CN103833781A - Preparation method of phenyl chlorosilane - Google Patents

Preparation method of phenyl chlorosilane Download PDF

Info

Publication number
CN103833781A
CN103833781A CN201410103908.5A CN201410103908A CN103833781A CN 103833781 A CN103833781 A CN 103833781A CN 201410103908 A CN201410103908 A CN 201410103908A CN 103833781 A CN103833781 A CN 103833781A
Authority
CN
China
Prior art keywords
phenyl
preparation
chlorosilane
disilane
reaction
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.)
Granted
Application number
CN201410103908.5A
Other languages
Chinese (zh)
Other versions
CN103833781B (en
Inventor
高俊杰
胡庆超
徐晓光
宋超
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.)
Shandong Dongyue organosilicon material Limited by Share Ltd
Institute of Process Engineering of CAS
Original Assignee
Shandong Dongyue Organic Silicon Material Co Ltd
Institute of Process Engineering of CAS
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 Shandong Dongyue Organic Silicon Material Co Ltd, Institute of Process Engineering of CAS filed Critical Shandong Dongyue Organic Silicon Material Co Ltd
Priority to CN201410103908.5A priority Critical patent/CN103833781B/en
Publication of CN103833781A publication Critical patent/CN103833781A/en
Application granted granted Critical
Publication of CN103833781B publication Critical patent/CN103833781B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Abstract

The invention relates to a preparation method of phenyl chlorosilane. The preparation method comprises the following steps: adding phenyl disilane and a catalyst into a reactor, uniformly mixing, then inhaling inert gas into the reactor and exhausting air, stirring, heating, continuously inhaling pyrolysis gas for reaction under a normal pressure condition, stopping the reaction, rectifying and separating the reaction liquid to prepare different types of phenyl chlorosilane monomers. The target products prepared by the method disclosed by the invention are various types of phenyl chlorosilane monomers; the method can be used for simultaneously preparing various types of high value-added phenyl chlorosilane such as methyl phenyl dichloromethylsilane, dimethyl phenyl chlorosilane, methyl diphenyl chlorosilane and the like; moreover, the yield is high, the yield of byproduct methyl chlorosilane is low, and high-value utilization of a silicon resource is realized.

