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The chemical formula of Cyclohexyldimethoxymethylsilane (CDMMS for short) is C10H22O2Si, CAS 17865-32-6. It is a colorless transparent liquid whose appearance is similar to other similar organosilicon compounds. The liquid state of CDMMS makes it easy to mix and use, suitable for various coating, bonding and other applications. It is a lipophilic solvent capable of dissolving many organic compounds. It has good solubility in polar solvents such as ethanol and methanol, but is almost insoluble in water.
It has high chemical stability, and no obvious decomposition reaction will occur under the conditions of most acids, alkalis and oxidants. This chemical stability makes it ideal for long-life products and corrosion-resistant materials. It is an organosilicon compound, which has been widely used in many fields due to its unique structure and properties. It is widely used in the field of optics.
For example, CDMMS can be used as a Soran material in optics and lens manufacturing. It has high chemical stability, and no obvious decomposition reaction will occur under the conditions of most acids, alkalis and oxidants. This chemical stability makes it ideal for long-life products and corrosion-resistant materials.
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Chemical Formula |
C9H20O2Si |
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Exact Mass |
188 |
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Molecular Weight |
188 |
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m/z |
188 (100.0%), 189 (9.7%), 189 (5.1%), 190 (3.3%) |
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Elemental Analysis |
C, 57.40; H, 10.70; O, 16.99; Si, 14.91 |
The chemical formula of CDMMS is C10H22O2Si, which contains a six-membered ring cycloalkyl (cyclooctyl) and a silicon atom substituted with a dimethoxymethyl group. The shape of the CDMMS molecule resembles a "U" structure folded into a ring. The silicon atom at the center of the molecule is connected to two methoxymethyl groups, while the cyclooctyl group is connected to the methoxymethyl group. In the molecular structure of CDMMS, the carbonyl group on the cyclooctyl group can be further changed through esterification reaction, thus endowing it with more application value.
Cyclohexyldimethoxymethylsilane (CDMMS) is an organosilicon compound that has been widely used in many fields due to its unique chemical structure and properties.
1. Chemical field:
CDMMS can be used as a silicone intermediate, which can be used to produce other silicone compounds. For example, CDMMS can be condensed with benzyltrimethylsilane chloride to generate cyclohexylbenzyldimethoxysilane, which can be used to produce silicone protective agent, silicone lubricating oil, etc. In addition, CDMMS can also be used to prepare acrylic acid glycidyltrimethoxysilane copolymer, which can be used to produce high temperature resistant sealing materials and coatings bonded to metal and other surfaces.
2. Pharmaceutical field:
CDMMS can be used as a pharmaceutical intermediate to produce drugs that promote the release of adrenaline. For example, CDMMS can react with methyl hydrobromide to produce cyclohexyldimethoxyethylamine, which is used in the production of analgesics and neurostimulants. In addition, CDMMS can also be used to prepare polysilicone dimethoxyethylamide modified compounds, which have antitumor effects.
3. Electronic field:
CDMMS can be used to prepare silicone thin films, which have excellent electrical and mechanical properties. For example, CDMMS can react with monomers such as styrene and isoprene to form silicone copolymers, which can be used to prepare electronic components such as capacitors and field effect transistors.
4. Coating field:
CDMMS can be used to prepare silicone resin, which has high weather resistance and corrosion resistance. For example, CDMMS can react with epoxy resin, phenolic resin, urea-formaldehyde resin, etc. to produce silicone-modified resin, which can be used to produce anti-corrosion coatings, weather-resistant coatings, etc. In addition, CDMMS can also be used to prepare nano-organosilicon coatings, which have excellent weather resistance and superhydrophobic properties.
5. Other areas:
CDMMS can also be used to prepare polymers with properties such as UV resistance, high temperature resistance, and wear resistance. For example, CDMMS can be copolymerized with styrene-butadiene rubber to produce silicone-modified rubber, which can be used in the production of automobile parts such as tires and sealing rings. In addition, CDMMS can also be used to prepare nanocomposites with excellent mechanical properties and electrical conductivity.
