Ethyl vinyl ether

Last updated
Ethyl vinyl ether
Ethyl vinylether.svg
Names
Preferred IUPAC name
Ethoxyethene
Other names
Ethoxyethylene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.382 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-718-4
PubChem CID
RTECS number
  • KO0710000
UNII
UN number 1302
  • InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3
    Key: FJKIXWOMBXYWOQ-UHFFFAOYSA-N
  • CCOC=C
Properties
C4H8O
Molar mass 72.107 g·mol−1
Appearancecolorless liquid
Density 0.7589 g/mL
Melting point −116 °C (−177 °F; 157 K)
Boiling point 33 °C (91 °F; 306 K)
8.3 g/L at 15°C
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H225, H319, H335, H412
P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
202 °C (396 °F; 475 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Contents

Use of ethyl vinyl ether in the synthesis of glutaraldehyde. Glutaraldehyde synthesis.svg
Use of ethyl vinyl ether in the synthesis of glutaraldehyde.

Preparation and reactions

Ethyl vinyl ether is made by reaction of acetylene and ethanol in presence of a base. [1]

The alkene portion of the molecule is reactive in many ways. It is prone to polymerization, leading to formation of polyvinyl ethers. Polymerization is typically initiated with Lewis acids such as boron trifluoride. [2]

Ethyl vinyl ether participates in many reactions of interest to organic synthesis. [3] 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.

Ethyl vinyl ether also participates in inverse demand [4+2] cycloaddition reactions.

Deprotonation with butyl lithium 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 anesthetics. The acute LD50 for the closely related methyl vinyl ether is greater than 4 g/kg (rats, oral). [1]

Related Research Articles

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R−O−R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

Acrylates are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH2=CHCO−2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.

<span class="mw-page-title-main">Isobutylene</span> Unsaturated hydrocarbon compound (H2C=C(CH3)2)

Isobutylene is a hydrocarbon with the chemical formula (CH3)2C=CH2. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.

<i>n</i>-Butyllithium Chemical compound

n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry.

<span class="mw-page-title-main">1-Bromobutane</span> Chemical compound

1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.

<span class="mw-page-title-main">Butyraldehyde</span> Chemical compound

Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.

<span class="mw-page-title-main">Enol ether</span> Class of chemical compounds

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 the reagent 3,4-dihydropyran and the monomers methyl vinyl ether and ethyl vinyl ether.

<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

Hydroperoxides or peroxols are compounds of the form ROOH, which contain the hydroperoxy functional group (–OOH). The hydroperoxide anion and the neutral hydroperoxyl radical (HOO·) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)COOH. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Caprolactone</span> Chemical compound

ε-Caprolactone or simply caprolactone is a lactone possessing a seven-membered ring. Its name is derived from caproic acid. This colorless liquid is miscible with most organic solvents and water. It was once produced on a large scale as a precursor to caprolactam.

<span class="mw-page-title-main">Allyl bromide</span> Chemical compound

Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, synthetic perfumes and other organic compounds. Physically, allyl bromide is a colorless liquid with an irritating and persistent smell, however, commercial samples are yellow or brown. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.

<span class="mw-page-title-main">Allyl acetate</span> Chemical compound

Allyl acetate is an organic compound with formula C3H5OC(O)CH3. This colourless liquid is a precursor to especially allyl alcohol, which is a useful industrial intermediate. It is the acetate ester of allyl alcohol.

Methyl vinyl ether is an organic compound with the chemical formula CH3OCH=CH2. A colorless gas, it is the simplest enol ether. It is used as a synthetic building block, as is the related compound ethyl vinyl ether (a liquid at room temperature).

In industrial chemistry, carboalkoxylation is a process for converting alkenes to esters. This reaction is a form of carbonylation. A closely related reaction is hydrocarboxylation, which employs water in place of alcohols

<span class="mw-page-title-main">Vinyl propionate</span> Chemical compound

Vinyl propionate is the organic compound with the formula CH3CH2CO2CH=CH2. This colorless liquid is the ester of propionic acid and vinyl alcohol. It is used to produce poly(vinyl propionate) as well as copolymers with acrylate esters, vinyl chloride, and vinyl acetate, some of which are used in paints. The compound resembles vinyl acetate.

<span class="mw-page-title-main">Polyvinyl ether</span>

Polyvinyl ethers are a class of organic polymers derived from vinyl ethers. Common monomers include methyl vinyl ether and ethyl vinyl ether, the polymer having the formula [CH2CH(OR)]n (R = methyl, ethyl). Commercial interest has also focused on polymers derived from ethyl, isobutyl, octadecyl substituents in place of methyl. Like other vinyl polymers, the polymers exhibit tacticity. Polymerization is typically initiated with Lewis acids such as boron trifluoride.

α,β-Unsaturated carbonyl compound Functional group of organic compounds

α,β-Unsaturated carbonyl compounds are organic compounds with the general structure (O=CR)−Cα=Cβ-R. Such compounds include enones and enals, but also carboxylic acids and the corresponding esters and amides. In these compounds the carbonyl group is conjugated with an alkene. Unlike the case for carbonyls without a flanking alkene group, α,β-unsaturated carbonyl compounds are susceptible to attack by nucleophiles at the β-carbon. This pattern of reactivity is called vinylogous. Examples of unsaturated carbonyls are acrolein (propenal), mesityl oxide, acrylic acid, and maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction.

References

  1. 1 2 Ernst Hofmann; Hans‐Joachim Klimisch; René Backes; Regina Vogelsang; Lothar Franz; Robert Feuerhake (2011). "Vinyl Ethers". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_435.pub.
  2. Gerd Schröder (2012). "Poly(Vinyl Ethers)". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_011.
  3. Percy S. Manchand (2001). "Ethyl Vinyl Ether". EEROS. doi:10.1002/047084289X.re125. ISBN   0-471-93623-5.