Description

A kind of preparation method of phenyl chlorosilane
Technical field
The present invention relates to a kind of preparation method of phenyl chlorosilane, belong to organosilane monomer preparing technical field.
Background technology
Organosilicon material has many excellent properties and the specific functions such as good temperature tolerance, radioprotective, intermiscibility, is widely used in the every field such as science and techniques of defence, aerospace, chemical industry, medicine.Compare with the organosilicon material of preparing take methyl chlorosilane monomer as raw material, the organosilicon material of preparing with phenyl chlorosilane monomer has the characteristics such as more excellent temperature tolerance, radioprotective, intermiscibility, makes the characteristic of organosilicon material have great lifting.
The preparation method of phenyl chlorosilane mainly comprises: condensation method, Grignard method, Wurtz method, catalystic pyrolysis etc.
Patent documentation CN101628917A discloses the synthesis technique that a kind of condensation method is prepared phenyl chlorosilane monomer, adopting chlorobenzene, methyl hydrogen dichlorosilane is raw material, chloroform is catalyzer, at 0.2-0.8Mpa, under 350-600 ℃ of condition, prepares dichloromethyl phenylsilane.But the reaction conditions of the method High Temperature High Pressure is high to equipment and operator's security requirement, has increased production cost, especially generate the by product benzene of a large amount of strong carinogenicity, be extremely unfavorable for industrial production.
Patent documentation US6541651 and patent documentation CN102225949A have all adopted Grignard legal system for phenyl chlorosilane.Under oxygen free condition, take chlorobenzene and MAGNESIUM METAL as raw material, in alkyl oxide, make phenyl-magnesium-chloride, and then react and obtain dichloromethyl phenylsilane with METHYL TRICHLORO SILANE.This method adopts a large amount of organic solvents, and Grignard reagent is very active, easily blasts, and dangerous high, the subsequent disposal of a large amount of metal halogens of generation bothers very much, and the product finally generating is difficult separation also.
Patent documentation CN101077877A discloses the alcoholysate octadecyloxy phenyl TMOS for phenyl chlorosilane monomer with Wurtz legal system, specifically, take chlorobenzene and methyl alkoxy silane as raw material, condensation reaction occurs under the effect of sodium and obtain octadecyloxy phenyl TMOS.The shortcoming of these class methods is that raw material ratio is more expensive, and methyl alkoxy silane is higher than chlorosilane price, is that raw material reacts acutely if adopt chlorosilane, and the difficult control of process, easily causes danger, the use of excess sodium, complex operation step and more dangerous in the time of subsequent disposal.
It is catalyzer that patent documentation US3772347 and patent documentation CN101195633A disclose employing noble metal platinum or palladium and complex compound thereof, and the scission reaction of catalysis disilane and chlorine aromatic hydrocarbons, prepares phenyl chlorosilane monomer.But this class reaction gained target product kind is more single, generate the by product methyl chlorosilane monomer of equivalent simultaneously, required catalyzer is expensive, is difficult to cyclically utilizing, and production cost is high.
Therefore, the novel process that needs a kind of phenyl chlorosilane monomer of design and development to prepare, this technique is reaction conditions gentleness not only, simple to operate, raw material is cheaply easy to get, and the kind of gained target product phenyl chlorosilane monomer is many, productive rate is high, and by product is few, can realize the higher value application of silicon resource.
Summary of the invention
The present invention is directed to the deficiencies in the prior art, a kind of preparation method of phenyl chlorosilane is provided.
The present invention is achieved through the following technical solutions:
A preparation method for phenyl chlorosilane, comprises the steps:
By phenyl disilane and catalyzer (10～100) in mass ratio: 1 adds in reactor, mix, then in reactor, pass into rare gas element exhausted air, be heated with stirring to 100～200 ℃, under condition of normal pressure, continue to pass into splitting gas 8～24h, the mol ratio of splitting gas and phenyl disilane is (1～8): 1, stopped reaction, carries out rectifying separation to reaction solution, makes different types of phenyl chlorosilane monomer;
Described phenyl disilane structural formula is as follows:
Me mPh nX 3-m-nSiSiMe aPh bX 3-a-b
Wherein: m, n, a, b is 0～3 integer, and n+b>=1, m+n+a+b < 6, Me is-CH 3, Ph is-C 6h 5, X is Cl or Br;
Described catalyzer is one or more the mixing in polyethers, quaternary ammonium salt, organic amine, crown ether, quaternary ammonium hydroxide or season phosphonium salt;
Described splitting gas is HX, X 2, CH 3the mixing of one or more in X, wherein X is Cl or Br.
