LEVULINIC ACID

Levulinic Acid white flake crystals, hygroscopic. 
Levulinic Acid clear yellowish liquid after melting.
Levulinic Acid is easily soluble in water and alcohol, ether organic solvents.

CAS Number: 123-76-2
Molecular Formula: C5H8O3
Molecular Weight: 116.12
EINECS Number: 204-649-2

Synonyms: LEVULINIC ACID, 4-Oxopentanoic acid, 123-76-2, Laevulinic acid, Pentanoic acid, 4-oxo-, 4-Oxovaleric acid, Levulic acid, 3-Acetylpropionic acid, 4-Ketovaleric acid, gamma-Ketovaleric acid, Acetopropionic acid, Laevulic acid, LEVA, Levulinsaeure, Valeric acid, 4-oxo-, beta-Acetylpropionic acid, 4-oxo-pentanoic acid, USAF CZ-1, Propionic acid, 3-acetyl-, 4-Oxopentansaeure, Acidum laevulinicum, FEMA No. 2627, 3-Acetylpropionsaeure, 3-Ketobutane-1-carboxylic acid, Acetylpropionic acid, .beta.-Acetylpropionic acid, NSC 3716, Pentanoic acid, 4-oxo, g-Ketovalerate, .gamma.-Ketovaleric acid, UNII-RYX5QG61EI, b-Acetylpropionate, NSC-3716, EINECS 204-649-2, g-Ketovaleric acid, BRN 0506796, b-Acetylpropionic acid, DTXSID8021648, CHEBI:45630, AI3-03377, RYX5QG61EI, Valeric acid, 4-oxo-(levulinic acid), LEVULINIC ACID [MI], LEVULINIC ACID [FCC], LEVULINIC ACID [FHFI], DTXCID701648, NSC3716, laevulinate, levulate, levulinate, 4-03-00-01560 (Beilstein Handbook Reference), 4-ketovalerate, 4-oxovalerate, gamma-ketovalerate, 3-acetylpropionate, beta-acetylpropionate, CALCIUM LEVULATE, Levulinic acid, calcium salt, CAS-123-76-2, MFCD00002796, Laevulinsaeure, Diasporal, levulenic acid, 4Oxopentansaeure, 4Oxovaleric acid, 4Ketovaleric acid, 4oxopentanoic acid, 4-Oxopentanoicacid, 3Acetylpropionsaeure, gammaOxovaleric acid, magnesium laevulinate, gammaKetovaleric acid, 4-ketopentanoic acid, Valeric acid, 4oxo, 3Acetylpropionic acid, gammaOxopentanoic acid, Pentanoic acid, 4oxo, betaAcetylpropionic acid, Levulinic acid, 98%, Propionic acid, 3acetyl, Levulinic acid (Standard), 3Ketobutane1carboxylic acid, 3-Ketobutane-1-carboxylate, WLN: QV2V1, SCHEMBL20868, LEVULINIC ACID [INCI], Levulinic acid, >=97%, FG, CHEMBL1235931, BDBM82191, HY-Y0839R, Levulinic acid, analytical standard, HY-Y0839, Levulinic acid, natural, 99%, FG, Tox21_201483, Tox21_302729, BBL027404, GEO-04255, LMFA01060006, s6207, STK802043, AKOS000119608, DB02239, PB48051, 4-Oxopentanoic acid, 4-ketovaleric acid, NCGC00249052-01, NCGC00256314-01, NCGC00259034-01, VS-08535, PENTANOIC ACID,4-OXO MFC5 H8 O3, DB-003710, PENTANOIC ACID,4-OXO MFC5 H8 O3, CS-0015813, L0042, NS00012787, EN300-20219, D70802, SBI-0633496.0002, Q903322, SR-01000944838, J-004982, J-521643, SR-01000944838-1, F2191-0253, Z104477318, Laevulinic acid; 4-Oxopentanoic acid; 4-Oxovaleric acid; gamma-Ketovaleric acid; Levulic acid; 4-Oxo-pentanoic acid, 2-Acetopropionicacid;aevuL;Levulinic acid 4-oxopentanoic acid;sodium 4-oxopentanoate;4-Keto-n-valericacid;4-Oxo-pentanoic acid (levulinic acid);4-oxo-pentanoicaci;4-oxovaleric

Levulinic acid conventionally is derived from refined petroleum but technological advances now permit the production of levulinic acid from biomass. 
Suitable feedstocks from the forest industry include pulp and paper mill residues, sawmill and logging residues, and solid municipal waste. It takes approximately 2 kg of cellulose to produce 1 kg of levulinic acid. 
Obtaining enough raw materials to support the production of levulinic acid from biomass is not a foreseeable concern; Canada currently produces over 75 million tonnes of logging residues annually which, in turn, could produce 19 million tonnes of levulinic acid.

