Vinyl acetate



Vinyl acetate
IUPAC name Vinyl acetate
Other names Acetic acid vinyl ester, acetoxyethene, VyAc, VAM, zeset T, VAM vinyl acetate monomer, acetic acid ethenyl ester, 1-acetoxyethylene
Identifiers
CAS number 108-05-4
SMILES C=COC(C)=O
Properties
Molecular formula C4H6O2
Molar mass 86.09 g/mol
Appearance Colourless liquid
Density 0.934 g/cm3
Melting point

-93 °C

Boiling point

72.7 °C

Hazards
NFPA 704
3
2
2
 
R-phrases R11
S-phrases S33
Flash point -8°C
Autoignition
temperature 		427 °C
Explosive limits 2.6–13.40%
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Vinyl acetate is the polyvinyl acetate. Like other industrially significant compounds, vinyl acetate has numerous names and acronymns.

Preparation

The major industrial route involves the reaction of ethylene and palladium catalyst.[1] It is also prepared by the gas-phase addition of acetic acid to acetylene.[1]

Polymerization

It can be polymerized, either by itself to make polyvinyl acetate or with other RAFT (or more specifically MADIX) polymerization offers a convenient method of controlling the synthesis of PVA by the addition of a xanthate chain transfer agent.

Other derivatives

Vinyl acetate undergoes many of the reactions anticipated for an Diels-Alder and 2+2 cycloadditions.

References

  1. ^ G. Roscher "Vinyl Esters" in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.
  2. ^ D. Swern and E. F. Jordan, Jr “Vinyl Laurate and Other Vinyl Esters” Organic Syntheses, Collected Volume 4, p.977 (1963). http://www.orgsyn.org/orgsyn/pdfs/CV4P0977.pdf
 
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