CN111909193B - Phenyl trimethylsilane and preparation method thereof - Google Patents
Phenyl trimethylsilane and preparation method thereof Download PDFInfo
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- CN111909193B CN111909193B CN202010948383.0A CN202010948383A CN111909193B CN 111909193 B CN111909193 B CN 111909193B CN 202010948383 A CN202010948383 A CN 202010948383A CN 111909193 B CN111909193 B CN 111909193B
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- KXFSUVJPEQYUGN-UHFFFAOYSA-N trimethyl(phenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC=C1 KXFSUVJPEQYUGN-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 75
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000005054 phenyltrichlorosilane Substances 0.000 claims abstract description 61
- 239000000463 material Substances 0.000 claims abstract description 60
- 239000006227 byproduct Substances 0.000 claims abstract description 57
- 239000000126 substance Substances 0.000 claims abstract description 49
- 239000000047 product Substances 0.000 claims abstract description 35
- 239000005055 methyl trichlorosilane Substances 0.000 claims abstract description 33
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 32
- 238000005086 pumping Methods 0.000 claims abstract description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 25
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 18
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims abstract description 12
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000000843 powder Substances 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 claims description 5
- GDCCFQMGFUZVKK-UHFFFAOYSA-N 1-butyl-2h-pyridine Chemical compound CCCCN1CC=CC=C1 GDCCFQMGFUZVKK-UHFFFAOYSA-N 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 abstract description 4
- 239000010703 silicon Substances 0.000 abstract description 4
- 239000002699 waste material Substances 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 13
- 239000002994 raw material Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- GTPDFCLBTFKHNH-UHFFFAOYSA-N chloro(phenyl)silicon Chemical compound Cl[Si]C1=CC=CC=C1 GTPDFCLBTFKHNH-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- DZPJVKXUWVWEAD-UHFFFAOYSA-N [C].[N].[Si] Chemical compound [C].[N].[Si] DZPJVKXUWVWEAD-UHFFFAOYSA-N 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- XHIHMDHAPXMAQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butylpyridin-1-ium Chemical group CCCC[N+]1=CC=CC=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XHIHMDHAPXMAQK-UHFFFAOYSA-N 0.000 description 1
- NELRINSZCVVEAD-UHFFFAOYSA-N chloro-ethenyl-methylsilane Chemical compound C[SiH](Cl)C=C NELRINSZCVVEAD-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007777 multifunctional material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000005053 propyltrichlorosilane Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses phenyl trimethylsilane and a preparation method thereof, which relate to the technical field of organic silicon and comprise the following steps: s1, pumping high-boiling substances of phenyl trichlorosilane into a batching kettle A by using a pump, and adding methyl trichlorosilane to obtain a first mixed material; s2, driving byproducts in the synthesis of the methyl monomers into a batching kettle B, and adding a catalyst and CuCl powder to obtain a second mixed material; s3, pressurizing and heating the tubular reactor, pumping the second mixed material into the tubular reactor, pumping the first mixed material into the tubular reactor, and reacting the first mixed material with the second mixed material; s4, removing low-boiling substances from the product, recovering unreacted byproducts and methyltrichlorosilane, decoloring and filtering the product to obtain phenyltrimethylsilane. The invention has the advantages that the high-boiling and low-boiling byproduct waste of the organic silicon, which causes serious hidden trouble to the safety and the environment, is converted into a high-value product, and the process is simple and efficient and the product content is high.
Description
Technical Field
The invention relates to the technical field of organic silicon, in particular to phenyl trimethylsilane and a preparation method thereof.
