CN112375097A - Synthetic method of isopropenyl oxotrimethylsilane - Google Patents

Synthetic method of isopropenyl oxotrimethylsilane Download PDF

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CN112375097A
CN112375097A CN202011325504.2A CN202011325504A CN112375097A CN 112375097 A CN112375097 A CN 112375097A CN 202011325504 A CN202011325504 A CN 202011325504A CN 112375097 A CN112375097 A CN 112375097A
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Prior art keywords
acetone
oxotrimethylsilane
isopropenyl
trimethylchlorosilane
chloride
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CN112375097B (en
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丁冰
梁秋鸿
杨静
葛利伟
姜林炜
曾小龙
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Jiangxi Chenguang New Materials Co ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • C07F7/1872Preparation; Treatments not provided for in C07F7/20
    • C07F7/188Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)

Abstract

The invention provides a synthesis method of isopropenyl oxotrimethylsilane. The synthesis method of isopropenyl oxotrimethylsilane comprises the following steps: mixing trimethylchlorosilane, a solvent and a catalyst uniformly, adding an acid-binding agent, and reacting under ultrasonic waves. The method provided by the invention can obviously shorten the reaction time, improve the reaction efficiency and save the cost.

Description

Synthetic method of isopropenyl oxotrimethylsilane
Technical Field
The invention relates to the technical field of synthesis of silane cross-linking agents, and particularly relates to a synthesis method of isopropenyl oxotrimethylsilane.
Background
Isopropenyloxysilanes are common and important crosslinking agents in silicone rubbers. Most of isopropenyloxysilanes researched at present are triisopropenoxysilane, most of carbon functional groups are phenyl, methyl, vinyl and propyl, and triisopropenoxysilane contains three hydrolyzable functional groups, so that the triisopropenoxysilane has remarkable advantages as a crosslinking agent and a dealcoholization crosslinking agent of the acetone-free silicone rubber, such as: high hydrolytic activity, complete cross-linking reaction, high sulfurizing speed, high heat resistance, high storage stability, etc.
In the prior art, the isopropenyloxysilane synthesis route: 1) chlorosilane, acetone, metallic sodium and organic amine acid-binding agent (triethylamine, tripropylamine, hexamethylenetetramine, pyridine, pyrrole, tributylamine, etc.); 2) chlorosilanes, acetone, organic amine acid scavengers and lewis acids (zinc chloride, cuprous chloride, nickel chloride, palladium chloride, aluminum chloride, etc.). In the two types of synthesis reactions, the reaction temperature needs to reach the boiling point of a solvent (usually 50-90 ℃), the reaction temperature is high, the reaction conditions are harsh, the risk of using metallic sodium is high, the reaction needs to last for 24-50 h, and the yield is concentrated on 45-60% and is low.
Isopropenyl oxotrimethylsilane can be used as an end-capping agent such as silicone oil, can also replace hexamethyldisiloxane to be used as a treating agent of modified powder, can also be used as a silicon-based reagent (also called silanization reagent) to replace trimethylchlorosilane (TMCS for short), has the advantages of high safety and stability, stronger silanization effect and the like, and has been used for synthesizing beta-alkoxy ketone (such as camphor type beta-alkoxy-beta-unsaturated ketone) with optical activity to be applied to medicine synthesis. However, currently, there is less research on isopropenyloxotrimethylsilane.
Disclosure of Invention
The first purpose of the invention is to provide a method for synthesizing isopropenyloxotrimethylsilane. The synthesis method comprises the following steps: mixing trimethylchlorosilane, a solvent and a catalyst uniformly, adding an acid-binding agent, and reacting under ultrasonic waves.
The invention innovatively uses ultrasonic waves to synthesize isopropenyl oxotrimethylsilane, can obviously shorten the reaction time, improve the reaction efficiency and save the cost.
In a preferred embodiment of the present invention, the power of the ultrasonic wave is 100 to 300w, and the frequency is 20 to 200 KHz. Preferably, the power of the ultrasonic wave is 200-250 w, and the frequency is 50-100 KHz.
In a preferred embodiment of the invention, the reaction time is 30 min-5 h, and the reaction temperature is 25-50 ℃. Preferably, the reaction time is 1-2 h, and the reaction temperature is 35-40 ℃.
In a preferred embodiment of the present invention, the solvent is 80 to 300 wt%, preferably 100 to 200 wt% of the mass of trimethyl monochloromethane. The solvent commonly used in the art, such as one or more of toluene, benzene, cyclohexane, n-hexane, petroleum ether, dioxane, acetone, and DMF, preferably acetone, can be selected for use in the present invention.
In a preferred embodiment of the present invention, the catalyst is a lewis acid, and the lewis acid is preferably one or more of zinc chloride, cuprous chloride, nickel chloride, palladium chloride, and aluminum chloride, and is further preferably cuprous chloride.
In a preferred embodiment of the invention, the acid-binding agent is one or more of triethylamine, tripropylamine, hexamethylenetetramine, 4-dimethylaminopyridine, quinoline, pyridine and pyrrole, preferably triethylamine.
In a preferred embodiment of the present invention, the molar ratio of trimethylchlorosilane to acid-binding agent is 1: (1-5), preferably 1: (1.2-1.5), wherein the catalyst is 0.5-5 wt% of trimethylchlorosilane by mass, and preferably 1-2 wt%.
