CN117186143A - Preparation method of siloxane containing electron withdrawing functional groups - Google Patents

Preparation method of siloxane containing electron withdrawing functional groups Download PDF

Info

Publication number
CN117186143A
CN117186143A CN202311090321.0A CN202311090321A CN117186143A CN 117186143 A CN117186143 A CN 117186143A CN 202311090321 A CN202311090321 A CN 202311090321A CN 117186143 A CN117186143 A CN 117186143A
Authority
CN
China
Prior art keywords
catalyst
electron withdrawing
siloxane
temperature
ether
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202311090321.0A
Other languages
Chinese (zh)
Inventor
王子超
韩兆萌
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shanghai Rukun New Material Co Ltd
Original Assignee
Shanghai Rukun New Material Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shanghai Rukun New Material Co Ltd filed Critical Shanghai Rukun New Material Co Ltd
Priority to CN202311090321.0A priority Critical patent/CN117186143A/en
Publication of CN117186143A publication Critical patent/CN117186143A/en
Pending legal-status Critical Current

Links

Abstract

The application relates to the technical field of C07F7/18, in particular to a preparation method of siloxane containing electron withdrawing functional groups, which comprises the following steps: reacting the compound (I) with an ether substance in the presence of a catalyst to obtain siloxane; wherein the compound (I) has the structure ofThe siloxane has the structure ofn is any integer from 1 to 5, R 1 Is any one of nitro, cyano, fluorine, chlorine, bromine, iodine, alkynyl, aryl and acetyl, R 2 Is C 1‑5 Alkyl or acetyl. The preparation method disclosed by the application is simple to operate, mild in reaction conditions, good in intermediate stability, not easy to cause side reaction, and simple in product separation and purification.

