Dimethyl maleate

Dimethyl maleate is an organic compound with the formula C6H8O4. It is the dimethyl ester of maleic acid.

Not to be confused with dimethyl malonate.
Dimethyl maleate
Skeletal formula of dimethyl maleate
Ball-and-stick model of the dimethyl maleate molecule
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
3D model (JSmol)
471705
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.862
EC Number
  • 210-848-5
RTECS number
  • EM6300000
UNII
  • InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3- checkY
    Key: LDCRTTXIJACKKU-ARJAWSKDSA-N checkY
  • InChI=1/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-
    Key: LDCRTTXIJACKKU-ARJAWSKDBU
  • O=C(OC)\C=C/C(=O)OC
Properties
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)
slightly soluble
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H314, H317, H335
P260, P261, P264, P270, P271, P272, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P333+P313, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
1
0
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).
checkY verify (what is checkY☒N ?)
Infobox references

Synthesis

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

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

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

See also

References
  1. "Dimethyl maleate", Chemical Land 21
  2. "Dimethyl maleate Archived 2008-07-24 at the Wayback Machine", Bimax Chemicals Ltd.
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