Vinyl acetate

Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, an important industrial polymer.
Production.
The worldwide production capacity of vinyl acetate was estimated at 6,969,000 tonnes/year in 2007, with most capacity concentrated 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. Celanese is the largest producer (ca 25% of the worldwide capacity), while other significant producers include China Petrochemical Corporation (7%), Chang Chun Group (6%), and LyondellBasell (5%).
It is a key ingredient in furniture glue.
Preparation.
Vinyl acetate is the acetate ester of vinyl alcohol. Since vinyl alcohol is highly unstable (with respect to acetaldehyde), the preparation of vinyl acetate is more complex than the synthesis of other acetate esters. 
The major industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst.
<chem> 2 C2H4 + 2 CH3CO2H + O2 -> 2 CH3CO2CHCH2 + 2 H2O</chem>
The main side reaction is the combustion of organic precursors. 
Mechanism.
Isotope labeling and kinetics experiments suggest that the mechanism involves PdCH2CH2OAc-containing intermediates. Beta-hydride elimination would generate vinyl acetate and a palladium hydride, which would be oxidized to give hydroxide.
Alternative routes.
Vinyl acetate was once prepared by hydroesterification. This method involves the gas-phase addition of acetic acid to acetylene in the presence of metal catalysts. By this route, using mercury(II) catalysts, vinyl acetate was first prepared by Fritz Klatte in 1912. Another route to vinyl acetate involves thermal decomposition of ethylidene diacetate:
<chem>(CH3CO2)2CHCH3 -> CH3CO2CHCH2 + CH3CO2H </chem>
Polymerization.
It can be polymerized to give polyvinyl acetate (PVA). With other monomers it can be used to prepare various copolymers such as ethylene-vinyl acetate (EVA), vinyl acetate-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 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 or a dithiocarbamate chain transfer agent.
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 generated 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. The alkene also undergoes Diels-Alder and 2+2 cycloadditions.
With an iridium catalyst, vinyl acetate can undergo transesterification, giving access to vinyl ethers:
Toxicity evaluation.
Tests suggest that vinyl acetate is of low toxicity. For rats (oral) LD50 is 2920 mg/kg.
On January 31, 2009, the Government of Canada's final assessment concluded that exposure to vinyl acetate is not harmful to human health. This decision under the Canadian Environmental Protection Act (CEPA) was based on new information received during the public comment period, as well as more recent information from the risk assessment conducted by the European Union.
In the context of large-scale release into the environment, it is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), under which it "does not meet toxicity criteria but because of its acute lethality, high production volume [or] known risk is considered a chemical of concern." By this law, it is subject to strict reporting requirements by facilities which produce, store, or use it in quantities greater than 1000 pounds.