Levulinic acid
| Levulinic acid[1] | |
|---|---|
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| IUPAC name 4-Oxopentanoic acid | |
| Other names Levulinic acid, Laevulinic acid, β-Acetylpropionic acid, 3-Acetopropionic acid, β-acetylpropionic acid, γ-ketovaleric acid, 4-oxopentanoic acid | |
| Identifiers | |
| CAS number | 123-76-2  |
| PubChem | 11579 |
| ChemSpider | 11091 |
| UNII | RYX5QG61EI |
| DrugBank | DB02239 |
| ChEBI | CHEBI:45630 |
| ChEMBL | CHEMBL1235931  |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C5H8O3 |
| Molar mass | 116.11 g/mol |
| Density | 1.1447 g/cm3 |
| Melting point | 33–35 °C |
| Boiling point | 245–246 °C |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH3C(O)CH2CH2CO2H. It is classified as a keto acid. This white crystalline solid is soluble in water and polar organic solvents. It is derived from degradation of cellulose and is a potential precursor to biofuels.[2]
Synthesis
Related to its original synthesis,[3] levulinic acid is prepared by heating sucrose with concentrated acid.[4] The process proceeds via the intermediacy of glucose, which isomerizes to fructose and then undergoes dehydration to hydroxymethylfurfural (HMF). Other sugar-derivatives can be used in this process including levulose (D-fructose), inulin and starch. HMF hydrolyzes to formic acid and levulinic acid:
- HOCH2C4H2OCHO + 2 H2O → HCO2H + CH3C(O)CH2CH2CO2H
Reactions and applications
Levulinic acid is the precursor to pharmaceuticals, plasticizers, and various other additives.[5]
Potential biofuels can be prepared from levulinic acid including methyltetrahydrofuran, valerolactone, and ethyl levulinate. Dehydration of levulinic acid gives angelica lactone.[6]
Other occurrence and niche uses
Levulinic acid is used in cigarettes to increase nicotine delivery in smoke and binding of nicotine to neural receptors.[7]
Safety
Levulinic acid is relatively nontoxic, with an LD50 of 1850 mg/kg.[5]
References
- ↑ The Merck Index, 15th Ed. (2013), p. 1018, Monograph 5526, O'Neil: The Royal Society of Chemistry. Available online at: http://www.rsc.org/Merck-Index/monograph/mono1500005526
- ↑ Biorefineries – Industrial Processes and Products. Status Quo and Future Directions. Vol. 1, Edited by Birgit Kamm, Patrick R. Gruber, Michael Kamm. 2006, WILEY-VCH, Weinheim. ISBN 3-527-31027-4
- ↑ A. Freiherrn, V. Grote, B. Tollens, "Untersuchungen über Kohlenhydrate. I. Ueber die bei Einwirkung von Schwefelsäure auf Zucker entstehende Säure (Levulinsäure)" Justus Liebigs Annalen der Chemie volume 175, pp. 181-204 (1875). doi: 10.1002/jlac.18751750113
- ↑ B. F. McKenzie (1941), "Levulinic acid", Org. Synth.; Coll. Vol. 1: 335
- ↑ 5.0 5.1 Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a18 313
- ↑ George W. Huber, Sara Iborra, = Avelino Corma "Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering" Chemical Reviews 2006, vol. 106, 4044-4098. doi:10.1021/cr068360d
- ↑ Doris Cullen et al., A Guide to Deciphering the Internal Codes Used by the Tobacco Industry, Report No. 03-05, Harvard School of Public Health, Division of Public Health Practice, Tobacco Research Program, August 2005, http://legacy.library.ucsf.edu/resources/harvard_monograph.pdf
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This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press