Levulinic acid

Base Information

• Chemical Name: Levulinic acid
• CAS No.: 123-76-2
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 2918.30
• European Community (EC) Number: 204-649-2
• NSC Number: 3716
• UNII: RYX5QG61EI
• DSSTox Substance ID: DTXSID8021648
• Nikkaji Number: J10.067F
• Wikipedia: Levulinic_acid
• Wikidata: Q903322
• RXCUI: 6379
• Metabolomics Workbench ID: 1530
• ChEMBL ID: CHEMBL1235931
• Mol file: 123-76-2.mol

Synonyms:4-oxopentanoic acid, 4-ketovaleric acid;calcium levulate;calcium levulinate;Diasporal;gamma-ketovaleric acid;levulinic acid;levulinic acid, ammonium salt;levulinic acid, calcium salt;levulinic acid, sodium salt;Magnesium Diasporal;magnesium laevulinate;magnesium levulinate

Chemical Property of Levulinic acid

Chemical Property:

• Appearance/Colour: clear yellowish liquid after melting
• Vapor Pressure: 1 mm Hg ( 102 °C)
• Melting Point: 30-33 °C(lit.)
• Refractive Index: 1.438 - 1.442
• Boiling Point: 242.9 °C at 760 mmHg
• PKA: pKa 4.65(H2O,t = 25,c=0.03-0.001) (Uncertain)
• Flash Point: 115 °C
• PSA: 54.37000
• Density: 1.129 g/cm³
• LogP: 0.44020
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: 675g/l
• Water Solubility.: Soluble in water ( 675g/L at 20°C).
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

Levulinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,C
• Hazard Codes: Xn,C
• Statements: 22-36/37/38-34-R34-R22
• Safety Statements: 26-45-36/37/39-S45-S36/37/39-S26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(=O)CCC(=O)O
• Uses: Levulinic acid is a biomass product and its derivatives, such as ethyl levulinate and alkyl levulinate, can be used as fuel additives. levulinic acid is used for calcium levulinate in pharmaceuticals, as esters in solvents and plasticizers, and for making valerolactone. As its uses expand, it will probably be made from cellulosic wastes. Mesitonic acid, a homolog of levulinic acid is obtained by boiing mesityl oxide with KCN. Hydrogenation of levulinic acid can produce other useful chemicals. Valeric-g-lactone, which is an effective solvent with extensive uses, can be obtained in very high yields. This compound may be hydrogenated to 1,4-pentandiol, which upon dehydration yields 1,3-pentadine (piperylene). Piperylene is known to polymerize to a rubbery mass and is therefore a source of synthetic rubber (Ghorpade and Hanna 1997). Levulinic acid is a precursor for the synthesis of useful intermediates such as γ-valerolactone, ethyl levulinate, pentanoic acid and 2-methyl-tetrahydrofuran. Derivatization and esterification of levulinic acid results in potential biofuels. It can also be used in: The preparation of catalytic composite to synthesize 5-hydroxymethylfurfural and furfural. The synthesis of a commercial fragrance, fraistone. The synthesis of pyrrolidone derivatives via reductive amination. The total synthesis of mycobacterial arabinogalactan. Levulinic acid may be used as an analytical reference standard for the quantification of the analyte in the following:Soy sauce using liquid chromatography coupled to mass spectrometry (LC–MS).Liquid food samples using gas chromatography with flame ionization detection (GC-FID). Replenisher (calcium). Levulinic acid is a precursor for the synthesis of useful intermediates such as γ-valerolactone, ethyl levulinate, pentanoic acid and 2-methyl-tetrahydrofuran. Derivatization and esterification of levulinic acid results in potential biofuels.It can also be used in:The preparation of catalytic composite to synthesize 5-hydroxymethylfurfural and furfural.The synthesis of a commercial fragrance, fraistone.The synthesis of pyrrolidone derivatives via reductive amination.The total synthesis of mycobacterial arabinogalactan.
• Description: Levulinic acid has a tart, whiskey taste. It may be synthesized by the action of more or less concentrated HCL on sucrose, glucose, or fructose; hence, its reported presence in caramels.

