2-Methylsuccinic acid: Difference between revisions
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'''2-Methylsuccinic acid''' is an [[organic compound]] with the formula HO<sub>2</sub>CCH(CH<sub>3</sub>)CH<sub>2</sub>CO<sub>2</sub>H. A white solid, it is the simplest [[chiral]] [[dicarboxylic acid]]. It is a recurring component of urban aerosols.<ref>{{cite journal|title=Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere|authors=Kawamura, Kimitaka; Ikushima, Kouichi|journal=Environmental Science and Technology|year=1993|volume=27|pages= |
'''2-Methylsuccinic acid''' is an [[organic compound]] with the formula HO<sub>2</sub>CCH(CH<sub>3</sub>)CH<sub>2</sub>CO<sub>2</sub>H. A white solid, it is the simplest [[chiral]] [[dicarboxylic acid]]. It is a recurring component of urban aerosols.<ref>{{cite journal|title=Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere|authors=Kawamura, Kimitaka; Ikushima, Kouichi|journal=Environmental Science and Technology|year=1993|volume=27|pages=2227–35|doi=10.1021/es00047a033}}</ref> Salts and esters of 2-methylsuccinic acid are called '''2-methylsuccinates'''. |
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==Preparation== |
==Preparation== |
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It can be prepared by partial [[hydrogenation]] of [[itaconic acid]] over [[Raney nickel]].<ref>{{cite journal|title=3-Methylthiophene|authors=R. F. Feldkamp, B. F. Tullar|journal=Org.Synth.|year=1954 |volume=34|page=73|doi=10.15227/orgsyn.034.0073}}</ref> Alternatively, [[hydrocyanation]] of ethyl [[crotonate]] affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and [[nitrile]] substituents.<ref>{{cite journal|journal=Org. Synth.|year=1946|volume=26|page=54|doi=10.15227/orgsyn.026.0054|title=Methylsuccinic acid|author=George Bosworth Brown}}</ref> |
It can be prepared by partial [[hydrogenation]] of [[itaconic acid]] over [[Raney nickel]].<ref>{{cite journal|title=3-Methylthiophene|authors=R. F. Feldkamp, B. F. Tullar|journal=Org. Synth.|year=1954 |volume=34|page=73|doi=10.15227/orgsyn.034.0073}}</ref> Alternatively, [[hydrocyanation]] of ethyl [[crotonate]] affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and [[nitrile]] substituents.<ref>{{cite journal|journal=Org. Synth.|year=1946|volume=26|page=54|doi=10.15227/orgsyn.026.0054|title=Methylsuccinic acid|author=George Bosworth Brown}}</ref> |
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==References== |
==References== |
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Revision as of 01:57, 10 March 2019
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| Names | |
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| Other names
Pyrotartaric acid; 2-methylbutanedioic acid; propane-1,2-dicarboxylic acid
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.144 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C5H8O4 | |
| Molar mass | 132.115 g·mol−1 |
| Appearance | White solid |
| Melting point | 117.5 °C (243.5 °F; 390.6 K) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Methylsuccinic acid is an organic compound with the formula HO2CCH(CH3)CH2CO2H. A white solid, it is the simplest chiral dicarboxylic acid. It is a recurring component of urban aerosols.[1] Salts and esters of 2-methylsuccinic acid are called 2-methylsuccinates.
Preparation
It can be prepared by partial hydrogenation of itaconic acid over Raney nickel.[2] Alternatively, hydrocyanation of ethyl crotonate affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and nitrile substituents.[3]
References
- ^ "Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere". Environmental Science and Technology. 27: 2227–35. 1993. doi:10.1021/es00047a033.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ "3-Methylthiophene". Org. Synth. 34: 73. 1954. doi:10.15227/orgsyn.034.0073.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ George Bosworth Brown (1946). "Methylsuccinic acid". Org. Synth. 26: 54. doi:10.15227/orgsyn.026.0054.