methyl methacrylate

Methyl methacrylate
IUPAC name	methyl 2-methylprop-2-enoate
Other names	MMA, 2-(methoxycarbonyl)-1-propene
Identifiers
CAS number	80-62-6 Y
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
MSDS	External MSDS
Main hazards	flammable
Flash point	2 °C (autoignition 435 °C)
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methyl methacrylate is an organic compound with the formula CH₂=C(CH₃)COOCH₃. This colourless liquid, the methyl ester of methacrylic acid (MAA) is a monomer produced on a large scale for the production of polymethyl methacrylate (PMMA).

Production

The compound is manufactured by several methods, the principal one being the acetone cyanohydrin (ACH) route, using acetone and hydrogen cyanide as raw materials. The intermediate cyanohydrin is converted with sulfuric acid to a sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate and MMA. Although widely used, the ACH route coproduces substantial amounts of ammonium sulfate. Some producers start with an isobutylene or, equivalently, tert-butanol, which is sequentially oxidized first to methacrolein and then to methacrylic acid, which is then esterified with methanol. Propene can be carbonylated in the presence of acids to isobutyric acid, which undergoes subsequent dehydrogenation.^[1] The combined technologies afford more than 3 billion kilograms per year. MMA can also be prepared from methyl propionate and formaldehyde.^[2]

Uses

The principal application, consuming approximately 80% of the MMA, is the manufacture of polymethyl methacrylate acrylic plastics (PMMA). Methyl methacrylate is also used for the production of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for PVC.

See also

• Acrylate
• Methacrylates
• (Meth)acrylates
• PMMA

References

1. ^ 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
2. ^ 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

External links

• Methacrylate Producers Association (MPA)
• National Pollutant Inventory - Methyl methacrylate fact sheet
• Basic Acrylic Monomer Manufacturers (BAMM)