Levulinic acid
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Names | |
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IUPAC name
4-Oxopentanoic acid
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Other names
Levulinic acid, Laevulinic acid, β-Acetylpropionic acid, 3-Acetopropionic acid, β-acetylpropionic acid, γ-ketovaleric acid, 4-oxopentanoic acid
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Identifiers | |
3D model (JSmol)
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DrugBank | |
ECHA InfoCard | 100.004.228 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C5H8O3 | |
Molar mass | 116.11 g/mol |
Density | 1.1447 g/cm3 |
Melting point | 33–35 °C |
Boiling point | 245–246 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 is soluble in water, ethanol, and diethyl ether. It is derived from degradation of cellulose and is a potential precursor to biofuels.[2]
Synthesis and uses
Related to its original synthesis,[3] levulinic acid is prepared in the laboratory by heating sucrose with concentrated hydrochloric acid.[4] The process proceeds via the intermediacy of glucose, which is isomerized to fructose and then hydroxymethylfurfural. Other sugar-derivatives can be used in this process including levulose (D-fructose), inulin and starch as well as other acids such as sulfuric.
Levulinic acid is a potential precursor to nylon-like polymers, synthetic rubbers, and plastics. It is a versatile synthetic intermediate, e.g., in the synthesis of pharmaceuticals. It is a precursor in the production of other chemical commodities such as methyltetrahydrofuran, valerolactone, and ethyl levulinate. Dehydration of levulinic acid gives α-Angelica lactone (CAS#591-12-8). The first manufacturing facility able to produce levulinic acid at an industrial scale is Green Future based in Caserta, Italy.[citation needed]
Niche uses
Levulinic acid is also a photosensitizer for photodynamic therapy.
Levulinic acid is used in cigarettes to increase nicotine delivery in smoke and binding of nicotine to neural receptors.[5]
For the biogen production of fuel, bacteria are genetically modified, to be able to feed on levulinic acid rather than sugar.[6]
Safety
Levulinic acid is relatively nontoxic, with an LD50 of 1850 mg/kg.[citation needed]
References
- ^ Merck Index, 11th Edition, 5352
- ^ 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". Organic Syntheses; Collected Volumes, vol. 1, p. 335.
- ^ Doris Cullen et al., A Guide to Deciphering the Internal Codes Used by the Tobacco Industry, Harvard School of Public Health Division of Public Health Practice Tobacco Research Program, August 2005.
- ^ http://biomassmagazine.com/articles/7831/researchers-design-microbes-that-make-biofuels-without-sugar
- public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.
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