Dimethyl oxalate, also known as oxalic acid dimethyl ester, chemical formula C4H6O4, chemical formula C4H6O4, is a colorless monoclinic crystal or colorless crystalline powder. Slightly soluble in cold water, but decomposes in hot water, soluble in organic solvents such as alcohols and ethers. Classified as a toxic substance, its toxicity level is classified as poisoning. The oral LD50 value of rats is 500mg/kg, indicating that it has certain toxic effects on organisms. The application of dimethyl oxalte as an important chemical and pharmaceutical raw material is often used to prepare various organic solvents, extractants, adhesives, plasticizers, and various pharmaceutical intermediates. For example, it is used to synthesize vitamin B13, hydrogenation to prepare methyl acetate, ethylene glycol, and replace diethyl oxalate to synthesize sulfamethoxazole.
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Chemical Formula |
C4H6O4 |
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Exact Mass |
118 |
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Molecular Weight |
118 |
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m/z |
118 (100.0%), 119 (4.3%) |
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Elemental Analysis |
C, 40.68; H, 5.12; O, 54.19 |
Dimethyl oxalate (DMO), also known as dimethyl oxalte, is an important organic compound with a wide range of applications.
Important reagents and solvents in organic synthesis
It plays an important role in organic synthesis and is commonly used as a reagent and solvent, participating in various chemical reactions.
(1) Esterification and acylation reactions
It can be used as a reagent in esterification and acylation reactions, reacting with alcohol compounds to produce ester compounds, or reacting with acid anhydrides to produce acylation products. This type of reaction is very common in organic synthesis and is used to prepare various ester compounds.
(2) Condensation reaction
It can also undergo condensation reactions with certain ketone compounds to generate compounds with special structures and properties. This type of reaction has important applications in drug synthesis and natural product synthesis.
(3) Solvent action
Due to its ability to dissolve various organic compounds such as resins, dyes, and coatings, it is often used as a solvent in organic synthesis. In the dye industry, DMO is commonly used in extraction, precipitation, and crystallization processes to assist in the separation and purification of target compounds.
Important raw materials for synthetic materials
It is also widely used in the field of synthetic materials and is one of the important raw materials for synthesizing polyester and polyester fibers.
(1) Polyester material
Can react with diols to produce polyester. This type of polyester material has good physical and chemical properties, such as high strength, high toughness, wear resistance, corrosion resistance, etc., and is therefore widely used in the manufacture of plastics, coatings, plastic films, and other products.
(2) Polyester fiber
The polyester synthesized from it can be further processed into polyester fibers. Polyester fibers have excellent textile properties such as wear resistance, wrinkle resistance, easy washing and drying, and are therefore widely used in the textile industry to make products such as clothing, curtains, carpets, etc.
Application of pharmaceutical intermediates
It also has important applications in the field of medicine, as it can be used as an intermediate for synthesizing some drugs.
(1) Synthesis of Vitamin B12
Vitamin B12 is an important water-soluble vitamin that plays a crucial role in human health. It can be used as one of the intermediates for synthesizing vitamin B12 and participate in its synthesis process.
(2) Synthesis of other drugs
In addition to vitamin B12, it can also be used to synthesize various other drugs, such as tetraethyl oxalate. These drugs have wide application value in the medical field, used to treat various diseases.
Synthetic raw materials for pesticides and insecticides
It also has applications in the field of pesticides and insecticides, and can be used as a raw material for synthesizing some pesticides and insecticides.
(1) Synthesis of pesticides
It can be used to synthesize various pesticides, which have different insecticidal, bactericidal, or herbicidal effects. By using reasonable formulas and application methods, crop diseases and pests can be effectively controlled, and crop yield and quality can be improved.
(2) Synthesis of insecticides
It can also be used to synthesize some insecticides, which have strong killing effects on pests. Reasonable use of insecticides in agricultural production can effectively protect crops from pest infestations.
Composition of dyes and inks
It also has applications in the fields of dyes and inks, and can be used as one of the components of dyes and inks.
(1) Synthesis of dyes
It can be used to synthesize various dyes, which have bright colors and good dyeing performance. They are widely used in industries such as textiles, printing and dyeing, providing rich colors for products such as textiles and paper.
(2) Preparation of Ink
It can also be used as one of the components of ink to prepare various types of ink. These inks have good fluidity and stability, which can meet different writing and printing needs.
Application of Catalysts
It can also be used as a catalyst in certain catalytic reactions to promote the progress of the reaction.
(1) Synthesis of esters, ethers, and amides
It can be used as a catalyst in the synthesis of esters, ethers, and amides. It can reduce the activation energy of the reaction, increase the reaction rate and yield.
(2) Other catalytic reactions
In addition to the above-mentioned catalytic reactions, it can also be used in other types of catalytic reactions, such as redox reactions, addition reactions, etc. By selecting appropriate catalysts and reaction conditions, efficient and green chemical synthesis processes can be achieved.