Description

Preparation method of siloxane containing electron withdrawing functional groups
Technical Field
The application relates to the technical field of C07F7/18, in particular to a preparation method of siloxane containing electron withdrawing functional groups.
Background
The siloxane containing electron withdrawing functional groups is a common silane coupling agent, is an important intermediate for preparing amino propyl trimethoxy silane (HP-540), and is also high-performance oil-resistant silicone sealant. The traditional dimethyl silicone rubber has poor oil resistance, after the silicone rubber is immersed in oil, oil substances can permeate the silicone rubber and act on molecular chains to diffuse mutually to destroy a network structure and generate a swelling effect, and meanwhile, some soluble additives are dissolved to change the network structure, so that the performance of the silicone rubber is poor. In order to make up for the deficiency and maintain other excellent performances, students at home and abroad have made many related researches. Mainly from the following aspects. (1) grafting modification, and introducing polar groups. The fluorosilicone rubber not only has a plurality of excellent performances of the traditional silicone rubber, but also has outstanding oil resistance, but the synthesis process is difficult to control, and the cost is high, so that the fluorosilicone rubber is difficult to popularize and apply. The electron-withdrawing functional group is introduced as a hot spot in recent researches, and the electron-withdrawing functional group modified polydimethyl polysiloxane is novel heat-resistant and oil-resistant silicone rubber, has good stability to common oil, solvent oil and fuel, and can be used at the temperature of-70-260 ℃. (2) Blending modification, and blending with other rubber with good oil resistance to obtain the blending rubber. Currently, in many research systems, common materials that improve the oil resistance of silicone rubber are acrylate rubber (ACM), fluororubber (FKM), and ethylene-vinyl acetate copolymers of the rubber (EVM) and plastic (EVA) type. However, silicone rubber is generally poor in compatibility with the above classes and phase separation is liable to occur. (3) The requirements on raw materials are high, for example, the low molecular weight silicon rubber is selected, and zinc oxide, cerium oxide and the like are selected, so that the oil resistance can be improved to a certain extent.
CN201911409954.7 proposes a preparation method of cyano silane: under the vacuum of-0.1 MPa, dropping methanol, reacting with 2-cyanoethyl trichlorosilane, and absorbing the generated HCl by alkali liquor to obtain the product. However, in the reaction process, a large amount of HCl gas is generated to react with raw material alcohol to generate water, so that not only can raw material chlorosilane be hydrolyzed, but also target product alkoxysilane is initiated to be hydrolyzed, and a large amount of powder is generated in the reaction process; it is also difficult to avoid the addition of methanol to cyano to form imine byproducts. In addition, the HCl produced has a very high solubility in the alkoxysilane of the final product, which leads to increased difficulties in post-reaction treatment and increased production costs. And the alkali liquor is used for removing acid to finally obtain the alkoxy silane with low acid value, and the reaction process and the preparation cost are increased.
Therefore, it is desirable to provide a preparation method that is simple to operate, low in cost, and free of HCl gas generation.
Disclosure of Invention
For the purpose ofThe first aspect of the present application provides a method for preparing a siloxane containing an electron withdrawing functional group, comprising: reacting the compound (I) with an ether or ester substance in the presence of a catalyst to obtain siloxane; wherein the compound (I) has the structure ofThe siloxane has the structure->n is any integer from 1 to 5, R 1 Is any one of nitro, cyano, fluorine, chlorine, bromine, iodine, alkynyl, aryl and acetyl, R 2 Is C 1-5 Alkyl or acetyl.
C in the application 1-5 Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, and n-butyl.
In one embodiment, the siloxanes obtained may be exemplified by
Etc.
In one embodiment, the catalyst is selected from one or more of palladium catalyst, platinum catalyst, rhodium catalyst, ruthenium catalyst, cobalt catalyst, iron catalyst, manganese catalyst, bismuth catalyst, aluminum catalyst, zinc catalyst, titanium catalyst, tin catalyst.
Preferably, the palladium catalyst is selected from one or more of tris (dibenzylideneacetone) dipalladium, palladium acetate, (tetra) triphenylphosphine palladium, 1' -bis-diphenylphosphine ferrocene palladium dichloride.
Preferably, the platinum catalyst is selected from one or more of platinum chloride, platinum oxide, chloroplatinic acid, and metallic platinum.
Preferably, the rhodium catalyst is selected from one or more of rhodium chloride, rhodium tetrafluoroborate, rhodium acetate and rhodium metal.
Preferably, the ruthenium catalyst is selected from one or more of rhodium hydroxide, rhodium chloride and metallic ruthenium.
