gamma-Valerolactone

Base Information

• Chemical Name: gamma-Valerolactone
• CAS No.: 108-29-2
• Deprecated CAS: 57129-69-8
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29322980
• European Community (EC) Number: 203-569-5
• NSC Number: 33700
• UN Number: 1224
• UNII: O7056XK37X
• DSSTox Substance ID: DTXSID0047618
• Nikkaji Number: J5.072E
• Wikipedia: Gamma-Valerolactone
• Wikidata: Q845530
• Pharos Ligand ID: VK4JAPF8T9B3
• Metabolomics Workbench ID: 4342
• ChEMBL ID: CHEMBL195593
• Mol file: 108-29-2.mol

Synonyms:4-valerolactone;gamma-valerolactone

Chemical Property of gamma-Valerolactone

Chemical Property:

• Appearance/Colour: colorless to pale yellow clear liquid
• Vapor Pressure: 0.235mmHg at 25°C
• Melting Point: -31 °C(lit.)
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 206.624 °C at 760 mmHg
• Flash Point: 74.98 °C
• PSA: 26.30000
• Density: 1.05 g/cm³
• LogP: 0.71190
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform, Methanol
• Water Solubility.: MISCIBLE
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 88.1
• Transport DOT Label: Flammable Liquid

Purity/Quality:

≥99% ^*data from raw suppliers

γ-Valerolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 39-26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Lactones
• Canonical SMILES: CC1CCC(=O)O1
• Chemical Composition and Structure: The chemical formula of Gamma-valerolactone (GVL) is C5H8O2. It is a lactone, specifically a five-membered cyclic ester, with a molecular weight of approximately 100.12 g/mol.
• Physical Properties: Gamma-valerolactone (GVL) is a colorless liquid with a high boiling point (480 K) and low vapor pressure (0.28 Torr at 296 K). It has a relatively large oxygen content, making it favored as a gasoline substitute or additive.
• Uses and Mechanism of Action: As a green solvent: Gamma-valerolactone (GVL) is praised for its solvent properties and can potentially replace harmful solvents in various applications, such as in the manufacture of polymers, pharmaceuticals, paint and coating formulations, cosmetics, and agrochemicals.^[1]; As a biofuel additive: Gamma-valerolactone (GVL) has been investigated as a potential additive to gasoline due to its desirable physical and chemical properties. It has been shown to reduce emissions and improve octane ratings in fuel blends.^[2]
• Production Methods: GVL can be produced from levulinic acid, which can be obtained from lignocellulosic biomass. Ionic liquids have been investigated as catalysts for the hydrogenation of levulinic acid to GVL.
• References: [1] The green platform molecule gamma-valerolactone – ecotoxicity, biodegradability, solvent properties, and potential applications; DOI 10.1039/D0GC04353B; [2] Ionic liquids for the sustainable transformation of levulinic acid to gamma-valerolactone (GVL); DOI 10.1016/j.cogsc.2022.100607

Technology Process of gamma-Valerolactone

There total 412 articles about gamma-Valerolactone 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: 16.8%

propan-1-ol (71-23-8) + 4-oxopentanoic acid ethyl ester (539-88-8) → n-propyl levulinate (645-67-0) + 5-methyl-dihydro-furan-2-one (108-29-2)

Guidance literature:

With graphene oxide-supported zirconia; at 180 ℃; for 3h; under 7500.75 Torr; Inert atmosphere; Sealed tube; Autoclave;

DOI:10.1007/s10562-019-02835-2

Reference yield:

4-bromo-valeric acid (1450-80-2) + water (7732-18-5) → hydrogen bromide (10035-10-6,12258-64-9) + 5-methyl-dihydro-furan-2-one (108-29-2)

Guidance literature:

Reference yield:

4-bromo-valeric acid (1450-80-2) → hydrogen bromide (10035-10-6,12258-64-9) + 5-methyl-dihydro-furan-2-one (108-29-2)

Guidance literature:

upstream raw materials:

5-methyl-2-furanone

1,4-Pentanediol

pent-4-enoic acid

4-hydroxyvaleric amide

Downstream raw materials:

4-(2,5-Dimethylphenyl)valeriansaeure

6-(Phenylsulfonyl)-2-hydroxyundecan-5-one

2-(4'-hydroxy-1'-oxopentyl)-N,N-bis-(methylethyl)benzamide

α-(diphenylmethylsilyl)-γ-valerolactone

Refernces

• 1、 Bourne, Richard A.,Stevens, James G.,Ke, Jie,Poliakoff, Martyn. "Maximising opportunities in supercritical chemistry: The continuous conversion of levulinic acid to γ-valerolactone in CO2". . p. 4632 - 4634. Retrieved 2007.
• 2、 Kumar, V. Vijay,Naresh,Deepa,Bhavani, P. Ganga,Nagaraju,Sudhakar,Chary,Venugopal,Tardio,Bhargava. "Influence of W on the reduction behaviour and Br?nsted acidity of Ni/TiO2catalyst in the hydrogenation of levulinic acid to valeric acid: Pyridine adsorbed DRIFTS study". . p. 169 - 176. Retrieved 2017.
• 3、 Wojciechowska, Joanna,J?drzejczyk, Marcin,Grams, Jacek,Keller, Nicolas,Ruppert, Agnieszka M.. "Enhanced Production of Γ-Valerolactone with an Internal Source of Hydrogen on Ca-Modified TiO2 Supported Ru Catalysts". . p. 639 - 650. Retrieved 2019.
• 4、 Verma, Sanny,Baig, R. B. Nasir,Nadagouda, Mallikarjuna N.,Varma, Rajender S.. "Sustainable Strategy Utilizing Biomass: Visible-Light-Mediated Synthesis of γ-Valerolactone". . p. 690 - 693. Retrieved 2016.
• 5、 Du, Xian-Long,Bi, Qing-Yuan,Liu, Yong-Mei,Cao, Yong,Fan, Kang-Nian. "Conversion of biomass-derived levulinate and formate esters into γ-valerolactone over supported gold catalysts". . p. 1838 - 1843. Retrieved 2011.
• 6、 Jefford, Charles W.,Wang, Ying. "Selective, Heterogeneous Oxidation of Alcohols and Diols with Potassium Permanganate". . p. 634 - 635. Retrieved 1988.
• 7、 Bui, Linh,Luo, Helen,Gunther, William R.,Román-Leshkov, Yuriy. "Domino reaction catalyzed by zeolites with Br?nsted and Lewis acid sites for the production of γ-valerolactone from furfural". . p. 8022 - 8025. Retrieved 2013.
• 8、 Yang, Xiaohai,Xiang, Xiaomin,Chen, Hongmei,Zheng, Hongyan,Li, Yong-Wang,Zhu, Yulei. "Efficient Synthesis of Furfuryl Alcohol and 2-Methylfuran from Furfural over Mineral-Derived Cu/ZnO Catalysts". . p. 3023 - 3030. Retrieved 2017.
• 9、 Bhatia, Anita,Kannan, Muthukumar,Muthaiah, Senthilkumar. "Ruthenium-Promoted Acceptorless and Oxidant-Free Lactone Synthesis in Aqueous Medium". . p. 721 - 725. Retrieved 2019.
• 10、 Lomate, Samadhan,Sultana, Asima,Fujitani, Tadahiro. "Effect of SiO2 support properties on the performance of Cu-SiO2 catalysts for the hydrogenation of levulinic acid to gamma valerolactone using formic acid as a hydrogen source". . p. 3073 - 3083. Retrieved 2017.