Important raw material for advanced aperture nickel templates
It also has applications in the manufacturing of electronic components and display devices, and can be used as an important raw material for advanced aperture nickel templates.
(1) Preparation of Aperture Nickel Template
Advanced aperture nickel templates can be prepared using dimethyl oxalate. These templates have precise patterns and structures that can meet the high-precision requirements in the manufacturing of electronic components and display devices.
(2) Manufacturing of electronic components and display devices
Advanced aperture nickel templates have wide applications in the manufacturing of electronic components and display devices. They can be used to manufacture various types of electronic components and display devices, such as integrated circuits, liquid crystal displays, etc. These products have an important position and role in the modern electronics industry.
Application of Aromatic Agents
With fragrance, it is also commonly used to manufacture perfume and other aromatic products.
(1) Preparation of perfume
It can be used to prepare various types of perfume. There are different aromas and persistence that can meet the needs of different consumers. Perfume products with unique fragrance can be prepared by reasonable formula and modulation method.
(2) Manufacturing of other aromatic products
In addition to perfume, it can also be used to manufacture other aromatic products, such as air fresheners, aromatic oils, etc. These products can emit pleasant aromas, improve indoor environment and atmosphere, and enhance people's quality of life.
Application of plasticizers
DMO plasticizer (also known as DOA) is widely used in various materials such as plastics and rubber.
(1) Application in rubber
In rubber, it is mainly used to adjust the hardness and flexibility of materials. It can make rubber materials have better elasticity and flexibility while maintaining a certain strength. This is of great significance for improving the comfort and service life of rubber products.
Specific application examples include the processing and molding processes of rubber materials such as NBR and EPDM. Among these materials, dimethyl oxalate plasticizer can effectively adjust the hardness and flexibility of the materials to meet practical application requirements.
(2) Applications in plastics
In plastics, it is mainly used to improve the plasticity and flowability of materials. It can make it easier for plastic to flow and fill molds during processing and molding, resulting in better molding effects and appearance quality. At the same time, it can also improve the flexibility and ductility of plastics, making them have better impact resistance and wear resistance.
Specific application examples include the processing and molding processes of materials such as PVC, PS, AS, etc. Among these materials, the processing performance and physical and mechanical properties can be effectively improved, making them have a wider range of application fields and market prospects.
The application of DMO as an important chemical and pharmaceutical raw material is often used to prepare various organic solvents, extractants, adhesives, plasticizers, and various pharmaceutical intermediates. For example, it is used to synthesize vitamin B13, hydrogenation to prepare methyl acetate, ethylene glycol, and replace diethyl oxalate to synthesize sulfamethoxazole. If DMO is used instead of diethyl oxalate as the starting material, 5-methyl-3-formylisoxazole can be produced through multiple reactions such as Kjeldahl, acidification, cyclization, and ammonolysis without changing other production processes and raw materials. The resulting product is then inspected and analyzed, and it is found that there is no difference in product quality; Meanwhile, due to the lower price of DMO compared to diethyl oxalate, the production cost of the product has been reduced and its competitiveness in the market has been improved.
DMO can also react with ammonia to produce oxamide, which can be used as a stabilizer for nitrocellulose products and as a gas generator and cooling agent in gas generators. Oxalamide can also be used as a slow-release nitrogen fertilizer. Preparation of nitric oxide and carbonylation to synthesize DMO. Using carbon monoxide as the raw material for carbonylation reaction, sodium nitrite and dilute nitric acid are fully reacted in the NO preparation reactor to produce nitric oxide. Together with the carbon monoxide used for stirring, it is supplemented to the DMO circulation system for esterification and carbonylation, ultimately synthesizing DMO;
Specifically, it includes the following process steps:
The concentration of dilute nitric acid in the NO production process is controlled at 50-65%, the concentration of sodium nitrite solution is controlled at 30-45%, the purity of CO is not less than 98.5%, and the ratio of CO to generated NO is CO: NO=1-8;
Before the esterification reaction, an independent gas mixer is set up to fully mix oxygen with a purity greater than 99% with the circulating gas and initiate the oxidation reaction of NO. Then, the mixed gas 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 installed at the top, and the condensate is fully refluxed. The methanol content in the refluxed liquid is greater than 99%. A reboiler is installed at the bottom, and the temperature of the tower kettle is 70-120 ° C; Fresh methanol is added to the reflux tank with a purity of not less than 99.8%;
The gas coming out of the top of the esterification reactor is treated by a gas purifier, and after removing impurities, it is mixed with the raw material CO and enters the carbonylation reactor at a pressure of 0.1-0.5 MPa and a reaction temperature of 120-150, ultimately producing DMO;
The material coming out of the carbonylation reactor enters the methanol washing tower, and the dimethyl oxalate in the mixed gas is washed away using liquid methanol; The tower is equipped with a tower top cooler and a tower kettle reboiler, with a tower top temperature of 10-20 and a tower kettle temperature of 70-110. Fresh methanol is added to the reflux tank, and the molar ratio of methanol for alcohol washing to the mixed gas volume is 1:4-8;
The mixed gas from the top of the methanol washing tower is separated by a gas-liquid separator with a separation accuracy of 5-30 μ m, and then pressurized by a circulating gas compressor and sent to the esterification reactor;
The material coming out from the bottom of the methanol washing tower enters the DMO refining tower, with a tower top temperature of 60-75 and a tower kettle temperature of 150-170. DMO product is obtained at the bottom of the tower, and methanol, dimethyl carbonate, and water are obtained at the top of the tower.
