Ethyl vinyl ether

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 Edit this at Wikidata
EC Number
  • 203-718-4
PubChem CID
  • 8023
RTECS number
  • KO0710000
UNII
  • 6235C9592H
UN number 1302
CompTox Dashboard (EPA)
  • DTXSID3029609 Edit this at Wikidata
InChI
  • InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3
    Key: FJKIXWOMBXYWOQ-UHFFFAOYSA-N
  • 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
 GHS02: FlammableGHS07: Exclamation mark
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
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
Chemical compound

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.

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. ^ a b 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.