Everything about Vinyl Acetate totally explained
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| FlashPt = -8°C
| ExploLimits = 2.6–13.40%
| Autoignition = 427 °C
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Vinyl acetate is the
organic compound with the
formula CH
3COOCH=CH
2. 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.
(External Link
) It is also prepared by the gas-phase addition of acetic acid to acetylene.
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 can't 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, CH
3CH(OAc)
2. It undergoes transesterification with a variety of
carboxylic acids. 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
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
May 17,
2008 from the Government of Canada may label it toxic, along with as many as sixteen other substances.
Further Information
Get more info on 'Vinyl Acetate'.
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