Ethyl vinyl ether

Ethyl vinyl ether
Names
Preferred IUPAC name
Ethoxyethene
Other names
Ethoxyethylene, Vinamar
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.382 Edit this at Wikidata
EC Number
  • 203-718-4
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
Appearance colorless 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:
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
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.

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.