Preferably, the cobalt catalyst is selected from one or more of cobalt acetate, cobalt oxide and metallic cobalt.
Preferably, the iron catalyst is selected from one or more of ferric chloride, ferric bromide, ferric iodide, ferric oxide, ferric triflate, ferric sulfate, ferric nitrate, ferric carbonate, ferric phosphate, ferric acetate, ferric sulfide, ferric fluoride, and the corresponding ferrous salts.
Preferably, the manganese catalyst is selected from one or more of manganese chloride, manganese oxide and manganese metal.
Preferably, the bismuth catalyst is selected from one or more of bismuth chloride, bismuth bromide, bismuth iodide, bismuth oxide, bismuth triflate, bismuth sulfate, bismuth nitrate, bismuth carbonate, bismuth phosphate, bismuth acetate, bismuth sulfide, bismuth fluoride.
Preferably, the aluminium catalyst is selected from one or more of aluminium chloride, aluminium bromide, aluminium iodide, aluminium oxide, aluminium triflate, aluminium sulphate, aluminium nitrate, aluminium carbonate, aluminium phosphate, aluminium acetate, aluminium sulphide, aluminium fluoride.
Preferably, the zinc catalyst is selected from one or more of zinc chloride, zinc bromide, zinc iodide, zinc oxide, zinc triflate, zinc sulfate, zinc nitrate, zinc carbonate, zinc phosphate, zinc acetate, zinc sulfide, zinc fluoride.
Preferably, the titanium catalyst is selected from one or more of titanium chloride, titanium bromide, titanium iodide, titanium oxide, titanium triflate, titanium sulfate, titanium nitrate, titanium carbonate, titanium phosphate, titanium acetate, titanium sulfide, titanium fluoride.
Preferably, the tin catalyst is selected from one or more of tin chloride, tin bromide, tin iodide, tin oxide, tin triflate.
In one embodiment, the molar ratio of compound (I), catalyst, ether or ester is 1 (0.001-0.1): (4-10), preferably 1:0.1:5.
In one embodiment, the reaction temperature is 0 to 150 ℃, preferably 0 to 110 ℃, and examples thereof include 0 ℃,5 ℃, 15 ℃, 20 ℃, 25 ℃, 40 ℃, 45 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃, 90 ℃, 100 ℃, 110 ℃, 120 ℃, 130 ℃, 140 ℃, 150 ℃, and the like.
In one embodiment, a method for preparing a siloxane containing electron withdrawing functionality comprises: adding a catalyst and an ether or ester substance into a reaction container, and performing a reaction by adopting a program temperature control under the protection of inert gas, namely: cooling to 0 ℃, dropwise adding the compound (I) at a controlled temperature of 0-5 ℃, preserving heat for 0.5-1.5h at 0-5 ℃ after the dropwise adding, and preserving heat for 10-12h after the temperature is raised to 25-150 ℃ to obtain siloxane, wherein the temperature of the preserved heat after the temperature is raised is preferably 25-110 ℃.
When R is 2 Is C 1-5 In the case of alkyl radicals, the ether or ester species are selected from C 2-5 Such as one or more of alkyl isopropyl ether, alkyl n-butyl ether, alkyl cyclopentyl ether, alkyl cyclohexyl ether, alkyl phenyl ether, glycol ether, orthoformate, orthoacetate, orthopropionate, alkoxymethane, alkoxyethane, alkoxypropane.
Alkyl carbon number and R in ether material 2 The alkyl groups have the same carbon number. For example, when R 2 In the case of methyl, the ether or ester is selected from one or more of methyl isopropyl ether, methyl n-butyl ether, methyl tert-butyl ether, methyl cyclopentyl ether, methyl cyclohexyl ether, methyl phenyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, trimethyl orthoformate, trimethyl orthoacetate, trimethyl orthopropionate, dimethoxymethane, dimethoxyethane and dimethoxypropane. When R is 2 In the case of ethyl, the ether material is selected from one or more of diethyl ether, ethyl isopropyl ether, ethyl n-butyl ether, ethyl tert-butyl ether, ethyl cyclopentyl ether, ethyl cyclohexyl ether, ethyl phenyl ether, ethylene glycol diethyl ether, diethylene glycol diethyl ether, triethyl orthoformate, triethyl orthoacetate, triethyl orthopropionate, diethoxymethane, diethoxyethane and diethoxypropane.
When R is 2 In the case of acetyl, the ether or ester is selected from one or more of ethyl acetate, isopropyl acetate, n-butyl acetate, t-butyl acetate, cyclopentyl acetate, cyclohexyl acetate, phenyl acetate, ethylene glycol diacetate, diethylene glycol diacetate, methylene diacetate, ethylene diacetate and propylene diacetate.
In the preparation process of the siloxanes according to the application, after the reaction has been completed, the person skilled in the art can carry out conventional rectification operations.
In one embodiment, the process for preparing compound (I) can be referred to in the literature (Organometallics, 1989,8,549-550), and comprises the following main steps: and (3) reacting the trichlorosilane with electron-withdrawing alkane containing terminal alkene under the conditions of cuprous oxide and tetramethyl ethylenediamine, concentrating and distilling to obtain the compound (I).
In a preferred embodiment, the process for the preparation of compound (I) comprises: adding cuprous oxide and tetramethyl ethylenediamine into a reaction vessel, controlling the temperature to be 0-5 ℃ under the protection of inert gas, adding trichlorosilane and electron-withdrawing alkane containing terminal alkene, heating to 25 ℃ after heat preservation for 1-3 hours, continuously preserving heat for 1-3 hours, and obtaining the compound (I) through reduced pressure distillation.
