Levulinic acid
Levulinic acid
CAS: 123-76-2
Molecular Formula: C5H8O3
Levulinic acid - Names and Identifiers
| Name | Levulinic acid |
| Synonyms | aevuL 4-oxovaleric Levulic Acid laevulic acid Levulinic acid 4-oxopentanoate 4-oxovaleric acid 4-oxo-pentanoicaci 4-Oxopentanoic acid 2-Acetopropionicacid 4-Keto-n-valericacid 4-Ketopentanoic acid 4-Oxopentanoic acid) sodium 4-oxopentanoate 2-methyl-3-oxobutanoic acid calcium bis(4-oxopentanoate) Levulinic acid 4-oxopentanoic acid Levulinic acid,(4-Ketopentanoic acid 4-Oxo-pentanoic acid (levulinic acid) |
| CAS | 123-76-2 |
| EINECS | 204-649-2 |
| InChI | InChI=1/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)/p-1 |
| InChIKey | JOOXCMJARBKPKM-UHFFFAOYSA-N |
Levulinic acid - Physico-chemical Properties
| Molecular Formula | C5H8O3 |
| Molar Mass | 116.12 |
| Density | 1.134 g/mL at 25 °C (lit.) |
| Melting Point | 30-33 °C (lit.) |
| Boling Point | 245-246 °C (lit.) |
| Flash Point | 280°F |
| JECFA Number | 606 |
| Water Solubility | Soluble in water ( 675g/L at 20°C). |
| Solubility | 675g/l |
| Vapor Presure | 1 mm Hg ( 102 °C) |
| Appearance | White crystal |
| Color | Clear yellow |
| Merck | 14,5472 |
| BRN | 506796 |
| pKa | pKa 4.65(H2O,t = 25,c=0.03-0.001) (Uncertain) |
| Storage Condition | Store below +30°C. |
| Sensitive | Light Sensitive |
| Refractive Index | n20/D 1.439(lit.) |
| MDL | MFCD00002796 |
| Physical and Chemical Properties | Character: white flaky crystal with hygroscopicity. melting point 37.2 ℃ boiling point 139~140 ℃ relative density 1.1335 refractive index 1.4396 soluble in water and alcohol, ether organic solvents. |
| Use | Used as raw materials for medicines, spices, coatings, and as solvents |
Levulinic acid - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R34 - Causes burns |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | 3261 |
| WGK Germany | 3 |
| RTECS | OI1575000 |
| TSCA | Yes |
| HS Code | 29183000 |
| Hazard Class | 8 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 1850 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
Levulinic acid - Upstream Downstream Industry
| Raw Materials | Starch potato Furfuryl alcohol |
| Downstream Products | Indomethacin 4,4'-Azobis(4-cyanovaleric acid) |
Levulinic acid - Reference
| Reference Show more | 1. Zhang Xifeng, Wang Xinxin, Zhang Qingting, Luo Guanghong. Temperature-sensitive eutectic solvent aqueous two-phase extraction separation of peony seed meal polysaccharides for oil [J]. Chinese grease, 2020,45(12):93-99. 2. Chen, Jianqiu, et al. "Investigations into the production of volatile compounds in Korla fragrant pears (Pyrus sinkiangensis Yu)." Food chemistry 302 (2020): 125337.https://doi.org/10.1016/j.foodchem. 2019.125337 3. Wang, Tianyang, et al. "Metabolomic profile perturbations of serum, lung, bronchoalveolar lavage fluid, spleen and feces in LPS-induced acute lung injury rats based on HPLC-ESI-QTOF-MS." Analytical and bioanalytical chemistry 412.5 (2020): 1215-1234. 4. [IF=5.686] Wendi Dong et al."Rare-Earth Metal Yttrium-Modified Composite Metal Oxide Catalysts for High Selectivity Synthesis of Biomass-Derived Lactic Acid from Cellulose."ChemCatChem. 2022 Apr 14 |
Levulinic acid - Nature
Open Data Verified Data
White Flake Crystal, flammable, hygroscopic. Soluble in water and alcohol, ether organic solvents. Distillation at atmospheric pressure hardly decomposes, and if heated for a long time, water is lost to become unsaturated Y-lactone. Melting point 37.2 °c. Boiling point 139~140 deg C (lkPa). The relative density was 1.1335. Refractive index 4396.
Last Update：2024-01-02 23:10:35
Levulinic acid - Preparation Method
Open Data Verified Data
The cellulose residue or waste sweet potato residue from the production of furfural from cottonseed shells or corncob is hydrolyzed with hydrochloric acid under pressure (above 150 ℃, 350 ~ 500kPa), filtered and vacuum distilled to obtain a finished product. In addition, furfuryl alcohol in the presence of hydrochloric acid, pressure hydrolysis can also be prepared this product.
Last Update：2022-01-01 10:31:35
Levulinic acid - Introduction
Sensitive to light. It's hygroscopic. Distillation under normal pressure hardly decomposes, and long-term heating loses water molecules to form unsaturated γ-lactone. Easily soluble in water, alcohols and ethers, almost insoluble in aliphatic hydrocarbons. Low toxicity, half lethal dose (rat, oral) 1850mg/kg.
