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M-Tolyl isocyanate, molecular formula C8H7NO, CAS number 621-29-4, is a colorless to pale yellow transparent liquid and an important organic compound. Organic compounds containing isocyanate groups in their molecular structure are commonly referred to as isocyanates. Organic isocyanate is an important organic synthesis intermediate, which is widely used in pesticides, dyes, coatings, leather polish, adhesives, artificial leather, polyurethane waterproof materials, potting materials, soft and hard foam, elastomers, acrylic carbamate and other polymer materials. The production of isocyanates has attracted attention from countries around the world, and its output has been increasing year by year. Among them, the application level of plastic products such as polyurethane has become one of the indicators to measure a country's comprehensive national strength and modernization level.
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Chemical Formula |
C8H7NO |
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Exact Mass |
133 |
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Molecular Weight |
133 |
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m/z |
133 (100.0%), 134 (8.7%) |
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Elemental Analysis |
C, 72.17; H, 5.30; N, 10.52; O, 12.02 |
Isocyanate m-toluene ester (also known as M-Tolyl isocyanate, m-TDI, chemical formula C9H7NO2) is an important organic synthesis intermediate with a wide range of applications.
Application in Polyurethane Industry
Isocyanate methyl methacrylate plays a crucial role in the polyurethane industry. Polyurethane is a polymer formed by the reaction of isocyanates and polyols, and as an important diisocyanate, it can react with polyols to form polyurethane prepolymers. These prepolymers can be further processed to produce a variety of polyurethane products, such as foam, elastomer, adhesives and coatings.
(1) Foam material: polyurethane foam is widely used in construction, automobile, furniture and other industries due to its excellent thermal insulation, sound insulation and cushioning properties. As the key raw material of foam production, it plays an important role in improving the performance and stability of foam.
(2) Elasticity: Polyurethane elastomers have excellent properties such as high strength, high elasticity, wear resistance, and oil resistance, and are suitable for manufacturing rubber products such as tires, seals, and conveyor belts. The use can enhance the comprehensive performance of elastomers and extend their service life.
(3) Adhesive: Polyurethane adhesive has the advantages of high bonding strength, good chemical resistance, and fast curing speed, and is widely used in fields such as automotive, electronics, aerospace, etc. As one of the main components of adhesives, it plays an important role in improving bonding effectiveness and curing speed.
(4) Coatings: Polyurethane coatings have excellent weather resistance, chemical resistance, and decorative properties, and are suitable for coating surfaces such as building exterior walls, car bodies, and furniture. Use can enhance the adhesion and durability of coatings.
Applications in the fields of medicine and pesticides
It can also serve as an intermediate for pharmaceuticals and pesticides, providing key raw materials for the development of new drugs and pesticides.
(1) In the field of medicine, it can be used to synthesize compounds with specific pharmacological activities, which have potential application value in the treatment of osteoporosis, anti-tumor, antiviral and other aspects. For example, certain drugs based on it can significantly reduce the risk of vertebral and hip fractures, providing effective osteoporosis treatment options for postmenopausal women.
(2) Pesticide field: In the field of pesticides, it can be used to synthesize pesticides with weed control, insecticidal, bactericidal and other effects. These pesticides play an important role in agricultural production, helping to improve crop yield and quality. For example, Beet Ning is a herbicide that uses it as an intermediate and has advantages such as high efficiency, low toxicity, and environmental friendliness.
Application in the synthesis of polymer materials
It also has wide applications in the synthesis of polymer materials and can be used to synthesize various high-performance polymer materials.
(1) Polyurethane waterproof material: Polyurethane waterproof material has excellent waterproof and weather resistance, suitable for waterproofing projects such as roofs, basements, bathrooms, etc. The use can improve the flexibility and bonding strength of waterproof materials, enhancing the waterproof effect.
(2) Sealing material: Polyurethane sealing material has excellent insulation performance, chemical resistance, and seismic resistance, and is suitable for sealing protection of electronic components. As one of the key raw materials for sealing materials, it plays an important role in improving the sealing effect and protective performance.
(3) Leather polish: Polyurethane leather polish has excellent glossiness and wear resistance, suitable for surface treatment of leather products. Using can enhance the glossiness and durability of leather polish, making leather products more beautiful and durable.
(4) Artificial leather: Polyurethane artificial leather has a similar appearance and performance to natural leather, and is widely used in clothing, footwear, luggage and other fields. Isocyanate methyl methacrylate, as one of the main raw materials for synthetic leather, plays an important role in improving the softness, elasticity, and wear resistance of synthetic leather.
There are various methods for the synthesis of amino acid esters, including nitrobenzene reduction functionalization, aromatic amine oxidation functionalization, and methoxy functionalization of aromatic amines. M-toluene isocyanate is an important isocyanate mainly used in the manufacture of polyurethane materials, and can be used as a substitute in certain situations. In addition, it can also serve as an important intermediate for pharmaceuticals and pesticides.
Moreover, m-tolyl isocyanate is also an important intermediate for pharmaceuticals and pesticides. Developing a skin wound dressing with a bilayer structure based on polysiloxane supramolecular elastomers and its preparation method. The steps of this method are as follows:
Amino terminated polydimethylsiloxane reacts with hexamethylene diisocyanate to obtain polydimethylsiloxane supramolecular elastomers for use as flexible substrate layers;
Carboxyl terminated polydimethylsiloxane reacts successively with monofunctional and bifunctional primary amine compounds to obtain siloxane oligomers containing secondary amine groups;
Siloxanes oligomers are then reacted successively with m-toluene isocyanate and hexamethylene diisocyanate to obtain polysiloxane supramolecular elastomers used as adhesive layers;
Then, double-layer polysiloxane supramolecular elastomer film dressings were prepared through hot pressing and cold pressing molding processes.
