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Pure M-Cresol, also known as 3-methylphenol, is an organic compound with the chemical formula C7H8O and CAS 108-39-4. It is typically a colorless or pale yellow liquid with a unique phenolic odor. Solubility exhibits certain peculiarities. It is slightly soluble in water, but its solubility increases significantly at high temperatures. For example, at 20 ℃, its solubility in water is about 20g/L; At 40 ℃, the solubility can reach 2.5%; At 100 ℃, it reaches as high as 5.5%. It is also easily soluble in caustic soda and commonly used organic solvents such as ethanol, ether, etc. Can be miscible with sodium hydroxide aqueous solution, acetone, chloroform, etc. Mainly used as an intermediate for pesticides, it produces insecticides such as fenthion, fenthion, methomyl, and chlorpyrifos. It is also an intermediate for color films, resins, plasticizers, and fragrances. It can also be used as a disinfectant, fumigant, photographic developer, etc.
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Chemical Formula |
C7H8O |
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Exact Mass |
108 |
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Molecular Weight |
108 |
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m/z |
108 (100.0%), 109 (7.6%) |
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Elemental Analysis |
C, 77.75; H, 7.46; O, 14.79 |
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Toluene reacts with sulfuric acid, heats up, adds toluene, heats up for isomerization, and alkali melts cresol. The m-cresol and p-cresol obtained from the above reaction are re evaporated in a high-efficiency distillation tower, and a narrow fraction of 201 ~ 208 ℃ is cut, that is, a mixture of m-cresol and p-cresol is obtained; Dilute the material with benzene, add urea, react, centrifugal filtration, and wash it twice with benzene or toluene to obtain a white solid complex of m-cresol urea. Hydrolyze the complex with toluene, take the upper liquid layer, evaporate toluene and water under normal pressure in the distillation tower, and then distillate in vacuum to obtain Pure M-Cresol with a content of more than 95%.
This method is the earliest industrialized method with mature process route. It was used in foreign countries in the early stage. However, due to the large amount of acid and alkali consumed by this method, the amount of three wastes is large, the equipment corrosion is serious, and the solid materials need to be treated many times in the process, which makes the continuous production more difficult, and the quality is poor. It is not superior to the isopropyl toluene method in technology and economy.
Toluene is used as raw material, propylene is alkylated in the presence of catalyst, and then it is obtained by oxidation and acidolysis. Alkylation alkylation with aluminum trichloride as catalyst can obtain meta isomers with high yield. The oxidants used in the oxidation of isopropyl toluene include air, pure oxygen or hydrogen peroxide. Generally, air oxidation is more economical. The oxidation reaction is carried out in the presence of initiator (benzoyl peroxide or azodiisobutyronitrile), and the mass of isopropyl toluene is added; Isopropyl toluene hydroperoxide is about 85% - 90%. Decompose isopropyl toluene. Hydrogen peroxide decomposes into cresol and acetone in the presence of sulfuric acid.
The mixed cresol synthesized by this method has m-and p-isomers of about 6:4. The composition of the decomposition solution after acid decomposition is about 34.2% acetone, 30.7% m-and p-mixed cresol, and 6.9% isopropyl toluene, α- Methyl styrene 3.9%, peroxide 4.4%. The boiling point difference between o-cresol, m-cresol and p-cresol is large, so it can be separated by selecting appropriate equipment. However, m-cresol and p-cresol have very similar boiling points, so fractionation method cannot be used for separation.
Good results can be obtained. The process is to alkylate mixed cresol with isobutene in the presence of catalyst to obtain a mixture of Di tert butyl m-cresol and di tert butyl p-cresol. The product obtained by tertiary butylation of cresol is a complex mixture, in which there are unreacted cresol and isobutene polymers in addition to mono tertiary butyl cresol isomers and di tertiary butyl isomers, which can be distilled and separated by using their boiling point differences. After separation, 4,6-di-tert-butyl m-cresol can be dehydrocarbonized and decomposed into m-cresol and isobutene in the presence of catalyst after heating to 202 ℃. The content of m-cresol in the product can reach more than 98%, and the recovery rate is about 95%. The recovery rate of isobutene is more than 95%, which can be recycled. Using this method to separate m-cresol, 2,6-di-tert-butyl-p-cresol antioxidant can also be produced.
M-Cresol (CAS number 108-39-4), as an important organic chemical raw material, has shown wide application value in various fields such as pesticides, pharmaceuticals, fragrances, polymer materials, dyes, preservatives, etc. due to its unique chemical structure and reactivity.
1. Pesticide field: Key intermediates for highly efficient and low toxicity insecticides
It is the core raw material for synthesizing pyrethroids, organophosphates, and carbamate insecticides. The methyl and phenolic hydroxyl groups in its molecular structure can participate in various chemical reactions, generating intermediates with high biological activity.
