![]() | |
![]() | |
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 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
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: | |
![]() ![]() | |
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): | |
LD50 (median dose) | 1850 mg/kg [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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]
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.
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]
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 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.
The former term “levulose” for fructose gave levulinic acid its name.