Levulinic acid is an organic compound that is classified as a keto acid, with the chemical formula C5H8O3. 
Levulinic Acid is derived from the dehydration of carbohydrates, such as glucose, and can be found naturally in a variety of sources, including plant-based materials like wood, corn, and other agricultural byproducts. 
Levulinic Acid is a colorless to light yellow liquid with a mild, sweet odor and is known for its versatility in industrial and pharmaceutical applications.

Levulinic Acid is a multipurpose platform chemical that is currently used in a wide variety of applications. 
The potential of levulinic acid is formidable, as can be seen by the diversity and quantity of literature regarding its transformation into different chemicals. 
Development in industrial production of levulinic acid from lignocellulosic biomass has resulted in a surge of interest in levulinic acid as a cheap, readily available, biobased material. 

This minireview will analyse the application of levulinic acid as a reagent in polymer chemistry. 
Levulinic acid has been used in step-growth polymerization, chain-growth polymerization, as a post polymerization functionality, and finally as a method to introduce post polymerisation modificationto sustainable polymers.
Levulinic Acid is an oxopentanoic acid with the oxo group in the 4-position. 

Levulinic Acid has a role as a plant metabolite. 
It is a straight-chain saturated fatty acid and an oxopentanoic acid. 
It is a conjugate acid of a 4-oxopentanoate.

Levulinic Acid may be synthesized by the action of more or less concentrated HCL on sucrose, glucose, or fructose; hence, its reported presence in caramels.
Accurately weigh about 1.0 g of the sample, and put it into a 250ml Erlenmeyer flask containing 75~100ml water, add phenolphthalein test solution; apply 0.5 mol/L sodium hydroxide for titration to until it began to appear pink and maintain 15 s.
Levulinic Acid is one of the top twelve chemicals listed by the US Department of Energy that can be derived from biomass. 

Levulinic Acid serves as a building block and platform chemical for producing a variety of chemicals, fuels and materials which are currently produced in fossil based refineries. 
Levulinic Acid is a key strategic chemical, as fuel grade chemicals and plastic substitutes can be produced by its catalytic conversion. 
Levulinic Acid, or 4-oxopentanoic acid, is prepared from natural sugar (saccharide) sources (e.g., starch, cellulose, or cane sugar) by boiling the saccharide in a strong acid such as HCl. 

It gets its name from the sugar levulose, another name for fructose. 
It is used in the manufacture of nylon, synthetic rubber, plastics, and pharmaceuticals.
Levulinic Acid, is a biogenic product of hexose acid hydrolysis, produced from renewable or bio-based resources.

Levulinic Acid is reported to react with a variety of compounds to result in products, which are widely used in pharmaceuticals, personal care products, electronics, plasticizers, antifouling compounds, fuels, solvents, polymers, anti-freeze agents, batteries, coatings, biologically active materials, corrosion inhibitors, adsorbents, etc.
Levulinic Acid is also employed as a chemical intermediate in the production of biodegradable polymers, fuel extenders, herbicides, flavors, antibiotics and useful 5-carbon compounds.

Levulinic acid is often used as an intermediate in the production of various chemicals, including solvents, plasticizers, and resins. 
It can also be used in the synthesis of biofuels, such as levulinate esters, which are considered potential alternatives to petroleum-based fuels.
It serves as a precursor for the synthesis of other bio-based chemicals, including γ-valerolactone, a compound with potential uses in sustainable energy and chemicals.

Due to its antimicrobial and anti-inflammatory properties, levulinic acid is increasingly being used in cosmetics and skincare formulations, such as moisturizers, lotions, and sunscreens. 
It helps to improve skin texture and provide hydration.
Levulinic acid is utilized in pharmaceutical research and development, including the creation of active pharmaceutical ingredients (APIs) and in formulations that treat certain skin conditions or act as preservatives.

As a bio-based compound, levulinic acid contributes to the circular economy, where renewable resources are used to produce high-value chemicals, reducing dependency on fossil fuels and promoting environmental sustainability. 
However, the environmental impact of its production depends on the methods used to extract and process the biomass, as well as the energy required for its conversion into usable forms.

