Ethyl levulinate

Base Information

• Chemical Name: Ethyl levulinate
• CAS No.: 539-88-8
• Deprecated CAS: 1790637-12-5
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• Hs Code.: 2918.30 Oral rat LD50: >5 gm/kg
• European Community (EC) Number: 208-728-2
• NSC Number: 24876,8863
• UNII: 7BU24CSS2G
• DSSTox Substance ID: DTXSID8047058
• Nikkaji Number: J1.595D
• Wikipedia: Ethyl_levulinate
• Wikidata: Q27268032
• RXCUI: 1313748
• Metabolomics Workbench ID: 49041
• ChEMBL ID: CHEMBL3182933
• Mol file: 539-88-8.mol

Synonyms:ethyl 4-ketovalerate;ethyl 4-oxopentanoate;ethyl acetylpropanoate;ethyl levulinate

Chemical Property of Ethyl levulinate

Chemical Property:

• Appearance/Colour: clear yellowish liquid
• Vapor Pressure: 0.249mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: 1.420 - 1.425
• Boiling Point: 205.499 °C at 760 mmHg
• Flash Point: 919 °C
• PSA: 43.37000
• Density: 0.996 g/cm³
• LogP: 0.91870
• Storage Temp.: 2-8°C
• Solubility.: H2O: freely soluble
• Water Solubility.: Soluble in water.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

99% ^*data from raw suppliers

Ethyl levulinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CCC(=O)C
• Uses: Solvent for cellulose acetate and starch ethers, flavoring. Ethyl levulinate is used to develop a preparative HPLC method to preserve wine aromas and isolates fruity characteristics of red wine aroma extracts Ethyl levulinate was used to develop a preparative HPLC method to preserve wine aromas and isolates fruity characteristics of red wine aroma extracts.

Technology Process of Ethyl levulinate

There total 198 articles about Ethyl levulinate 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: 100.0%

ethanol (64-17-5) + levulinic acid (123-76-2) → 4-oxopentanoic acid ethyl ester (539-88-8)

Guidance literature:

With Zirconium Exchanged Phosphotungstic Acid; at 120 ℃; for 2h; Temperature;

DOI:10.1007/s10562-019-02862-z

Reference yield: 96.92%

(2-furyl)methyl alcohol (98-00-0,25212-86-6,93793-62-5) + ethanol (64-17-5) → 4-oxopentanoic acid ethyl ester (539-88-8)

Guidance literature:

With MCM-41; amberlyst-15; In ethyl acetate; at 15 - 80 ℃; for 5h; Temperature; Solvent; Reagent/catalyst;

Reference yield: 84.0%

D-Fructose (57-48-7,18875-34-8) + ethanol (64-17-5) → 4-oxopentanoic acid ethyl ester (539-88-8)

Guidance literature:

With poly(p-styrenesulfonic acid)-grafted carbon nanotubes; at 120 ℃; for 24h; Reagent/catalyst; chemoselective reaction; Sealed tube; Green chemistry;

DOI:10.1039/c3gc41139g

upstream raw materials:

diazomethane

5-methyl-2-furanone

ethanol

(2-furyl)methyl alcohol

Downstream raw materials:

Ethyl levulinate ethylene ketal

(2-methyl-5-oxo-tetrahydro-furan-2-yl)-acetic acid ethyl ester

4-(diamino-[1,3,5]triazin-2-yl)-butan-2-one

dihydro-5-butyl-5-methyl-2-(3H)-furanone

Refernces

• 1、 Ganji, Parameswaram,Roy, Sounak. "Conversion of levulinic acid to ethyl levulinate using tin modified silicotungstic acid supported on Ta2O5". . . Retrieved 2020.
• 2、 Li, Xiaoning,Li, Yehui,Wang, Xiang,Peng, Qingrui,Hui, Wei,Hu, Aiyun,Wang, Haijun. "Zr-DBS with Sulfonic Group: A Green and Highly Efficient Catalyst for Alcoholysis of Furfuryl Alcohol to Ethyl Levulinate". . p. 2622 - 2630. Retrieved 2021.
• 3、 Fan, Jingdeng,Gao, Lijing,Hu, Feng,Qu, Xumin,Wei, Ruiping,Wu, Yuanfeng,Xiao, Guomin,Zhang, Zongqi. "Tuning the Catalytic Activity of UiO-66 via Modulated Synthesis: Esterification of Levulinic Acid as a Test Reaction". . . Retrieved 2020.
• 4、 Bosilj, Monika,Schmidt, Johannes,Fischer, Anna,White, Robin J.. "One pot conversion of glucose to ethyl levulinate over a porous hydrothermal acid catalyst in green solvents". . p. 20341 - 20344. Retrieved 2019.
• 5、 Song, Daiyu,Sun, Yingnan,Zhang, Qingqing,Zhang, Panpan,Guo, Yihang,Leng, Jiyan. "Fabrication of propylsulfonic acid functionalized SiO2 core/PMO shell structured PrSO3H-SiO2@Si(R)Si nanospheres for the effective conversion of D-fructose into ethyl levulinate". . p. 36 - 46. Retrieved 2017.
• 6、 An, Sai,Song, Daiyu,Lu, Bo,Yang, Xia,Guo, Yi-Hang. "Morphology Tailoring of Sulfonic Acid Functionalized Organosilica Nanohybrids for the Synthesis of Biomass-Derived Alkyl Levulinates". . p. 10786 - 10798. Retrieved 2015.
• 7、 Yan, Kai,Wu, Guosheng,Wen, Jiali,Chen, Aicheng. "One-step synthesis of mesoporous H4SiW12O 40-SiO2 catalysts for the production of methyl and ethyl levulinate biodiesel". . p. 58 - 63. Retrieved 2013.
• 8、 Zhang, Zhi,Yuan, Hong,Wang, Yunjie,Ke, Yihu. "Preparation and characterisation of ordered mesoporous SO4 2?/Al2O3 and its catalytic activity in the conversion of furfuryl alcohol to ethyl levulinate". . . Retrieved 2019.
• 9、 Drache, Franziska,Cirujano, Francisco G.,Nguyen, Khoa D.,Bon, Volodymyr,Senkovska, Irena,Llabrés I Xamena, Francesc X.,Kaskel, Stefan. "Anion Exchange and Catalytic Functionalization of the Zirconium-Based Metal-Organic Framework DUT-67". . p. 5492 - 5500. Retrieved 2018.
• 10、 Chen, Qifeng,Duan, Ran,Gao, Guanggang,Gao, Guoming,Hu, Xun,Lv, Mingxuan,Shao, Yuewen,Wang, Yi,Zhang, Shu,Zhao, Hui. "Crystal facet-dependent activity of h-WO3for selective conversion of furfuryl alcohol to ethyl levulinate". . p. 26923 - 26934. Retrieved 2020.