Background
Phenyl trichlorosilane Chinese is known as mono phenyl trichlorosilane, commonly known as phenyl chlorosilane and phenyl trichlorosilane, and the molecular formula is C 6 H 5 SiCl 3 . Phenyl trichlorosilane is a chemical intermediate with very wide application, can be used for preparing various coupling agents, is also one of important monomers for preparing organosilicon polymers, and has obvious effects of improving the performance of polyorganosiloxane, in particular improving the heat resistance, chemical stability, irradiation resistance and the like of organosilicon products. The organosilicon monomer is the raw material for preparing silicone oil, silicone rubber, silicone resin and silane coupling agent, and thousands of organosilicon products can be produced from several basic monomers, including methyl chlorosilane (methyl monomer for short), phenyl chlorosilane (phenyl monomer for short), methyl vinyl chlorosilane, ethyl trichlorosilane, propyl trichlorosilane, vinyl trichlorosilane, gamma-chloropropyl trichlorosilane, fluorosilicone monomer and the like. Among them, methylchlorosilanes are the most important, and their use amounts account for the total monomerThe amount is more than 90 percent. Along with the rapid development of the world organosilicon industry, the requirements on the phenyl trichlorosilane and the hydrogen-containing double seal heads are increasingly larger, high-boiling byproducts generated in the synthesis process of the phenyl trichlorosilane and byproducts generated in the production process of the hydrogen-containing double seal heads are also more and more, the commercial value of the high-boiling substances and the byproducts is always low, a large amount of the high-boiling substances and the byproducts are accumulated and blocked, so that serious environmental protection and safety problems are caused, and effective resources are wasted greatly, so that the utilization of the byproducts becomes a serious obstacle for restricting the further development of the organosilicon industry.
Phenyl trimethyl silane is transparent liquid and has molecular formula of C 9 H 14 Si, density: 0.873g/mL, boiling point: the preparation method is characterized in that bromobenzene, iodobenzene and hexamethyldisilane are usually used for reaction at 168-170 ℃, and can be used as raw materials for preparing novel multi-functional materials with high hardness, low friction coefficient, low k value, wide optical band gap, corrosion resistance and the like, such as silicon carbon nitrogen (SiCxNy) and the like.
Disclosure of Invention
The invention aims to at least solve one of the technical problems in the prior art and provides a method for preparing phenyl trimethylsilane by using phenyl trichlorosilane high-boiling residues, byproducts in methyl monomer synthesis and methyl trichlorosilane as raw materials.
The technical scheme of the invention is as follows:
the phenyltrimethylsilane comprises high-boiling materials of phenyltrichlorosilane and byproducts in the synthesis of methyl monomers, and the phenyltrimethylsilane content in the obtained products is 70-85%.
A method for preparing phenyl trimethylsilane, comprising the following steps:
s1, pumping high-boiling-point substances of phenyl trichlorosilane into a batching kettle A by using a pump, adding methyl trichlorosilane, and stirring and uniformly mixing to obtain a first mixed material;
s2, adding byproducts in the synthesis of the methyl monomers into a batching kettle B, adding a catalyst and CuCl powder, and uniformly stirring to obtain a second mixed material;
s3, pressurizing and heating the tubular reactor, pumping the second mixed material into the tubular reactor, and then pumping the first mixed material into the tubular reactor, wherein the first mixed material and the second mixed material react to generate a product;
s4, removing low-boiling substances from the product, recovering unreacted byproducts and methyltrichlorosilane, and decoloring and filtering the product to obtain phenyltrimethylsilane.
Further, in the first mixed material, the mass ratio of the phenyl trichlorosilane high-boiling substance to the methyl trichlorosilane is 1:0.2-0.5.
Further, the byproducts in the synthesis of the methyl monomer comprise 55 to 65 weight percent of CH 4 The mass ratio of the Si, phenyl trichlorosilane high-boiling substance to the byproduct in the synthesis of the methyl monomer is 1:2-3.
Further, the catalyst is one or more of triethylamine chloroaluminate hydrochloride, 1-methyl-3-butyl imidazole chloroaluminate, N-butyl pyridine chloroaluminate and aluminum trichloride, and the addition amount of the catalyst is 1-5 wt% of phenyl trichlorosilane high-boiling residues.
Further, the addition amount of the CuCl powder is 1-5 wt% of the phenyltrichlorosilane high-boiling-point substance.
Further, in the step S3, the second mixed material is horizontally fed into the tubular reactor, and the feeding direction of the first mixed material and the second mixed material is 90 °.
Further, in the step S3, the pressure in the tubular reactor is 0.2-2.0 Mpa, and the temperature is 280-660 ℃.
