Maleic anhydride

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Template:Chembox E numberTemplate:Chembox SolubilityInWater
Maleic anhydride
IUPAC name Maleic anhydride
3D model (JSmol)
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RTECS number UE5950000
Molar mass 98.06 g/mol
Appearance white crystals
Density 1.314 g/cm3
Melting point
Boiling point
EU classification {{{value}}}
R-phrases R22, R34, R42/43
S-phrases (S2), S22, S26,
S36/37/39, S45
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


Maleic anhydride (cis-butenedioic anhydride, toxilic anhydride, dihydro-2,5-dioxofuran) is an organic compound with the formula C4H2O3. In its pure state it is a colourless or white solid with an acrid odour.

Maleic anhydride was traditionally manufactured by the oxidation of benzene or other aromatic compounds. Due to rising benzene prices, most maleic anhydride plants now use n-butane as a feedstock. As of 2006, only few smaller plants continue to use benzene:

CH3CH2CH2CH3 + 3.5 O2 → C2H2(CO)2O + 4 H2O

Characteristic reactions

The chemistry of maleic anhydride is very rich, reflecting its ready availability and bifunctional reactivity.

  • It hydrolyzes, producing maleic acid, cis-HO2CCH=CHCO2H. With alcohols, the half-ester is generated, e.g., cis-HO2CCH=CHCO2CH3.
  • Maleic anhydride is a potent dienophile in Diels-Alder reactions.
  • Maleic anhydride (MA) is an excellent ligand for low-valent metal complexes, examples being Pt(PPh3)2(MA) and Fe(CO)4(MA).

External links

de:Maleinsäureanhydrid it:Anidride maleica fi:Maleiinianhydridi