Maleic anhydride

Encyclopedia : M : MA : MAL : Maleic anhydride

>
Maleic anhydride

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)
Dipole moment ? D
Hazards
MSDS External MSDS
EU classification Corrosive (C)
NFPA 704
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, ε_r, 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)
[Chemical infoboxInfobox disclaimer and references]

Maleic anhydride

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)
Dipole moment	? D
Hazards
MSDS	External MSDS
EU classification	Corrosive (C)
NFPA 704
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, ε_r, 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) [Chemical infoboxInfobox disclaimer and references]

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-HO₂CH=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

For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].

From Wikipedia, the Free Encyclopedia. Original article here. Support Wikipedia by contributing or donating.
All text is available under the terms of the GNU Free Documentation License See Wikipedia Copyrights for details.