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Dimethyl sulfoxide liquid (DMSO) is a sulfur-containing organic compound with the molecular formula of c2h6os. It is a colorless and odorless transparent liquid at room temperature. It is a hygroscopic flammable liquid. It has the characteristics of high polarity, high boiling point, good thermal stability, aprotic and miscible with water. It can be soluble in most organic substances such as ethanol, propanol, benzene and chloroform. It is known as "universal solvent". Heating in the presence of acid will produce a small amount of methyl mercaptan, formaldehyde, dimethyl sulfur, methanesulfonic acid and other compounds. It can decompose at high temperature, react violently with chlorine, and burn in the air to produce a light blue flame. Dmso dimethyl sulfoxide can be used as organic solvent, reaction medium and organic synthesis intermediate. It can also be used as dyeing solvent, dye remover, dyeing carrier of synthetic fiber and absorbent for recycling acetylene and sulfur dioxide.
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Chemical Formula |
C2H6OS |
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Exact Mass |
78 |
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Molecular Weight |
78 |
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m/z |
78 (100.0%), 80 (4.5%), 79 (2.2%) |
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Elemental Analysis |
C, 30.75; H, 7.74; O, 20.48; S, 41.03 |
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Due to its reputation as a universal solvent and its wide application in life, dimethyl sulfoxide has been tried a variety of synthetic methods under the surge of demand and economic pull. In this paper, we will list two of them.
1. Dimethyl sulfoxide liquid process
Dimethyl sulfide / ether was prepared by reacting dimethyl sulfate with sodium sulfide / sodium chloride; Sulfuric acid reacts with nitrite / sodium to produce dioxygen / nitrous oxide; The crude dimethyl sulfoxide is obtained by oxidation of dimethyl sulfide / ether with dioxygen / nitrogen, then neutralized and distilled to obtain refined dimethyl sulfoxide. In addition, dimethyl sulfoxide was produced from dimethyl / sulfide by anodic oxidation.
Refining method: after vacuum distillation of dimethyl sulfoxide, add alumina and put it overnight. Use a distillation tower with a height of 50cm and filled with ceramic saddle filler to conduct vacuum distillation at 266.6~399.9pa and 50 ℃, and collect the middle distillate. Or heat dimethyl sulfoxide and CaH2 together for one day, dry them with molecular sieve after vacuum distillation, and then carry out vacuum distillation under nitrogen flow. It can also be refined by step crystallization.
2. Nitrogen dioxide method
In methanol and hydrogen sulfide γ- Dimethyl sulfide is formed under the action of alumina; Sulfuric acid reacts with sodium nitrite to produce nitrogen dioxide; Dimethyl sulfide reacts with nitrogen dioxide in gas-liquid phase at 60-80 ℃ to produce crude dimethyl sulfoxide, or it is oxidized directly with oxygen to produce crude dimethyl sulfoxide, and then refined to produce the finished product of dimethyl sulfoxide through vacuum distillation. This method is an advanced production method.
Dimethyl sulfoxide liquid (DMSO) is an important nonprotic polar solvent which is soluble in both water and organic solvents. Widely used as solvent and reaction reagent, it has high selective extraction ability. Dimethyl sulfoxide itself has anti-inflammatory, analgesic, diuretic, sedative and other functions. It can be directly used as the raw material and carrier of some drugs in the pharmaceutical industry. Known as a "panacea", it is often added to drugs as an active component of analgesic drugs.
1. Chemical synthesis
Reaction solvent: As a solvent in organic synthesis, it helps to improve reaction rate and yield. Transition metal halides such as chromium chloride and manganese chloride, as well as common halides such as potassium chloride and sodium chloride, have a certain solubility in dimethyl sulfoxide (DMSO), which makes them applicable in the field of organic chemistry
Catalysts and reagents: In certain chemical reactions, they can act as catalysts or reactants themselves.
Aggregation reaction: It is used as a processing solvent and spinning solvent in acrylonitrile polymerization reaction, and also plays an important role in polyurethane synthesis and spinning process. In addition, it is also used as a synthetic solvent for polyamide, polyimide, and polysulfone resins, as well as an extraction solvent for aromatic hydrocarbons and butadiene, and a solvent for synthesizing chlorofluoroaniline.
2. Research and laboratory applications
Cell culture: used for cell culture and preservation, especially during cryopreservation.
Analytical chemistry: In chromatographic analysis, used as a sample solvent or mobile phase component.
3. In the field of agriculture
The applications in the field of agriculture mainly include the following aspects:
As a reaction solvent, it is suitable for high and low temperature reactions to improve the conversion rate and yield in pesticide synthesis, such as the synthesis of herbicides and insecticides.
Application in the synthesis of organic fluorine compounds: accelerating and catalyzing fluorination reactions, improving the synthesis efficiency of fluorine-containing pesticide intermediates.
As a penetrant and enhancer of pesticides, dimethyl sulfoxide enhances the penetration performance of pesticides, such as preventing fruit tree rot and killing heart worms.