adverse reaction
Dimethyl Oxalate (DMO) is an important organic compound with wide applications in pharmaceuticals, organic synthesis, and other fields. However, its toxicity and potential adverse reactions cannot be ignored. The following elaborates on its adverse reactions from multiple systems and provides prevention and management recommendations.
Skin system adverse reactions
Irritation reaction: Dimethyl Oxalate is irritating to the skin and may cause symptoms such as redness, itching, pain, or dryness upon contact. These reactions typically occur within minutes to hours after exposure, and the severity of symptoms is positively correlated with the concentration and duration of exposure.
Inflammatory response: Long term or repeated exposure to Dimethyl Oxalate may lead to skin inflammation, manifested as thickening, flaking, cracking, or formation of blisters. These inflammatory reactions may further develop into contact dermatitis, affecting the quality of life of patients.
Adverse reactions in the ocular system
Stimulating reaction: Dimethyl Oxalate has a strong irritant effect on the eyes, which may cause symptoms such as conjunctival congestion, tearing, pain, photophobia, or blurred vision upon contact. These reactions usually occur immediately after exposure, and the severity of symptoms is closely related to the concentration and duration of exposure.
Serious damage: High concentrations or prolonged exposure to Dimethyl Oxalate may cause severe eye damage such as corneal epithelial injury, corneal ulcers, or perforation. These injuries may cause permanent vision loss and require urgent treatment.
Research data: Animal experiments have shown that Dimethyl Oxalate has severe eye irritation in rabbits, causing corneal opacity and conjunctival edema.
Respiratory system adverse reactions
Stimulating reaction: Inhalation of Dimethyl Oxalate vapor or dust may cause respiratory irritation, manifested as coughing, difficulty breathing, sore throat, or chest tightness. These reactions usually occur within minutes to hours after inhalation, and the severity of symptoms is positively correlated with inhalation concentration and time.
Toxic effects: Long term or repeated inhalation of Dimethyl Oxalate may cause toxic effects on lung tissue, leading to serious respiratory diseases such as pulmonary edema, chemical pneumonia, or pulmonary fibrosis. These diseases may affect the patient's respiratory function and even endanger their life.
Adverse reactions to the digestive system
Gastrointestinal irritation: Ingestion of Dimethyl Oxalate may cause gastrointestinal irritation, manifested as nausea, vomiting, abdominal pain, or diarrhea. These reactions usually occur within minutes to hours after ingestion, and the severity of symptoms is related to the amount of food ingested and individual differences.
Serious damage: Ingestion of Dimethyl Oxalate at high concentrations or in large quantities may cause serious damage such as gastrointestinal perforation, bleeding, or shock. These injuries may endanger the patient's life and require urgent treatment.
Dimethyl oxalate, a seemingly simple chemical intermediate, plays a multifaceted role in modern industry. From its synthesis via esterification or oxidative carbonylation to its applications in ethylene glycol production, pharmaceuticals, and fuel cells, DMO exemplifies the intersection of chemistry and sustainability. While safety and environmental concerns necessitate careful handling, ongoing innovations in process optimization and circular economy integration promise a brighter, greener future for this versatile compound. As research progresses, dimethyl oxalate is poised to remain a cornerstone of industrial chemistry, driving progress across diverse sectors.
Frequently Asked Questions
What is the formula for dimethyl oxalate?
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Dimethyl oxalate is an organic compound with the formula (CO 2CH 3) 2 or (CH 3) 2C 2O 4. It is the dimethyl ester of oxalic acid. Dimethyl oxalate is a colorless or white solid that is soluble in water.
Should I stop eating spinach because of oxalates?
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Key takeaways:
But, if you're prone to certain types of kidney stones, it's best to eat a low-oxalate diet. Foods that are high in oxalate include spinach, rhubarb, rice bran, buckwheat, almonds, and miso. Many other foods also have oxalate, but you can eat them in moderation.
Is avocado high in oxalates?
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The only berry that is very high in oxalate is raspberries (look at the list). On the other hand, people do not realize avocado, oranges, dates, and even grapefruit and kiwi are very high and need caution. This doesn't mean you can never have these healthy treats.
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