Methyl levulinate

Base Information

• Chemical Name: Methyl levulinate
• CAS No.: 624-45-3
• Molecular Formula: C6H10 O3
• Molecular Weight: 130.144
• Hs Code.: 2918300090
• European Community (EC) Number: 210-846-4
• NSC Number: 24874
• UNII: 3Q95S830W6
• DSSTox Substance ID: DTXSID80211455
• Nikkaji Number: J45.094D
• Wikidata: Q27257899
• Metabolomics Workbench ID: 49440
• Mol file: 624-45-3.mol

Synonyms:levulinic acid, methyl ester;methyl levulinate;methyl-4-oxopentanoate;methyl-4-oxovalerate

Chemical Property of Methyl levulinate

Chemical Property:

• Appearance/Colour: Colorless liquid with a pleasant odor.
• Vapor Pressure: 0.408mmHg at 25°C
• Melting Point: 237 °C
• Refractive Index: n20/D 1.422
• Boiling Point: 193-195 ºC
• Flash Point: 72°C
• PSA: 43.37000
• Density: 1.051
• LogP: 0.52860
• Storage Temp.: Refrigerator
• Solubility.: It is soluble in ethanol, ether, acetone and benzene.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

Methyl Levulinate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)CCC(=O)OC
• Uses: Methyl levulinate is mainly used as raw material on perfume.

Technology Process of Methyl levulinate

There total 236 articles about Methyl 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: 69.0%

methanol (67-56-1) + D-Fructose (57-48-7,18875-34-8) → 5-(methoxymethyl)-2-furaldehyde (1917-64-2) + levulinic acid methyl ester (624-45-3)

Guidance literature:

With poly(p-styrenesulfonic acid)-grafted carbon nanotubes; at 100 ℃; for 24h; chemoselective reaction; Sealed tube; Green chemistry;

DOI:10.1039/c3gc41139g

Reference yield: 58.2%

methanol (67-56-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 5-(methoxymethyl)-2-furaldehyde (1917-64-2) + levulinic acid methyl ester (624-45-3)

Guidance literature:

methanol; 5-hydroxymethyl-2-furfuraldehyde; sulfuric acid; In water; at 60 ℃; for 2h;

In methanol; water; at 220 ℃; for 0.0666667h; under 48754.9 Torr; Product distribution / selectivity;

Reference yield: 56.4%

methanol (67-56-1) + α-D-fructofuranose (10489-79-9) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + 5-(methoxymethyl)-2-furaldehyde (1917-64-2) + levulinic acid methyl ester (624-45-3) + 2-(dimethoxymethyl)-5-(methoxymethyl)furan (110339-34-9)

Guidance literature:

With C₇H₇NO₂*3H⁽¹⁺⁾*O₄₀PW₁₂^(3-); at 120 ℃; for 10h; Reagent/catalyst; Catalytic behavior; Sealed tube;

DOI:10.1039/c8ra02278j

upstream raw materials:

diazomethane

5-methyl-2-furanone

methanol

(2-furyl)methyl alcohol

Downstream raw materials:

5-methoxy-2-methyl-1-(phenylmethyl)-1H-indol-3-ylacetic acid

methyl 3-chlorolevulinate

(+/-)-1,4-bis-phenylcarbamoyloxy-pentane

(R)-5-methyl-2-oxotetrahydrofuran

Refernces

• 1、 Zhou, Lipeng,Zou, Haojie,Nan, Jiaxu,Wu, Lin,Yang, Xiaomei,Su, Yunlai,Lu, Tianliang,Xu, Jie. "Conversion of carbohydrate biomass to methyl levulinate with Al 2(SO4)3 as a simple, cheap and efficient catalyst". . p. 13 - 16. Retrieved 2014.
• 2、 Adam, Waldemar,Griesbeck, Axel G.,Gollnick, Klaus,Knutzen-Mies, Karen. "1,2-Dioxetanes Derived from 4,5-Dimethyl-2,3-dihydrofuran and 4,5-Dimethyl-2,3-dihydrothiophene: Synthesis via Photooxygenation, Activation Parameters, and Excitation Properties". . p. 1492 - 1495. Retrieved 1988.
• 3、 Deng, Weiping,Liu, Mi,Zhang, Qinghong,Tan, Xuesong,Wang, Ye. "Acid-catalysed direct transformation of cellulose into methyl glucosides in methanol at moderate temperatures". . p. 2668 - 2670. Retrieved 2010.
• 4、 Zhao, Wenguang,Ding, Hui,Tian, Yi,Xu, Qiong,Liu, Xianxiang. "Efficient alcoholysis of furfuryl alcohol to n-butyl levulinate catalyzed by 5-sulfosalicylic acid". . p. 1339 - 1345. Retrieved 2021/02/26.
• 5、 Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He. "Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water". . p. 4327 - 4337. Retrieved 2021/05/31.