In a preferred embodiment of the present invention, the method for synthesizing isopropenyloxotrimethylsilane comprises the steps of:
mixing trimethylchlorosilane, toluene and catalyst nickel chloride uniformly under ultrasonic wave, dropwise adding an acid-binding agent and acetone into the mixture, and reacting under ultrasonic wave; wherein the power of the ultrasonic wave is 200-250 w, and the frequency is 50-100 KHz; the reaction time is 1-2 h, and the reaction temperature is 35-40 ℃.
The invention has the beneficial effects that:
the invention innovatively synthesizes isopropenyl oxotrimethylsilane by using ultrasonic waves, and can obviously shorten the reaction time, improve the reaction efficiency, save the cost and have obvious economic effect by optimizing the power, the frequency and various parameters of the ultrasonic waves.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is isooctane), the ultrasonic power is 250w, and the frequency is 50 KHz. 108.64g of trimethylchlorosilane and 1.1g of cuprous chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is heated to 40 ℃, the mixture of 150g of acetone and 131.54g of triethylamine is dropwise added through a constant pressure dropping funnel while ultrasonic treatment is carried out, the upper opening of the three-mouth flask is connected with a condenser tube for keeping, the acetone volatilization is reduced, the temperature of a reaction solution is maintained at 40 ℃, the reaction solution is kept for 30min, ultrasonic treatment is continued for 1h, the mass percentage content of the trimethylchlorosilane in a GC spectrogram is sampled and tested, the acetone and the triethylamine which are not reacted are filtered, and 113.58g of isopropenyl oxotrimethylsilane is collected through reduced pressure rectification, the GC content is 98.12%, and the reaction yield is 87.2%.
Example 2
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is petroleum ether with a boiling range of 90-120 ℃), the ultrasonic power is 200w, and the frequency is 100 KHz. 108.64g of trimethylchlorosilane and 1.1g of cuprous chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is uniformly mixed, the mixture is heated to 40 ℃, the mixture of 150g of acetone and 131.54g of triethylamine is dropwise added through a constant pressure dropping funnel while ultrasonic treatment is carried out, the upper opening of a three-mouth flask is connected with a condenser tube for keeping, the acetone volatilization is reduced, the temperature of a reaction solution is maintained at 40 ℃, the reaction solution is kept for 30min, ultrasonic treatment is continuously carried out for 1h, the mass percentage content of the trimethylchlorosilane in a GC spectrogram is sampled and tested, the acetone and the triethylamine which are not reacted are filtered, the acetone and the triethylamine are distilled and recovered, 110.84g of isopropenyl oxotrimethylsilane is collected by reduced pressure.
Example 3
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is isooctane), the ultrasonic power is 100w, and the frequency is 200 KHz. 108.64g of trimethylchlorosilane and 1.1g of cuprous chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is uniformly mixed, the mixture is heated to 40 ℃, the mixture of 150g of acetone and 131.54g of triethylamine is dropwise added through a constant pressure dropping funnel while ultrasonic treatment is carried out, the upper opening of a three-mouth flask is connected with a condenser tube for keeping, the acetone volatilization is reduced, the temperature of a reaction solution is maintained at 40 ℃, the reaction solution is kept for 30min, ultrasonic treatment is continuously carried out for 1h, the mass percentage content of the trimethylchlorosilane in a GC spectrogram is sampled and tested, the acetone and the triethylamine which are not reacted are filtered, the acetone and the triethylamine are distilled and recovered, 91.96g of isopropenyl oxotrimethylsilane is collected by reduced pressure.
Example 4
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is isooctane), the ultrasonic power is 300w, and the frequency is 20 KHz. 108.64g of trimethylchlorosilane and 1.1g of cuprous chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is uniformly mixed, the mixture is heated to 40 ℃, the mixture of 150g of acetone and 131.54g of triethylamine is dropwise added through a constant pressure dropping funnel while ultrasonic treatment is carried out, the upper opening of a three-mouth flask is connected with a condenser tube for keeping, the acetone volatilization is reduced, the temperature of a reaction solution is maintained at 40 ℃, the reaction solution is kept for 30min, ultrasonic treatment is continuously carried out for 1h, the mass percentage content of the trimethylchlorosilane in a GC spectrogram is sampled and tested, the acetone and the triethylamine which are not reacted are filtered, 94.17g of isopropenyl oxotrimethylsilane is collected by reduced pressure rectification, and the reaction yield is 72.3.
Example 5
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is isooctane), the ultrasonic power is 250w, and the frequency is 50 KHz. 108.64g of trimethylchlorosilane and 2.17g of cuprous chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is heated to 40 ℃, a mixed solution of 108.6g of acetone and 121.4g of triethylamine is dropwise added through a constant pressure dropping funnel while carrying out ultrasonic treatment, the upper opening of a three-mouth flask is connected with a condenser tube for keeping, the acetone volatilization is reduced, the temperature of a reaction solution is maintained at 40 ℃, the dropwise addition lasts for 30min, the ultrasonic treatment is continued for 1h, the mass percentage of the trimethylchlorosilane in a GC spectrogram is sampled and tested, the acetone and the triethylamine which are not reacted are filtered, 102.12g of isopropenyl oxotrimethylsilane is collected by reduced pressure rectification, and the reaction yield is 78.4%.
