Dimethyl maleate

Dimethyl maleate can be synthesized from maleic anhydride and methanol, with sulfuric acid acting as acid catalyst, via a nucleophilic acyl substitution for the monomethyl ester, followed by a Fischer esterification reaction for the dimethyl ester.

Dimethyl maleate is used in many organic syntheses as a dienophile for diene synthesis.

[1] Dimethyl maleate has also found use in applications where improvements in the hardness and toughness of polymer films are desired.

This includes, in particular, the improvement of anti-blocking properties of copolymers of vinyl acetate with DMM.

It is also used as an internal modifier to increase the glass transition temperature of styrene or vinyl chloride polymers.

Skeletal formula of dimethyl maleate
Ball-and-stick model of the dimethyl maleate molecule
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code