Levulinic acid

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Levulinic acid[1]
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 123-76-2 YesY
PubChem 11579
ChemSpider 11091 YesY
UNII RYX5QG61EI YesY
DrugBank DB02239
ChEBI CHEBI:45630 YesY
ChEMBL CHEMBL1235931 N
Jmol-3D images Image 1
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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

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[edit]

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[edit]

Levulinic acid is used in cigarettes to increase nicotine delivery in smoke and binding of nicotine to neural receptors.[7]

Safety[edit]

Levulinic acid is relatively nontoxic, with an LD50 of 1850 mg/kg.[5]

References[edit]

  1. ^ 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
  2. ^ 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
  3. ^ 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
  4. ^ B. F. McKenzie (1941), Levulinic acid, Org. Synth. ; Coll. Vol. 1: 335 
  5. ^ a b Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a18 313
  6. ^ 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
  7. ^ 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