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	S16, S23, S29, 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 organic compound with the formula CH₃COOCH=CH₂. This colorless liquid with a pungent odor is the precursor to an important polymer 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 acetic acid with oxygen in the presence of a palladium catalyst.[1] It is also prepared by the gas-phase addition of acetic acid to acetylene.G. Roscher "Vinyl Esters" in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.

Polymerization

It can be polymerized, either by itself to make polyvinyl acetate or with other monomers to prepare copolymers such as ethylene-vinyl acetate. Due to the instability of the radical, attempts to control the polymerization via most \'living/controlled\' radical processes have proved problematic. However, 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 alkene and an ester. Bromine adds to give the dibromide. Hydrogen halides add to give 1-haloethyl acetates, which cannot be generate by other methods because of the non-availability of the corresponding halo-alcohols. Acetic acid adds in the presence of palladium catalysts to give ethylidene diacetate, CH₃CH(OAc)₂. It undergoes transesterification with a variety of carboxylic acids.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 The alkene also undergoes Diels-Alder and 2+2 cycloadditions.

Ethylene + Acetic Acid + Oxygen ---------> Vinyl Acetate + Water

C2H4 + CH3COOH + 1/2 O2 ---------> CH3COOC2H3 + H2O

But also By products are made

Ethylene + Oxygen -----------------> Carbon Dioxide + Water C2H4 + O2 -----------------> CO2 + H2O

References

External links

• CID 7904 from PubChem
• EPA health assessment information on vinyl acetate

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