Dimethyl maleate is an organic compound with the formula C₆H₈O₄. It is the (Z)-isomer of the dimethyl ester of fumaric acid.

Synthesis[edit]

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.

Applications[edit]

Dimethyl maleate is used in many organic syntheses as a dienophile for diene synthesis. It is used as an additive and intermediate for plastics, pigments, pharmaceuticals, and agricultural products. It is also an intermediate for the production of paints, adhesives, and copolymers.^[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.^[2]

Chemistry[edit]

Hydrolysis of dimethyl maleate gives maleic acid, or possibly the maleic acid monomethyl ester. Hydration of the same compound gives malic acid.

See also[edit]

• Dimethyl fumarate


• Maleic acid


• Malic acid

References[edit]

Dimethyl maleate

Names
Preferred IUPAC name Dimethyl (2Z)-but-2-enedioate
Other names Dimethyl maleate Maleic acid dimethyl ester Methyl maleate sipomer DMM 2-Butenedioic acid, dimethyl ester 2-Butenedioic acid (Z)-,dimethyl ester
Identifiers
CAS Number	624-48-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:35460 Y
ChemSpider	4436352 Y
ECHA InfoCard	100.009.862
EC Number	210-848-5
InChI InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3- Y Key: LDCRTTXIJACKKU-ARJAWSKDSA-N Y InChI=1/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3- Key: LDCRTTXIJACKKU-ARJAWSKDBU
SMILES O=C(OC)C=C/C(=O)OC
Properties
Chemical formula	C6H8O4
Molar mass	144.13 g/mol
Appearance	clear, colorless, oily liquid
Density	1.15 g/cm3
Melting point	−17 °C (1 °F; 256 K)
Boiling point	204 to 207 °C (399 to 405 °F; 477 to 480 K)
Solubility in water	slightly soluble
Hazards
EU classification (DSD) (outdated)	Harmful (H)
NFPA 704
Flash point	95 °C (203 °F; 368 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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