Technology Process of Levulinic acid

There total 524 articles about Levulinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

4-pentynoic acid (6089-09-4) → 5-methylenedihydrofuran-2-one (10008-73-8) + levulinic acid (123-76-2)

Guidance literature:

With (1-(4-((triethylammonium chloride)methyl)benzyl)-3-mesityl-2,3-dihydro-1H-imidazol-2-yl)gold(I)chloride; In water; at 20 ℃; for 24h; pH=7;

DOI:10.1039/c5ob01286d

Reference yield: 35.0%

α-cellulose → furfural (98-01-1) + β-D-glucose (492-61-5) + levulinic acid (123-76-2)

Guidance literature:

With sulfuric acid; hydrogen; In water; at 160 ℃; for 5h; under 37503.8 Torr; Autoclave;

DOI:10.1039/c000075b

Reference yield: 30.4%

α-cellulose → furfural (98-01-1) + β-D-glucose (492-61-5) + DL-xylose (53106-52-8) + levulinic acid (123-76-2)

Guidance literature:

With phosphoric acid; hydrogen; In water; at 160 ℃; for 5h; under 37503.8 Torr; Autoclave;

DOI:10.1039/c000075b

upstream raw materials:

(2-furyl)methyl alcohol

tetrachloromethane

5-methyl-2,3-dihydro-furan-2,3-diol

5-hydroxymethyl-2-furfuraldehyde

Downstream raw materials:

4,4-bis(5-methylfuran-2-yl)pentanoic acid

3-acetyl-4-furan-2-yl-but-3-enoic acid

(E)-4-oxo-6-phenylhex-5-enoic acid

3-acetyl-4-phenyl-but-3-enoic acid

Refernces

• 1、 Candu, Natalia,El Fergani, Magdi,Verziu, Marian,Cojocaru, Bogdan,Jurca, Bogdan,Apostol, Nicoleta,Teodorescu, Cristian,Parvulescu, Vasile I.,Coman, Simona M.. "Efficient glucose dehydration to HMF onto Nb-BEA catalysts". . p. 109 - 116. Retrieved 2019.
• 2、 Tan, Jin,Wang, Haiyong,Ma, Longlong,Wang, Chenguang,Liu, Qiying,Zhang, Qi,He, Minghong. "Selective yields of furfural and hydroxymethylfurfural from glucose in tetrahydrofuran over Hβ zeolite". . p. 24534 - 24540. Retrieved 2018.
• 3、 Szabolcs, Armin,Molnar, Mark,Dibo, Gabor,Mika, Laszlo T.. "Microwave-assisted conversion of carbohydrates to levulinic acid: An essential step in biomass conversion". . p. 439 - 445. Retrieved 2013.
• 4、 Wang,Tan,Zhu,Miao,Kong,Sun. "One-pot catalytic conversion of microalgae (Chlorococcum sp.) into 5-hydroxymethylfurfural over the commercial H-ZSM-5 zeolite". . p. 452 - 460. Retrieved 2016.
• 5、 Thapa, Indira,Mullen, Brian,Saleem, Ammar,Leibig, Cora,Baker, R. Tom,Giorgi, Javier B.. "Efficient green catalysis for the conversion of fructose to levulinic acid". . p. 70 - 79. Retrieved 2017.
• 6、 Liu, Qishun,Yang, Fengli,Yin, Heng,Du, Yuguang. "Conversion of saccharides into levulinic acid and 5-hydroxymethylfurfural over WO3-Ta2O5 catalysts". . p. 49760 - 49763. Retrieved 2016.
• 7、 Yang, Lisha,Yang, Xiaokun,Tian, Elli,Lin, Hongfei. "Direct Conversion of Cellulose into Ethyl Lactate in Supercritical Ethanol-Water Solutions". . p. 36 - 41. Retrieved 2016.
• 8、 Dussan, Karla,Girisuta, Buana,Lopes, Marystela,Leahy, James J.,Hayes, Michael H. B.. "Effects of Soluble Lignin on the Formic Acid-Catalyzed Formation of Furfural: A Case Study for the Upgrading of Hemicellulose". . p. 492 - 504. Retrieved 2016.
• 9、 Li, Jiang,Ding, Dao-Jun,Xu, Lu-Jiang,Guo, Qing-Xiang,Fu, Yao. "The breakdown of reticent biomass to soluble components and their conversion to levulinic acid as a fuel precursor". . p. 14985 - 14992. Retrieved 2014.
• 10、 China, H.,Dohi, T.,Fujitake, M.,Kageyama, N.,Kikushima, K.,Yatabe, H.. "New syntheses of haloketo acid methyl esters and their transformation to halolactones by reductive cyclization". . p. 1804 - 1810. Retrieved 2020.