Typical application cases:
Imidacloprid insecticides: By reacting with chlorinated phenoxyl compounds, Pure m-cresol is generated, which further synthesizes highly efficient and low toxicity insecticides such as permethrin and cypermethrin. This type of insecticide has contact and stomach toxicity effects on pests, and is environmentally friendly, making it a mainstream insecticide variety worldwide.
Organophosphorus insecticides: react with trichlorfon to produce intermediates such as fenitrothion and fenthion, which are used to control pests on crops such as rice and cotton. Its mechanism of action is to inhibit the activity of insect acetylcholinesterase, leading to nerve conduction blockade.
Aminomethyl ester insecticides: react with isocyanate compounds to produce intermediates such as imidacloprid, and have the characteristic of quickly knocking down pests.
Technical advantages:
Selective regulation: By adjusting reaction conditions such as temperature and catalyst, the substitution position of meta cresol can be controlled to optimize product activity.
Green synthesis process: using microchannel reactors or enzyme catalysis technology can reduce the generation of by-products and improve atomic utilization efficiency.
2. Pharmaceutical field: raw materials for the synthesis of vitamin E and antibacterial drugs
The application in the field of medicine focuses on the synthesis of vitamin E, antibiotics, and local anesthetics. The phenolic hydroxyl group can participate in redox reactions, while the methyl group can introduce steric hindrance to regulate molecular activity.
Typical application cases:
Vitamin E synthesis: Methyl cresol undergoes methylation, oxidation, and other steps to produce 2,4,6-trimethylphenol, which is further synthesized into trimethylhydroquinone to ultimately produce vitamin E (α - tocopherol). Vitamin E has antioxidant properties and is widely used in health products and cosmetics.
Antibacterial drug synthesis: Reacts with chlorinated compounds to Pure m-cresol intermediates such as tetrabromocresol, which are used to prepare topical antibacterial drugs such as tinea powder. Its mechanism of action is to disrupt the structure of bacterial cell membranes and inhibit bacterial growth.
Local anesthetics: react with amino compounds to produce local anesthetics such as benzocaine, used for surface anesthesia of the skin and mucous membranes.
Technological breakthrough:
Continuous production: The continuous methylation and oxidation reaction of meta cresol is achieved through a fixed bed reactor, shortening the production cycle and improving product quality.
Chiral synthesis: Using chiral catalysts, vitamin E derivatives with specific stereoisomers can be synthesized to enhance drug activity.
3. Spice field: Chemical synthesis alternatives to natural flavors
Meta cresol is a key raw material for the synthesis of natural fragrances such as thymol and menthol. Its phenolic hydroxyl group can participate in esterification, etherification and other reactions, generating compounds with special aromas.
Typical application cases:
Thymol synthesis: m-cresol is produced by catalytic hydrogenation, oxidation and other steps to produce thymol, which is used for flavoring perfume, soap and oral care products. Thymol has antibacterial and preservative effects, which can extend the shelf life of products.
Synthesis of menthol: m-cresol reacts with isopropylaluminum to produce thymol, which is further hydrogenated to produce L-menthol.
L-menthol is the main component of cooling agents and is widely used in chewing gum, toothpaste, and cosmetics.
Essence intermediate: m-cresol reacts with acetic anhydride to produce m-tolyl acetate, which is used to enhance the flavor of food and beverages.
Technological frontiers:
Biocatalytic synthesis: Enzyme catalyzed technology is used to achieve highly selective conversion of meta cresol to thymol, reducing the generation of by-products.
Green solvent system: Using ionic liquids or supercritical carbon dioxide as solvents, it can replace traditional organic solvents and reduce environmental pollution.
4. Polymer materials field: raw materials for the synthesis of phenolic resins and antioxidants
Meta cresol is an important raw material for the synthesis of phenolic resins, epoxy resins, and antioxidants. Its phenolic hydroxyl group can react with aldehydes or epichlorohydrin to produce polymer materials with heat resistance and mechanical properties.
Typical application cases:
Phenolic resin synthesis: m-cresol and formaldehyde are condensed under acidic or alkaline conditions to produce phenolic resin, which is used to manufacture electric wood, coatings, and adhesives.
Phenolic resin has excellent heat resistance and electrical insulation properties, and is widely used in the electronics and automotive industries.
Epoxy resin curing agent: m-cresol reacts with epichlorohydrin to produce m-cresol type epoxy resin, which is used in composite materials and electronic packaging materials.
Antioxidant synthesis: m-cresol reacts with tert butyl chloride to produce 6-tert-butyl-3-methylphenol, which is further synthesized into antioxidants such as CA and antioxidant 300 for use in plastics, rubber, and lubricants.
