Methyl methacrylate
From Wikipedia, the free encyclopedia
| Methyl methacrylate | |
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| IUPAC name | methyl 2-methylprop-2-enoate |
| Other names | MMA, 2-(methoxycarbonyl)-1-propene |
| Identifiers | |
| CAS number | [80-62-6] |
| RTECS number | OZ5075000 |
| SMILES | CC(=C)C(=O)OC |
| Properties | |
| Molecular formula | C5H8O2 |
| Molar mass | 100.12 g/mol |
| Appearance | colourless liquid |
| Density | 0.94 g/cm³ |
| Melting point |
-48 °C (225 K) |
| Boiling point |
101 °C (374 K) |
| Solubility in water | 1.5 g/100 ml (25 °C) |
| Viscosity | 0.6 cP at 20 °C |
| Structure | |
| Dipole moment | 1.6-1.97 D |
| Hazards | |
| Main hazards | flammable |
| Flash point | 2 °C (autoignition 435 °C) |
| 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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Methyl methacrylate is an organic compound with the formula CH2=C(CH3)CO2CH3. This colourless liquid, the methyl ester of methacrylic acid (MMA) is the monomer for the production of the transparent plastic polymethyl methacrylate (PMMA).
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[edit] Production
Major producers worldwide include Cyro, Arkema, BASF, Dow Chemical, Lucite, Celanese and Rohm and Haas, Mitsubishi Rayon, and Sumitomo. The United States production in 1993 amounted to 600 thousand metric tonnes per annum (mt/a), and the worldwide production in 2005 was estimated at 3.2 million mt/a.
Most producers apply an acetone cyanohydrin (ACH) route, with acetone and hydrogen cyanide as raw materials. The intermediate cyanohydrin is converted with sulfuric acid to a sulfate ester of the methacrylamide, hydrolysis of which gives ammonium bisulfate and MAA. Some Asian producers start with an isobutylene or, equivalently, tert-butanol, which is oxidized to methacrolein, and again oxidized to methacrylic acid. MAA is then esterified with methanol to MMA. Propene can be carbonylated in the presence of acids to isobutyric acid]], which undergoes subsequent dehydrogenation.[1]
A newer palladium-catalysed MMA production technology, announced 18th September 2007, uses a homogeneous palladium-phosphine catalyst. Lucite's Alpha process uses ethylene, carbon monoxide, and methanol as raw materials to produce methyl propionate, which is then combined with formaldehyde to produce MMA and water.[2]
[edit] Uses
The principal application of methyl methacrylate is the manufacture of polymethyl methacrylate acrylic plastics. Also methyl methacrylate is used for the production of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for PVC.
Methyl methacrylate polymers and co-polymers are used for waterborne coatings, such as latex house paint. It is also used in adhesive formulations.
A modern application is the use in plates that keep light spread evenly across LCD computer and TV screens.
Methyl methacrylate is also used to prepare corrosion casts of anatomical organs, such as coronary arteries of the heart.
[edit] References
- ^ William Bauer, Jr. "Methacrylic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. DOI: 10.1002/14356007.a16_441. Article Online Posting Date: June 15, 2000
- ^ http://www.chemsystems.com/reports/search/docs/abstracts/0405-2_abs.pdf
- Chemical data on Chemicalland
- US Environmental Protection Agency, 1994 data
- Intox Cheminfo data
- SRI Consulting PEP report
