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Overview: Dimethylformamide is abbreviated as DMF. A compound formed by the substitution of the hydroxyl group of formic acid with a dimethylamine group, with the molecular formula HCON(CH3)2. It is a colorless, transparent, high-boiling-point liquid with a faint amine smell and a relative density of 0.9445 at 25ºC. Melting point: -61ºC. Boiling point: 152.8ºC. Flash point: 57.78ºC. The vapor density is 2.51. Vapor pressure: 0.49kpa(3.7 MMHG at 25ºC). The autoignition point is 445ºC. The explosion limit of the mixture of vapor and air is 2.2 to 15.2%. It can cause combustion and explosion when exposed to open flames or high heat. It can react violently with concentrated sulfuric acid and fuming nitric acid, and even explode. It is miscible with water and most organic solvents. It is a commonly used solvent in chemical reactions. Pure dimethylformamide is odorless, but industrial-grade or deteriorated dimethylformamide has a fishy smell because it contains impurities of dimethylamine. The name comes from the fact that it is a dimethyl substitution of formamide (the amide of formic acid), and both methyl groups are located on the N (nitrogen) atom. Dimethylformamide is a high-boiling-point polar (hydrophilic) aprotic solvent that can promote the progress of the SN2 reaction mechanism. Dimethylformamide is produced using formic acid and dimethylamine. Dimethylformamide is unstable in the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid (especially at high temperatures), and hydrolyzes into formic acid and dimethylamine. It is stable both in air and when heated to boiling. However, when the temperature exceeds 350ºC, it loses water and generates carbon monoxide and dimethylamine. N, N-dimethylformamide is an excellent aprotic polar solvent that can dissolve most organic and inorganic substances. It is miscible with water, alcohols, ethers, aldehydes, ketones, esters, halogenated hydrocarbons and aromatics, etc. The positively charged end of the N, n-dimethylformamide molecule is surrounded by methyl groups, forming a spatial barrier that prevents negative ions from approaching and only associates with positive ions. The activity of exposed negative ions is much greater than that of solvated negative ions. Many ionic reactions are more likely to occur in N, N-dimethylformamide than in common protonic solvents. For example, at room temperature, carboxylate salts react with halogenated hydrocarbons in N, N-dimethylformamide to produce high-yield esters, which are particularly suitable for the synthesis of steric hindrance esters. Purification and water removal methods: DMF can be mixed freely with most organic solvents and water, and has good solubility for both organic and inorganic compounds. N, N-dimethylformamide contains a small amount of moisture. Some decomposition occurs during atmospheric distillation, generating dimethylamine and carbon monoxide. Decomposition accelerates in the presence of acid or base. So after adding solid potassium hydroxide (sodium) and leaving it at room temperature for several hours, it will partially decompose. Therefore, the most commonly used materials are calcium sulfate, magnesium sulfate, barium oxide, silica gel or molecular sieves for drying, followed by vacuum distillation, and the fraction at 76ºC/4800Pa(36mmHg) is collected. If the water content is relatively high, one-tenth of its volume of benzene can be added. The water and benzene can be distilled off under normal pressure and below 80ºC. Then, it can be dried with anhydrous magnesium sulfate or barium oxide, and finally subjected to vacuum distillation. The purified N, N-dimethylformamide should be stored away from light. If free amines are present in N, N-dimethylformamide, the color produced by 2, 4-dinitrofluorobenzene can be used for inspection. The uses of dimethylformamide: Dimethylformamide is an excellent solvent for various polymers such as polyethylene, polyvinyl chloride, polyacrylonitrile, and polyamide. It can be used in the wet spinning of synthetic fibers such as polyacrylonitrile fibers and the synthesis of polyurethane. Used for plastic film making; It can also be used as a paint remover for removing paint. It can also dissolve some low-solubility pigments, endowing the pigments with the characteristics of dyes. Dimethylformamide is used for the extraction of aromatics and for the separation and recovery of butadiene from the carbon four fraction and isoprene from the carbon five fraction. It can also be used as an effective reagent for the separation of non-hydrocarbon components from paraffin. It has good selectivity for the solubility of isophthalic acid and terephthalic acid: the solubility of isophthalic acid in dimethylformamide is greater than that of terephthalic acid. Solvent extraction or partial crystallization in dimethylformamide can separate the two. In the petrochemical industry, dimethylformamide can be used as a gas absorbent to separate and refine gases. In the polyurethane industry, it is used as a washing and curing agent, mainly in the production of wet-process synthetic leather. As a solvent in the acrylic fiber industry, it is mainly used in the dry spinning production of acrylic fibers. In the electronics industry, it is used for quenching tin-plated components and cleaning circuit boards, etc. Other industries include carriers of hazardous gases, solvents for drug crystallization, adhesives, etc. In organic reactions, dimethylformamide is not only widely used as a solvent for the reactions but also an important intermediate in organic synthesis. It can be used to produce acetamiprid in the pesticide industry. In the pharmaceutical industry, it can be used in the production of