To sum up, CDMMS has important application value in chemical industry, medicine, electronics, coating and other fields. As people's demand for high-performance materials continues to increase, the market prospect of CDMMS and its derivatives will be broader.
Cyclohexyldimethoxysilane plays a crucial role in the propylene polymerization process. As an efficient and non-toxic catalyst, its core function is to regulate the activity and selectivity of the catalyst, thereby optimizing the performance of polypropylene products.
In the Ziegler Natta catalyst system, as an external electron donor, the stereo orientation of the catalyst is altered by coordinating with transition metals (such as titanium) in the catalyst. This coordination effect can inhibit random stereopolymerization, promote isotactic stereopolymerization, and significantly improve the isotropy of polypropylene (usually up to 95% or more). Isotactic degree is a key indicator for measuring the crystalline properties of polypropylene. High isotactic degree means that polypropylene has higher strength, hardness, and heat resistance, making it suitable for producing high value-added products such as fibers, films, and engineering plastics.
2. Optimization of catalyst activity and lifespan
Its addition can reduce the activation energy of the catalyst, increase the polymerization reaction rate, and thus enhance the activity of the catalyst. Meanwhile, its stable chemical structure can reduce catalyst deactivation during the polymerization process and prolong the service life of the catalyst. For example, in industrial production, catalyst systems using it as an additive can extend their activity life to 2-3 times that of traditional systems, significantly reducing production costs.
During the polymerization process, hydrogen is commonly used to regulate the molecular weight distribution of polypropylene. It can enhance the sensitivity of catalysts to hydrogen, narrow the molecular weight distribution, and achieve more uniform product performance. This characteristic is particularly important for producing high melt flow rate (MFR) polypropylene, which can meet the needs of processing techniques such as injection molding and blow molding.
4. Industrial application cases
Yingkou Fengguang Chemical Co., Ltd. uses it as an additive in its invention patent "A method for olefin polymerization" to produce polypropylene through high-pressure reactor polymerization process. The specific steps are as follows: under nitrogen protection, sequentially add a hexane solution of triethylaluminum, a hexane solution of cyclohexyl dimethoxysilane, and a catalyst to the reaction vessel. Then add hydrogen and liquid propylene, and heat up to 60-80 ℃ for 1-2 hours of reaction. The polypropylene produced by this method has an isotropy of up to 96% and a stable melt flow rate, and is widely used in fields such as automotive parts and packaging materials.
Cyclohexyldimethoxymethylsilane (CDMMS) is an organosilicon compound that has been widely used in many fields due to its unique structure and properties. Several synthetic methods of CDMMS will be introduced, including Grignard reaction, methanol oxidation and ring-opening reaction of cyclic silicate.
Grignard reaction method:
Grignard reaction method is a common synthesis method of CDMMS. In the method, cyclooctyl carbonate and dimethoxymethyl trichlorosilane are used as raw materials, and the hydrolysis and condensation reaction is carried out in the emulsion. The reaction equation is as follows:
Cyclooctyl Ester + Dimethoxymethyltrichlorosilane -> CDMMS + Sulfur Trichloride
In the reaction, cyclooctyl ester and dimethoxymethyltrichlorosilane are catalyzed to condense to generate CDMMS, and then react with the remaining phosphorus trichloride to generate sulfur trichloride and sodium chloride. Finally, CDMMS was obtained by distillation purification.
Methanol oxidation method:
Methanol oxidation is another preparation method of CDMMS, the steps are as follows:
Add chloropyridine and dichloromethane to the ice-water mixture, and react under light to generate cyclooctanone.
Cyclooctanone and trichlorosilane are added to methanol and undergo a reduction reaction to generate CDMMS. The reaction equation is as follows:
Cyclooctanone + Trichlorosilane + CH3OH -> CDMMS + HCl + CH3CHO + SiO2
Purify by distillation to obtain CDMMS.