Melting point: 30-33 °C (lit.)
Boiling point: 245-246 °C (lit.)
Density: 1.134 g/mL at 25 °C (lit.)
vapor pressure: 1 mm Hg ( 102 °C)
refractive index: n20/D 1.439(lit.)
FEMA: 2627 | LEVULINIC ACID
Flash point: 280 °F
storage temp.: Store below +30°C.
solubility: 675g/l
form: Liquid After Melting
pka: pKa 4.65(H2O,t = 25,c=0.03-0.001) (Uncertain)
color: Clear yellow
Odor: at 100.00 %. sweet caramel acidic acetoin buttery
Odor Type: caramellic
Water Solubility: Soluble in water ( 675g/L at 20°C).
Sensitive: Light Sensitive
Merck: 14,5472
JECFA Number: 606
BRN: 506796
InChIKey: JOOXCMJARBKPKM-UHFFFAOYSA-N
LogP: -0.498

Levulinic Acid, often referred to as 4-oxopentanoic acid, is a versatile and important organic compound that plays a key role in various industries due to its unique chemical properties. 
It is typically produced by the acid-catalyzed dehydration of sugars, particularly hexoses like glucose, through a process known as acid hydrolysis or pyrolysis. 
This makes it a renewable resource derived from biomass, and it is often considered part of the green chemistry movement due to its bio-based origins and potential for sustainable applications.

The residue during the manufacturing of furfural with cotton seed shell or corncob sugar (furfural residue) or waste taro residue, through pressured hydrolysis with dilute acid, can be used to produce levulinic acid. 
The furfural residue was added to 10% dilute hydrochloric acid, the solidified solution was 1: 1.75, mixed and put into the hydrolysis pot, steamed at a pressure of 0.2MPa for 8-10 h. 
The diluted solution is then filtered and concentrated to a concentration of about 50%. 

Levulinic Acid is further subject to vacuum distillation for collecting the fraction above 130 ℃ (2.67kPa) to obtain the finished product. 
Raw material consumption quota: potato tacar 7,000 kg/t, hydrochloric acid (fold 100%) 1800kg/t. 
Another method is manufacturing through the rearrangement and hydrolysis of sugar alcohol.

4% hydrochloric acid solution was added to the reaction pot, stir and heat to 97-100 ℃, slowly add the mixture of furfuryl alcohol, ethanol and water. 
After addition, stir 30 min. The filtrate was concentrated at 80 ° C (21.3 kPa) under reduced pressure to give crude levulinic acid. 
Then apply vacuum distillation, collect the fraction of 160-170 ° C (2.67kPa), and then re-distill once, to obtain the refined levulinic acid with the yield of about 75%.

Levulinic acid is considered one of the "top value-added chemicals" that can be derived from biomass. 
Levulinic Acid can be used as an intermediate in the production of a variety of chemicals, including levulinate esters (which have potential as biofuels), solvents, and plasticizers. 
Levulinic Acid has been identified as a key chemical for replacing petrochemicals in the manufacturing of products like plastics and synthetic fibers.

Levulinic acid is used as a starting material for the synthesis of γ-valerolactone (GVL), a compound that is considered a promising bio-based fuel and solvent. 
GVL can be converted into high-energy-density fuels and is an attractive candidate for use in alternative energy applications, offering a renewable and sustainable fuel source.
Levulinic acid has applications in the agricultural sector, where it is used as a natural herbicide or plant growth regulator. 

Levulinic Acid can help to control weeds, particularly in crops like corn, by acting as an environmental herbicide that is safer for the ecosystem compared to traditional synthetic herbicides.
In the food industry, Levulinic Acid is sometimes used as a flavoring agent or as a precursor in the production of various food additives.
In cosmetic formulations, levulinic acid is used for its antimicrobial properties, which help preserve products by inhibiting the growth of harmful bacteria and fungi. 

Additionally, it has mild anti-inflammatory and hydrating effects, which makes it a useful ingredient in moisturizers, lotions, and anti-aging skincare products. 
Levulinic Acid is particularly beneficial in products aimed at sensitive skin.
It also helps improve the penetration of other ingredients in the skin, enhancing the effectiveness of other active components in the formulation.

Levulinic acid has been investigated for use in pharmaceutical formulations, particularly for its potential as a preservative in both topical and oral medications due to its antimicrobial properties.
Levulinic acid derivatives have also shown promise as anti-inflammatory agents, and there is ongoing research into its potential therapeutic effects in treating skin conditions such as eczema or acne.
Levulinic acid and its derivatives can be used to produce biodegradable polymers that can serve as alternatives to petroleum-based plastics. 

These biodegradable polymers have applications in packaging materials, medical devices, and other products where environmental sustainability is a priority.
Levulinic acid fits well into the field of green chemistry because it is derived from renewable sources like plant biomass, and its production is seen as a more sustainable alternative to petrochemical-based processes. 
The development of processes to create levulinic acid and its derivatives from lignocellulosic biomass (such as wood, agricultural waste, or grasses) further supports its potential as a building block for sustainable materials and chemicals.

