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Vinyl acetate monomer

Vinyl acetate
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Ethenyl acetate
Systematic IUPAC name
Ethenyl ethanoate
Other names
Acetic acid vinyl ester, vinyl ethanoate, acetoxyethene, VyAc, VAM, zeset T, VAM vinyl acetate monomer, acetic acid ethenyl ester, 1-acetoxyethylene
Identifiers
108-05-4 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:46916 N
ChemSpider 7616 N
ECHA InfoCard 100.003.224
EC Number 203-545-4
KEGG C19309 YesY
MeSH C011566
PubChem 7904
UNII L9MK238N77 N
Properties
C4H6O2
Molar mass 86.09 g/mol
Appearance Colorless liquid
Density 0.934 g/cm3
Melting point −93.5 °C (−136.3 °F; 179.7 K)
Boiling point 72.7 °C (162.9 °F; 345.8 K)
-46.4·10−6 cm3/mol
Hazards
Safety data sheet ICSC 0347
R-phrases R11
S-phrases S16, S23, S29, S33
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −8 °C (18 °F; 265 K)
427 °C (801 °F; 700 K)
Explosive limits 2.6–13.40%
US health exposure limits (NIOSH):
PEL (Permissible)
 none
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Vinyl acetate is an organic compound with the formula CH3CO2CHCH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate, an important polymer in industry. Unlike many other acetate esters, the odor of vinyl acetate is thoroughly disagreeable and is not used to any substantial degree as an odorant.

The worldwide production capacity of vinyl acetate monomer (VAM) was estimated at 6,154,000 tonnes/annum 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.

The major industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst.

The main side reaction is the combustion of organic precursors. 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 Klatte in 1912. Another route to vinyl acetate involves thermal decomposition of ethylidene diacetate:

It can be polymerized to give polyvinyl acetate (PVA). With other monomers can be used to prepare 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.


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Wikipedia

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