Preferably, the molar ratio of the trichlorosilane to the terminal alkene-containing electron withdrawing alkane is 1:1.
Preferably, the molar ratio of cuprous oxide, tetramethyl ethylenediamine and trichlorosilane is 0.15: (0.3-0.5): 1, more preferably 0.15:0.45:1.
Compared with the prior art, the application has the following beneficial effects:
(1) The preparation method of the siloxane containing the electron withdrawing functional group solves the problems of high risk, high difficulty in product separation and purification, harsh reaction conditions and the like in the traditional synthesis method;
(2) In the preparation method, the dropping temperature of the compound (I) is controlled to be 0-5 ℃, then the temperature is raised again for reaction after the reaction is carried out for a period of time at 0-5 ℃, and the yield of the obtained target product is high;
(3) The application can continuously improve the yield of the target product by regulating and controlling the catalyst and the ether or ester substances;
(4) According to the application, through the reaction of the compound (I) and the ether substance, the generation of HCl caused by the alcoholysis reaction of chlorosilane and alcohol is avoided, and the method not only avoids the hydrolysis of a target product, but also reduces the cost;
(5) The preparation method disclosed by the application is simple to operate, mild in reaction conditions, good in intermediate stability, not easy to cause side reaction, and simple in product separation and purification.
Detailed Description
The present application is illustrated by the following specific embodiments, but is not limited to the specific examples given below.
Examples
The central control analysis was determined by gas chromatography. The product was measured by gas chromatography, moisture meter, ion chromatography and colorimeter.
The gas chromatography was performed using HP-5 from Shimadzu corporation, 30 m.times.0.32 mm.times.0.25 μm as a column, and the ion chromatography was performed using SH-AC-4 from Siemens Fed corporation, 250 mm.times.4.6 mm; the guard column SH-AG-4, 50mm×4.6mm; the suppressor shi-a-5 was analyzed using the conventional method of the kaleidoscope company, and the colorimeter was analyzed using the conventional method of the hash company.
Example 1
Example 1 provides a method for preparing (2-phenylethyl) trimethoxy silane by using styrene and trichlorosilane as raw materials and manganese chloride as a catalyst, wherein the synthesis reaction formula is as follows:
the preparation steps of the (2-phenylethyl) trimethoxysilane are as follows:
21.45g of cuprous oxide and 52.2g of tetramethyl ethylenediamine are accurately weighed, cooled to 0 ℃ under the protection of nitrogen, 135.5g of trichlorosilane (purity 99%, 1 mol) and 104g of styrene are weighed, uniformly mixed, added into a 250ml constant pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the dropping is carried out for 4 hours, the temperature is kept for 2 hours, the temperature is slowly raised to room temperature, the temperature is kept for 2 hours, and 215.6g of intermediate is obtained through reduced pressure distillation.
11.6g of manganese chloride and 400g of methyl tert-butyl ether (MTBE) are added into a 1000ml four-mouth bottle, cooled to 0 ℃ under the protection of nitrogen, 215.6g of intermediate is added into a constant pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the drop is carried out for 2 hours, the temperature is kept for 1 hour, the temperature is slowly raised to room temperature, the temperature is kept for 10 hours, chloride ions are 18670ppm, after the decompression and desolventization, the colorless transparent liquid (14) is obtained by rectification, the purity of GC is 99.3wt%, and the yield is 84.2wt%. The chloride ion content was 10ppm.
Example 2
Example 2 provides a process for the preparation of (4-cyanobutyl) triacetoxysilane starting from pentenenitrile and trichlorosilane, with cobalt chloride as catalyst, the synthesis reaction being as follows:
the preparation steps of the (2-phenylethyl) trimethoxysilane are as follows:
21.45g of cuprous oxide and 52.2g of tetramethyl ethylenediamine are accurately weighed, cooled to 0 ℃ under the protection of nitrogen in a 250ml four-neck flask, 135.5g of trichlorosilane (purity 99%, 1 mol) and 81g of pentenenitrile are weighed, uniformly mixed, added into a 250ml constant-pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the dropping time is 4 hours, the temperature is kept for 2 hours, the temperature is slowly raised to room temperature, the temperature is kept for 2 hours, and 193.6g of intermediate is obtained through reduced pressure distillation.