Preferred according to the present invention, described polyethers is: H (OCH 2cH 2) 3oH, H (OCH 2cH 2) 5oH or R (OCH 2cH 2) 4oR; Described quaternary ammonium salt is: tetramethyl ammonium chloride, tetrabutyl ammonium sulfate or Dodecyl trimethyl ammonium chloride; Described organic amine is: nitrogen nitrogen xylidine, tri-n-amyl amine or tri-n-butylamine; Described crown ether is: cyclodextrin, 15-crown ether-5 or hexaoxacyclooctadecane-6-6; Described quaternary ammonium hydroxide is: Tetramethylammonium hydroxide, trimethylammonium ethyl ammonium hydroxide or dimethyl ethyl styroyl ammonium hydroxide; Described season phosphonium salt is: tetramethyl-bromide phosphine, tetrabutyl phosphonium bromide phosphine or tetraphenylphosphonium chloride.
Preferred according to the present invention, the mass ratio of described phenyl disilane and catalyzer is (40～80): 1.
Preferred according to the present invention, described temperature is 130～180 ℃.
Preferred according to the present invention, the mol ratio of splitting gas and phenyl disilane is (1～5): 1.
Preferred according to the present invention, described rare gas element is nitrogen, helium, neon or argon gas.
Above-mentioned phenyl disilane can adopt prior art preparation, also can adopt with the following method preparation in proportion:
The by product organosilicon high-boiling product of industrial " direct method " being produced to methyl chlorosilane generation carries out rectifying, and the cut of getting 130-170 ℃ obtains disilane Me 2clSiSiMeCl 2, MeCl 2siSiMeCl 2, Me 2clSiSiMe 2the mixed solution (three's mol ratio is 1:1:0.5) of Cl.Under the protection of nitrogen, 184g Na is added in 2130g toluene, add 10.65g Palmiticacid simultaneously; be stirred and heated to 105 ℃, be prepared into basic metal sand, 450g chlorobenzene is added in the basic metal sand of preparation; molecular balance 2h, obtains phenyl an alkali metal salt, and phenyl an alkali metal salt is joined to 529g Me 2clSiSiMeCl 2, MeCl 2siSiMeCl 2, Me 2clSiSiMe 2in the mixed solution of Cl (three's mol ratio is 1:1:0.5), add 2.05g tetrabutyl phosphonium bromide phosphine, under the condition of 50 ℃ simultaneously, after reaction 5h, stopped reaction, is cooled to room temperature, obtain the mixture of phenyl disilane, contain 247g Me through gas chromatographic analysis 2phSiSiMePhCl, 105.8g MePhClSiSiMePh 2, 155.5g MePhClSiSiClMePh, 91.4g Me 2phSiSiMe 2cl;
The phenyl disilane that aforesaid method makes is to contain Me 2phSiSiMePhCl, MePhClSiSiMePh 2, MePhClSiSiClMePh and Me 2phSiSiMe 2the mixture of tetra-kinds of phenyl disilane of Cl, can directly utilize it to carry out subsequent reactions, also can be separated into after single component by prior art, then carry out subsequent reactions.
Compared with prior art, tool of the present invention has the following advantages:
1) kind of gained target product phenyl chlorosilane monomer of the present invention is many, can prepare the multiple high added value phenyl chlorosilanes such as dichloromethyl phenylsilane, 3,5-dimethylphenyl chlorosilane, methyldiphenyl base chlorosilane simultaneously, and productive rate is high, the productive rate of by product methyl chlorosilane is low, has realized the higher value application of silicon resource;
2) reaction process gentleness of the present invention, simple to operate, do not adopt organic solvent, in reaction process without the generation of carcinogenic by product benzene;
3) catalyst for cracking of the present invention is marketable material, is cheaply easy to get, and reactant phenyl disilane adopts organosilicon high-boiling product preparation, and cost is low, is beneficial to suitability for industrialized production.
Embodiment
Below in conjunction with embodiment, technical scheme of the present invention is further elaborated, but institute of the present invention protection domain is not limited to this.
Utilize gas chromatograph-mass spectrometer to analyze each disilane component concentration of the disilane mixture that obtains through rectifying of organosilicon high-boiling product, and the content of the component concentration of each phenyl chlorosilane monomer, by product benzene in gained reaction solution in each embodiment.
Raw material phenyl disilane in embodiment is to contain Me 2phSiSiMePhCl, MePhClSiSiMePh 2, MePhClSiSiClMePh and Me 2phSiSiMe 2the mixture of tetra-kinds of phenyl disilane of Cl, can adopt prior art preparation, also can adopt with the following method preparation in proportion:
The by product organosilicon high-boiling product of industrial " direct method " being produced to methyl chlorosilane generation carries out rectifying, and the cut of getting 130-170 ℃ obtains disilane Me 2clSiSiMeCl 2, MeCl 2siSiMeCl 2, Me 2clSiSiMe 2the mixed solution (three's mol ratio is 1:1:0.5) of Cl.Under the protection of nitrogen, 184g Na is added in 2130g toluene, add 10.65g Palmiticacid simultaneously; be stirred and heated to 105 ℃, be prepared into basic metal sand, 450g chlorobenzene is added in the basic metal sand of preparation; molecular balance 2h, obtains phenyl an alkali metal salt, and phenyl an alkali metal salt is joined to 529g Me 2clSiSiMeCl 2, MeCl 2siSiMeCl 2, Me 2clSiSiMe 2in the mixed solution of Cl (three's mol ratio is 1:1:0.5), add 2.05g tetrabutyl phosphonium bromide phosphine, under the condition of 50 ℃ simultaneously, after reaction 5h, stopped reaction, is cooled to room temperature, obtain the mixture of phenyl disilane, contain 247g Me through gas chromatographic analysis 2phSiSiMePhCl, 105.8g MePhClSiSiMePh 2, 155.5g MePhClSiSiClMePh, 91.4g Me 2phSiSiMe 2cl.
