Name | Ethyl pyruvate |
Synonyms | PAEE PYR ET ETHYL PYRUVATE Ethyl pyruvate RARECHEM AL BI 0116 ETHYL 2-OXOPROPANOATE ethyl 2-oxopropanoate Ethyl 2-oxopropionate ETHYL 2-OXOPROPIONATE ETHYL 2-OXOPROPRIONATE PYRUVIC ACID ETHYL ESTER Pyruvic acid ethyl ester Brenztraubensaeure-ethylester Ethyl pyruvate,(Pyruvic acid ethyl ester) |
CAS | 617-35-6 |
EINECS | 210-511-2 |
InChI | InChI=1/C5H8O3/c1-3-8-5(7)4(2)6/h3H2,1-2H3 |
InChIKey | XXRCUYVCPSWGCC-UHFFFAOYSA-N |
Molecular Formula | C5H8O3 |
Molar Mass | 116.12 |
Density | 1.045 g/mL at 25 °C (lit.) |
Melting Point | -58 °C |
Boling Point | 144 °C (lit.) |
Flash Point | 114°F |
JECFA Number | 938 |
Water Solubility | Miscible with water, ethanol and ether. |
Solubility | 10g/l |
Vapor Presure | 2.36hPa at 25℃ |
Appearance | Liquid |
Color | Clear pale yellow |
Merck | 14,8021 |
BRN | 1071466 |
Storage Condition | Store at +2°C to +8°C. |
Stability | Volatile |
Refractive Index | n20/D 1.404(lit.) |
Physical and Chemical Properties | Density 1.06 boiling point 144°C refractive index 1.404-1.406 flash point 45°C |
Use | For the manufacture of pharmaceutical indole Xinan and pesticide thiabendazole |
Risk Codes | 10 - Flammable |
Safety Description | 16 - Keep away from sources of ignition. |
UN IDs | UN 3272 3/PG 3 |
WGK Germany | 3 |
TSCA | Yes |
HS Code | 29183000 |
Hazard Note | Flammable/Irritant |
Hazard Class | 3 |
Packing Group | III |
Toxicity | LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rat > 2000 mg/kg |
FEMA | 2457 | ETHYL PYRUVATE |
LogP | 0.435 at 22.5℃ |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
product description | ethyl pyruvate (English pyruvate), molecular formula is CH3COCOOC2H5, also known as ethyl 2-oxopropionate, is a colorless and transparent liquid at room temperature, has fresh and sweet flower and fruit aroma, and can be used in the blending of flavors such as apples, citrus and chocolate. It is an extremely important organic synthesis intermediate. It is used in medicine (synthetic thiamine drugs), pesticides (herbicides produced by DuPont, thiamine fungicides), food (can be used as preservatives, preservatives, etc.), Cosmetics and other industries have a wide range of uses. Ethyl pyruvate has a good effect on inhibiting the formation of tyrosinase in the epidermis, so it can prevent the formation of epidermal melanin and whiten the skin. It can also be added to the air freshener as an efficient active ingredient, which can effectively remove ammonia and methyl mercaptan in the air, and the smell is fresh and natural. Ethyl pyruvate has excellent performance in forming heterocyclic compounds. It is a raw material and intermediate that is difficult to replace in pesticide synthesis. It is widely used in the synthesis of fungicides and herbicides. Oxazolone derivatives synthesized from ethyl pyruvate are also good fungicides, which can effectively inhibit and kill fungi at a concentration of 5.0 × 10-4. Pyruvate is the main raw material for the production of tryptophan, phenylalanine, protein sugar and vitamin B. It is the raw material for the biosynthesis of L-dopa (dopa is used to treat Parkinson's syndrome) is the starter of ethylene polymer It is also the raw material for the preparation of grain protectants. An efficient herbicide was synthesized from pyruvate. The herbicide has excellent selectivity, good removal effect on sedge, Setaria and other weeds, and is safe for crops. As a feed and food additive, it has a good antiseptic and fresh-keeping function. At present, a small amount of it is used in the preservation of feed and fruit wine in China. Ethyl pyruvate itself has a special fragrance, which can be used in flavors and fragrances. It is also an important raw material for synthetic resins and plastics. Pyruvate ester products can also be used as special solvents for electronic materials, and foreign demand for applications in this area has increased rapidly. |
toxicity | GRAS(FEMA). |
usage limit | FEMA(mg/kg): beverage 50; Cold drinks 20~150; Candy 35; Baked products 40. The right amount is limited (FDA,§ 172.515,2001). |
use | ethyl pyruvate is an intermediate of the fungicide thiabendazole. Used in organic synthesis. It can be used to manufacture medicine indole and pesticide thiabendazole. At the same time, it is an important pharmaceutical and chemical intermediate, widely used in medicine, pesticides, flavors and fragrances, food additives, air fresheners, fine chemicals and other industries. It can be used to synthesize cardiovascular dilators and other drugs; it can also be used for whitening and nourishing skin cosmetics, which can promote skin wound healing, prevent and treat skin diseases characterized by cracking, peeling and scaling; it can be used as an air freshener The high-efficiency active ingredient in it can effectively remove ammonia and methyl mercaptan in the air; it has a special fragrance, so it can be used in flavors and fragrances; it is also an important raw material for synthetic resins and plastics. |
production method | obtained by oxidation of ethyl lactate with potassium permanganate. There are several preparation methods. Gas phase oxidation of ethyl lactate The gas phase oxidation of ethyl lactate is carried out in the presence of a catalyst, and MoO3 as a catalyst shows higher selectivity than other metal oxides. In addition, the binary oxide catalyst contains molybdenum oxides such as Fe2O3-MoO3 and TeO2-MoO3 for the synthesis of pyruvate. It has high selectivity (temperature 300 ℃, selectivity exceeds 90%). If SnO2-MoO3 is used as a catalyst, it can be carried out at a lower temperature of 250 ℃. SnO2-MoO3 catalyst can also be used as a catalyst for liquid phase oxidation of lactate. The reaction temperature is 130 ℃, the reaction time is 3h, the conversion rate of ethyl lactate is 38.4%, and the selectivity is 98.9% to generate ethyl pyruvate. Liquid phase oxidation of ethyl lactate ethyl lactate in the presence of a small amount of bromine as catalyst, and oxidation is carried out with H2O2 as oxidant. For example, 50% H2O2 is added dropwise to a stirred and illuminated dichloromethane solution containing ethyl lactate and bromine, the reaction temperature is 25 ℃, the H2O2 dropwise time is about 1.5h, and the reaction is continued for 3h after dropwise addition. The solution is neutralized with NaHCO3 and washed with Na2SO3 solution to destroy and remove ethyl lactate peroxide, then concentrate and distill under reduced pressure to obtain ethyl pyruvate. Acrylate oxide acrylate is oxidized to pyruvate by H2O2 in the presence of Cr or V compound catalyst. For example, isopropyl acrylate is stirred and added with H2O2 in acetonitrile solvent in the presence of chromium triacetoacetate. The reaction temperature is 50 ℃ for 8h to obtain isopropyl pyruvate. The selectivity is 99.1% and the conversion rate is 87.9%. Another example is methyl acrylate added to triethylamine in the presence of chromium triacetoacetate or chromic acid for 20h, the temperature is 40 ℃, the selective 72%, the conversion rate is 82%, and methyl pyruvate is obtained. In addition, acetone aldehyde and methanol react in the gas phase in the presence of nickel phosphate catalyst to obtain methyl pyruvate. |