Further, in the step S4, the low-boiling-point substances are removed from the product at the temperature of 80-120 ℃ and under the pressure of-0.095 to-0.075 Mpa, unreacted byproducts and methyltrichlorosilane are recovered, and then active oxygen is used for decoloring and filtering to obtain phenyltrimethylsilane.
Further, the content of phenyl trichlorosilane in the obtained product is 70-85%.
The invention has at least one of the following beneficial effects:
the invention uses byproduct waste generated by preparing hydrogen-containing double seal heads from phenyl trichlorosilane high-boiling residues and low-boiling residues and methyl trichlorosilane as raw materials, and the phenyl trichlorosilane high-boiling residues are cracked, disproportionated and directionally converted into phenyl trimethylsilane by virtue of a tubular reactor under the actions of high temperature and high pressure and a catalyst. The invention provides a method for converting high-boiling and low-boiling byproduct wastes of organic silicon with serious hidden danger to safety and environment into high-value products, which has the advantages of simple and efficient process, high product content, 70-85% of phenyltrichlorosilane in the products, high yield and easy realization of industrial large-scale continuous production.
Detailed Description
The following "phenyltrichlorosilane high boiling residue" is a high boiling by-product produced during the production of phenyltrichlorosilane, and the following examples and comparative examples use the same batch of high boiling by-product produced during the production of phenyltrichlorosilane.
The following "by-product in methyl monomer synthesis" is a by-product produced by rectifying low-boiling residue collected during rectification of mixed monomer in methyl monomer (methylchlorosilane) production process, and its main component is CH 4 Si, and CH 4 The ratio of Si in the by-product is 55-65 wt%, and the following examples and comparative examples use the same batch of by-product produced in the process of producing hydrogen-containing double heads using low boiling substances.
The invention provides a method for preparing phenyl trimethylsilane by utilizing organosilicon byproducts, which comprises the following steps:
s1, pumping the phenyl trichlorosilane high-boiling substance into a batching kettle A by a pump, adding methyl trichlorosilane, wherein the mass ratio of the phenyl trichlorosilane high-boiling substance to the methyl trichlorosilane is 1:0.2-0.5, and stirring for 5-10 min to obtain a first mixed material.
S2, adding byproducts in the synthesis of the methyl monomer into a batching kettle B, wherein the mass ratio of the phenyltrichlorosilane high-boiling residues to the byproducts in the synthesis of the methyl monomer is 1:2-3, adding 1-5wt% of catalyst of the phenyltrichlorosilane high-boiling residues and 1-5wt% of CuCl powder of the phenyltrichlorosilane high-boiling residues, wherein the catalyst is one or more of triethylamine chloroaluminate hydrochloride, 1-methyl-3-butylimidazole chloroaluminate, N-butylpyridine chloroaluminate and aluminum trichloride, and stirring for 5-10 min to mix uniformly to obtain a second mixed material.
S3, pressurizing the tubular reactor to 0.2-2.0 Mpa, heating to 280-660 ℃, horizontally pumping the second mixed material into the tubular reactor, vertically pumping the first mixed material into the tubular reactor, enabling the feeding direction of the first mixed material and the feeding direction of the second mixed material to be 90 degrees, enabling the mixed materials to react under the action of high temperature and high pressure and a catalyst, and enabling phenyl trichlorosilane high-boiling substances to be cracked in the reactor and to react with CH in byproducts 4 Si undergoes disproportionation reaction to directionally produce a phenyltrimethylsilane-containing product.
S4, removing low-boiling substances from the obtained product at the temperature of 80-120 ℃ under the pressure of minus 0.075 to minus 0.095Mpa, recycling unreacted low-boiling byproducts and methyltrichlorosilane for continuous reaction, and then decoloring and filtering by using active oxygen to obtain phenyltrimethylsilane, wherein the recycled low-boiling byproducts and methyltrichlorosilane can be recycled for continuous reaction.
The present invention will be described in further detail with reference to the following specific examples, but the present invention is not limited to the following specific examples.
