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Revision as of 11:54, 23 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 455758515 of page Levulinic_acid for the Chem/Drugbox validation project (updated: 'ChEMBL').		Latest revision as of 06:02, 20 April 2024 edit Solomonfromfinland (talk | contribs)Extended confirmed users16,041 edits remove space
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
	| Verifiedfields = changed		| Verifiedfields = changed
			| Watchedfields = changed
	| verifiedrevid = 402200795		| verifiedrevid = 462091509
	| Name = Levulinic acid		| Name = Levulinic acid
	| Reference = <ref>'']'', 11th Edition, '''5352'''</ref>
			| Reference = <ref>''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</ref>
	| ImageFile = Levulinic Acid Structural Formulae.svg		| ImageFile = Levulinic Acid Structural Formulae.svg
	| ImageSize = 180px
			| ImageSize = 180px
	| ImageName = Skeletal formula		| ImageName = Skeletal formula
	| ImageFile1 = Levulinic-acid-3D-balls.png		| ImageFile1 = Levulinic-acid-3D-balls.png
	| ImageName1 = Ball-and-stick model		| ImageName1 = Ball-and-stick model
	| IUPACName = 4-Oxopentanoic acid		| PIN = 4-Oxopentanoic acid
	| OtherNames = Levulinic acid, Laevulinic acid, β-Acetylpropionic acid, 3-Acetopropionic acid, β-acetylpropionic acid, γ-ketovaleric acid, 4-oxopentanoic acid		| OtherNames = Levulinic acid, β-Acetylpropionic acid, 3-Acetopropionic acid, β-acetylpropionic acid, γ-ketovaleric acid
	| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|Section1 = {{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 11091		| ChemSpiderID = 11091
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = <!-- blanked - oldvalue: 1235931 -->		| ChEMBL = 1235931
	| PubChem = 11579		| PubChem = 11579
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = RYX5QG61EI		| UNII = RYX5QG61EI
	| InChI = 1/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)		| InChI = 1/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
	| InChIKey = JOOXCMJARBKPKM-UHFFFAOYAR		| InChIKey = JOOXCMJARBKPKM-UHFFFAOYAR
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)		| StdInChI = 1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = JOOXCMJARBKPKM-UHFFFAOYSA-N		| StdInChIKey = JOOXCMJARBKPKM-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 123-76-2		| CASNo = 123-76-2
	| DrugBank_Ref = {{drugbankcite|changed|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB02239		| DrugBank = DB02239
	| ChEBI_Ref = {{ebicite|changed|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 45630		| ChEBI = 45630
	| SMILES = CC(=O)CCC(=O)O		| SMILES = CC(=O)CCC(=O)O
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>5</sub>H<sub>8</sub>O<sub>3</sub>		| Formula = C<sub>5</sub>H<sub>8</sub>O<sub>3</sub>
	| MolarMass = 116.11 g/mol		| MolarMass = 116.11 g/mol
	| Density = 1.1447 g/cm<sup>3</sup>		| Density = 1.1447 g/cm<sup>3</sup>
	| MeltingPt = 33-35 °C		| MeltingPtC = 33 to 35
			| MeltingPt_notes =
	| BoilingPt = 245-246 °C
			| BoilingPtC = 245 to 246
⚫	}}
	}}		}}
		⚫	}}
			'''Levulinic acid''', or 4-oxopentanoic acid, is an ] with the ] CH<sub>3</sub>C(O)CH<sub>2</sub>CH<sub>2</sub>CO<sub>2</sub>H. It is classified as a ]. This white crystalline solid is soluble in water and polar organic solvents. It is derived from degradation of ] and is a potential precursor to ]s,<ref>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}}</ref> such as ].<ref>{{Cite journal|last1=Leal Silva|first1=Jean Felipe|last2=Grekin|first2=Rebecca|last3=Mariano|first3=Adriano Pinto|last4=Maciel Filho|first4=Rubens|title=Making Levulinic Acid and Ethyl Levulinate Economically Viable: A Worldwide Technoeconomic and Environmental Assessment of Possible Routes|journal=Energy Technology|volume=6|issue=4|language=en|pages=613–639|doi=10.1002/ente.201700594|issn=2194-4296|year=2018}}</ref>