Embodiment 1
The mixture of the raw material phenyl disilane of above-mentioned preparation (is wherein contained to 247g Me 2phSiSiMePhCl, 105.8g MePhClSiSiMePh 2, 155.5g MePhClSiSiClMePh, 91.4g Me 2phSiSiMe 2cl), be added in the cracking still with material filling type separation column, and then add 6.00g tetraphenylphosphonium chloride, pass into nitrogen 30min, discharge the air in cracking still, be warming up to 200 ℃, continue to pass into gaseous state Br 2, Br 2with the molar ratio of phenyl disilane mixture be 1:1, under normal pressure after successive reaction 24h, stopped reaction, the reaction solution obtaining is the mixture of phenyl chlorosilane monomer.
By gas-chromatography, this mixture is analyzed, calculated Me 2the yield of PhSiBr is that the yield of 25.9%, MePhSiBrCl is 44.6%, MePh 2the yield of SiBr is 6.2%, Me 2the yield of SiBrCl is 8.3%, and the total recovery of phenyl-halide silane monomer is 76.7%, and no coupling product benzene generates.
The mixture of above-mentioned phenyl-halide silane monomer is carried out to rectifying, get respectively the cut of 218 ℃, 228 ℃, 316 ℃, obtain respectively product Me 2phSiBr, MePhSiBrCl, MePh 2siBr.
Embodiment 2
The mixture of the raw material phenyl disilane of above-mentioned preparation (is wherein contained to 247g Me 2phSiSiMePhCl, 105.8gMePhClSiSiMePh 2, 155.5g MePhClSiSiClMePh, 91.4g Me 2phSiSiMe 2cl), be added in the cracking still with material filling type separation column, and then add 29.98g tri-n-amyl amine, pass into nitrogen 10min, discharge the air in cracking still, be warming up to 130 ℃, continue to pass into Cl 2, Cl 2with the molar ratio of phenyl disilane be 4:1, under normal pressure after successive reaction 12h, stopped reaction, the reaction solution obtaining is the mixture of phenyl chlorosilane monomer.
By gas-chromatography, this mixture is analyzed, calculated Me 2the yield of PhSiCl is 27.4%, MePhSiCl 2yield be 47.2%, MePh 2the yield of SiCl is 6.6%, Me 2siCl 2yield be 8.78%, the total recovery of phenyl chlorosilane is: 81.2%, no coupling product benzene generate.
The mixture of above-mentioned phenyl chlorosilane monomer is carried out to rectifying, get respectively the cut of 196 ℃, 206 ℃, 296 ℃, obtain respectively product Me 2phSiCl, MePhSiCl 2, MePh 2siCl.
Embodiment 3
The mixture of the raw material phenyl disilane of above-mentioned preparation (is wherein contained to 247g Me 2phSiSiMePhCl, 105.8g MePhClSiSiMePh 2, 155.5g MePhClSiSiClMePh, 91.4g Me 2phSiSiMe 2cl), be added in the cracking still with material filling type separation column, and then add 8.57g tetramethyl-bromide phosphine, pass into nitrogen 20min, discharge the air in cracking still, be warming up to 150 ℃, continue to pass into CH 3cl, CH 3the molar ratio of Cl and phenyl disilane is 3:1, under normal pressure after successive reaction 19h, and stopped reaction, the reaction solution obtaining is the mixture of phenyl chlorosilane monomer.
By gas-chromatography, this mixture is analyzed, calculated Me 2the yield of PhSiCl is 62.2%, MePhSiCl 2yield be 10.7%, MePh 2the yield of SiCl is 6.4%, Me 2siCl 2yield be 8.6%, the total recovery of phenyl chlorosilane is: 79.3%, no coupling product benzene generate.
The mixture of above-mentioned phenyl chlorosilane monomer is carried out to rectifying, get respectively the cut of 196 ℃, 206 ℃, 296 ℃, obtain respectively product Me 2phSiCl, MePhSiCl 2, MePh 2siCl.
Embodiment 4
The mixture of the raw material phenyl disilane of above-mentioned preparation (is wherein contained to 247g Me 2phSiSiMePhCl, 105.8g MePhClSiSiMePh 2, 155.5g MePhClSiSiClMePh, 91.4g Me 2phSiSiMe 2cl), be added in the cracking still with material filling type separation column, and then add 59.97g tetramethyl ammonium chloride, and pass into nitrogen 5min, discharge the air in cracking still, be warming up to 100 ℃, continue to pass into HCl gas, the molar ratio of HCl and phenyl disilane is 5:1, under normal pressure after successive reaction 8h, stopped reaction, the reaction solution obtaining is the mixture of phenyl chlorosilane monomer.
By gas-chromatography, this mixture is analyzed, calculated Me 2the yield of PhSiCl is 28%, MePhSiCl 2yield be 48.2%, MePh 2the yield of SiCl is 6.7%, and the total recovery of phenyl chlorosilane is: 82.9%, and no coupling product benzene generates.
The mixture of above-mentioned phenyl chlorosilane monomer is carried out to rectifying, get respectively the cut of 196 ℃, 206 ℃, 296 ℃, obtain respectively product Me 2phSiCl, MePhSiCl 2, MePh 2siCl.