Adding 1.17g of cobalt chloride and 533g of methyl acetate into a 1000ml four-mouth bottle, cooling to 0 ℃ under the protection of nitrogen, adding 193.6g of intermediate into a constant pressure dropping funnel, slowly dropping into a reaction bottle, controlling the temperature to be 0-5 ℃, dropping for 2 hours, preserving heat for 1 hour, slowly raising the temperature to 50 ℃, preserving heat for 10 hours, keeping the temperature for 23120ppm of chloride ion, decompressing and desolventizing, rectifying to obtain 232.5g of colorless transparent liquid with the GC purity of 99.0wt% and the yield of 81.0wt%. The chloride ion content was 11ppm.
Example 3
Example 3 provides a method for preparing (2-butanone group) triethoxysilane by using methyl acrylate and trichlorosilane as raw materials and ruthenium chloride as a catalyst, wherein the synthesis reaction formula is as follows:
the preparation steps of the (2-butanone group) triethoxysilane are as follows:
21.45g of cuprous oxide and 52.2g of tetramethyl ethylenediamine are accurately weighed, cooled to 0 ℃ under the protection of nitrogen, 135.5g of trichlorosilane (purity 99%, 1 mol) and 86g of methyl acrylate are weighed, uniformly mixed, added into a 250ml constant-pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the dropping time is 4 hours, the temperature is kept for 2 hours, the temperature is slowly raised to room temperature, the temperature is kept for 2 hours, and 183.4g of intermediate is obtained through reduced pressure distillation.
0.19g of anhydrous ruthenium chloride and 918g of ethyl tertiary butyl ether are added into a 2000ml four-mouth bottle, cooled to 0 ℃ under the protection of nitrogen, 183.4g of intermediate is added into a constant pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled between 0 ℃ and 5 ℃, the drop is carried out for 2 hours, the temperature is kept for 1 hour, the temperature is slowly raised to 70 ℃, the temperature is kept for 10 hours, chlorine ions 16630ppm are decompressed and desolventized, and colorless transparent liquid (2) 184.2g with GC purity of 99.1wt% and yield of 78.7wt% is obtained by rectification. The chloride ion content was 11ppm.
Example 4
Example 4 provides a method for preparing (2-butanone group) triethoxysilane by using methyl acrylate and trichlorosilane as raw materials and palladium chloride as a catalyst, wherein the synthesis reaction formula is as follows:
the preparation steps of the (2-butanone group) triethoxysilane are as follows:
21.45g of cuprous oxide and 52.2g of tetramethyl ethylenediamine are accurately weighed, cooled to 0 ℃ under the protection of nitrogen, 135.5g of trichlorosilane (purity 99%, 1 mol) and 86g of methyl acrylate are weighed, uniformly mixed, added into a 250ml constant-pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled to be 0-5 ℃, the dropping time is 4 hours, the temperature is kept for 2 hours, the temperature is slowly raised to room temperature, the temperature is kept for 2 hours, and 181.2g of intermediate is obtained through reduced pressure distillation.
16.0g of anhydrous palladium chloride and 400g of ethyl tertiary butyl ether are added into a 1000ml four-mouth bottle, cooled to 0 ℃ under the protection of nitrogen, 181.2g of intermediate is added into a constant pressure dropping funnel, slowly dropped into a reaction bottle, the temperature is controlled between 0 ℃ and 5 ℃, the drop is carried out for 2 hours, the temperature is kept for 1 hour, the temperature is slowly increased to 60 ℃, the temperature is kept for 10 hours, chloride ions are 17640ppm, after decompression and desolventizing, 187.7g of colorless transparent liquid (2) is obtained by rectification, the GC purity is 98.9wt%, and the yield is 80.2wt%. The chloride ion content was 12ppm.
Example 5
Example 5 provides a process for the preparation of nitroethylene and trichlorosilane starting materials, the process conditions being substantially the same as those of example 1, except that the second reaction catalyst was changed to ferric triflate, and the corresponding compound was obtained in a yield of 71.3wt%. GC purity was 98.1wt% and chloride ion was 10ppm.
Example 6
Example 6 provides a process for the preparation of 1-bromohexene and trichlorosilane starting from essentially the same conditions as in example 1, except that the second reaction catalyst was replaced by zinc nitrate, and the corresponding compound was obtained in 80.2wt% yield. GC purity was 98.7wt% and chloride ion was 12ppm.
Example 7
Example 8 provides a process for preparing styrene and trichlorosilane as starting materials under substantially the same conditions as in example 1, except that the second step of reaction was changed to chloroplatinic acid, methyl tertiary ether was changed to isopropyl tertiary butyl ether, the temperature of the resulting mixture was still 0-5 ℃, the reaction temperature was kept at 110 ℃, and the corresponding compound was obtained in the same manner, with a yield of 69.3wt%. GC purity was 98.0wt% and chloride ion was 10ppm.
Example 8
Example 8 provides a process for the preparation of styrene and trichlorosilane starting materials under substantially the same conditions as in example 1, except that the catalyst of the second reaction step was changed to bismuth chloride, methyl tertiary ether was changed to n-amyl ether, the reaction temperature was 120 ℃, and the corresponding compound was obtained in a yield of 46.1wt%. GC purity 95.2wt% and chloride ion 18ppm.

