Methyl methacrylate


Methyl methacrylate
Methyl methacrylate
Identifiers
CAS number 80-62-6 YesY
ChemSpider 6406 YesY
UNII 196OC77688 YesY
KEGG C14527 N
ChEBI CHEBI:34840 N
ChEMBL CHEMBL49996 YesY
RTECS number OZ5075000
Jmol-3D images Image 1
Properties
Molecular formula C5H8O2
Molar mass 100.12 g mol−1
Appearance Colorless liquid
Density 0.94 g/cm³
Melting point

-48 °C, 225 K, -54 °F

Boiling point

101 °C, 374 K, 214 °F

Solubility in water 1.5 g/100 ml
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 (36 °F)
Autoignition
temperature
435 °C (815 °F)
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
 N methacrylate (verify) (what is: YesY/N?)
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 poly(methyl methacrylate) (PMMA).

Contents

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. Also used in fracture repair in small exotic animal species using internal fixation.

Shortage

In 2010 the world experienced an MMA shortage, believed to be due to production facilities shutting down for economic reasons. One of the largest producers, Dow Chemical, surprised many purchasers when they announced a six month shut down of their plant that produced 60% of MMA.[3]

See also

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
  3. ^ http://www.npr.org/templates/story/story.php?storyId=127095942

External links


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Look at other dictionaries:

  • methyl methacrylate — n a volatile flammable liquid ester C5H8O2 that polymerizes readily and is used esp. as a monomer for acrylic resin * * * a methyl ester of methacrylic acid, which polymerizes to form polymethyl methacrylate; used in the manufacture of acrylic… …   Medical dictionary

  • methyl methacrylate — noun 1. : a volatile flammable liquid ester CH2 . C(CH3)COOCH3 that polymerizes readily (as in the presence of a peroxide) 2. or methyl methacrylate resin : an acrylic resin made by polymerization of monomeric methyl methacrylate * * * Chem. a… …   Useful english dictionary

  • methyl methacrylate — metilmetakrilatas statusas T sritis chemija formulė CH₂=C(CH₃)COOCH₃ atitikmenys: angl. methyl methacrylate rus. метилметакрилат; метиловой эфир метакриловой кислоты ryšiai: sinonimas – 1 (metoksikarbonil) 1 metiletilenas …   Chemijos terminų aiškinamasis žodynas

  • methyl methacrylate — noun The methyl ester of methacrylic acid, CH:C(CH)COOCH, used as a monomer in the manufacture of polymethyl methacrylate plastics …   Wiktionary

  • methyl methacrylate — noun Date: 1933 a volatile flammable liquid C5H8O2 that polymerizes readily and is used especially as a monomer for resins …   New Collegiate Dictionary

  • methyl methacrylate — Chem. a colorless, volatile, flammable, water insoluble, liquid, unsaturated ester, C5H8O2, that polymerizes readily to a clear plastic. Cf. Lucite, Plexiglas. [1930 35] * * * …   Universalium

  • methyl methacrylate — meth′yl methac′rylate n. chem. a colorless, volatile, flammable liquid, C5H8O2, an unsaturated ester of methacrylic acid that polymerizes readily to a clear plastic • Etymology: 1930–35 …   From formal English to slang

  • methyl methacrylate — /mɛθəl məˈθækrəleɪt/ (say methuhl muh thakruhlayt) noun a colourless volatile liquid, CH2C(CH3)COOCH3, which polymerises to form a clear, transparent thermoplastic, as perspex or plexiglas …   Australian English dictionary

  • Methyl methacrylate (data page) — This page provides supplementary chemical data on Methyl methacrylate. Contents 1 Material Safety Data Sheet 2 Structure and properties 3 Thermodynamic properties 4 Spectr …   Wikipedia

  • methyl methacrylate resin — noun see methyl methacrylate 2 …   Useful english dictionary