Application in other organic synthesis reactions: Accelerating reaction rates in nucleophilic substitution reactions, electrophilic substitution reactions, etc. is of great significance for pesticide synthesis.
Other uses in the field of pesticides: such as spraying soybean with dimethyl sulfoxide aqueous solution to increase yield, and enhancing the fumigation and sterilization power of formaldehyde, thereby expanding the application of dimethyl sulfoxide in the field of pesticides.
4. Medical field
Cryoprotectant: As a cryoprotectant, it plays an important role in cell biology and biomedical research, used to protect cells and other biological samples from low-temperature damage, such as the cryopreservation of peripheral blood hematopoietic stem cells and immature mouse testicular germ cells.
Antibacterial and anti-inflammatory: It has certain antibacterial and bactericidal effects, is effective against various pathogenic bacteria, and has anti-inflammatory effects, which can reduce inflammatory reactions and tissue damage, such as treating systemic inflammation caused by yeast polysaccharides, rat cystitis, and hemorrhagic cystitis.
Analgesia: It has analgesic effects and can be used to relieve pain and discomfort, such as treating postherpetic neuralgia.
Antitumor: As a cell differentiation inducer, it can be used to treat various tumors, such as inhibiting the growth of human lung adenocarcinoma A549 cells, inducing the differentiation of human liver cancer HepG2 cells into normal cells, promoting the killing effect of ALA-PDT on A431 cells, and inhibiting mouse skin squamous cell carcinoma.
Central nervous system diseases: can be used to treat head and spinal cord injuries, stroke, memory impairment and other related diseases, such as slowing down functional decline in Alzheimer's disease patients, improving the efficacy of ischemic stroke animal models, promoting peripheral nerve regeneration and repairing spinal cord injuries in rats.
Dermatology: It can promote wound healing and treat various skin diseases, such as promoting the healing of refractory wounds in diabetes mice, and improving the bonding strength of dental dentin with fluorosis.
Nuclear radiation protection effect: It has a nuclear radiation protection effect and can reduce the damage of radioactive substances to human cells, such as protecting against bone marrow type acute radiation disease and intestinal type acute radiation disease, preventing radiation-induced oral mucosal inflammation, and radiation damage to the reproductive system of male mice.
Diabetes: it can be used to induce bone marrow mesenchymal stem cells to differentiate into islet cells, providing new ideas for the treatment of diabetes.
Oral medicine: may become a potential treatment option for preventing radiation-induced oral mucositis.
5. Industrial applications
(1) Application in petroleum processing
Dimethyl sulfoxide was first used as an extraction solvent in aromatic hydrocarbon extraction using the IFP method in France, which was presented at the Warsaw Thirty Five Nation Chemical Conference.
Its advantages are:
1. High selectivity for aromatic hydrocarbons;
2. Unrestricted miscibility of aromatic hydrocarbons at room temperature;
3. The extraction temperature is low and does not react with alkanes, alkenes, or water;
4. Non corrosive and non-toxic;
5. The extraction process is simple, with few equipment and energy saving;
6. Insoluble olefins are suitable for oilseeds with high olefin content;
7. Solvent recovery can be achieved through reverse extraction.
Dimethyl sulfoxide liquid is insoluble in alkanes and is therefore used in the refining of food wax and edible white oil, as well as in the detection of cancer drugs.
Acetylene is easily soluble, with 33 liters of acetylene dissolved per liter of dimethyl sulfoxide, while acetone can only dissolve 25 liters of acetylene. Dimethyl sulfoxide has a high boiling point and is easy to recover and regenerate. Therefore, it is used in the recovery of petroleum gas acetylene and the production of dissolved acetylene.
Organic sulfides, aromatic hydrocarbons, and alkynes are easily soluble and commonly used in lubricating oil and diesel refining.
(2) Application in synthetic fibers
The application of acrylic fiber spinning was first patented by Toyo Rayon Co., Ltd. in Japan, which polymerized acrylonitrile in dimethyl sulfoxide without separation and directly sprayed it in a water bath to obtain fluffy, soft, and easily dyed synthetic wool. Its advantages include simplified process, high solubility, high boiling point of solvents, non toxicity, easy recycling, good product performance, and low cost. Some acrylic fiber factories in Yuci, Dalian, and Beijing, Shanxi, China use this process for production. Recently, polypropylene nitrile has also been used in the production of carbon fiber. It is used for refining terephthalate in the production of polyester resin abroad. In addition, dimethyl sulfoxide spinning and acrylonitrile copolymerization are used in the production of chloroprene.
(3) Application in dyes
Jilin Dye Factory has significantly improved its production capacity and yield after using dimethyl sulfoxide. It has been reported that adding dimethyl sulfoxide to printing and dyeing can achieve uniform dyeing and eliminate color difference.
