CH3OCOCOOCH3
Dimethyl oxalate
CAS: 553-90-2
Molecular Formula: C4H6O4
CH3OCOCOOCH3 - Names and Identifiers
| Name | Dimethyl oxalate |
| Synonyms | CH3OCOCOOCH3 Methyl oxalate Dimethyl oxalate Tricholomic acid Dihydro-ibotenic acid dimethyl ethanedioate OXALIC ACID METHYL ESTER Oxalic acid dimethyl ester OXALIC ACID DIMETHYL ESTER OXALIC ACID BIS-METHYL ESTER Ethanedioicaciddimethylester Ethanedioicacid,dimethylester Dimethyl ester of oxalic acid Ethanedioc acid dimethyl ester |
| CAS | 553-90-2 |
| EINECS | 209-053-6 |
| InChI | InChI=1/C4H6O4/c1-7-3(5)4(6)8-2/h1-2H3 |
| InChIKey | LOMVENUNSWAXEN-UHFFFAOYSA-N |
CH3OCOCOOCH3 - Physico-chemical Properties
| Molecular Formula | C4H6O4 |
| Molar Mass | 118.09 |
| Density | 1.148 g/mL at 25 °C (lit.) |
| Melting Point | 50-54 °C (lit.) |
| Boling Point | 163.5 °C (lit.) |
| Flash Point | 167°F |
| Water Solubility | 60 G/L (25 ºC) |
| Solubility | ethanol: soluble50mg/mL, clear to very slightly hazy, colorless |
| Vapor Presure | 3 hPa (20 °C) |
| Appearance | Crystalline Solid |
| Specific Gravity | 1.148 |
| Color | Colorless to white |
| Merck | 14,6106 |
| BRN | 1071744 |
| PH | 1 (60g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, acids, bases, reducing agents. |
| Refractive Index | n20/D 1.39(lit.) |
| Physical and Chemical Properties | Colorless monoclinic crystal. Melting point 54 ℃, boiling point 163.5 ℃, relative density 1.1479(54 ℃), refractive index 1.379(82.1 ℃), flash point 75 ℃. Soluble in alcohol and ether, soluble in about 17 parts of water, decomposed in hot water. |
| Use | Mainly used in pharmaceutical, pesticide, organic synthesis, also used as plasticizer |
CH3OCOCOOCH3 - Risk and Safety
| Risk Codes | R36/38 - Irritating to eyes and skin. R36 - Irritating to the eyes R22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S24/25 - Avoid contact with skin and eyes. S23 - Do not breathe vapour. |
| UN IDs | 1759 |
| WGK Germany | 3 |
| RTECS | RO2850000 |
| TSCA | Yes |
| HS Code | 2917 11 00 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
CH3OCOCOOCH3 - Upstream Downstream Industry
| Raw Materials | Oxalic acid Oxalic acid Methyl alcohol |
| Downstream Products | sulfamethoxazole |
CH3OCOCOOCH3 - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | dimethyl oxalate chemical formula CH3OOCCOOCH3. Melting point 50~54 ℃, boiling point 163.5 ℃, relative density 1.148, refractive index 1.379. Soluble in ether, benzene, chloroform, slightly soluble in water. Condensation reaction can be carried out with certain ketones. Dimethyl oxalate is mainly used in organic synthesis, and can also be used in plasticizers, pharmaceuticals, pesticides and other industries. Carbon monoxide gas phase catalytic coupling synthesis of dimethyl oxalate as a part of the synthesis gas to ethylene glycol technology, has become an important research topic in the field of carbon chemistry and organic chemical industry in China. |
| application | dimethyl oxalate, as an important chemical and pharmaceutical raw material, is often used to prepare various organic solvents, extractants, adhesives, plasticizers and various pharmaceutical intermediates, such as for the synthesis of vitamin B13, hydrogenation to prepare methyl glycolate, ethylene glycol, instead of diethyl oxalate to synthesize sulfamethoxazole, etc. For example, dimethyl oxalate is used instead of diethyl oxalate as the starting raw material, and without changing the rest of the production process and raw materials, 5-methyl -3-formyl isoxazole is produced through multi-step reactions such as Krechellol, acidification, cyclization and ammonolysis, and the obtained products are inspected and analyzed, and it is found that there is no difference in product quality; at the same time, because the price of dimethyl oxalate is lower than that of diethyl oxalate, the production cost of the product is reduced, improved its competitiveness in the market. Dimethyl oxalate can also react with ammonia to produce oxalamide, oxalamide can be used as a stabilizer for nitrocellulose products, and can be used as a gas agent and cooling agent in the gas generator, and oxalamide can also be used as slow-release nitrogen fertilizer. |