Claims (6)

1. a preparation method for phenyl chlorosilane, is characterized in that, comprises the steps:
By phenyl disilane and catalyzer (10～100) in mass ratio: 1 adds in reactor, mix, then in reactor, pass into rare gas element exhausted air, be heated with stirring to 100～200 ℃, under condition of normal pressure, continue to pass into splitting gas 8～24h, the mol ratio of splitting gas and phenyl disilane is (1～8): 1, stopped reaction, carries out rectifying separation to reaction solution, makes different types of phenyl chlorosilane monomer;
Described phenyl disilane structural formula is as follows:
Me mPh nX 3-m-nSiSiMe aPh bX 3-a-b
Wherein: m, n, a, b is 0～3 integer, and n+b>=1, m+n+a+b < 6, Me is-CH 3, Ph is-C 6h 5, X is Cl or Br;
Described catalyzer is one or more the mixing in polyethers, quaternary ammonium salt, organic amine, crown ether, quaternary ammonium hydroxide or season phosphonium salt;
Described splitting gas is HX, X 2, CH 3the mixing of one or more in X, wherein X is Cl or Br.
2. preparation method as claimed in claim 1, is characterized in that, described polyethers is: H (OCH 2cH 2) 3oH, H (OCH 2cH 2) 5oH or R (OCH 2cH 2) 4oR;
Described quaternary ammonium salt is: tetramethyl ammonium chloride, tetrabutyl ammonium sulfate or Dodecyl trimethyl ammonium chloride;
Described organic amine is: nitrogen nitrogen xylidine, tri-n-amyl amine or tri-n-butylamine; Described crown ether is: cyclodextrin, 15-crown ether-5 or hexaoxacyclooctadecane-6-6;
Described quaternary ammonium hydroxide is: Tetramethylammonium hydroxide, trimethylammonium ethyl ammonium hydroxide or dimethyl ethyl styroyl ammonium hydroxide;
Described season phosphonium salt is: tetramethyl-bromide phosphine, tetrabutyl phosphonium bromide phosphine or tetraphenylphosphonium chloride.
3. preparation method as claimed in claim 1, is characterized in that, the mass ratio of described phenyl disilane and catalyzer is (40～80): 1.
4. preparation method as claimed in claim 1, is characterized in that, described temperature is 130～180 ℃.
5. preparation method as claimed in claim 1, is characterized in that, the mol ratio of described splitting gas and phenyl disilane is (1～5): 1.
6. preparation method as claimed in claim 1, is characterized in that, described rare gas element is nitrogen, helium, neon or argon gas.
CN201410103908.5A 2014-03-19 2014-03-19 Preparation method of phenyl chlorosilane Active CN103833781B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410103908.5A CN103833781B (en) 2014-03-19 2014-03-19 Preparation method of phenyl chlorosilane

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201410103908.5A CN103833781B (en) 2014-03-19 2014-03-19 Preparation method of phenyl chlorosilane

Publications (2)

Publication Number Publication Date
CN103833781A true CN103833781A (en) 2014-06-04
CN103833781B CN103833781B (en) 2017-05-10

Family

ID=50797711

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410103908.5A Active CN103833781B (en) 2014-03-19 2014-03-19 Preparation method of phenyl chlorosilane

Country Status (1)

Country Link
CN (1) CN103833781B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111909193A (en) * 2020-09-10 2020-11-10 江西星火狮达科技有限公司 Phenyl trimethylsilane and preparation method thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB794086A (en) * 1955-11-22 1958-04-30 Gen Electric Improvements relating to organohalogenomonosilanes
US3772347A (en) * 1971-12-15 1973-11-13 Dow Corning Transition metal catalyzed silylations
US5288892A (en) * 1992-06-19 1994-02-22 Wacker-Chemie Gmbh Separation of methylchlorosilanes from high boiling residues of methylchlorosilane synthesis
CN101195633A (en) * 2007-12-07 2008-06-11 浙江大学 Method for producing methyl phenyl dichloresilane
CN101628917A (en) * 2009-07-28 2010-01-20 江苏宏达新材料股份有限公司 Method for preparing methyldiphenylchlorosilane and reactor thereof
CN102584882A (en) * 2012-02-17 2012-07-18 嘉兴学院 Method for preparing methyl phenyl dichlorosilane

