Vinyl acetate

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Vinyl acetate
Image:Vinyl acetate.png
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	Image:NFPA 704.svg 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.

1 Preparation
2 Polymerization
3 Other derivatives
4 References
5 External links

[edit] 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.^[1]

[edit] 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.

[edit] 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.^[2] 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

[edit] References

^ G. Roscher "Vinyl Esters" in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.
^ 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