Methyl Acrylate - Production, Reactions, and Uses

Production, Reactions, and Uses

It is produced by acid-catalysed esterification of acrylic acid, which in turn is produced by oxidation of propylene. Owing to its tendency to polymerize, samples typically contain an inhibitor such as hydroquinone.

The compound undergoes transesterification to give a variety of other acrylate esters. The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope (b.p. 62-63 °C). Several other esters are precursors to useful polymers.

Methyl acrylate is a classic Michael acceptor, which means that it adds nucleophiles at its terminus. For example in the presence of a base catalyst, it adds hydrogen sulfide to give the thioether:

2 CH₂CHCO₂CH₃ + H₂S → S(CH₂CH₂CO₂CH₃)2

It is also a good dienophile.

Methyl acrylate is the precursor to fibers that are woven to make carpets. Acrylates are also used in the preparation of polyamidoamine (PAMAM) dendrimers typically by Michael addition with a primary amine.