Vinyl acetate
IUPAC name	Ethenyl acetate
Systematic name	Ethenyl ethanoate
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 Y
PubChem	7904
SMILES	C=COC(C)=O
Properties
Molecular formula	C4H6O2
Molar mass	86.09 g/mol
Appearance	Colorless liquid
Density	0.934 g/cm3
Melting point	-93 °C, 180 K, -135 °F
Boiling point	72.7 °C, 346 K, 163 °F
Hazards
MSDS	ICSC 0347
R-phrases	R11
S-phrases	S16, S23, S29, S33
NFPA 704	3 2 2
Flash point	-8°C
Autoignition temperature	427 °C
Explosive limits	2.6–13.40%
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Vinyl acetate is an organic compound with the formula CH₃COOCH=CH₂. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate, an important polymer in industry.

Contents 1 Preparation 2 Polymerization 3 Other reactions 4 Possible label as "toxic" in Canada 5 References 6 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]

Ethylene + acetic acid + 1/2 O₂ → Vinyl acetate + H₂O

But byproducts are also generated:

Ethylene + 3 O₂ → 2 CO₂ + 2 H₂O

Vinyl acetate is also prepared by the gas-phase addition of acetic acid to acetylene.^[2]

[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 reactions

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.^[3] The alkene also undergoes Diels-Alder and 2+2 cycloadditions.

[edit] Possible label as "toxic" in Canada

Due to research done by the International Agency for Research on Cancer that the substance could be linked to cancer in lab rats, a draft report due from the Government of Canada may label it toxic, along with as many as sixteen other substances.^[4]

[edit] References

1. ^ Y.-F. Han, D. Kumar, C. Sivadinarayana, and D.W. Goodman (2004). "Kinetics of ethylene combustion in the synthesis of vinyl acetate over a Pd/SiO2 catalyst". Journal of Catalysis 224: 60–68. doi:10.1016/j.jcat.2004.02.028. http://www.chem.tamu.edu/rgroup/goodman/pdf%20files/442_joc-224-04-60.pdf. 
2. ^ G. Roscher "Vinyl Esters" in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.
3. ^ D. Swern and E. F. Jordan, Jr (1963). "Vinyl Laurate and Other Vinyl Esters". Organic Syntheses, Collected Volume 4: 977. http://www.orgsyn.org/orgsyn/pdfs/CV4P0977.pdf. 
4. ^ "Chewing gum substance could be toxic". Vancouver Sun. 2008-05-13. p. A4. 

[edit] External links

• EPA health assessment information on vinyl acetate