Supriya Ghosh (Editor)

Methacrylic acid

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Abbreviations
  
MAA

Formula
  
C4H6O2

Boiling point
  
161 °C

Density
  
1.02 g/cm³

Molar mass
  
86.06 g/mol

Melting point
  
15 °C

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Appearance
  
Colorless liquid or solid

Methacrylic acid meaning


Methacrylic acid, abbreviated MAA, is an organic compound. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA) and poly(methyl methacrylate) (PMMA). The methacrylates have numerous uses, most notably in the manufacture of polymers with trade names such as Lucite and Plexiglas. MAA occurs naturally in small amounts in the oil of Roman chamomile.

Contents

Production and properties

More than 3 million tons of methyl methacrylate (MMA) are produced annually. In one route, acetone cyanohydrin is converted to methacrylamide sulfate using sulfuric acid. That compound is hydrolyzed to methacrylic acid, or it can be converted into methyl methacrylate in one step. In the second route, isobutylene or tert-butanol are oxidized to methacrolein, then methacrylic acid. Methacrolein for this purpose can also be obtained from formaldehyde and ethylene. Isobutyric acid can also be dehydrogenated to methacrylic acid.

Methacrylic acid was first obtained in the form of its ethyl ester by treating phosphorus pentachloride with oxyisobutyric ester (A synonym for beta-hydroxy-butyric acid or 3-hydroxybutyric acid) . It is, however, more readily obtained by boiling citra- or meso-brompyrotartaric acids with alkalis. It crystallizes in prisms. When fused with an alkali, it forms propanoic acid. Sodium amalgam reduces it to isobutyric acid. A polymeric form of methacrylic acid was described in 1880.

References

Methacrylic acid Wikipedia