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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). MAA occurs naturally in small amounts in the oil of Roman chamomile.

Production

In the most common route, methacrylic acid is prepared from acetone cyanohydrin, which is converted to methacrylamide sulfate using sulfuric acid. This derivative in turn is hydrolyzed to methacrylic acid, or esterified to 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.

It can also be prepared by decarboxylation of itaconic acid, citraconic acid, and mesaconic acid by decarboxylation. Such green precursors are not of commercial value. It is, however, obtained by boiling citra- or meso-brompyrotartaric acids with alkalis.

Reactions

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[3]) . 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.