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Maleic anhydride - Revision history
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<p><b>New page</b></p><div>{{Chembox new<br />
| Name = Maleic anhydride<br />
| ImageFileL1 = Maleic anhydride.png<br />
| ImageSizeL1 = 80px<br />
| ImageNameL1 = Maleic anhydride<br />
| ImageFileR1 = Maleic anhydride-3d.png<br />
| ImageSizeR1 = 150px<br />
| IUPACName = Maleic anhydride<br />
| Section1 = {{Chembox Identifiers<br />
| SMILES = O=C1C=CC(=O)O1<br />
| CASNo = 108-31-6<br />
| RTECS = UE5950000<br />
}}<br />
| Section2 = {{Chembox Properties<br />
| Formula = C<sub>4</sub>H<sub>2</sub>O<sub>3</sub><br />
| MolarMass = 98.06 g/mol<br />
| Appearance = white crystals<br />
| Solubility = 40 g/100 ml at ? °C<br />
| MeltingPtC = 53<br />
| BoilingPtC = 202<br />
| Density = 1.314 g/cm<sup>3</sup><br />
}}<br />
| Section3 = {{Chembox Structure<br />
| Dipole =<br />
}}<br />
| Section7 = {{Chembox Hazards<br />
| ExternalMSDS =[http://www.jtbaker.com/msds/englishhtml/m0364.htm MSDS at J. T. Baker]<br />
| EUClass = Corrosive ('''C''')<br />
| NFPA-H = 3<br />
| NFPA-R = 1<br />
| NFPA-F = 1<br />
| RPhrases = {{R22}}, {{R34}}, {{R42/43}}<br />
| SPhrases = {{S2}}, {{S22}}, {{S26}},<br />{{S36/37/39}}, {{S45}}<br />
| FlashPt = 102 °C<br />
}}<br />
| Section8 = {{Chembox Related<br />
| Function = [[acid anhydride]]s<br />
| OtherFunctn = [[Succinic anhydride]]<br />
| OtherCpds = [[Maleic acid]]<br />
}}<br />
}}<br />
{{CMG}}<br />
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==Overview==<br />
'''Maleic anhydride''' (''cis''-butenedioic anhydride, toxilic anhydride, dihydro-2,5-dioxofuran) is an [[organic compound]] with the formula C<sub>4</sub>H<sub>2</sub>O<sub>3</sub>. In its pure state it is a colourless or white solid with an acrid odour.<br />
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Maleic anhydride was traditionally manufactured by the [[organic oxidation|oxidation]] of [[benzene]] or other [[aromatic compound]]s. 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:<br />
:CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> + 3.5 O<sub>2</sub> → C<sub>2</sub>H<sub>2</sub>(CO)<sub>2</sub>O + 4 H<sub>2</sub>O<br />
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==Characteristic reactions==<br />
The chemistry of maleic anhydride is very rich, reflecting its ready availability and bifunctional reactivity.<br />
*It hydrolyzes, producing [[maleic acid]], ''cis''-HO<sub>2</sub>CCH=CHCO<sub>2</sub>H. With alcohols, the half-ester is generated, e.g., ''cis''-HO<sub>2</sub>CCH=CHCO<sub>2</sub>CH<sub>3</sub>. <br />
*Maleic anhydride is a potent [[dienophile]] in [[Diels-Alder reaction]]s.<br />
*Maleic anhydride (MA) is an excellent ligand for low-valent metal complexes, examples being Pt(PPh<sub>3</sub>)<sub>2</sub>(MA) and Fe(CO)<sub>4</sub>(MA).<br />
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==References==<br />
<references/><br />
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==External links==<br />
*{{ICSC|0799|07}}<br />
*{{PGCH|0376}}<br />
*[http://www.oehha.ca.gov/air/chronic_rels/pdf/maleic.pdf Chronic toxicity summary]<br />
*[http://www.osha.gov/dts/sltc/methods/organic/org086/org086.html Maleic anhydride at Occupational Safety & Health Administration]<br />
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[[Category:Acid anhydrides]]<br />
[[Category:Oxygen heterocycles]]<br />
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[[de:Maleinsäureanhydrid]]<br />
[[fr:Anhydride maléïque]]<br />
[[it:Anidride maleica]]<br />
[[ja:無水マレイン酸]]<br />
[[fi:Maleiinianhydridi]]<br />
[[pt:Anidrido maléico]]<br />
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