Methyl 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. T ...
with the chemical formula CH
3OCH=CH
2. A colorless gas, 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 includ ...
. It is used as a synthetic building block, as is the related compound
ethyl vinyl ether
Ethyl vinyl ether is an organic compound with the chemical formula CH3CH2OCH=CH2. It is the simplest enol ether that is liquid at room temperature. It is used as a synthetic building block and a monomer.
Preparation and reactions
Ethyl vinyl e ...
(a liquid at room temperature).
Preparation
Methyl vinyl ether can be made by reaction of
acetylene and
methanol in presence of a base.
Reactions
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 molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...
, leading to formation of
polyvinyl ethers. Polymerization is typically initiated with
Lewis acids such as
boron trifluoride.
This mode of reactivity is analogous to the way
vinyl acetate
Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate and ethene-vinyl acetate copolymers, important industrial polymers.
Production
The worldwide production capacity of v ...
and
vinyl chloride
Vinyl chloride is an 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 (PVC ...
can be polymerized to form
polyvinyl acetate
Polyvinyl acetate (PVA, PVAc, poly(ethenyl ethanoate)), commonly known as wood glue, PVA glue, white glue, carpenter's glue, school glue, or Elmer's glue in the US, is a widely available adhesive used for porous materials like wood, paper, and ...
and
polyvinyl chloride, respectively.
Methyl vinyl ether also participates in
+2cycloaddition
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". T ...
reactions.
Its reaction with
acrolein is the first step in the commercial synthesis of
glutaraldehyde
Glutaraldehyde is an organic compound with the formula . The molecule consists of a five carbon chain doubly terminated with formyl (CHO) groups. It is usually used as a solution in water, and such solutions exists as a collection of hydrates, c ...
.
The alkene can be deprotonated at the vinyl carbon adjacent to the oxygen.
In particular, this approach allows the synthesis of a variety of acyl derivatives of silicon, germanium, and tin that cannot be made easily by other routes.
Toxicity
The toxicity of vinyl ethers has been heavily investigated because
divinyl ether
Divinyl ether is the organic compound with the formula O(CH=CH2)2. It is a colorless, volatile liquid that has mainly been of interest as an inhalation anesthetic. It is prepared by treating bis(chloroethyl) ether with base.
History
The anal ...
has been used as an
anesthetic
An anesthetic (American English) or anaesthetic (British English; see spelling differences) is a drug used to induce anesthesia — in other words, to result in a temporary loss of sensation or awareness. They may be divided into two ...
. 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 methyl vinyl ether is greater than 4 g/kg (rats, oral).
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References
{{reflist
Ethers
Vinyl compounds