Vinyl acetate

Vinyl acetate

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
CAS Number	108-05-4 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:46916 N
ChemSpider	7616 N
ECHA InfoCard	100.003.224
EC Number	203-545-4
KEGG	C19309 Y
MeSH	C011566
PubChem CID	7904
UNII	L9MK238N77 N
InChI InChI=1S/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3 N Key: XTXRWKRVRITETP-UHFFFAOYSA-N N InChI=1/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3 Key: XTXRWKRVRITETP-UHFFFAOYAB
SMILES C=COC(C)=O
Properties
Chemical formula	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)
Magnetic susceptibility (χ)	-46.4·10−6 cm3/mol
Hazards
Safety data sheet	ICSC 0347
R-phrases	R11
S-phrases	S16, S23, S29, S33
NFPA 704	3 2 2
Flash point	−8 °C (18 °F; 265 K)
Autoignition temperature	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 YN ?)
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.