Levulinic acid

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Levulinic acid [1]
Skeletal formula Levulinic Acid Structural Formulae.svg
Skeletal formula
Ball-and-stick model Levulinic-acid-3D-balls.png
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.228 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) Yes check.svgY
    Key: JOOXCMJARBKPKM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
    Key: JOOXCMJARBKPKM-UHFFFAOYAR
  • CC(=O)CCC(=O)O
Properties
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)
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H315, H317, H318, H319
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P305+P354+P338, P317, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P501
Lethal dose or concentration (LD, LC):
1850 mg/kg [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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, [3] such as ethyl levulinate. [4]

Contents

Synthesis

Levulinic acid was first prepared in 1840 by Dutch chemist Gerardus Johannes Mulder by heating fructose with hydrochloric acid. [5] The first commercial production of levulinic acid began as a batchwise process in an autoclave by starch manufacturer A. E. Staley in the 1940s. [6] In 1953 Quaker Oats developed a continuous process for the production of levulinic acid. [7] In 1956 it was identified as a platform chemical with high potential. [8] and in 2004 the US Department of Energy (U.S. DoE) identified levulinic acid as one of the 12 potential platform chemicals in the biorefinery concept. [9]

The synthesis of levulinic acid from hexoses (glucose, fructose) or starch in dilute hydrochloric acid or sulfuric acid. [5] [10] [11] [12] In addition to formic acid further, partly insoluble, by-products are produced. These are deeply colored and their complete removal is a challenge for most technologies.

Synthesis levulinic acid.svg

Many concepts for the commercial production of levulinic acid are based on a strong acid technology. The processes are conducted in a continuous manner at high pressures and temperatures. Lignocellulose is an inexpensive starting material. Levulinic acid is separated from the mineral acid catalyst by extraction. Levulinic acid is purified by distillation. [13]

Reactions and applications

Levulinic acid is used as a precursor for pharmaceuticals, plasticizers, and various other additives. [2] The largest application of levulinic acid is its use in the production of aminolevulinic acid, a biodegradable herbicide used in South Asia. Another key application is the use of levulinic acid in cosmetics. Ethyl levulinate, a primary derivative of levulinic acid, is extensively used in fragrances and perfumes. Levulinic acid is a chemical building block or starting material for a wide variety of other compounds [14] including γ-valerolactone and 2-methyl-THF. [9]

Levulinic acid family.svg

Other occurrence and niche uses

Levulinic acid is used in cigarettes to increase nicotine delivery in smoke and binding of nicotine to neural receptors. [15]

Levulinic acid, in its cyclic alternate structure, was the first pseudoacid to be described as such.

Etymology

The former term "levulose" for fructose gave levulinic acid its name.

References

  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. 1 2 Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a18_313
  3. ↑ 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
  4. ↑ 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.
  5. 1 2 Mulder, G. J. (1840). "Untersuchungen über die Humussubstanzen" [Investigations on humic substances]. J. Prakt. Chem. (in German). 21 (1): 203–240. doi:10.1002/prac.18400210121.
  6. ↑ A. E. Staley, Mfg. Co. (Decatur, Ill.); Levulinic Acid 1942 [C.A. 36, 1612]
  7. ↑ U.S. patent 2,813,900
  8. ↑ R. H. Leonard, Ind. Eng. Chem. 1331, (1956).
  9. 1 2 The Pacific Northwest National Laboratory and The National Renewable Energy Laboratory (Aug 2004). "Volume I-Results of Screening for Potential Candidates from Sugars and Synthesis Gas" (PDF). Top Value Added Chemicals from Biomass. U.S. Department of Energy.
  10. ↑ 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
  11. ↑ B. F. McKenzie (1941). "Levulinic acid". Organic Syntheses ; Collected Volumes, vol. 1, p. 335.
  12. ↑ S.L. Suib, New and Future Developments in Catalysis – Catalytic Biomass Conversion, Elsevier, (2013). ISBN   978-0-444-53878-9
  13. ↑ U.S. patent 5,608,105
  14. ↑ Bozell, Joseph J.; Petersen, Gene R. (2010-04-06). "Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy's "Top 10" revisited". Green Chemistry. 12 (4): 539–554. doi:10.1039/b922014c.
  15. ↑ 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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