Claims (10)

1. The preparation method of the siloxane containing the electron withdrawing functional group is characterized by comprising the step of reacting chlorosilane containing the electron withdrawing functional group with a non-aqueous reagent under the action of a catalyst, wherein the non-aqueous reagent is an ether or ester substance.
2. The method for producing an electron withdrawing-functional group-containing siloxane according to claim 1, wherein the structure of the electron withdrawing-functional group-containing siloxane is:n is any integer from 1 to 5, R 1 Is any one of nitro, cyano, fluorine, chlorine, bromine, iodine, alkynyl, aryl and acetyl, R 2 Is C 1-5 Alkyl or acetyl.
3. The method for producing an electron withdrawing group-containing siloxane according to any one of claims 1 to 2, wherein the electron withdrawing group-containing chlorosilane structure is: :
n is any integer from 1 to 5, R 1 Is any one of nitro, cyano, fluorine, chlorine, bromine, iodine, alkynyl, aryl and acetyl.
4. A method for preparing a siloxane containing an electron withdrawing functionality according to any one of claims 1 to 3, wherein said catalyst is one or more of palladium catalyst, platinum catalyst, rhodium catalyst, ruthenium catalyst, cobalt catalyst, iron catalyst, manganese catalyst, bismuth catalyst, aluminum catalyst, zinc catalyst, titanium catalyst, tin catalyst.
5. The method for producing an electron withdrawing group-containing siloxane according to any one of claims 1 to 4, wherein the molar ratio of the electron withdrawing group-containing chlorosilane, catalyst, ether or ester is 1 (0.001 to 0.1): (4-10), preferably 1:0.1:5.
6. The method for producing an electron withdrawing-functional siloxane according to any one of claims 1 to 5, wherein the reaction temperature is 0 to 110 ℃.
7. The method for preparing a siloxane containing electron withdrawing functionality according to claim 6, wherein the reaction process adopts a programmed temperature control, namely comprising: adding a catalyst and ether or ester substances into a reaction container, cooling to 0 ℃ under the protection of inert gas, then dropwise adding chlorosilane containing electron-withdrawing functional groups at the controlled temperature of 0-5 ℃, after the dropwise adding, preserving the heat for 0.5-1.5h at the temperature of 0-5 ℃, and preserving the heat for 10-12h after the temperature is raised to 25-110 ℃ to obtain siloxane.
8. The method according to any one of claims 1 to 7, wherein the separation and purification step is carried out after the completion of the reaction step.
9. The method for producing an electron withdrawing group-containing siloxane according to any one of claims 1 to 8, wherein the electron withdrawing group-containing chlorosilane is obtained by reacting trichlorosilane with an electron withdrawing alkane containing terminal alkene under the condition of a catalyst.
10. A siloxane containing electron withdrawing functionality, wherein the siloxane is prepared by the preparation method of any one of claims 1-9, and the content of chloride ions in the siloxane is below 20ppm, preferably below 15 ppm.
CN202311090321.0A 2023-08-28 2023-08-28 Preparation method of siloxane containing electron withdrawing functional groups Pending CN117186143A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202311090321.0A CN117186143A (en) 2023-08-28 2023-08-28 Preparation method of siloxane containing electron withdrawing functional groups

