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Methyltetrahydrofuran (2-MeTHF) is an organic compound, CAS 96-47-9, The chemical formula is C5H10O. It is a colorless and transparent liquid. It is highly flammable at room temperature and pressure, and can be used for higher temperature chemical reactions compared to tetrahydrofuran,. Easy to dissolve in water and organi solvents such as ethanol, ether, benzene, chloroform, etc. Therefore, it can be used as a substitute for tetrahydrofuran in specific applications. It can be produced by catalytic hydrogenation of furfural intermediate products generated from sugars. Sometimes sold as biofuels. Mainly used as a solvent for resins, natural rubber, ethyl cellulose, and vinyl chloroacetate copolymers. It is also a raw material for the pharmaceutical industry, which can be used to synthesize the anti hemorrhoid drug piperaquine phosphate.
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Chemical Formula |
C5H10O |
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Exact Mass |
86 |
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Molecular Weight |
86 |
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m/z |
86 (100.0%), 87 (5.4%) |
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Elemental Analysis |
C, 69.72; H, 11.70; O, 18.57 |
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Methyltetrahydrofuran is synthesized by various methods, which can be divided into diol method, lactone method and furfural method according to different starting materials.
Dihydric alcohol method:
It can be prepared by dehydration of 2 ‑ methyl ‑ 1,4 ‑ butanediol with pentaethoxyphosphorus as catalyst and dichloromethane as solvent. This method has mild conditions, high yield and relatively low requirements for equipment. However, raw materials are rare and easy to cause environmental pollution, so it is difficult to popularize.
Lactone method:
It can be prepared by dissolving lactone in alcohol solution with hydrated zirconia as catalyst. This method has short process and high yield, but the reaction conditions are harsh, and a large amount of heavy metal pollution will be generated.
Furfural method:
The most remarkable feature is that it can be prepared from furfural, an important agricultural and sideline product. The process is mature, the technology is stable, and the cost is low, which opens up a broad prospect for the deep processing of agricultural and sideline products. However, using furfural as raw material requires harsh reaction conditions, especially high pressure requirements and high equipment investment.
Specific method:
Method 1:
Add copper nitrate and nickel nitrate into the silicon oxide aqueous solution in proportion. After stirring uniformly at room temperature, adjust the pH by adding precipitant until the precipitation of Cu and Ni ions is complete, and then continue stirring. The obtained solution was filtered, dried and calcined to prepare a catalyst precursor. The precursor was passed with hydrogen, and the catalyst bed was heated to prepare a Cu based catalyst Cu Ni / SiO2.
Cu based catalyst Cu Ni / SiO2 was added to the continuous fixed bed reactor. The reaction temperature was 160 ℃, the pressure was 2.8MPa, the molar ratio of hydrogen to levulinate was 80, the mass space velocity of levulinate was 1.0h-1, the conversion of levulinate was 100%, and the selectivity of 2-MeTHF was 97.8%.
Method 2:
Weigh RuCl3 and ZnCl2, add pure water to prepare an aqueous solution, put it into a flask, then add activated carbon carrier, seal it, put it in a constant temperature water bath, and then heat up and stir. Then adjust the pH value of the solution to 9 with NaOH, reduce and filter with analytical pure formaldehyde, wash the filter cake with deionized water until there is no chloride ion in the filtrate, and put the filter cake into a vacuum oven for drying to obtain the composite catalyst.
Preparation of 2-methf: add 100g and 1g of MEF (1% of the mass of MEF) of the composite catalyst prepared as above into the pressure reactor, and carry out liquid phase hydrogenation reaction under the conditions of reaction temperature of 100 ° C and reaction pressure of 4.0Mpa; After the hydrogen absorption is terminated, the reaction liquid is cooled to 20 ℃, the excess hydrogen is evacuated, and the reaction product is filtered to remove the catalyst after being replaced twice with nitrogen. The filtrate is sampled for gas phase analysis. The content of 2-MeTHF is 26.7%, and the content of 2-methylfuran is 70.1%.
Methyltetrahydrofuran (chemical formula C ₅ H ₁₀ O) is an important organic compound that is a colorless and transparent liquid at room temperature and pressure. It has an ether like odor and turns pale yellow to brown when exposed to light, light, or stored for a long time. It is soluble in water and easily soluble in organic solvents such as ethanol, ether, benzene, and chloroform.