iodiazine, doxycycline, cortisone, vitamin B6, iodoside, pinazine, thiouracil, N-formyl sarcomatosin, anti-tumor line, methoxyl mustard, benazine mustard, cyclohexanethylurea, fufluracil, hemostatic cycloacid, betamethasone, megesterone, cholvitasol, chlorpheniramine and sulfonamide drugs. Dimethylformamide plays a catalytic role in hydrogenation, dehydrogenation, dehydration and dehalogenation reactions, reducing the reaction temperature and improving the purity of the product. Universal solvent - Dimethylformamide Dimethylformamide is mainly used as a low-volatility solvent. Dimethylformamide is used in the manufacturing of propylene fibers and plastics. In the pharmaceutical industry, it is also used to manufacture pesticides, adhesives, artificial leather, fibers, films and surface coatings, etc. Dimethylformamide is a reagent for the Bouveault aldehyde synthesis reaction and the Vilsmeier-Haack reaction (another useful aldehyde synthesis reaction). In the nuclear magnetic resonance spectrum, the protons on the methyl group of dimethylformamide form two single peaks because the rotation rate of the carbonyl carbon-nitrogen bond is very slow in the time scale of nuclear magnetic resonance. The bond order of the carbonyl carbon-nitrogen bond is greater than one, while that of the amide carbon-oxygen bond is less than two. In the infrared spectrum of amides, the C=O band is usually less than 1700cm-1 because the C=O bond is weakened due to the electron density of oxygen supplied from nitrogen. Dimethylformamide can penetrate most plastics and cause them to expand, so it is often used as one of the components of paint removers. Dimethylformamide is also known as a "universal solvent", but it also has its limitations. With a high boiling point of 154ºC, it is quite suitable as a solvent for many polymer materials. However, in organic synthesis, careful selection is necessary as it is often encountered that the solvent cannot be completely removed. In addition, it can be miscible with water. Simple solvent recovery methods are difficult to dehydrate. When costs are not a concern, it can be washed off with water. However, when conducting small-scale trials, the feasibility of large-scale production should be considered. It is necessary to calculate the cost and the wastewater treatment plan. The preparation of N, N-dimethylformamide (DMF) can be directly synthesized from CO and (CH3)2NH, which is called the one-step method. That is, using sodium methoxide as the catalyst, CO and (CH3)2NH are synthesized at 120ºC and 1.8MPa. Toxicity of dimethylformamide Acute toxicity: LD50:400mChemical Book kg/kg(oral administration in rats); 5000mg/kg(rabbit transcutaneous). LC50:9400mg/m ³, 2 hours (inhaled by mice). When humans inhale 30 to 60ppm, they may experience digestive tract symptoms, abnormal liver function, jaundice, increased urobilinogen, and proteinuria. When a person inhales 10 to 20ppm(sometimes 30ppm), they experience headache, loss of appetite, nausea, and normal liver function and electrocardiogram. Subacute and chronic toxicity: In rats inhaled 2500mg/m3,6h/d for 5 days, 80% died and liver and lung lesions occurred; When people inhale 5.1-49mg/m ³ for 3 years, they develop neurasthenia syndrome, low blood pressure and changes in liver function. Metabolism: After being absorbed through various pathways,N, N-dimethylformamide (DMF) is mainly metabolized in the liver and excreted relatively quickly. The main target organ is the liver, and there is also certain damage to the kidneys. The demethylation mainly occurs through the mixed functional oxidase of microsomes in the liver, removing one methyl group. The metabolic products are methylformamide and formamide, and the metabolism is rapid. Formamide remains in the blood for a slightly longer period and is then metabolized into formic acid and ammonia for excretion. Some dimethylformamide is excreted in its original form through urine and exhalation. Health hazard: Irritating to the eyes, skin and respiratory tract. Steam can cause mild to moderate irritation symptoms in the eyes and upper respiratory tract. Contaminated skin can cause burns of varying degrees, with wrinkled skin, pale complexion, and a burning sensation. In severe cases, it can cause skin swelling and intense burning pain. Contaminating the eyes causes burning pain, tearing and conjunctival congestion. In severe cases, it can cause corneal necrosis. Gastrointestinal symptoms: Patients often experience loss of appetite, nausea, vomiting, abdominal discomfort and constipation, etc. In a few cases, there is pain in the middle and upper abdomen. Liver: During acute poisoning, liver damage is often more prominent. Patients experience significant fatigue, distension and pain in the upper right abdomen, discomfort, jaundice, and the liver gradually enlarges with tenderness. Routine liver function tests show abnormalities, among which serum transaminase levels increase significantly. The lesion is generally not serious and can gradually alleviate after treatment. The condition can be fully recovered within a few weeks. Severe acute poisoning: It is characterized by severe toxic liver disease. Occupational poisoning is rare. When exposed to high concentrations, especially with severely contaminated skin that has not been thoroughly washed off in time, one should be alert to the possibility of severe poisoning. Emergency response principles: Leave the scene, remove contaminated clothing, and immediately rinse with clean water if the skin is contaminated. There is no specific antidote. It mainly protects the liver. Symptomatic treatment, such as hemorrhagic gastroenteritis. Adrenal glucocorticoids can be used for those with severe poisoning. Preventive measures: The production process