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Levulinic acid is used as a precursor for pharmaceuticals, plasticizers, and various other additives.
Synonyms: 4-Oxovaleric acid; NSC 3716
4.5
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 123-76-2 |
Formula : | C5H8O3 |
M.W : | 116.12 |
SMILES Code : | C(C(C)=O)CC(O)=O |
Synonyms : |
4-Oxovaleric acid; NSC 3716
|
MDL No. : | MFCD00002796 |
InChI Key : | JOOXCMJARBKPKM-UHFFFAOYSA-N |
Pubchem ID : | 11579 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H317-H318 |
Precautionary Statements: | P261-P264-P270-P272-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88 %Chromat. | With caesium carbonate In toluene for 2 h; | General procedure: Esterification of levulinic acid was carried out in a 50mL round bottom flask equipped with a reflux condenser. In a typical catalytic reaction the catalyst (40mg) was added to a mixture of levulinic acid and ethanol with the molar ratio of LA: alcohol=1:8 (ethanol acts as reagent cum solvent) and the mixture was magnetically stirred at 333K for 2h. A portion of the reaction mixture was separated after the scheduled reaction time through filtration and the filtrate was then analyzed through the gas chromatography (GC) equipped with a flame-ionized detector and a capillary column. All compounds were characterized on the basis of their spectroscopic data (1H NMR) and by comparison with those reported in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | In diethyl ether; at 20℃; | To a stirred solution of levulinic acid (2.8 g, 19.5 mmol) in 65 mL of ether at 0° C. was slowly added methyl magnesium bromide (3M, 13 mL, 39 mmol). The resulting solution was allowed to stir overnight at room temperature. The solution was cooled to 0° C., decomposed with 50percent sulfuric acid, extracted with ether, dried over magnesium sulfate, and concentrated to give 5,5-dimethyl-dihydro-furan-2-one (400 mg, 18percent) as a brown oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen; at 199.84℃; under 30003.0 Torr; for 4h;Autoclave;Catalytic behavior; | In a typical reaction, the batch autoclave reactor was loaded with catalyst, substrate, and solvent, purged three times with argon after which the reaction mixture was heated to reaction temperature and charged with H2 to 40?bar. This was taken as the starting point of the reaction. After the reaction was cooled to room temperature, the H2 was released, and 2?wtpercent anisole was added as internal standard. The catalyst was separated by centrifugation, filtration, and finally washed with acetone. The reaction products were analyzed using a Shimadzu GC-2010A gas chromatograph equipped with a CP-WAX 57-CB column (25?m?×?0.2?mm?×?0.2?mum) and FID detector. Products were identified with a GC?MS from Shimadzu with a CP-WAX 57CB column (30?m?×?0.2?mm?×?0.2?mum). The gas-phase reaction products were analyzed by an online dual channel Varian CP4900 micro-GC equipped with a COX column and TCD detector, for analysis of H2, CO2, CO, and CH4. Dioxane runs were performed with 10?wtpercent levulinic acid (2.5?g, 21.5?mmol) in dioxane (22.5?g) over a series of 1?wtpercent Ru catalysts (0.3?g) containing different supports. The reactions were run in a 50?mL Parr batch autoclave at a temperature of 473?K for 4?h using a hydrogen pressure 40?bar and a stirring speed of 1600?rpm. 2-Ethylhexanoic acid runs were performed with 10?wtpercent levulinic acid (6.0?g, 51.7?mmol) in 2-ethylhexanoic acid (54?g) with 1?wtpercent Ru catalysts (0.6?g). The reactions were run in 100?mL Parr batch autoclave at a temperature of 473?K for 10?h using a hydrogen pressure 40?bar and a stirring speed of 1600?rpm. 1?mL of solution was sampled at various intervals during the reaction. Reactions with intermediates GVL (2.2?g, 21.5?mmol) or PEA (2.2?g, 21.5?mmol) in EHA (22.8?g) were conducted with 0.3?g of catalyst in the 50?mL Parr batch autoclave. Finally, neat LA runs were performed with LA (20?g, 172?mmol) over 1?wtpercent Ru catalysts (0.3?g or 0.5?g). The reactions were run in a 50?mL Parr batch autoclave at a temperature of 473?K for 4?h and 10?h using a hydrogen pressure 40?bar and a stirring speed of 1600?rpm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11%Spectr. | With formic acid; dodecacarbonyl-triangulo-triruthenium; at 120℃; for 12h; | General procedure: In a typical experiment, a 25-mL Schlenk flask equipped with a Rotaflo valve and a magnetic stirrer was charged with 0.760 g of LA (6.54 mmol), 5 mg (Ru3CO12, 0.007 mmol), 3.27 mmol of amine (alkyl, aryl amine) and 315 mg of FA (6.54 mmol) at room temperature. This was heated at 120 C for 12 h. The mixture eventually dissolved in THF and was analyzed by CG-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12%Spectr.; 9%Spectr.; 5%Spectr. | With toluene-4-sulfonic acid; for 20h;Reflux; | General procedure: To a 25-mL Schlenk flask equipped with a Rotaflo valve and a magnetic stirrer was charged 2-alkynylaniline (0.26 mmol), 1.5 equiv. of p-toluenesulfonic monohydrate, 2.6 equiv. of LA and 3 mL of ethanol. The solution