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Maleic anhydride

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Maleic anhydride[1]
Maleic anhydride
Maleic anhydride
Names
IUPAC name
Furan-2,5-dione
Identifiers
3D model (JSmol)
ECHA InfoCard 100.003.247 Edit this at Wikidata
RTECS number
  • UE5950000
  • O=C1C=CC(=O)O1
Properties
C4H2O3
Molar mass 98.06 g/mol
Appearance White crystals
Density 1.48 g/cm3
Melting point 52.8 °C (127.0 °F; 325.9 K)
Boiling point 202 °C (396 °F; 475 K)
Reacts
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Flash point 102 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. As of 2006, only a few smaller plants continue to use benzene; due to rising benzene prices, most maleic anhydride plants now use n-butane as a feedstock:

2 CH3CH2CH2CH3 + 7 O2 → 2 C2H2(CO)2O + 8 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).

References

  1. ^ Merck Index, 11th Edition, 5586.
  • International Chemical Safety Card 0799
  • NIOSH Pocket Guide to Chemical Hazards. "#0376". National Institute for Occupational Safety and Health (NIOSH).
  • Chronic toxicity summary
  • Maleic anhydride at Occupational Safety & Health Administration
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