is reactive in many ways. It is prone to

polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are ...

, leading to formation of

polyvinyl ether Polyvinyl ethers are a class of Organic compound, organic polymers derived from enol ether, vinyl ethers. Common monomers include methyl vinyl ether and ethyl vinyl ether, the polymer having the formula H2CH(OR) (R = methyl, ethyl). Commercial ...

s. Polymerization is typically initiated with

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any sp ...

s such as

boron trifluoride Boron trifluoride is the inorganic compound with the formula BF3. This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure and bondin ...

. Ethyl vinyl ether participates in many reactions of interest to

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

. With catalytic amounts of acids, ethyl vinyl ether adds to alcohols to give the mixed acetal: :EtOCH=CH₂ + ROH → EtOCH(OR)CH₃ This alcohol protection reaction is akin to the behavior of

dihydropyran In organic chemistry, dihydropyran refers to two heterocyclic compounds with the chemical formula, formula C5H8O: *3,4-Dihydropyran, 3,4-Dihydro-2''H''-pyran *3,6-dihydro-2''H''-pyran Nomenclature In IUPAC names, "dihydro" refers to the two adde ...

. Ethyl vinyl ether also participates in inverse demand +2

cycloaddition In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of th ...

reactions. Deprotonation with

butyl lithium Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis: * ''n''-Butyllithium, abbreviated BuLi or nBuLi * ''sec''-Butyllithium, abbreviated ''sec''-BuLi or sBuLi, has 2 stereoisomers, ...

gives the acetyl anion equivalent: :EtOCH=CH₂ + BuLi → EtOC(Li)=CH₂ + BuH

Toxicity

The toxicity of vinyl ethers has been heavily investigated because they have been used as

inhalation anesthetic An inhalational anesthetic is a chemical compound possessing general anesthetic properties that can be delivered via inhalation. They are administered through a face mask, laryngeal mask airway or tracheal tube connected to an anesthetic vapori ...

s. The acute

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the ...

for the closely related methyl vinyl ether is greater than 4 g/kg (rats, oral).

References

{{reflist Ethers Vinyl compounds