			== Synthesis ==
			Levulinic acid was first prepared in 1840 by Dutch chemist ] by heating ] with hydrochloric acid.<ref name=":0">{{Cite journal|title = Untersuchungen über die Humussubstanzen|language = German|trans-title=Investigations on humic substances|last = Mulder|first = G. J.|authorlink = Gerardus Johannes Mulder|journal = ]|doi = 10.1002/prac.18400210121|year = 1840|volume = 21|issue = 1|pages = 203–240| url=https://zenodo.org/record/1427786 }}</ref> The first commercial production of levulinic acid began as a batchwise process in an autoclave by ] manufacturer ] in the 1940s.<ref>A. E. Staley, Mfg. Co. (Decatur, Ill.); Levulinic Acid 1942 </ref> In 1953 Quaker Oats developed a continuous process for the production of levulinic acid.<ref>{{US patent|2813900}}</ref> In 1956 it was identified as a platform chemical with high potential.<ref>R. H. Leonard, Ind. Eng. Chem. 1331, (1956).</ref> 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.<ref name=":1">{{Cite web|url = http://www.nrel.gov/docs/fy04osti/35523.pdf|work = Top Value Added Chemicals from Biomass |title=Volume I-Results of Screening for Potential Candidates from Sugars and Synthesis Gas |date =Aug 2004 |author=The Pacific Northwest National Laboratory and The National Renewable Energy Laboratory |publisher=U.S. Department of Energy }}</ref>
			The synthesis of levulinic acid from ]s (], ]) or starch in dilute ] or ].<ref name=":0" /><ref>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}}</ref><ref>{{OrgSynth |author = B. F. McKenzie|title = Levulinic acid|collvol = 1|collvolpages = 335|year = 1941|prep = cv1p0335}}</ref><ref>S.L. Suib, New and Future Developments in Catalysis – Catalytic Biomass Conversion, Elsevier, (2013). {{ISBN|978-0-444-53878-9}}</ref> In addition to ] further, partly insoluble, by-products are produced. These are deeply colored and their complete removal is a challenge for most technologies.
			]
			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. ] is an inexpensive starting material. Levulinic acid is separated from the mineral acid ] by ]. Levulinic acid is purified by ].<ref>{{US patent|5608105}}</ref>
			==Reactions and applications==
			Levulinic acid is used as a precursor for pharmaceuticals, plasticizers, and various other additives.<ref name=Ullmann>Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a18_313}}</ref> The largest application of levulinic acid is its use in the production of ], a biodegradable ] used in South Asia. Another key application is the use of levulinic acid in cosmetics. ], 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<ref>{{Cite journal|title = Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy's "Top 10" revisited|journal = Green Chemistry|volume = 12|issue = 4|pages = 539–554|doi = 10.1039/b922014c|first1 = Joseph J.|last1 = Bozell|first2 = Gene R.|last2 = Petersen|date = 2010-04-06}}</ref> including ] and ].<ref name=":1" />
			]
			===Other occurrence and niche uses===
			Levulinic acid is used in cigarettes to increase ] delivery in smoke and binding of nicotine to neural receptors.<ref>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</ref>
			Levulinic acid, in its cyclic alternate structure, was the first ] to be described as such.
			== Etymology ==
			The former term “levulose” for fructose gave levulinic acid its name.
			== Safety ==
			Levulinic acid is relatively nontoxic, with an {{LD50}} of 1850&nbsp;mg/kg.<ref name=Ullmann/>
			== References ==
			{{reflist}}
			* {{cite EB1911 |wstitle=Rubber |volume=23 |page=802 |first=Wyndham Rowland |last=Dunstan}}
			]
			]