| Preparation | Nitric oxide is prepared and carbonylated to synthesize dimethyl oxalate. The raw material carbon monoxide of the carbonylation reaction is stirred as a gas, and sodium nitrite and dilute nitric acid are fully reacted in the NO preparation reactor to produce nitric oxide, which is supplemented with the carbon monoxide used for stirring to the dimethyl oxalate circulation system for esterification, Carbonylation, finally synthesis of dimethyl oxalate; specifically including the following process steps: ①The concentration of dilute nitric acid in the NO preparation process is controlled at 50-65%, the concentration of sodium nitrite solution is controlled at 30-45%, and the purity of CO is not less than 98.5%, the ratio of CO to the generated NO CO: NO = 1-8;② Before the esterification reaction, an independent gas mixer is set up to fully mix the oxygen with a purity greater than 99% with the circulating gas and initially generate the oxidation reaction of NO, and then the mixture enters the esterification reactor to generate methyl nitrite; Among them, the esterification reactor adopts a packed tower with 10-40 theoretical plates, a cooler is set on the top, the condensate is fully refluxed, and the methanol content in the reflux is greater than 99%, A reboiler is set at the bottom, and the temperature of the tower kettle is 70-120 ℃; Fresh methanol is added in a reflux tank with a purity of not less than 99.8%. (3) The gas from the top of the esterification reactor is treated by a gas purifier, and after removing impurity components, it is mixed with the raw material CO and enters the carbonylation reactor at a pressure of 0.1-0.5MPa and a reaction temperature of 120-150 ℃, resulting in dimethyl oxalate; (4) The materials from the carbonylation reactor enter the methanol washing tower, use liquid methanol to wash dimethyl oxalate in the mixed gas; The tower is equipped with a tower top cooler and a tower kettle reboiler. The tower top temperature is 10-20 ℃, the tower kettle temperature is 70-110 ℃, fresh methanol is added to the reflux tank, and the molar ratio of the amount of alcohol washed methanol to the amount of mixed gas is 1: 4-8;⑤ The mixed gas from the top of the methanol washing tower is separated by a vapor-liquid separator with a separation accuracy of 5-30μm, and then pressurized by a circulating gas compressor to the esterification reactor; ⑥ The materials from the bottom of the methanol washing tower enter the dimethyl oxalate refining tower. The top temperature of the tower is 60-75 ℃, and the temperature of the tower kettle is 150-170 ℃. The bottom of the tower obtains dimethyl oxalate products. The top of the tower is methanol, dimethyl carbonate and water. |
| use | for organic synthesis. It is used as an intermediate of vitamin B13 and also as a plasticizer. Mainly used in pharmaceuticals, pesticides, organic synthesis, and also used as a plasticizer Used in the preparation of pure methanol, and also used as a plasticizer |
| Production method | It is obtained by esterification of oxalic acid and methanol in the presence of sulfuric acid. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 500 mg/kg |
| flammability hazard characteristics | high heat, open flame flammable, can act with oxidant |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants and food additives |
| fire extinguishing agent | foam, carbon dioxide, dry powder, sand |
| spontaneous combustion temperature | 480°C |
Last Update：2024-04-09 21:04:16
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Raw Materials for CH3OCOCOOCH3
Downstream Products for CH3OCOCOOCH3