1.1 Resin, rubber, and cellulose solvents
Mainly used as a solvent for resins, natural rubber, ethyl cellulose, and chloroacetic acid vinyl acetate copolymers. In the resin processing, it can dissolve various resins, making the resin have good fluidity and processability, which facilitates the molding and processing of the resin. For example, in the manufacturing of coatings, adhesives, and other products, as a solvent, the viscosity of the resin can be adjusted to give the product better coating and bonding properties. In the processing of natural rubber, it can dissolve rubber, promote the mixing of rubber with other additives, and improve the quality and performance of rubber products. For polymer materials such as ethyl cellulose and chloroacetic acid vinyl acetate copolymers, they can also exhibit good solubility, providing convenience for the processing and application of these materials.
1.3 Alternative to traditional toxic solvents
Can be used as a green solvent to replace traditional toxic solvents such as benzene, toluene, chloroform, etc. Benzene, toluene, chloroform and other solvents have high toxicity and volatility, causing serious harm to the environment and human health. And it has low toxicity and volatility, with minimal environmental pollution, meeting the requirements of modern chemical industry for green chemistry. In the fields of synthetic fragrances, new materials, etc., using it as a solvent can reduce the health hazards to operators, lower environmental pollution, and ensure product quality and performance.
3.1 Reaction solvent
It is commonly used as a reaction solvent in organi synthesis. It is stable and not easily decomposed over a wide temperature range, providing a stable reaction environment for organi synthesis reactions. The choice of reaction solvent has a significant impact on the yield and selectivity of organi synthesis reactions. It can dissolve various organi reactants and catalysts, promote contact and reaction between reactants, and improve reaction efficiency. For example, in some organi synthesis reactions such as nucleophilic substitution reactions and addition reactions, acting as a solvent can make the reaction proceed more smoothly, resulting in higher yields and better selectivity.
3.3 Storage and Transfer of Organic Reagents
Can be used for storage and transfer of organi reagents. It can effectively protect the activity of organi reagents and prevent them from deteriorating or decomposing during storage and transmission. In some organi synthesis experiments that require high stability of reagents, using them as storage and transfer media can ensure the quality and performance of reagents. At the same time, it can also conveniently transfer reagents from one container to another, improving the efficiency and accuracy of experiments.
3.2 Catalyst Carrier and Electrolyte Additives
It can also be used as a catalyst carrier and electrolyte additive in organi synthesis. As a catalyst carrier, it can uniformly disperse the catalyst in the reaction system, improving the activity and stability of the catalyst. In some catalytic reactions, the dispersed state of the catalyst has a significant impact on the efficiency of the reaction. As a carrier, it can facilitate better contact between the catalyst and the reactants, promoting the progress of the reaction. As an electrolyte additive, it can improve the performance of electrolytes, enhance the charging and discharging efficiency and cycle life of batteries. For example, in secondary lithium batteries, as an electrolyte additive, it can improve the ion conductivity of the electrolyte, reduce the internal resistance of the battery, and thus enhance the performance of the battery.
4.1 Automotive Fuel Additives
Can be used in automotive fuel additives. It is inherently more stable and has lower volatility, making it suitable for use as engine fuel. Furfural and other furan based compounds (such as furfuryl alcohol, 2-methylfuran, tetrahydrofurfuryl alcohol) have a tendency to polymerize and are quite volatile, which gives them certain advantages as fuel additives. It can improve the combustion performance of fuel, enhance the power output and fuel economy of the engine. At the same time, it can also reduce engine exhaust emissions and lower environmental pollution.
4.2 Alternative fuel components
It is a component of electrolytes and alternative fuels in secondary lithium batteries. In secondary lithium batteries, it can improve the performance and safety of the battery as an electrolyte. With the rapid development of new energy equipment such as electric vehicles, the demand for high-performance batteries is constantly increasing. As an electrolyte additive or component, it can improve the charging and discharging efficiency, cycle life, and safety of batteries, providing support for the development of new energy equipment. As a component of alternative fuels, it can provide new options for energy diversification and sustainable development.
5.1 Organic solar cell electrolyte
Can be used as an electrolyte for organi solar cells, helping to improve their photoelectric conversion efficiency. Organi solar cells are a new type of solar cell with advantages such as low cost, light weight, and flexible preparation. Electrolytes play an important role in transferring charges in organi solar cells. As an electrolyte, it can improve the charge transfer performance, enhance the photoelectric conversion efficiency of the battery, and provide a new approach for the development of organi solar cells.
5.2 Cosmetics and perfume industry
Methyltetrahydrofuran can be used in cosmetics and perfume industry to prepare fragrance or increase the stability of products. In cosmetics, it can serve as a solvent or fragrance carrier, allowing the fragrance to be evenly dispersed in the product, enhancing its aroma persistence and stability. In the perfume industry, it can be compounded with other perfume ingredients to produce perfume products with unique fragrance. Of course, when applied in these fields, corresponding regulations and standards must be followed to ensure product quality and safety.
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