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB794086A (en) * 1955-11-22 1958-04-30 Gen Electric Improvements relating to organohalogenomonosilanes
US3772347A (en) * 1971-12-15 1973-11-13 Dow Corning Transition metal catalyzed silylations
US5288892A (en) * 1992-06-19 1994-02-22 Wacker-Chemie Gmbh Separation of methylchlorosilanes from high boiling residues of methylchlorosilane synthesis
CN101195633A (en) * 2007-12-07 2008-06-11 浙江大学 Method for producing methyl phenyl dichloresilane
CN101628917A (en) * 2009-07-28 2010-01-20 江苏宏达新材料股份有限公司 Method for preparing methyldiphenylchlorosilane and reactor thereof
CN102584882A (en) * 2012-02-17 2012-07-18 嘉兴学院 Method for preparing methyl phenyl dichlorosilane

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111909193A (en) * 2020-09-10 2020-11-10 江西星火狮达科技有限公司 Phenyl trimethylsilane and preparation method thereof
CN111909193B (en) * 2020-09-10 2023-06-06 江西星火狮达科技有限公司 Phenyl trimethylsilane and preparation method thereof

Also Published As

Publication number Publication date
CN103833781B (en) 2017-05-10

Similar Documents

Publication Publication Date Title
González-Sebastián et al. Nickel-catalyzed hydrosilylation of CO2 in the presence of Et3B for the synthesis of formic acid and related formates
Sadow et al. Catalytic Functionalization of Hydrocarbons by σ‐Bond‐Metathesis Chemistry: Dehydrosilylation of Methane with a Scandium Catalyst
CN102351894B (en) Preparation method of methylphenyldialkoxysilane
US9290525B2 (en) Method for producing cyclic silane compound or salt thereof, salt having cyclic silane dianion, and cyclic silane dianion salt-containing composition
CN104119371B (en) A kind of method of hydrosilylation of olefins
CN104258904B (en) Lewis acid-amine salt/ammonium salt mixed catalyst and applications thereof in hydrogenation and hydrosilation of carbon oxides
CN103298821A (en) Method of preparing a diorganodihalosilane
Tyagi et al. Transition‐Metal‐Free C− H Silylation: An Emerging Strategy
CN107973812B (en) A method of preparing aryl boric acid neopentyl glycol esters compound
CN102875585B (en) A kind of method preparing tetramethyl divinyl disiloxane
CN103833781A (en) Preparation method of phenyl chlorosilane
CN103524746B (en) A kind of Borazine aryne resin and preparation method thereof
CN103073581B (en) Method for compositing alkyl phosphonic acid dialkyl ester
CN103319296B (en) A kind of preparation method of tetramethyl biphenyl
CN102076700A (en) Production method for a linear or cyclic trisilaalkane
CN102850388A (en) A preparation method of silane coupling agent
CN103880873B (en) Method for preparing phenyldisilane from organic silicon high-boiling material
CN100560591C (en) A kind of method for preparing dichloromethyl phenylsilane
KR20190058653A (en) Manufacturing method of hydridosilane
CN102675234B (en) Synthetic method of sym-triazine derivative
CN105732692B (en) The synthetic method of aminomethyl phenyl dimethoxysilane
CN105198800A (en) Preparation method of pesticide intermediate, namely 2,3-dichloro-5-methylpyridine
CN100506826C (en) Triphenylacetylene silane novle synthesis method
CN111185236A (en) Application of aryloxy rare earth metal complex and borane in catalyzing carbon dioxide hydrosilation reduction reaction
CN102584882B (en) Method for preparing methyl phenyl dichlorosilane

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CP01 Change in the name or title of a patent holder

Address after: 256401 Tangshan, Shandong, Huantai Town, Zibo

Co-patentee after: Institute of Process Engineering, Chinese Academy of Sciences

Patentee after: Shandong Dongyue organosilicon material Limited by Share Ltd

Address before: 256401 Tangshan, Shandong, Huantai Town, Zibo

Co-patentee before: Institute of Process Engineering, Chinese Academy of Sciences

Patentee before: Shandong Dongyue Silicon Material co., Ltd.

CP01 Change in the name or title of a patent holder