should be as sealed as possible, with enhanced local suction and waste gas recovery. When maintaining equipment, anti-toxic masks should be used reasonably. This product should be kept away from concentrated alkaline solution to prevent the formation of another toxic substance - dimethylamine. Hazard Classification (GB5044-85) : Grade III (Moderate hazard). Chemical properties: Colorless and transparent liquid. It is a polar inert solvent. It can be mixed with water and most organic solvents at will except for halogenated hydrocarbons. Dimethylformamide is an excellent organic solvent, serving as a solvent for polyurethane, polyacrylonitrile, and polyvinyl chloride. It is also used as an extractant and as a raw material for the medicine and pesticide acetamiprid. It is used as an analytical reagent and as a solvent for ethylene resin and acetylene. Dimethylformamide is not only a widely used chemical raw material but also an excellent solvent with a wide range of applications. Dimethylformamide is an excellent solvent for a variety of polymers such as polyethylene, polyvinyl chloride, polyacrylonitrile, and polyamide, and can be used in the wet spinning of synthetic fibers such as polyacrylonitrile fibers and the synthesis of polyurethane. Used for plastic film making; It can also be used as a paint remover for removing paint. It can also dissolve some low-solubility pigments, endowing the pigments with the characteristics of dyes. Dimethylformamide is used for the extraction of aromatics and for the separation and recovery of butadiene from the carbon four fraction and isoprene from the carbon five fraction. It can also be used as an effective reagent for the separation of non-hydrocarbon components from paraffin. It has good selectivity for the solubility of isophthalic acid and terephthalic acid: the solubility of isophthalic acid in dimethylformamide is greater than that of terephthalic acid. Solvent extraction or partial crystallization in dimethylformamide can separate the two. In the petrochemical industry, dimethylformamide can be used as a gas absorbent to separate and refine gases. In organic reactions, dimethylformamide is not only widely used as a solvent for the reactions but also an important intermediate in organic synthesis. It can be used to produce acetamiprid in the pesticide industry. In the pharmaceutical industry, it can be used to synthesize iodiazine, doxycycline, cortisone, vitamin B6, iodoside, pinazine, thiouracil, N-formyl sarcomatosin, anti-tumor line, methoxyl mustard, benazine mustard, cyclohexaflurea, fufluracil, hemostatic cycloacid, betamethasone, megesterone, cholvitasone, chlorpheniramine, etc. Dimethylformamide plays a catalytic role in hydrogenation, dehydrogenation, dehydration and dehalogenation reactions, reducing the reaction temperature and improving the purity of the product. It is used as a non-aqueous solution titration solvent. Solvents for ethylene resin and acetylene. Photometric determination. Gas chromatography stationary liquid (maximum operating temperature 50ºC, solvent methanol), capable of separating and analyzing C2 to C5 hydrocarbons, and also able to separate n-isobutylene, cis-2-butene and trans-2-butene. Analysis of pesticide residues Organic synthesis Peptide synthesis. For the photographic industry. Production methods: Since the first synthesis of dimethylformamide by the reaction of formic acid with dimethylamine in 1899, various technological methods for synthesizing dimethylformamide from different raw materials have been developed, such as the dimethylamine-carbon monoxide method, formamide-dimethylamine method, hydrogen cyanide - methanol method, acetonitrile - methanol method, methyl formate - dimethylamine method, trichloroacetaldehyde - dimethylamine method, etc. However, at present, the industrial production abroad still mainly relies on the dimethylamine-carbon monoxide method. The methyl formate - dimethylamine method involves the esterification of formic acid with methanol to form methyl formate, which then undergoes a gas-phase reaction with dimethylamine to produce dimethylformamide. After distillation to recover methanol and unreacted methyl formate, the product is obtained through vacuum distillation. 2. The dimethylamine-carbon monoxide method is obtained by the direct reaction of dimethylamine and carbon monoxide under the action of sodium methoxide. The reaction conditions are 1.5-2.5MPa and 110-150ºC. The crude product is distilled to obtain the finished product. 3. Methyl formate is synthesized from carbon monoxide and methanol through carbonylation under high pressure and at a temperature of 80-100ºC. Then, it reacts with dimethylamine to form dimethylformamide, which is distilled to obtain the finished product. 4. The trichloroacetaldehyde method is obtained by the reaction of trichloroacetaldehyde with dimethylamine. Category: Flammable Liquid \ nToxicity Classification: Poisoning \ nAcute Toxicity \ nOral Administration - Rat \ nLD50 :2800 mg/kg Oral administration - Mouse LD50:3750 mg/kg Stimulation data - Eye - Rabbit 100 mg Severe Explosive Hazardous characteristics Explosive when mixed with air flammable Hazardous characteristics Flammable when exposed to open flame, high temperature, and strong oxidants. Combustion emits toxic nitrogen oxide fumes. Storage and transportation characteristics: Complete packaging, handle with care. The warehouse should be well-ventilated, kept away from open flames and high temperatures, and stored separately from oxidants and acids. The occupational standard for fire extinguishing agents such as foam, dry powder, carbon dioxide, and sand is TLV-VA 10PPM(30 mg/m ³). STEL20PPM(60 milligrams per cubic meter)
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