(4) Application in Coatings
It is commonly used as a solvent, co solvent, and antifreeze in water-based paints. Due to its good solubility in various resins, dimethyl sulfoxide is used as a solubilizer in some paints. The more important use is as a paint remover. Adding alkali or nitric acid to dimethyl sulfoxide can remove various paint films, including epoxy resin.
(5) Application in antifreeze
The freezing point of pure dimethyl sulfoxide is 18.45 ℃, and dimethyl sulfoxide containing 40% water does not freeze at -60 ℃. Moreover, dimethyl sulfoxide releases heat when mixed with water and snow. This property makes dimethyl sulfoxide a component of automotive antifreeze, brake fluid, and hydraulic fluid. Ethylene glycol antifreeze is no longer suitable for temperatures exceeding -40 ℃. And it has a lower boiling point than dimethyl sulfoxide, is toxic, and prone to gas blockage. Dimethyl sulfoxide antifreeze is used as a de icing agent, anti freezing agent for coatings, various latex, anti icing agent for gasoline and aviation fuel, anti freezing agent for bone marrow, blood, and low-temperature storage in the northern cold regions.
(6) Application in gas separation
Using dimethyl sulfoxide as a solvent for gas separation in petroleum processing, chemical exhaust gas recovery, and gas separation due to its solubility in aromatic hydrocarbons, alkynes, sulfides, nitrogen dioxide, and sulfur dioxide.
(7) Application in synthetic resin
Dimethyl sulfoxide is used as the polymerization solvent for polysulfone resin in production. It is soluble in many natural and synthetic resins, and can dissolve nylon, polyester, and polyvinyl chloride resins at medium heat. Used for artificial leather processing, it can also be used as a cleaning agent for polyurethane reaction vessels and a solvent for acrylonitrile copolymerization reaction.
(8) Application in coking by-products
In anthraquinone production, it is used for anthracene refining. Adding dimethyl sulfoxide to anthracene oil for extraction of refined anthracene can achieve a content of over 98% in one extraction, without the need for water reverse extraction to recover dimethyl sulfoxide. The process is simple. It has also been applied in naphthalene refining outside of China, for the recovery of organic sulfides in coke oven gas separation.
Using dimethyl sulfoxide as an extraction additive for gold, platinum, niobium, tantalum, rhenium, and radioactive elements to improve selectivity, solubility, and low-temperature crystallization as an antifreeze agent.
(9) Applied in the electronics industry
Electrolyte used for Farad level, ultra large capacity capacitors - liquid double-layer capacitors. Ordinary capacitors have only microfarad capacity, while this type of capacitor can reach 1-100 Farad. For example, 3-5V 10F capacitors from Japan and 1.6V 100F capacitors from the United States are used as energy storage components in solar power supply systems, as well as information protection power and memory components for electronic computers and robots. Dimethyl sulfoxide is widely used in the cleaning of electronic components and integrated circuits. It has the function of removing organic, inorganic, and polymer substances in one go, and is non-toxic, odorless, and easy to recycle.
It can also be used for the manufacturing of optoelectronic materials, liquid crystal displays, semiconductor devices, etc. With the continuous development of the electronic product market and the increasing demand for high-performance materials, the market demand in the electronics industry will also continue to expand.
Chemical properties of dimethyl sulfoxide:
1 . Dimethyl sulfoxide is reduced to form methyl sulfide. Oxidized to dimethylsulfone by strong oxidant;
2. when dimethyl sulfoxide contacts with acyl chloride substances such as cyanuric chloride, benzoyl chloride, acetyl chloride, phenyliodoyl chloride, thionyl chloride, thionyl chloride, phosphorus trichloride, etc., intense exothermic decomposition reaction occurs. Combine with nitric acid to form (CH3) 2SO · HNO3. Dimethyl sulfoxide can be regenerated by interaction with barium carbonate. React with concentrated hydroiodic acid to form dimethyl sulfur compound.
3. dimethyl sulfoxide has water absorption and needs to be dried before use.
Physical properties of dimethyl sulfoxide:
Colorless viscous liquid. Flammable, almost odourless, bitter and hygroscopic. It can dissolve common organic solvents except petroleum ether. It can be freely miscible with water, ethanol, acetone, acetaldehyde, pyridine, ethyl acetate, dibutyl phthalate, dioxane and aromatic compounds, but insoluble in aliphatic hydrocarbons other than acetylene. It has strong hygroscopicity. At 20 ℃, when the relative humidity is 60%, it can absorb water equivalent to 70% of its own weight from the air. This product is a weak oxidant. The water-free dimethyl sulfoxide is non corrosive to metals. For iron when containing water; Copper and other metals are corrosive, but not corrosive to aluminum. Stable to alkali. Heating in the presence of acid will produce a small amount of methyl mercaptan, formaldehyde and dimethyl sulfur; Methanesulfonic acid and other compounds. Dimethyl sulfoxide liquid can decompose at high temperature, react violently with chlorine, and burn in the air to produce a light blue flame.
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