Vinyl acetate
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2008-07-14T23:15:13Z
Benjah-bmm27
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[[ball-and-stick model]] of the molecule added
{{Chembox new
| Name = Vinyl acetate
| ImageFile = Vinyl_acetate.png
<!-- | ImageSize = 150px -->
| ImageName = Vinyl acetate
| ImageFile1 = Vinyl-acetate-3D-balls.png
| ImageSize1 = 230
| IUPACName = Vinyl acetate
| OtherNames = Acetic acid vinyl ester, acetoxyethene, VyAc, VAM, zeset T, VAM vinyl acetate monomer, acetic acid ethenyl ester, 1-acetoxyethylene
| Section1 = {{Chembox Identifiers
| SMILES = C=COC(C)=O
| CASNo = 108-05-4
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>2</sub>
| MolarMass = 86.09 g/mol
| Appearance = Colourless liquid
| Density = 0.934 g/cm<sup>3</sup>
| MeltingPt = -93 °C
| BoilingPt = 72.7 °C
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| NFPA-H = 2
| NFPA-R = 2
| NFPA-F = 3
| RPhrases = {{R11}}
| SPhrases = {{S16}}, {{S23}}, {{S29}}, {{S33}}
| FlashPt = -8°C
| ExploLimits = 2.6–13.40%
| Autoignition = 427 °C
}}
}}
'''Vinyl acetate''' is the [[organic compound]] with the [[Chemical formula|formula]] CH<sub>3</sub>COOCH=CH<sub>2</sub>. This colorless liquid with a pungent odor is the precursor to an important polymer [[polyvinyl acetate]]. Like other industrially significant compounds, vinyl acetate has numerous names and acronymns.
==Preparation==
The major industrial route involves the reaction of [[ethylene]] and [[acetic acid]] with [[oxygen]] in the presence of a [[palladium]] catalyst.[http://www.chem.tamu.edu/rgroup/goodman/pdf%20files/442_joc-224-04-60.pdf] It is also prepared by the gas-phase addition of acetic acid to acetylene.<ref>G. Roscher "Vinyl Esters" in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.</ref>
==Polymerization==
It can be polymerized, either by itself to make polyvinyl acetate or with other [[monomer]]s to prepare [[Heteropolymer|copolymers]] such as [[Ethylene-Vinyl Acetate|ethylene-vinyl acetate]]. Due to the instability of the radical, attempts to control the polymerization via most 'living/controlled' radical processes have proved problematic. However, [[RAFT (chemistry)|RAFT]] (or more specifically MADIX) polymerization offers a convenient method of controlling the synthesis of PVA by the addition of a xanthate chain transfer agent.
==Other derivatives==
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 generate 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, CH<sub>3</sub>CH(OAc)<sub>2</sub>. It undergoes transesterification with a variety of [[carboxylic acid]]s.<ref>D. Swern and E. F. Jordan, Jr “Vinyl Laurate and Other Vinyl Esters” Organic Syntheses, Collected Volume 4, p.977 (1963). http://www.orgsyn.org/orgsyn/pdfs/CV4P0977.pdf</ref> The alkene also undergoes [[Diels-Alder]] and 2+2 cycloadditions.
Ethylene + Acetic Acid + Oxygen ---------> Vinyl Acetate + Water
C2H4 + CH3COOH + 1/2 O2 ---------> CH3COOC2H3 + H2O
But also By products are made
Ethylene + Oxygen -----------------> Carbon Dioxide + Water
C2H4 + O2 -----------------> CO2 + H2O
==Possible label as "toxic" in Canada==
Due to research done by the [[International Agency for Research on Cancer]] that the substance could be linked to [[cancer]] in lab rats, a draft report due [[May 17]], [[2008]] from the Government of Canada may label it toxic, along with as many as sixteen other substances.<ref name="possible Canadian ban">{{cite news|title=Chewing gum substance could be toxic|date=2008-05-13|publisher=[[Vancouver Sun]]|page=A4}}</ref>
==References==
<references/>
==External links==
* {{PubChemLink|7904}}
* [http://www.epa.gov/iris/subst/0512.htm EPA health assessment information on vinyl acetate]
[[Category:Acetates]]
[[Category:Hazardous air pollutants]]
[[Category:Monomers]]
[[de:Vinylacetat]]
[[es:Acetato de vinilo]]
[[fr:Acétate de vinyle]]
[[id:Vinil asetat]]
[[it:Acetato di vinile]]
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[[ja:酢酸ビニル]]
[[pl:Octan winylu]]
[[pt:Acetato de vinila]]
[[fi:Vinyyliasetaatti]]