Citraconic acid
 | |
| Names | |
|---|---|
| IUPAC name
(2Z)-2-Methylbut-2-enedioic acid | |
| Other names
Citraconate; Methylmaleic acid; cis-Methylbutenedioic acid | |
| Identifiers | |
| 3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.007.145 |
| PubChem CID |
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| Properties | |
| C5H6O4 | |
| Molar mass | 130.10 g·mol−1 |
| Appearance | Monoclinic crystals[1] |
| Density | 1.62 g/cm3[1] |
| Melting point | ~90 °C (decomposition)[1] |
| Freely soluble[1] | |
| Hazards | |
| R-phrases (outdated) | R22[2] |
| S-phrases (outdated) | S36[2] |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Citraconic acid is an organic compound with the formula CH3C2H(CO2H)2. It is a white solid. It is the cis-isomer of mesaconic acid. It is one of the pyrocitric acids formed upon the heating of citric acid.[1] Citraconic acid can be produced, albeit inefficiently, by oxidation of xylene and methylbutanols. The acid displays the unusual property of spontaneously forming the anhydride, which, unlike maleic anhydride, is a liquid at room temperature.[3]
In the laboratory, citraconic acid can be produced by heating, itaconic acid anhydride to give citraconic acid anhydride, which can be hydrolyzed to citraconic acid.[4] The required itaconic acid anhydride is obtained by dry distillation of citric acid.
References
- 1 2 3 4 5 Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
- 1 2 Citraconic acid Archived January 19, 2012, at the Wayback Machine.
- ↑ Kurt Lohbeck; Herbert Haferkorn; Werner Fuhrmann; Norbert Fedtke (2005), "Maleic and Fumaric Acids", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a16_053
- ↑ R. L. Shriner; S. G. Ford; l. J. Roll (1931). "Citraconic Anhydride and Citraconic Acid". Org. Synth. 28: 28. doi:10.15227/orgsyn.011.0028.
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