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Send EmailLevulinic Acid, Oxopentanoic Acid, Acetylpropionic Acid, Acetopropionic Acid, Ketovaleric Acid, Oxovaleric Acid, NSC 3716, 123-76-2
Levulinic Acid – Overview
Levulinic acid is a bio-based keto acid with the molecular formula C₅H₈O₃. It appears as a white crystalline solid, soluble in water and polar organic solvents. Derived from cellulose hydrolysis, it plays a key role in sustainable chemistry and green industrial applications.
Physical & Chemical Properties
| Property | Value |
|---|---|
| Chemical Formula | C₅H₈O₃ |
| CAS Number | 123-76-2 |
| Molar Mass | 116.11 g/mol |
| Density | 1.1447 g/cm³ |
| Melting Point | 33–35°C |
| Boiling Point | 245–246°C |
| Water Solubility | 675 g/L (at 20°C) |
Production Methods
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Biomass Hydrolysis: Acid-catalyzed breakdown of lignocellulosic materials
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Catalysts: Sulfuric or hydrochloric acid commonly used
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Alternative Routes:
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Heterogeneous catalysts for cleaner conversion
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Ionic liquids for enhanced solubility and selectivity
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Agricultural waste and animal biomass as feedstock
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Applications by Sector
Biofuels
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Precursor for ethyl levulinate and GVL
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Reduces fossil fuel dependency
Pharmaceuticals
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Intermediate for aminolevulinic acid (ALA)
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Used in photodynamic therapy and dermatology
Cosmetics
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Moisturizer and pH regulator
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Found in creams, shampoos, deodorants
Polymers & Plastics
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Plasticizer in bio-based formulations
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Enhances flexibility and biodegradability
Agriculture
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Soil conditioner and microbial stimulant
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Potential use in organic pesticides
Food Industry (Under Research)
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Investigated as a preservative
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Possible use in food-contact packaging
Alternative Chemicals
| Compound | Use Case |
|---|---|
| Itaconic Acid | Bio-based polymers |
| Furfural | Solvents and resins |
| Succinic Acid | Bioplastics and pharma |
| Adipic Acid | Nylon production |
| γ-Valerolactone | Biofuel additive |
Synonyms & IUPAC Names
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4-Oxopentanoic acid
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β-Acetylpropionic acid
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γ-Ketovaleric acid
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4-Oxovaleric acid
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Acetopropionic acid
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Pentanoic acid, 4-oxo-
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NSC 3716
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Laevulinic acid
Levulinic Acid vs Alternative Bio-Based Chemicals – Technical Comparison Table
| Feature / Compound | Levulinic Acid | Itaconic Acid | Succinic Acid | Adipic Acid | γ-Valerolactone (GVL) | Furfural |
|---|---|---|---|---|---|---|
| Source | Cellulose, biomass | Glucose, sugar | Biomass, glucose | Petrochemical | Derived from Levulinic Acid | Hemicellulose |
| Production Method | Acid hydrolysis | Fermentation | Fermentation | Oxidation of cyclohexane | Hydrogenation of Levulinic Acid | Acid-catalyzed pyrolysis |
| Pharmaceutical Use | ALA precursor | Antimicrobial agent | API intermediate | Polymer additive | Solvent in drug delivery | Antibacterial agent |
| Cosmetic Use | Moisturizer, pH regulator | Stabilizer | Hydrating agent | Not used | Mild solvent | Fragrance component |
| Biofuel Potential | Ethyl levulinate | Low | Moderate | None | High (GVL fuel additive) | Low |
| Polymer Applications | Plasticizer | Bio-based polymer | Bioplastics | Nylon production | Solvent for polymer synthesis | Resin modifier |
| Advantages | Versatile, bio-based | Fermentable | Low toxicity | High mechanical strength | High energy density | Aromatic structure |
| Challenges | Cost of production | Stability issues | Market volatility | Fossil-based origin | Requires hydrogenation | Low yield efficiency |
Key Insights
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GVL is a direct derivative of Levulinic Acid and offers superior energy density for biofuel applications.
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Itaconic Acid is ideal for sustainable polymer development but has formulation limitations.
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Succinic Acid is GRAS-certified and widely used in food and pharma sectors.
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Adipic Acid remains essential for nylon and technical textiles, though fossil-derived.
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Furfural excels in resin and solvent applications due to its aromatic nature, but suffers from low conversion efficiency.
