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.

Use of ethyl vinyl ether in the synthesis of glutaraldehyde.

Ethyl vinyl ether

Names
Preferred IUPAC name Ethoxyethene
Other names Ethoxyethylene, Vinamar
Identifiers
CAS Number	109-92-2
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL116745
ChemSpider	7732
ECHA InfoCard	100.003.382
EC Number	203-718-4
PubChem CID	8023
RTECS number	KO0710000
UNII	6235C9592H
UN number	1302
CompTox Dashboard (EPA)	DTXSID3029609
InChI InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 Key: FJKIXWOMBXYWOQ-UHFFFAOYSA-N
SMILES CCOC=C
Properties
Chemical formula	C4H8O
Molar mass	72.107 g·mol−1
Appearance	colorless liquid
Density	0.7589 g/mL
Melting point	−116 °C (−177 °F; 157 K)
Boiling point	33 °C (91 °F; 306 K)
Solubility in water	8.3 g/L at 15°C
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H225, H319, H335, H412
Precautionary statements	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
Autoignition temperature	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). Infobox references

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]

References

1. 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. ISBN 978-3527306732.
2. Gerd Schröder (2012). "Poly(Vinyl Ethers)". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_011. ISBN 978-3527306732.
3. Percy S. Manchand (2001). "Ethyl Vinyl Ether". EEROS. doi:10.1002/047084289X.re125. ISBN 0-471-93623-5.