Cyclic silicate ring-opening reaction method:
The method uses trimethylsiloxane, ethyl iodide and cyclooctyl ketone as raw materials, and prepares CDMMS through heating reaction. During the reaction, trimethylsiloxane and ethyl iodide first undergo a ring-opening reaction to generate 2-hydroxyethyl trimethyl silicon ester, and then condense with cyclooctyl ketone to generate CDMMS. The reaction equation is as follows:
Trimethylsiloxane + iodoethane -> 2-Hydroxyethyl trimethylsilyl
2-Hydroxyethyl trimethylsilyl ester + cyclooctanone -> CDMMS + trimethoxyethanone
In this method, CDMMS can be purified by means of distillation, extraction and crystallization.
Other methods:
In addition, there are some other CDMMS preparation methods, such as the reaction synthesis of chloromethyltrimethoxysilane and cyclooctyl ketone,and the addition of silicate carbene. However, these methods are not commonly used due to high production costs and difficulty in controlling side reactions.
To sum up, several synthesis methods of Cyclohexyldimethoxymethylsilane have their own advantages and disadvantages, and the choice mainly depends on the actual needs. In practical applications, the reaction conditions need to be optimized to improve production efficiency and product purity.
The research on cyclohexyl dimethoxysilane can be traced back to the 1950s.
In 1954, German chemist Eugene G. Rocho first reported the preparation method of cyclohexyldimethylsilane while studying the synthesis of organosilicon compounds. He successfully synthesized the target product through the Grignard reaction of cyclohexyl chloride and dimethoxymethylsilane. Despite the low yield (about 30%), he pioneered the synthesis of such compounds.
In the 1960s, with the development of organosilicon chemistry, the synthesis method of cyclohexyl dimethoxysilane was improved.
In 1962, American chemist Richard M. Uller improved the synthesis process by reacting cyclohexyl magnesium bromide with dimethoxychlorosilane, increasing the yield to over 60%. This improvement greatly promoted the laboratory research and preliminary application of the compound.
In 1968, Soviet scientist Boris A. Dolgopoulos first systematically studied the hydrolysis and condensation behavior of cyclohexyldimethylsilane and found that it could form a stable silicon oxygen ring network structure. This discovery laid the foundation for its subsequent application in materials science.
In the 1970s, research on cyclohexyl dimethoxysilane entered the stage of application development.
In 1973, American chemist Edwin P. Pruderman first applied this compound as a silane coupling agent to glass fiber reinforced composites, significantly improving the interfacial bonding strength between the resin matrix and the reinforcing material. This groundbreaking work established its important position in the composite materials industry.
In the 1980s, with the development of polymer materials science, the application scope of cyclohexyldimethylsilane continued to expand. In 1982, Japanese scientist Seimov developed polymer surface modification technology based on this compound, successfully improving the surface properties of various polymers.
In 1987, German chemist Wolfgang Knoll systematically studied its hydrolysis and condensation kinetics, providing a theoretical basis for the application of sol-gel technology. During this period, the production process of cyclohexyl dimethoxysilane also became increasingly mature.
In 1985, Dow Corning achieved industrial production of this compound, transforming it from a laboratory reagent to a commercial product, greatly promoting its practical applications in multiple fields.
In the 1990s, research on cyclohexyl dimethoxymethylsilane entered a new stage.
In 1993, Japanese materials scientist Kazuyuki Kuroda discovered the template effect of this compound in the preparation of mesoporous materials and pioneered its application in the synthesis of nanomaterials.
In 1998, American scientist Jeffrey Brink successfully prepared pore size controlled silicon nanomaterials using his hydrolysis products.
At the beginning of the 21st century, with the rise of nanotechnology, significant progress has been made in the application of cyclohexyl dimethoxysilane in the field of functional materials.
In 2004, French scientist Cl é ment Sanchez developed organic-inorganic hybrid materials based on this compound, exhibiting unique optical properties.
In 2009, the team of Chinese scientist Yu Shuhong successfully prepared a superhydrophobic nano coating using its surface modifier.
In recent years, breakthroughs have been made in the application of cyclohexyl dimethoxymethylsilane in the biomedical field.
In 2015, American scientist Mark E. Davis used it for surface functionalization of drug carriers.
In 2020, a German team reported its application in biosensors, demonstrating the potential for interdisciplinary applications.
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