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202311090321.0A CN117186143A (en) 2023-08-28 2023-08-28 Preparation method of siloxane containing electron withdrawing functional groups

Publications (1)

Publication Number Publication Date
CN117186143A true CN117186143A (en) 2023-12-08

Family

ID=88989754

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202311090321.0A Pending CN117186143A (en) 2023-08-28 2023-08-28 Preparation method of siloxane containing electron withdrawing functional groups

Country Status (1)

Country Link
CN (1) CN117186143A (en)

Similar Documents

Publication Publication Date Title
EP0693492B1 (en) Method for preparation of methacryloxypropyldimethylchlorosilane
JP2003516996A (en) Method for producing epoxy organosilicon compound
KR20200125664A (en) Silicon compound containing hexafluoroisopropanol group and method for producing same
CN101273049A (en) A method of manufacturing an organic silicon compound that contains a methacryloxy group or an acryloxy group
CN101039949B (en) Method of producing silylalkoxymethyl halide
CN102159583A (en) Method for producing (meth)acrylosilanes
JP5115729B2 (en) Organosilicon compound containing acetoacetate group protected with trialkylsilyl group and process for producing the same
JP3947772B2 (en) High purity organofunctional alkyl dialkoxysilane by reverse addition
CN117186143A (en) Preparation method of siloxane containing electron withdrawing functional groups
WEST et al. The preparation of organosilanes from dichlorosilane
JP5234909B2 (en) Alkoxy group-containing cage-type siloxane compound, silanol group-containing cage-type siloxane compound, and methods for producing them
CN107636000B (en) Process for the preparation of aqueous hydrolysates of aminoalkyl trialkoxysilanes
CN102898457B (en) Ethylphenyldiethoxysilane and preparation method thereof
JP3555646B2 (en) Method for producing chlorosilane containing acryloxy group or methacryloxy group
EP2099809B1 (en) Process for preparing organic silane compounds having beta-cyano ester group
JP4278725B2 (en) Process for producing α, ω-dihydrogenorganopentasiloxane
US5723643A (en) Method for the preparation of acryloxy- or methacryloxy-functional organosilicon compounds
EP1797103B1 (en) Preparation of an aminoaryl-containing organosilicon compound and intermediate used in its preparation
JP7126389B2 (en) Method for producing tertiary alkylsilane and method for producing tertiary alkylalkoxysilane
KR102169810B1 (en) Hydrocarbyloxydisilanes
JPS61100587A (en) Organosilicon compound
CN108440592B (en) Preparation method of 1, 5-divinyl-1, 1,3,3,5, 5-hexamethyl trisiloxane
Seyferth et al. The reaction of 3, 3-dichloroallyltrimethylsilane with n-butyllithium
CN102482300A (en) Synthesis of fluorocarbofunctional alkoxysilanes and chlorosilanes
JP4407822B2 (en) Method for producing tri (secondary alkyl) silane compound

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination