Vinyl acetate
From Wikipedia, the free encyclopedia
| Vinyl acetate | |
|---|---|
 |
|
| IUPAC name | Vinyl acetate |
| Other names | Acetic acid vinyl ester, acetoxyethene, VyAc, VAM, zeset T, VAM vinyl acetate monomer, acetic acid ethenyl ester, 1-acetoxyethylene |
| Identifiers | |
| CAS number | [108-05-4] |
| SMILES | C=COC(C)=O |
| Properties | |
| Molecular formula | C4H6O2 |
| Molar mass | 86.09 g/mol |
| Appearance | Colourless liquid |
| Density | 0.934 g/cm3 |
| Melting point |
-93 °C |
| Boiling point |
72.7 °C |
| Hazards | |
| NFPA 704 |
 3
2
2
|
| R-phrases | R11 |
| S-phrases | S16, S23, S29, S33 |
| Flash point | -8°C |
| Autoignition temperature |
427 °C |
| Explosive limits | 2.6–13.40% |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Vinyl acetate is the organic compound with the formula CH3COOCH=CH2. 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.
Contents |
[edit] Preparation
The major industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst.[1] It is also prepared by the gas-phase addition of acetic acid to acetylene.[1]
[edit] Polymerization
It can be polymerized, either by itself to make polyvinyl acetate or with other monomers to prepare copolymers such as 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 (or more specifically MADIX) polymerization offers a convenient method of controlling the synthesis of PVA by the addition of a xanthate chain transfer agent.
[edit] 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, CH3CH(OAc)2. It undergoes transesterification with a variety of carboxylic acids.[2] 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
[edit] 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.[3]
[edit] References
- ^ G. Roscher "Vinyl Esters" in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.
- ^ 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
- ^ "Chewing gum substance could be toxic", Vancouver Sun, 2008-05-13, p. A4.
