Vinyl acetate


Vinyl acetate

Chembox new
Name = Vinyl acetate
ImageFileL1 = Vinyl_acetate.png ImageSizeL1 = 120px
ImageNameL1 = Vinyl acetate
ImageFileR1 = Vinyl-acetate-3D-balls.png ImageSizeR1 = 150px
IUPACName = Ethenyl acetate
SystematicName = Ethenyl ethanoate
OtherNames = Acetic acid vinyl ester, acetoxyethene, VyAc, VAM, zeset T, VAM vinyl acetate monomer, acetic acid ethenyl ester, 1-acetoxyethylene
Section1 = Chembox Identifiers
SMILES = C=COC(C)=O
CASNo = 108-05-4
PubChem = 7904

Section2 = Chembox Properties
Formula = C4H6O2
MolarMass = 86.09 g/mol
Appearance = Colorless liquid
Density = 0.934 g/cm3
MeltingPtC = -93
BoilingPtC = 72.7

Section7 = Chembox Hazards
ExternalMSDS =
NFPA-H = 2
NFPA-R = 2
NFPA-F = 3
RPhrases = R11
SPhrases = S16, S23, S29, S33
FlashPt = -8°C
ExploLimits = 2.6–13.40%
Autoignition = 427 °C

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 (PVA), an important polymer in industry. Like many 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. [cite journal| author=Y.-F. Han, D. Kumar, C. Sivadinarayana, and D.W. Goodman | title = Kinetics of ethylene combustion in the synthesis of vinyl acetate over a Pd/SiO2 catalyst | journal = Journal of Catalysis | volume = 224 |year = 2004 |pages = 60–68 | url = http://www.chem.tamu.edu/rgroup/goodman/pdf%20files/442_joc-224-04-60.pdf| doi=10.1016/j.jcat.2004.02.028]

:Ethylene + acetic acid + 1/2 O2 → Vinyl acetate + H2OBut also 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. [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. [cite journal | author = D. Swern and E. F. Jordan, Jr |title = Vinyl Laurate and Other Vinyl Esters | journal = Organic Syntheses, Collected Volume 4 | pages = 977 |year = 1963 | url=http://www.orgsyn.org/orgsyn/pdfs/CV4P0977.pdf] The alkene also undergoes Diels-Alder and 2+2 cycloadditions.

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.cite news|title=Chewing gum substance could be toxic|date=2008-05-13|publisher="Vancouver Sun"|page=A4]

References

External links

* [http://www.epa.gov/iris/subst/0512.htm EPA health assessment information on vinyl acetate]


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