Example 6
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is isooctane), the ultrasonic power is 250w, and the frequency is 50 KHz. 108.64g of trimethylchlorosilane and 1.1g of cuprous chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is heated to 40 ℃, the mixture of 217.3g of acetone and 151.8g of triethylamine is dropwise added into the mixture through a constant pressure dropping funnel while carrying out ultrasonic treatment, the upper opening of a three-mouth flask is connected with a condenser tube for keeping, the acetone volatilization is reduced, the temperature of a reaction solution is maintained at 40 ℃, the dropwise addition lasts for 30min, the ultrasonic treatment is continued for 1h, the mass percentage of the trimethylchlorosilane in a GC spectrogram is sampled and tested, the mass percentage is 0.28 percent, the acetone and the triethylamine which are not reacted are filtered, 103.94g of isopropenyl oxotrimethylsilane is collected through reduced pressure rectification, and the reaction yield is.
Example 7
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is isooctane), the ultrasonic power is 250w, and the frequency is 50 KHz. 108.64g of trimethylchlorosilane and 0.5g of cuprous chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is heated to 40 ℃, a mixed solution of 86.9g of acetone and 506.0g of triethylamine is dropwise added through a constant pressure dropping funnel while ultrasonic treatment is carried out, the upper opening of a three-opening flask is connected with a condenser tube for keeping, the acetone volatilization is reduced, the temperature of a reaction solution is maintained at 40 ℃, the dropwise addition lasts for 30min, ultrasonic treatment is continued for 1h, a sample is taken for testing the mass percentage content of the trimethylchlorosilane in a GC spectrogram to be 0.83%, the unreacted acetone and the unreacted triethylamine are filtered, 93.52g of isopropenyl oxotrimethylsilane is collected through reduced pressure rectification, and the reaction yield is 71.8%.
Example 8
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is isooctane), the ultrasonic power is 250w, and the frequency is 50 KHz. 108.64g of trimethylchlorosilane and 5.4g of cuprous chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is heated to 40 ℃, a mixed solution of 325.92g of acetone and 101.2g of triethylamine is dropwise added through a constant pressure dropping funnel while ultrasonic treatment is carried out, the upper opening of a three-opening flask is connected with a condenser tube for keeping, the acetone volatilization is reduced, the temperature of a reaction solution is maintained at 40 ℃, the dropwise addition lasts for 30min, ultrasonic treatment is continued for 1h, sampling is carried out to test the mass percentage content of the trimethylchlorosilane to be 1.47% in a GC spectrogram, the unreacted acetone and the unreacted triethylamine are filtered, and 78.80g of isopropenyl oxotrimethylsilane is collected through reduced pressure rectification, wherein the reaction yield is 60.5.
Example 9
The embodiment of the invention provides a synthesis method of isopropenyl oxotrimethylsilane, which comprises the following steps:
under the protection of nitrogen, a 2L three-neck flask is placed into an ultrasonic reactor (the ultrasonic medium is isooctane), the ultrasonic power is 250w, and the frequency is 50 KHz. 108.64g of trimethylchlorosilane and 1.6g of nickel chloride are added into a flask, the mixture is stirred and ultrasonically vibrated for 2min and then is uniformly mixed, the mixture is heated to 40 ℃, the mixture of 150g of toluene, 64g of acetone and 186.3g of tripropylamine is dropwise added through a constant pressure dropping funnel while ultrasonic treatment is carried out, the upper opening of the three-neck flask is connected with a condensing tube for keeping the temperature of the reaction solution at 40 ℃, the time of dropwise addition is 30min, ultrasonic treatment is continued for 1h, the mass percent of the trimethylchlorosilane in a GC spectrogram is sampled and tested, the acetone which is not reacted is filtered, distilled and recovered, 91.31g of isopropenyl oxotrimethylsilane is collected by reduced pressure rectification, and the reaction yield is 70.1%.
Comparative example 1
The comparative example provides a method for synthesizing isopropenyl oxotrimethylsilane, comprising the following steps:
under the protection of nitrogen, 108.64g of trimethylchlorosilane, 128g of toluene and 2.7g of cuprous chloride are added into a 2L three-neck flask, the mixture is heated to 40 ℃ after being stirred and mixed uniformly, a mixed solution of 197.5g of acetone and 333.9g of triethylamine is dripped through a constant-pressure dropping funnel, the upper opening of the three-neck flask is connected with a condenser tube for keeping, the volatilization of the acetone is reduced, the temperature of the reaction solution is kept at 40 ℃, the dripping time is 30min, the reaction is kept for 40h, the reaction is tested to be strongly acidic, the filtration is carried out, the unreacted trimethylchlorosilane and the acetone are distilled and recovered, 14.6g of isopropenyl oxotrimethylsilane is collected through reduced pressure rectification, and the.
Finally, the method of the present invention is only a preferred embodiment and is not intended to limit the scope of the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (9)

