Maleic anhydride
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| Maleic anhydride | |
|---|---|
 |
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| General | |
| Systematic name | Maleic anhydride |
| Molecular formula | C4H2O3 |
| Molar mass | 98.06 g/mol |
| Appearance | white crystals |
| CAS number | [108-31-6] |
| Properties | |
| Solubility in water | 40 g/100 ml at ? °C |
| Melting point | 53 °C (226K) |
| Boiling point | 202 °C (475K) |
| Density | 1.314g/cm3 |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Corrosive (C) |
| NFPA 704 |
1
3
1
|
| R-phrases | R22, R34, R42/43 |
| S-phrases | S2, S22, S26, S36/37/39, S45 |
| Flash point | 102 °C |
| RTECS number | UE5950000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related acid anhydrides | Succinic anhydride |
| Related compounds | Maleic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
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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:
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- CH3CH2CH2CH3 + 3.5 O2 → C2H2(CO)2O + 4 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] External links
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