Methyl vinyl ether
Encyclopedia
Methyl vinyl ether is an organic compound with the chemical formula C3H6O. It is the simplest chemical that contains both an alkene
group and an alkyl group with an ether
linkage. The compound can be made by reaction of acetylene
and methanol
in presence of a base.
The alkene portion of the molecule is reactive in many ways. It is prone to polymerization
, leading to formation of poly(methyl vinyl ether) (PMVE, CAS
: 9003-09-2). This mode of reactivity is analogous to the way vinyl acetate
and vinyl chloride
can be polymerized to form polyvinyl acetate
and polyvinyl chloride
, respectively. The alkene can also react in [4+2] cycloaddition
reactions. The reaction of it with acrolein
is the first step in the commercial synthesis of glutaraldehyde
.
The compound is useful as a synthon
for nucleophilic acylation
, via deprotonation of the alkene adjacent to the oxygen attachment. In particular, this approach allows synthesis of a variety of acyl derivatives of silicon, germanium, and tin that cannot be made easily by other routes.
Alkene
In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...
group and an alkyl group with an ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...
linkage. The compound can be made by reaction of acetylene
Acetylene
Acetylene is the chemical compound with the formula C2H2. 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 pure form and thus is usually handled as a solution.As an alkyne, acetylene is unsaturated because...
and methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
in presence of a base.
The alkene portion of the molecule is reactive in many ways. It is prone to polymerization
Polymerization
In polymer chemistry, polymerization is a process of reacting monomer molecules together in a chemical reaction to form three-dimensional networks or polymer chains...
, leading to formation of poly(methyl vinyl ether) (PMVE, CAS
CAS registry number
CAS Registry Numbersare unique numerical identifiers assigned by the "Chemical Abstracts Service" toevery chemical described in the...
: 9003-09-2). This mode of reactivity is analogous to the way vinyl acetate
Vinyl acetate
Vinyl acetate is an organic compound with the formula CH3COOCH=CH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate, an important polymer in industry.-Production:...
and vinyl chloride
Vinyl chloride
Vinyl chloride is the organochloride with the formula H2C:CHCl. It is also called vinyl chloride monomer, VCM or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride . At ambient pressure and temperature, vinyl chloride...
can be polymerized to form polyvinyl acetate
Polyvinyl acetate
Polyvinyl acetate, PVA, PVAc, poly, is a rubbery synthetic polymer with the formula n. It belongs to the polyvinyl esters family with the general formula -[RCOOCHCH2]-...
and polyvinyl chloride
Polyvinyl chloride
Polyvinyl chloride, commonly abbreviated PVC, is a thermoplastic polymer. It is a vinyl polymer constructed of repeating vinyl groups having one hydrogen replaced by chloride. Polyvinyl chloride is the third most widely produced plastic, after polyethylene and polypropylene. PVC is widely used in...
, respectively. The alkene can also react in [4+2] cycloaddition
Cycloaddition
A cycloaddition is a pericyclic chemical reaction, in which "two or more unsaturated molecules combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity." The resulting reaction is a cyclization reaction.Cycloadditions are usually described by the...
reactions. The reaction of it with acrolein
Acrolein
Acrolein is the simplest unsaturated aldehyde. It is produced widely but is most often immediately reacted with other products due to its instability and toxicity...
is the first step in the commercial synthesis of glutaraldehyde
Glutaraldehyde
Glutaraldehyde is an organic compound with the formula CH22. A pungent colorless oily liquid, glutaraldehyde is used to disinfect medical and dental equipment...
.
The compound is useful as a synthon
Synthon
A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. The term was coined by E.J. Corey...
for nucleophilic acylation
Acylation
In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
, via deprotonation of the alkene adjacent to the oxygen attachment. In particular, this approach allows synthesis of a variety of acyl derivatives of silicon, germanium, and tin that cannot be made easily by other routes.