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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.