Last Update：2022-10-16 17:12:53
Levulinic acid - Use
Open Data Verified Data
This product is mainly used as raw materials and solvents for resins, medicines, spices and coatings. In the pharmaceutical industry, its calcium salt can be made into intravenous injection and indomethacin. Its lower ester can be used as food flavor or tobacco flavor. The water-soluble resin can be produced by the acid, which is used in the production of filter paper in the paper industry. It can also be used for the preparation of pesticides (such as plant hormones, etc.), dyes and surfactants.
Last Update：2022-01-01 10:31:35
Levulinic acid - Safety
Open Data Verified Data
This product has low toxicity. It is packed in plastic barrels and reinforced with wooden cases. Store in a cool, dry and ventilated place. Stay away from the fire. According to the provisions of flammable chemicals storage and transportation.
Last Update：2022-01-01 10:31:35
Levulinic acid - Reference Information
| FEMA | 2627 | LEVULINIC ACID |
| LogP | -0.498 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| application | levulinic acid has a wide range of applications. Levulinic acid can react as a carboxylic acid and as a ketone. Through esterification, halogenation, hydrogenation, oxidative dehydrogenation, condensation, etc., various products are prepared, including resins, medicines, fragrances, solvents, coatings and inks, Rubber and plastic additives, lubricating oil additives, surfactants, etc. In the pharmaceutical industry, its calcium salt (calcium fructose) can be used for intravenous injection. As a nutritional medicine, it helps the formation of bone and maintains the normal excitability of nerves and muscles. It is also used to produce indomethacin and plant hormones. Bisphenol acid prepared from levulinic acid can be used to make water-soluble resin, which is used in the paper industry to produce filter paper. Levulinic acid is also an intermediate of pesticides and dyes. |
| content analysis | accurately weigh about 1.0g of the sample, put it into a 250ml triangular flask containing 75-100ml of water, add phenolphthalein test solution, titrate with 0.5mol/L sodium hydroxide until pink starts to appear and maintain for 15s. Each ml0.5mol/L sodium hydroxide solution is equivalent to 58.08mg of this product. |
| toxicity | GRAS(FEMA). |
| usage limit | FEMA(mg/kg): beverages, cold drinks, 14.0; Candy, baked goods, 53.0; Gelatin jelly, pudding, 4.0. FDA,§ 172.515(2000): The right amount is limited. |
| Preparation | A method for separating levulinic acid from monosaccharide hydrolysate, using ion exchange resin adsorption method to extract and separate high-purity levulinic acid from monosaccharide hydrolysate method. The technical solution is the following steps: the monosaccharide hydrolysate is used as the starting material, and the high content of levulinic acid is obtained by column chromatography separation, atmospheric concentration and vacuum distillation; the entire separation process is as follows: 1) The weakly basic anion exchange resin is loaded with a wet method, and then pretreated for standby; the monosaccharide hydrolysate is passed through a chromatography column, the flow rate is 0.5-3.0 times the bed volume/hour, and the temperature is 20-40 ℃;2) Rinse the chromatography column with deionized water, wash off the neutral impurities in the monosaccharide hydrolysate, the flow rate is 0.5~3.0 times the volume of the bed layer/hour, and the temperature is 20~40 ℃:3) Use 0.1~1.0mol/l The elution solution elutes levulinic acid adsorbed on the resin, the flow rate is 0.3~2.0 times the volume of the bed layer/hour, and the temperature is 20~40 ℃; the eluate is collected in sections, the high content of levulinic acid is obtained by combining the flow fraction of pure levulinic acid aqueous solution, concentration at normal pressure and rectification at 0.01 ~ 0.05MPa. |
| Use | Used as a raw material for medicines, fragrances, and coatings, and as a solvent As an important chemical raw material or solvent, it can be used in the production of medicines (intravenous injections, indomethacin, etc.), resins (bisphenol acid water-soluble resins), fragrances (edible fragrances or tobacco fragrances), paints, coatings, pesticides, dyes and surfactants, etc. Biochemical research. Manufacture of esters and drugs. Inhibitors of chlorophyll synthesis. Used as a biochemical reagent and also used in organic synthesis |
| production method | the residue (furfural residue) or waste sweet potato residue after sugar aldehyde production from cotton seed husk or corncob can be hydrolyzed with dilute acid to obtain levulinic acid. The glycolic residue is added into the 10% dilute hydrochloric acid, the curing solution is 1:1.75, mixed evenly, put into a hydrolysis pot, and steamed at 0.2MPa pressure for 8-10h. Then the hydrolyzed dilute liquid is filtered and concentrated to a concentration of about 50%. Then vacuum distillation is carried out, and fractions above 130 ℃(2.67kPa) are collected to obtain the finished product. Raw material consumption quota: sweet potato standard chartered 7000 kg/t, hydrochloric acid (converted into 100%)1800 kg/t. Another preparation method is made by rearrangement and hydrolysis of sugar alcohols. Add 4% hydrochloric acid solution to the reaction pot, stir and heat to 97-100 ℃, and slowly add the mixed solution of furfuryl alcohol, ethanol and water. After adding, stir for 30min. Filtration, the filtrate is concentrated under reduced pressure at 80 ℃(21.3kPa) to obtain crude levulinic acid solution. Then decompressed distillation, 160-170 ℃(2.67kPa) fractions were collected, and then redistilled to obtain refined levulinic acid with a yield of about 75%. |
Last Update：2024-04-09 02:00:06
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Raw Materials for Levulinic acid
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