Maleic anhydride
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maleic anhydride
(mə′lā·ik an′hī′drīd)
(organic chemistry) C4H2O3 Colorless crystals, soluble in acetone, hydrolyzing in water; used to form polyester resins. Also known as 2,5-furandione.
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Maleic anhydride
| Maleic anhydride[1] | |
|---|---|
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Furan-2,5-dione |
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| Identifiers | |
| CAS number | 108-31-6  |
| PubChem | 7923 |
| ChemSpider | 7635 |
| UNII | V5877ZJZ25 |
| EC-number | 203-571-6 |
| ChEBI | CHEBI:474859  |
| ChEMBL | CHEMBL374159 |
| RTECS number | UE5950000 |
| Jmol-3D images | Image 1 |
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| 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 |
 1
3
1
|
| Flash point | 102 °C |
| Related compounds | |
| Related acid anhydrides | Succinic anhydride |
| Related compounds | Maleic acid |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Maleic anhydride (cis-butenedioic anhydride, toxilic anhydride, 2,5-dioxofuran) is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid and 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
Reactions
The chemistry of maleic anhydride is very rich, reflecting its ready availability and bifunctional reactivity. It hydrolyzes, producing maleic acid, cis-HOOC–CH=CH–COOH. With alcohols, the half-ester is generated, e.g., cis-HOOC–CH=CH–COOCH3.
Maleic anhydride is a potent dienophile in Diels-Alder reactions. It is also a ligand for low-valent metal complexes, examples being Pt(PPh3)2(MA) and Fe(CO)4(MA).
Maleic anhydride dimerizes in a photochemical reaction to form cyclobutane tetracarboxylic dianhydride (CBTA). This compound is used in the production of polyimides and as an alignment film for liquid crystal displays.[2][3]
References
- ^ Merck Index, 11th Edition, 5586.
- ^ Horie, T.; Sumino, M.; Tanaka, T.; Matsushita, Y.; Ichimura, T.; Yoshida, J. I. (2010). "Photodimerization of Maleic Anhydride in a Microreactor Without Clogging". Organic Process Research & Development 14 (2): 100128104701019. doi:10.1021/op900306z.
- ^ Reaction conditions Horie et al 2010 reaction conditions: microreactor , mercury lamp, ethyl acetate solvent, 15 °C
External links
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