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| Names | |
|---|---|
| Preferred IUPAC name Ethenyl acetate | |
| Systematic IUPAC name Ethenyl ethanoate | |
Other names
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| Identifiers | |
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3D model (JSmol) | |
| 1209327 | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.003.224 |
| EC Number |
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| KEGG |
|
| MeSH | C011566 |
| UNII | |
| UN number | 1301 |
| |
| |
| Properties | |
| C4H6O2 | |
| Molar mass | 86.090 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Sweet, pleasant, fruity; may be sharp and irritating[1] |
| 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 | |
| GHS labelling: | |
   | |
| Danger | |
| H225,H332,H335,H351 | |
| P201,P202,P210,P233,P240,P241,P242,P243,P261,P271,P280,P281,P303+P361+P353,P304+P312,P304+P340,P308+P313,P312,P370+P378,P403+P233,P403+P235,P405,P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | −8 °C (18 °F; 265 K) |
| 427 °C (801 °F; 700 K) | |
| Explosive limits | 2.6–13.40% |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | none[2] |
| Safety data sheet (SDS) | ICSC 0347 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Vinyl acetate is anorganic compound with theformula CH3CO2CH=CH2. This colorless liquid is the precursor topolyvinyl acetate,ethylene-vinyl acetate copolymers,polyvinyl alcohol, and other important industrial polymers.[3]
The worldwide production capacity of vinyl acetate was estimated at 6,969,000tonnes/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).[4] The average list price for 2008 was US$1600/tonne.Celanese is the largest producer (ca 25% of the worldwide capacity), while other significant producers includeChina Petrochemical Corporation (7%), Chang Chun Group (6%), andLyondellBasell (5%).[4]
Vinyl acetate is mainly (80%) polymerized, and the resulting polymer is hydrolyzed to givepolyvinyl alcohol.[3]
Vinyl acetate is theacetateester ofvinyl alcohol. Since vinyl alcohol is highly unstable (with respect toacetaldehyde), the preparation of vinyl acetate is more complex than the synthesis of other acetate esters.
The major industrial route involves the reaction ofethylene andacetic acid withoxygen in the presence of apalladium catalyst.[5]
This method has replaced the addition of acetic acid to acetylene. The main side reaction is the combustion of organic precursors.
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.[6]
Vinyl acetate was once mainly prepared byhydroesterification, i.e., the addition of acetic acid toacetylene in the presence of metal catalysts. Using mercury(II) catalysts, vinyl acetate was first prepared byFritz Klatte in 1912.[3] Presently,zinc acetate is used as the catalyst:
Approximately 1/3 of the world's production relies on this route, which, because it is environmentally messy, is mainly practiced in countries with relaxed environmental regulations, such as China.
Another route to vinyl acetate involvesthermal decomposition ofethylidene diacetate:
It can be polymerized to givepolyvinyl acetate (PVAc). With othermonomers it can be used to prepare variouscopolymers such asethylene-vinyl acetate (EVA), vinyl acetate-acrylic acid (VA/AA),polyvinyl chloride acetate (PVCA), andpolyvinylpyrrolidone (Vp/Va copolymer, used inhair gels).[7] Due to the instability of the radical, attempts to control the polymerization by 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 axanthate or adithiocarbamate chain transfer agent.
Vinyl acetate is useful inorganic synthesis.[8]Transacetylation is used to obtain enantioenriched alcohols and esters. Iridium-catalyzed transacetylation have also been demonstrated:[9][10]
Transvinylation is also possible using vinyl acetate. It undergoesDiels-Alder reactions withdienes.
Vinyl acetate undergoes many of the reactions anticipated for analkene and anester.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 ofcarboxylic acids.[11] The alkene also undergoesDiels–Alder and 2+2 cycloadditions.
Vinyl acetate has low toxicity. OralLD50 for rats is 2920 mg/kg.[3]
On January 31, 2009, the Government of Canada's final assessment concluded that exposure to vinyl acetate is not harmful to human health.[12] This decision under theCanadian 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 anextremely 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 that produce, store, or use it in quantities greater than 1000 pounds.[13]
It has a sweet, pleasant, fruity smell, but the odor may be sharp and irritating to some people.
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