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Featured Results:
 Maleic hydrazide: Carcinogenic Potency Database
Maleic hydrazide: Carcinogenic Potency Database
potency.berkeley.edu
 Acid Anhydride Profile | YourLabTest.com
Acid Anhydride Profile | YourLabTest.com
yourlabtest.com
 
Maleic anhydride[1]
Maleic anhydride
Maleic anhydride-3d.png
IUPAC name
Identifiers
CAS number 108-31-6 Yes check.svgY
EC-number 203-571-6
RTECS number UE5950000
SMILES
InChI
InChI key FPYJFEHAWHCUMM-UHFFFAOYAP
ChemSpider ID 7635
Properties
Molecular formula C4H2O3
Molar mass 98.06 g/mol
Appearance White crystals
Density 1.48 g/cm3
Melting point

52.8 °C, 326 K, 127 °F

Boiling point

202 °C, 475 K, 396 °F

Solubility in water Reacts
Hazards
MSDS MSDS at J. T. Baker
EU classification Corrosive (C)
R-phrases R22, R34, R42/43
S-phrases (S2), S22, S26,
S36/37/39, S45
NFPA 704
NFPA 704.svg
1
3
1
 
Flash point 102 °C
Related compounds
Related acid anhydrides Succinic anhydride
Related compounds Maleic acid
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Maleic anhydride (cis-butenedioic anhydride, toxilic anhydride, dihydro-2,5-dioxofuran) is an organic compound with the formula C2H2(CO)2O. 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

[edit] 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).

[edit] References

  1. ^ Merck Index, 11th Edition, 5586.

[edit] External links




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