This film dressing has good breathability and water absorption, and its use as a chronic wound dressing is beneficial for the growth and regeneration of wound tissue, accelerating wound healing. This method uses polydimethylsiloxane as the raw material, which has no cytotoxicity or skin irritation, and has good biocompatibility. At present, most of the production of m-Tolyl isocynate at home and abroad adopts the traditional phosgene method, which has the disadvantages of using highly toxic raw material phosgene, producing a large amount of highly corrosive hydrochloric acid as a byproduct, residual chlorine affecting product quality, and waste discharge, and will eventually be eliminated. The domestic and international chemical industry is currently researching clean processes for the production of isocyanates, with the main development trend being the two-step method, which involves the synthesis of amino esters and the thermal decomposition of amino esters.
preparation:
Method 1:
1) Synthesis operation: Before the reaction, accurately weighed m-toluidine, catalyst sodium methoxide, and solvent methanol are added to a four necked flask. The air inside the flask is replaced, and the oil bath is heated to around ℃ and refluxed under stirring conditions. Timing begins. After the reaction is complete and cooled to room temperature, collect the reaction solution.
2) Post processing operation: Use hydrochloric acid to neutralize the reaction solution to the left and right, and then filter it. The purpose of adding hydrochloric acid is to convert the catalyst sodium methoxide dissolved in methanol into white sodium chloride precipitate.
Pour the obtained filtrate into a beaker for vacuum distillation until no distillate appears.
Stop distillation, cool down, and solid precipitates in the flask. If there is still too much liquid, filter to obtain a light yellow solid. Recrystallize with anhydrous ethanol to obtain white needle shaped crystals, which are the product of this experiment, and weigh.
Method 2:
1) Synthesis operation: The reaction between meta toluidine and dimethyl carbonate to synthesize meta toluidine methyl acetate is carried out in a stainless steel high-pressure reactor. Before the reaction, accurately weigh m-toluidine and catalyst and add them to the reaction kettle. Replace the air inside the kettle and heat it up under stirring conditions. Start timing after the temperature is constant.
2) Post processing operation: After the reaction is complete, fill the reaction kettle with cooling water to room temperature, open the pressure relief valve to release the pressure to zero, then open the high-pressure kettle and take out the reaction solution into a beaker.
Due to the need to lower the high-temperature reaction solution to room temperature, certain products may precipitate from the reaction solution. To completely dissolve these products and residual solids, they can be poured into a kettle for cleaning.
Mix the reaction solution poured in the previous step with the reaction solution from the previous step, and slowly heat until the product dissolves.
Immediately filter under low pressure in a hot funnel to remove solid residue containing catalyst, collect the residue, and then proceed with subsequent processing.
Pour the obtained filtered liquid into a flask for vacuum distillation until no liquid flows out, stop distillation, cool, and the solid precipitates in the flask. Weigh the crude oil.
Finally, the rough m-tolyl isocyanate was purified by recrystallization from anhydrous ethanol to obtain a white crystalline solid, which was then weighed
The development of polyurethane and its products is closely related to the development of isocyanate raw materials. Therefore, the research and development of isocyanates have extremely important strategic significance. Our clients are located in multiple countries and regions around the world, including Belgium, Poland, Germany, Czech Republic, United States, Japan, Switzerland, Ukraine, India, United Kingdom, etc. The purity, packaging, and price of the products provided may vary according to the customer's needs. For example, some customers require 99% purity with packaging specifications ranging from 5 grams to 1 kilogram, and the price varies depending on the packaging quantity and purchase quantity.
History of Isocyanates:
In 1849: Wurtz first synthesized alkyl isocyanates
In 1850: Hofmann synthesized phenyl isocyanates
In 1884, Hentschel developed the phosgene method (amine+phosgene → isocyanate)
In 1937, Bayer developed the synthesis of polyurethane
In 1947, DuPont began to produce polyurethane rigid foam
In 1952, TDI Industrialization (Goodyear, Lockheed, DuPont)
In 1958, China began researching TDI
In 1962, China's first TDI plant (500 tons/year)
Key milestones:
In 1884, the phosgene method was established, making it possible to synthesize all aromatic isocyanates, including m-methylphenyl isocyanates
Mid-20th century: Recognized as a byproduct in TDI/MDI production or through directed synthesis of toluidine
In 1958, China began research on isocyanates
In 2000, Wei Yunyang et al. used it for the synthesis of non peptide CCK antagonists
In 2003, Sun Yaquan et al. used coordination chemistry
In 2008, Chen Feng completed research on green synthesis technology at Nanjing University of Science and Technology
In 2018, Liang Bin applied it to modify cellulose whiskers
Frequently Asked Questions
What is methyl isocyanate used for?
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Methyl isocyanate (MIS) is a chemical used in the manufacture of polyurethane foam, pesticides and plastics. It usually is handled and shipped as a liquid, which is easily burned and explosive.
How toxic are isocyanates?
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Isocyanates include compounds classified as potential human carcinogens and known to cause cancer in animals. The main effects of hazardous exposures are occupational asthma and other lung problems, as well as irritation of the eyes, nose, throat, and skin.
Do isocyanates react with water?
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Many of these compounds are extremely flammable, toxic by inhalation, and irritants to skin, eyes and mucous membranes. Most isocyanates will react with water to generate toxic fumes, and when heated to high temperatures they may decompose to emit toxic nitric oxides and cyanide fumes.
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