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.

Levulinic Acid 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.
Levulinic Acid can be used as the raw materials of medicine, spices and paint, and used as solvent.
Levulinic acid can be used as both a carboxylic acid and can also be used as a ketone for reaction for making various kinds of products through esterification, halogenation, hydrogenation, oxidation dehydrogenation, condensation, etc., including resins, pharmaceuticals, spices, solvents, rubber and plastic additives, lubricants additives, surfactants and so on. 

In the pharmaceutical industry, its calcium salt (calcium fructose) can be used for intravenous injection. 
As a nutritional medicine, it helps to boost the formation of bone and maintain the normal excitability of nerves and muscles. 
Levulinic Acid can also used for the production of indomethacin and plant hormones. 

Levulinic acid manufactured bisphenol acid can be made of water-soluble resin, used in the paper industry to produce filter paper. 
Levulinic acid is also an intermediate of pesticides and dyes.
Used for biochemical reagents, but also for organic synthesis.

It can be used as an important chemical raw material or solvents. 
Levulinic Acid can be used for the manufacturing of medicine (intravenous injection, indomethacin, etc.), resin (bisphenol acid water-soluble resin), spices (spices or tobacco spices), paint, paint, pesticides, and surfactants.
Levulinic Acid can be used for biochemical research; manufacturing of esters and drugs. 

Levulinic Acid is also the inhibitor of chlorophyll synthesis.
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).

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.
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 is used as a precursor for the production of gamma-valerolactone (GVL), a bio-based fuel that can be converted into high-energy-density fuels, offering an alternative to petroleum-based fuels. 
This makes it an important compound in the development of renewable energy sources.
Levulinic acid is utilized as a natural herbicide and plant growth regulator. 

Levulinic Acid can help manage weeds and promote healthier crop growth. 
It is often considered an environmentally safer alternative to synthetic herbicides.
In cosmetics, levulinic acid is used for its antimicrobial properties to prevent bacterial and fungal growth in formulations. 

Levulinic Acid also has anti-inflammatory effects, making it ideal for use in skincare products targeting sensitive or irritated skin.
Levulinic acid enhances the hydration and penetration of other active ingredients, making it beneficial in moisturizers, lotions, sunscreens, and anti-aging products.
Levulinic acid and its derivatives are being explored for use as preservatives in pharmaceuticals due to their antimicrobial properties.

It has also shown potential in the treatment of skin conditions like eczema and acne, offering soothing and healing effects.
Levulinic Acid is sometimes used as a flavoring agent or as a precursor for food additives, contributing to the production of natural flavors.
It can also be employed in food processing and preservation, particularly for its antimicrobial properties.

Levulinic Acid can be used to produce biodegradable plastics and polymers that serve as alternatives to conventional petroleum-based plastics. 
These biodegradable materials have applications in packaging, medical devices, and other environmentally conscious products.
Due to its renewable nature, levulinic acid is part of efforts to reduce reliance on fossil fuels. 

Its production from biomass (such as wood, agricultural waste, or corn) supports the development of more sustainable, green chemical processes and contributes to the circular economy.
Levulinic Acid has potential applications in water treatment as a flocculant or coagulating agent, where it helps remove impurities and contaminants from water sources.

Levulinic acid is an important research tool in various fields, including organic chemistry and green chemistry, due to its versatile chemical structure and potential to be transformed into a wide range of valuable chemicals.
Levulinic acid is being explored as a potential additive in animal feed, where it can help improve the digestion and health of livestock by promoting a healthy gut microbiome.

Safety Profile:
Levulinic acid can cause irritation or mild chemical burns if it comes into direct contact with skin, especially in higher concentrations. 
Levulinic Acid may lead to redness, burning, or stinging sensations.
Wear protective gloves and avoid prolonged skin contact. 

If contact occurs, rinse the affected area thoroughly with water.
Levulinic Acid can be irritating to the eyes, causing redness, discomfort, or a burning sensation if it splashes into the eyes.
Wear safety goggles or face shields when handling the substance. 

If it gets into the eyes, rinse with water immediately and seek medical attention if necessary.
Levulinic acid in its vapor form or as a mist may cause irritation to the respiratory tract. 
Prolonged or high-level exposure could potentially lead to coughing, shortness of breath, or dizziness.

Use in a well-ventilated area, or consider using a fume hood when working with concentrated levulinic acid.
Although levulinic acid is not considered highly toxic, ingesting significant quantities could result in gastrointestinal distress, including nausea, vomiting, or diarrhea.
Avoid oral ingestion and keep the substance away from food or drink.