Methyl methacrylate
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| Methyl methacrylate | |
|---|---|
| Image:Methyl-methacrylate-skeletal.png Image:Methyl methacrylate-3d.png | |
| General | |
| Systematic name | methyl 2-methylprop-2-enoate |
| Other names | MMA, 2-(methoxycarbonyl)-1-propene |
| Molecular formula | C5H8O2 |
| SMILES | CC(=C)C(=O)OC |
| Molar mass | 100.12 g/mol |
| Appearance | clear colourless liquid |
| CAS number | [80-62-6] |
| Properties | |
| Density and phase | 0.94 g/cm³ |
| Solubility in water | 1.5 g/100 ml (25 °C) |
| In organic solvents | Soluble |
| Melting point | -48 °C (225 K) |
| Boiling point | 101 °C (374 K) |
| Basicity (pKb) | ? |
| Viscosity | 0.6 cP at 20 °C |
| Structure | |
| Dipole moment | 1.6-1.97 D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | flammable |
| Flash point | 2 °C (autoignition 435 °C) |
| R/S statement | R: ? S: ? |
| RTECS number | OZ5075000 |
| Supplementary data page | |
| Structure & properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | ? |
| Other cations | ? |
| Related ? | ? |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references | |
Methyl methacrylate is a chemical compound mostly known as the monomer for the production of the transparent plastic polymethyl methacrylate (PMMA).
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, and ammonium bisulphate as by-products. New technologies such as the carbonylation of ethylene with methanol and carbon monoxide to form methyl propionate, with secondary reactions with formaldehyde are applied as well.
Some Asian producers apply an isobutylene route. Isobutylene or tert-butanol is oxidized to methacrolein, and again oxidized to methacrylic acid (MAA). MAA is then esterified with methanol to MMA. A new palladium-catalysed MMA production technology was announced 18th September 2007. The technology uses a homogeneous palladium-phosphine catalyst to create MMA. Lucite's Alpha process uses ethylene, carbon monoxide and methanol as raw materials, with a homogeneous palladium-phosphine catalyst being used to prompt the reaction to create MMA.
Uses
The principal application of methyl methacrylate is the production of polymethyl methacrylate (PMMA) 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 latex house paint.
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.
References
- Chemical data on Chemicalland
- US Environmental Protection Agency, 1994 data
- Intox Cheminfo data
- SRI Consulting PEP report
External links
- Methacrylate Producers Association (MPA)
- National Pollutant Inventory - Methyl methacrylate fact sheet
- Basic Acrylic Monomer Manufacturers (BAMM)de:Methacrylsäuremethylester
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