Technical advantages:
High performance: By introducing nano fillers or copolymerization modification, the toughness and heat resistance of phenolic resin can be improved.
Low toxicity: Using halogen-free antioxidants can reduce the release of toxic gases during the combustion of polymer materials.
5. In the field of dyes and preservatives: Dark dyes are key raw materials for industrial preservatives
Meta cresol is an important raw material for the synthesis of diazo dyes, anthraquinone dyes, and industrial preservatives.
Pure m-cresol phenolic hydroxyl group can participate in reactions such as diazotization and coupling, generating dyes with bright colors and good fastness.
Typical application cases:
Synthesis of diazo dyes: m-cresol undergoes diazotization, coupling and other steps to generate dyes such as Direct Black 38, which are used for dyeing cotton, linen and other fibers. This type of dye has the characteristics of bright color and good fastness.
Synthesis of anthraquinone dyes: m-cresol reacts with anthraquinone intermediates to produce dyes such as Disperse Blue 79, which are used for dyeing polyester fibers. Anthraquinone dyes have excellent light and wash resistance.
Industrial preservatives: m-cresol reacts with brominated compounds to produce preservatives such as bromocresol purple, which are used for the preservation of metalworking fluids and coatings. Its mechanism of action is to inhibit microbial growth and prolong the service life of the product.
Technological breakthrough:
Digital color matching technology: By using a computer color matching system, precise color matching of meta cresol based dyes can be achieved, improving dyeing efficiency.
Nano anti-corrosion technology: Combining meta cresol based preservatives with nanoparticles can enhance the permeability and durability of preservatives.
1. Green synthesis process: continuous and biocatalytic technology
The traditional synthesis process of meta cresol, such as sulfonation alkali melting method, has problems of high energy consumption and large pollution. In recent years, continuous production and biocatalytic technology have become research hotspots.
Technical case:
Microchannel continuous reaction: Continuous sulfonation, alkali melting, and acid precipitation reactions of meta cresol are achieved through microreactors, reducing the reaction time from 7 hours to 2 hours, achieving a product purity of 99.5%, and reducing energy consumption by 30%.
Enzymatic synthesis: The methylation or oxidation reaction of meta cresol is catalyzed by lipase or oxidoreductase, which can achieve highly selective conversion and reduce the generation of by-products.
2. Preparation of high-purity products: Molecular sieve adsorption and crystallization separation technology
High purity meta cresol (≥ 99.5%) has important applications in the fields of medicine and electronics. Traditional distillation processes are difficult to separate m-cresol/p-cresol mixtures and require the use of molecular sieve adsorption or crystallization separation techniques.
Technical case:
Molecular sieve adsorption separation: ZSM-5 molecular sieve is used as the adsorbent to selectively adsorb p-cresol, achieving enrichment of m-cresol with a purity of 99.8%.
Crystallization separation technology: By controlling the temperature and solvent composition, the crystallization separation of meta cresol and para cresol can be achieved, with a product purity of 99.9%.
3. Development of functional materials: fluorescent probes and photothermal therapy materials
Meta cresol based fluorescent materials have shown great potential in the fields of biological imaging and photothermal therapy.
For example, CsPbBr ∝ nanocrystals (containing meta cresol structure) can be used for fluorescence imaging of living tumors, with their emission wavelength (520nm) shifted from the self fluorescence wavelength of biological tissues, resulting in a signal-to-noise ratio improvement of over 50%.
Technical advantages:
Multimodal imaging: By combining meta cresol based fluorescent materials with magnetic nanoparticles, fluorescence magnetic resonance dual-mode imaging can be achieved, improving diagnostic accuracy.
Photothermal therapy: Under near-infrared light irradiation, m-cresol based nanocrystals can generate local high temperatures, achieving photothermal ablation of tumors.
4. New energy materials: battery electrolytes and solid electrolytes
With the rapid development of the new energy industry, the application of meta cresol in the field of batteries is gradually expanding. For example, in lithium-ion batteries, meta cresol can be used as an additive to optimize the ion conductivity of the electrolyte, increasing the battery's cycle life from 500 to 800 cycles.
Technological breakthrough:
All solid state battery: Introducing Pure m-cresol into sulfide solid electrolyte can form a stable lithium ion conduction channel, increasing the ion conductivity from 10 ⁻⁴ S/cm to 10 ⁻³ S/cm.
Sodium ion battery: Using meta cresol as raw material, a bromine containing Prussian blue analog is synthesized as the positive electrode material for sodium ion batteries, which can achieve high capacity (120mAh/g) and long cycle life (1000 times).
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