was stirred for 20 h in ethanol reflux in an oil bath. The mixture was then dissolved in THF and analyzed by GC-MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; hexane; at 199.84℃; for 0.25h;Autoclave; Inert atmosphere; Ionic liquid;Kinetics; Catalytic behavior; | Cellulose degradation is carried out in a 150 mL stainlessautoclave as a batch reactor. Typically, 5 g cellulose, desig-nated amount of cooperative ILs (20 g bmimCl and 3.5 mmolC4H8SO3HmimHSO4), 10 mL methanol and 80 mL hexane are addedto the reactor. After displacing the air in the reactor with nitro-gen, the reactor is heated and kept at designated temperature for15 min, and then the mixture of IL and products are cooled to roomtemperature for separation.The product from the cellulose degradation forms two phasesin a separating funnel, and is first separated. The heavy componentfraction is then exacted by hexane for three times to remove theresidual volatile chemical in the IL. By collecting the extract andthe upper phase product, the hexane-soluble fraction is obtained.After a sequence of IL removal operations (extracted by CH2Cl2) anddilution with methanol, the nonvolatile product from the cellulosedissolution and degradation process is obtained as the methanol-soluble fraction. The volatile components are determined with agas chromatography mass spectrometry (GC-MS). The molecularweight distribution of the methanol-soluble fraction is measuredwith a gel permeation chromatography (GPC) and the particle sizeof this fraction was measured with the Malvern analysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With acetic acid; for 4h;Reflux; | General procedure: Compound 1 (10 mmol) was dissolved in acetic acid (30 mL), andlevulinic acid (15 mmol) was added to the stirred solution which wasthen refluxed for 4 h. After cooling to room temperature, the mixturewas poured into water (200 mL) and then the solution was treated with30% sodium hydroxide to slight acidity (pH = 5-6). The precipitatedsolid was filtered off, recrystallised from ethanol and dried in vacuo togive compound 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.3% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃;Inert atmosphere; | In nitrogen protection, 0 C conditions, <strong>[84605-18-5]cycloastragenol</strong> (300 mg, 0.61 mmol), DMAP (160 mg, 1.22 mmol) and levulinic acid (350 mg, 3.06 mmol) were dissolved in dry dichloromethane (9 mL) and DCC (630 mg, 3.06 mmol) was added to the system. The system was slowly warmed to room temperature and stirred until the TLC trace showed complete reaction of the starting material. The reaction was extracted with ethyl acetate and washed successively with 1 mol / l HCl, saturated sodium bicarbonate, saturated NaCl and dried over anhydrous sodium sulfate. The reaction mixture was suction filtered, and the crude product was concentrated under reduced pressure. The residue was purified by column chromatography to obtain Compound 2 (413 mg, 98.3%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.99% | Add 100kg of levulinic acid and 1000L of carbon tetrachloride to the reactor.After adding 176 kg of sodium bromide and stirring, slowly add 260 kg of hydrogen peroxide solution.Heat to 60C for 2.5 hours, add water to wash, and separate organic phase.The aqueous phase treats the wastewater. To the organic phase, 75 kg of ammonium dithiocarbamate, 1000 kg of water, and 22 kg of sodium carbonate were directly added for the cyclization reaction.The aqueous phase is acidified with pH=1.5, obtaining2-mercapto-4-methyl-5-thiazoleacetic acid 132 kg, purity 99.92%,Yield 80.99%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ruthenium supported on montmorillonite K10; at 120℃; under 30003 Torr;Autoclave; | General procedure: 160ml, Parr). Autoclave was flled with an appropriateamount of catalyst (10wt% in case of Ru catalysts, 20wt%in case of Ni catalysts, based on levulinic acid), levulinicacid (10g, Merck, 98%), internal standard-mesitylene(0.8g, Acros Organics, 99%) and 100ml of solvent-toluene,1,4-dioxane, heptane, cyclohexane, methanol, propan-2-ol, propan-1-ol, butan-1-ol, ethyl acetate (all Penta, p.a.),ethanol (Penta, 96.5%) or butan-2-ol (Lachema, 99%). Samplestaken during the reaction were centrifuged and analyzedusing gas chromatograph coupled with mass detector(Shimadzu 2010 Plus, GCMS-QP2010 Ultra) equipped withnonpolar column DB-5. Injector temperature was 250C,the programmed temperature program ranged from 80C to250C using rate 10Cmin-1, detector voltage was 0.8kVand ion source had temperature 220C. Experiments wererepeated two times and the error between these two measurementswas not higher than 8%. Reuse experiment: reactionmixture was centrifuged, catalyst was separated and washed3 times with toluene (10ml). Wet catalyst was mixed withfresh reactants and the reaction was performed as usual. |
Tags: 123-76-2 synthesis path| 123-76-2 SDS| 123-76-2 COA| 123-76-2 purity| 123-76-2 application| 123-76-2 NMR| 123-76-2 COA| 123-76-2 structure
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