Vinyl acetate 2031942 225696117 2008-07-14T23:15:13Z Benjah-bmm27 126395 [[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&ndash;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]] [[nl:Vinylacetaat]] [[ja:酢酸ビニル]] [[pl:Octan winylu]] [[pt:Acetato de vinila]] [[fi:Vinyyliasetaatti]]