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Ethyl levulinate

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Ethyl levulinate
Names
Preferred IUPAC name Ethyl 4-oxopentanoate
Other names Ethyl levulate
Ethyl laevulinate
Ethyl 4-ketovalerate
Ethyl 3-acetylpropionate
Ethyl 4-oxovalerate
Ethyl ketovalerate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.936 Edit this at Wikidata
EC Number
  • 208-728-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3Key: GMEONFUTDYJSNV-UHFFFAOYSA-N
  • InChI=1S/C7H12O3/c1-3-10-7(9)5-4-6(2)8/h3-5H2,1-2H3Key: GMEONFUTDYJSNV-UHFFFAOYSA-N
SMILES
  • CCOC(=O)CCC(=O)C
Properties
Chemical formula C7H12O3
Molar mass 144.170 g·mol
Density 1.016 g/cm
Melting point 25 °C (77 °F; 298 K)
Boiling point 203 to 205 °C (397 to 401 °F; 476 to 478 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Ethyl levulinate is an organic compound with the formula CH3C(O)CH2CH2C(O)OC2H5. It is an ester derived from the keto acid levulinic acid. Ethyl levulinate can also be obtained by reaction between ethanol and furfuryl alcohol. These two synthesis options make ethyl levulinate a viable biofuel option, since both precursors can be obtained from biomass: levulinic acid from 6-carbon polymerized sugars such as cellulose, and furfural from 5-carbon polymerized sugars such as xylan and arabinan.

References

  1. The Merck Index, (2013), Monograph M5144, O'Neil: The Royal Society of Chemistry. Available online at: https://www.rsc.org/Merck-Index/monograph/m5144
  2. "Metabocard for Ethyl levulinate". Human Metabolite Database.
  3. Leal Silva, Jean Felipe; Grekin, Rebecca; Mariano, Adriano Pinto; Maciel Filho, Rubens (2018). "Making Levulinic Acid and Ethyl Levulinate Economically Viable: A Worldwide Technoeconomic and Environmental Assessment of Possible Routes". Energy Technology. 6 (4): 613–639. doi:10.1002/ente.201700594. ISSN 2194-4296.
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