1. A method for synthesizing isopropenyl oxotrimethylsilane is characterized by comprising the following steps:
mixing trimethylchlorosilane, a solvent and a catalyst uniformly, adding an acid-binding agent, and reacting under ultrasonic waves.
2. The synthesis method according to claim 1, wherein the power of the ultrasonic wave is 100 to 300w, and the frequency is 20 to 200 KHz.
3. The synthesis method according to claim 1 or 2, wherein the reaction time is 30min to 5h, and the reaction temperature is 25 to 50 ℃.
4. The synthesis process according to any one of claims 1 to 3, characterized in that the catalyst is a Lewis acid, preferably the Lewis acid is one or more of zinc chloride, cuprous chloride, nickel chloride, palladium chloride, aluminium chloride, further preferably cuprous chloride.
5. A synthesis method according to any one of claims 1 to 4, characterized in that the acid-binding agent is one or more of triethylamine, tripropylamine, hexamethylenetetramine, 4-dimethylaminopyridine, quinoline, pyridine and pyrrole, preferably triethylamine.
6. The synthesis process according to any one of claims 1 to 5, characterized in that the molar ratio of trimethylchlorosilane to acid-binding agent is 1: (1-5), preferably 1: (1.2-1.5).
7. A synthesis process according to any one of claims 1 to 6, characterised in that the catalyst is from 0.5% to 5% by weight, preferably from 1% to 2% by weight, of trimethylchlorosilane parts by mass.
8. The synthesis method according to any one of claims 1 to 7, characterized in that the solvent is one or more of toluene, benzene, cyclohexane, n-hexane, petroleum ether, dioxane, acetone, DMF, preferably acetone.
9. The synthesis process according to any one of claims 1 to 8, characterized in that the solvent is 80 to 300 wt.%, preferably 100 to 200 wt.%, based on the mass of trimethyl monochloromethane.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105601660A (en) * 2016-03-15 2016-05-25 荆州市江汉精细化工有限公司 Preparation method of propyltriisoallyloxysilane
CN107936052A (en) * 2017-11-20 2018-04-20 湖北新蓝天新材料股份有限公司 A kind of preparation method of different alkane alkenyloxy group silane
CN109796487A (en) * 2018-12-14 2019-05-24 浙江开化合成材料有限公司 A kind of synthetic method of vinyltriisopropenyloxysilane
CN111269255A (en) * 2020-01-14 2020-06-12 浙江衢州硅宝化工有限公司 Preparation method of isopropenyloxysilane

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105601660A (en) * 2016-03-15 2016-05-25 荆州市江汉精细化工有限公司 Preparation method of propyltriisoallyloxysilane
CN107936052A (en) * 2017-11-20 2018-04-20 湖北新蓝天新材料股份有限公司 A kind of preparation method of different alkane alkenyloxy group silane
CN109796487A (en) * 2018-12-14 2019-05-24 浙江开化合成材料有限公司 A kind of synthetic method of vinyltriisopropenyloxysilane
CN111269255A (en) * 2020-01-14 2020-06-12 浙江衢州硅宝化工有限公司 Preparation method of isopropenyloxysilane

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHANGHE ZHANG ET AL.,: "Enantioselective N‑Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes", 《ORGANIC LETTERS》 *

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