This MedLibrary.org supplementary page on Vinyl acetate is provided directly from the open source Wikipedia as a service to our readers. Please see the note below on authorship of this content, as well as the Wikipedia usage guidelines. To search for other content from our encyclopedia supplement, please use the form below:
Related Sponsors
| Vinyl acetate | |
|---|---|
 |
 |
| IUPAC name | Ethenyl acetate |
| Systematic name | Ethenyl ethanoate |
| 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 |
| PubChem | |
| SMILES |
|
| Properties | |
| Molecular formula | C4H6O2 |
| Molar mass | 86.09 g/mol |
| Appearance | Colorless liquid |
| Density | 0.934 g/cm3 |
| Melting point |
-93 °C, 180 K, -135 °F |
| Boiling point |
72.7 °C, 346 K, 163 °F |
| 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 references |
|
Vinyl acetate is an organic compound with the formula CH3COOCH=CH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate (PVA), an important polymer in industry. Like many industrially significant compounds, vinyl acetate has numerous names and acronymns.
Contents |
Preparation
The major industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst.1
- Ethylene + acetic acid + 1/2 O2 → Vinyl acetate + H2O
But also byproducts are also generated:
- Ethylene + 3 O2 → 2 CO2 + 2 H2O
Vinyl acetate is also prepared by the gas-phase addition of acetic acid to acetylene.2
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.
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.3 The alkene also undergoes Diels-Alder and 2+2 cycloadditions.
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 from the Government of Canada may label it toxic, along with as many as sixteen other substances.4
References
- ^ Y.-F. Han, D. Kumar, C. Sivadinarayana, and D.W. Goodman (2004). "Kinetics of ethylene combustion in the synthesis of vinyl acetate over a Pd/SiO2 catalyst". Journal of Catalysis 224: 60–68. doi:, http://www.chem.tamu.edu/rgroup/goodman/pdf%20files/442_joc-224-04-60.pdf.
- ^ G. Roscher "Vinyl Esters" in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.
- ^ D. Swern and E. F. Jordan, Jr (1963). "Vinyl Laurate and Other Vinyl Esters". Organic Syntheses, Collected Volume 4: 977, http://www.orgsyn.org/orgsyn/pdfs/CV4P0977.pdf.
- ^ "Chewing gum substance could be toxic", Vancouver Sun (2008-05-13), p. A4.
External links
Wikipedia content modification information:
- This page was last modified on 5 November 2008, at 12:25.
Wikipedia Authorship and Review
Wikipedia content provided here is not reviewed directly by MedLibrary.org. Wikipedia content is authored by an open community of volunteers and is not produced by or in any way affiliated with MedLibrary.org.
Wikipedia Usage Guidelines
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article on "Vinyl acetate".
The URL for this specific entry is:
All Wikipedia text is available under the terms of the GNU Free Documentation License. (See Copyrights for details). Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc.