Vinyl acetate is an organic compound with the
formula CH3CO2CHCH2. A colorless liquid with a pungentodor, it is the
precursor to polyvinylacetate, an important polymer in industry. Unlike
many other acetateesters, the odor of vinyl acetate is thoroughly
disagreeable and is not used toany substantial degree as an odorant.
worldwide production capacity of vinyl acetate monomer(VAM) was
estimated at 6,154,000 tonnes/annum in 2007, with most
capacityconcentrated in the United States (1,585,000 all in Texas),
China (1,261,000),Japan (725,000) and Taiwan (650,000). The average list
price for 2008 was$1600/tonne. Celaneseis the largest producer (ca 25%
of the worldwide capacity), while othersignificant producers include
China Petrochemical Corporation(7%), Chang Chun Group (6%) and
It is a key ingredient in furniture-glue.
The major industrial route involves the reaction of ethyleneand acetic acidwith oxygenin the presence of a palladium catalyst.
C2H4 + CH3CO2H+ 1⁄2 O2 → CH3CO2CHCH2+ H2O
main side reaction is the combustion of organic precursors.
Vinylacetate was once prepared by hydroesterification. This method
involves thegas-phase addition of acetic acid to acetylenein the
presence of metal catalysts. By this route, using mercury(II)
catalysts,vinyl acetate was first prepared by Klatte in 1912. Another
route to vinylacetate involves thermal decomposition of ethylidene
(CH3CO2)2CHCH3→ CH3CO2CHCH2 + CH3CO2H
can be polymerized to give polyvinylacetate. With other monomers can be
used to prepare copolymerssuch as ethylene-vinyl acetate (EVA),
vinylacetate-acrylic acid (VA/AA), polyvinyl chloride acetate (PVCA),
and polyvinylpyrrolidone (Vp/Va Copolymer, used in hair gels).Due to the
instability of the radical, attempts to control the polymerizationvia
most 'living/controlled' radical processes have proved
problematic.However, RAFT (or more specifically MADIX)polymerization
offers a convenient method of controlling the synthesis of PVAby the
addition of a xanthate or a dithiocarbamate chain transfer agent.
acetate undergoes many of the reactions anticipated for an alkeneand an
ester.Bromineadds to give the dibromide. Hydrogen halides add to give
1-haloethyl acetates,which cannot be generated by other methods because
of the non-availability ofthe corresponding halo-alcohols. Acetic acid
adds in the presence of palladiumcatalysts to give ethylidene diacetate,
CH3CH(OAc)2. Itundergoes transesterification with a variety of
carboxylicacids.The alkene also undergoes Diels-Alderand 2+2
On January 31, 2009, the Government of Canada's final assessment concludedthat exposure to vinyl acetate is not considered to be harmful to human health.Thisdecision under the Canadian Environmental Protection Act (CEPA) was based onnew information received during the public comment period, as well as morerecent information from the risk assessment conducted by the European Union.