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Methyl methacrylate

Methyl methacrylate


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	clear 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

Methyl methacrylate is a chemical compound mostly known as the monomer for the production of the transparent plastic polymethyl methacrylate (PMMA).

Additional recommended knowledge

Safe Weighing Range Ensures Accurate Results

How to quickly check pipettes?

Daily Sensitivity Test

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. 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.

References

Chemical data on Chemicalland
US Environmental Protection Agency, 1994 data
Intox Cheminfo data
SRI Consulting PEP report

Categories: Carboxylate esters | Monomers

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Methyl_methacrylate". A list of authors is available in Wikipedia.