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Levulinic acid information


Levulinic acid[1]
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
4-Oxopentanoic acid
Other names
Levulinic acid, β-Acetylpropionic acid, 3-Acetopropionic acid, β-acetylpropionic acid, γ-ketovaleric acid
Identifiers
CAS Number
  • 123-76-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:45630 checkY
ChEMBL
  • ChEMBL1235931 ☒N
ChemSpider
  • 11091 checkY
DrugBank
  • DB02239 checkY
ECHA InfoCard 100.004.228 Edit this at Wikidata
PubChem CID
  • 11579
UNII
  • RYX5QG61EI checkY
CompTox Dashboard (EPA)
  • DTXSID8021648 Edit this at Wikidata
InChI
  • InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) checkY
    Key: JOOXCMJARBKPKM-UHFFFAOYSA-N checkY
  • InChI=1/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
    Key: JOOXCMJARBKPKM-UHFFFAOYAR
SMILES
  • CC(=O)CCC(=O)O
Properties
Chemical formula
C5H8O3
Molar mass 116.11 g/mol
Density 1.1447 g/cm3
Melting point 33 to 35 °C (91 to 95 °F; 306 to 308 K)
Boiling point 245 to 246 °C (473 to 475 °F; 518 to 519 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒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] such as ethyl levulinate.[3]

  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. ^ 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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Levulinic acid

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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...

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Mathieu Flamini

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GF Biochemicals, the first company in the world able to mass-produce levulinic acid. Born in Marseille, Flamini was a youth team player for his local professional...

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Keto acid

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Gamma-keto acids, Gamma-ketoacids, or 4-oxoacids have the ketone group at the third carbon from the carboxylic acid. Levulinic acid is an example. Keto acids appear...

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Valeric acid

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CH3CH2CH=CH2 → CH3CH2CH2CH2CHO → valeric acid It can also be produced from biomass-derived sugars via levulinic acid and this alternative has received considerable...

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Ethyl levulinate

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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...

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GF Biochemicals

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Flamini. It is the first company in the world able to mass-produce levulinic acid. The company worked with the University of Pisa for seven years on its...

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Green solvent

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tetrahydrofuran, toluene, DCM, and diethyl ether in some applications. Levulinic acid esters from the same source would have the potential to replace DCM...

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Nicotine salt

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most common acids used in the formation of nicotine salts were lactic acid, benzoic acid and levulinic acid. Benzoic acid is the most used acid to create...

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Biogasoline

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California, Davis, researchers used a feedstock of levulinic acid to create biogasoline. Levulinic acid is derived from cellulose material, such as corn...

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Hydroxymethylfurfural

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of levulinic acid from sugar and sulfuric acid. This remains the classical route, with 6-carbon sugars (hexoses) such as fructose undergoing acid catalyzed...

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Oxopentanoic acid

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Oxopentanoic acid may refer to: Levulinic acid (4-oxopentanoic acid) 3-Oxopentanoic acid This set index article lists chemical compounds articles associated...

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Ketovaleric acid

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Ketovaleric acid may refer to: α-Ketovaleric acid β-Ketovaleric acid (3-oxopentanoic acid) γ-Ketovaleric acid (levulinic acid) This set index article...

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Dicarbonyl

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component of the citric acid cycle and product of glucose metabolism (glycolysis). The corresponding aldehyde-acid is glyoxalic acid (HC(O)CO2H). The parent...

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Humin

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Branimir; Metelko, Biserka; Šunjić, Vitomir (1985-01-01). "Mechanism of levulinic acid formation". Tetrahedron Letters. 26 (17): 2111–2114. doi:10.1016/S0040-4039(00)94793-2...

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Diphenolic acid

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prepared by the condensation reaction of phenol with levulinic acid in the presence of hydrochloric acid. The equation for this synthesis is: 2 C6H5OH + CH3C(O)CH2CH2COOH...

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Biorefinery

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biological chemical treatment (MBCT) systems for the production of levulinic acid has been studied, the revenue from resource recovery and product generation...

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Pseudoacid

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(using the German Pseudosäuren) was levulinic acid (4-oxopentanoic acid). Unlike the parent (open-form) oxocarboxylic acid, the pseudoacid has a chiral center...

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Hemin

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deficits in such patients, thereby suppressing the activity of delta-amino-levulinic acid synthase (a key enzyme in the synthesis of the porphyrins) by biochemical...

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Ketonic decarboxylation

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ISBN 9780582462366. Pileidis, Filoklis D.; Titirici, Maria-Magdalena (2016). "Levulinic Acid Biorefineries: New Challenges for Efficient Utilization of Biomass"...

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Furfural

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Buchentheers. I." [On the breakdown of 2-methylfuran into the aldehyde of levulinic acid, pentanonal. Investigations into the components of tar from beech trees...

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Ketovalerate

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refer to: α-Ketovalerate (α-ketovaleric acid) β-Ketovalerate (3-oxopentanoic acid) γ-Ketovalerate (levulinic acid) This set index article lists chemical...

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List of additives in cigarettes

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oleoresin Lactic acid Lauric acid Lauric aldehyde Lavandin oil Lavender oil Lemon oil and extract Lemongrass oil L-Leucine Levulinic acid Liquorice root...

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Magnesium levulinate

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of levulinic acid, is a mineral supplement. Ganjyal G, Fang Q, Hanna MA (2007). "Freezing points and small-scale deicing tests for salts of levulinic acid...

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Photoelectrochemical process

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Fluorescein Rubrene 9,10-Diphenylanthracene Tetracene 13,13'-Dibenzantronile Levulinic Acid Fluorescence spectroscopy aka fluorometry or spectrofluorometry, is...

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Glutaconic acid

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lower melting point (130–132 °C). It can be prepared by bromination of levulinic acid followed by treatment of the dibromoketone with potassium carbonate...

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Construction of electronic cigarettes

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nicotine base and a weak acid such as benzoic acid or levulinic acid is used to form a nicotine salt. Benzoic acid is the most used acid to create a nicotine...

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