Example 1
A method for preparing phenyltrimethylsilane from organosilicon byproducts, comprising the steps of:
s1, pumping the phenyl trichlorosilane high-boiling substance into a batching kettle A by using a pump, adding methyl trichlorosilane, wherein the mass ratio of the phenyl trichlorosilane high-boiling substance to the methyl trichlorosilane is 1:0.2, and stirring for 5min to obtain a first mixed material.
S2, adding byproducts in the synthesis of the methyl monomer into a batching kettle B, wherein the mass ratio of the phenyltrichlorosilane high-boiling substance to the byproducts in the synthesis of the methyl monomer is 1:2, adding a catalyst with the weight percent of 1 percent of the phenyltrichlorosilane high-boiling substance and CuCl powder with the weight percent of 1 percent of the phenyltrichlorosilane high-boiling substance, wherein the catalyst is triethylamine chloroaluminate hydrochloride, and stirring for 5min to mix uniformly to obtain a second mixed material.
S3, pressurizing the tubular reactor to 0.2Mpa, heating to 280 ℃, horizontally pumping the second mixed material into the tubular reactor, and vertically pumping the first mixed material into the tubular reactor to generate a phenyltrimethylsilane-containing product.
S4, removing low-boiling substances from the obtained product at 80 ℃ under reduced pressure of-0.095 Mpa, recovering unreacted low-boiling byproducts and methyltrichlorosilane, and then decoloring and filtering by using active oxygen to obtain phenyltrimethylsilane.
Example 2
A method for preparing phenyltrimethylsilane from organosilicon byproducts, comprising the steps of:
s1, pumping the phenyl trichlorosilane high-boiling substance into a batching kettle A by a pump, adding methyl trichlorosilane, wherein the mass ratio of the phenyl trichlorosilane high-boiling substance to the methyl trichlorosilane is 1:0.3, and stirring for 6min to obtain a first mixed material.
S2, adding byproducts in the synthesis of the methyl monomer into a batching kettle B, wherein the mass ratio of the phenyltrichlorosilane high-boiling residues to the byproducts in the synthesis of the methyl monomer is 1:2.2, adding 2wt% of catalyst of the phenyltrichlorosilane high-boiling residues and 2wt% of CuCl powder of the phenyltrichlorosilane high-boiling residues, wherein the catalyst is 1-methyl-3-butylimidazole chloroaluminate, and stirring for 6min to obtain a second mixed material.
S3, pressurizing the tubular reactor to 0.6Mpa, heating to 350 ℃, horizontally pumping the second mixed material into the tubular reactor, and vertically pumping the first mixed material into the tubular reactor to generate a phenyltrimethylsilane-containing product.
S4, removing low-boiling substances from the obtained product at 90 ℃ under reduced pressure of-0.09 Mpa, recovering unreacted low-boiling byproducts and methyltrichlorosilane, and then decoloring and filtering by using active oxygen to obtain phenyltrimethylsilane.
Example 3
A method for preparing phenyltrimethylsilane from organosilicon byproducts, comprising the steps of:
s1, pumping the phenyl trichlorosilane high-boiling substance into a batching kettle A by a pump, adding methyl trichlorosilane, wherein the mass ratio of the phenyl trichlorosilane high-boiling substance to the methyl trichlorosilane is 1:0.35, and stirring for 7min to obtain a first mixed material.
S2, adding byproducts in the synthesis of the methyl monomer into a batching kettle B, wherein the mass ratio of the phenyltrichlorosilane high-boiling residues to the byproducts in the synthesis of the methyl monomer is 1:2.5, adding 3wt% of catalyst of the phenyltrichlorosilane high-boiling residues and 3wt% of CuCl powder of the phenyltrichlorosilane high-boiling residues, wherein the catalyst is N-butylpyridinium chloroaluminate, and stirring for 7min to mix uniformly to obtain a second mixed material.
S3, pressurizing the tubular reactor to 1Mpa, heating to 450 ℃, horizontally pumping the second mixed material into the tubular reactor, and vertically pumping the first mixed material into the tubular reactor to generate a phenyltrimethylsilane-containing product.
S4, removing low-boiling substances from the obtained product at 100 ℃ under reduced pressure of-0.085 Mpa, recovering unreacted low-boiling byproducts and methyltrichlorosilane, and then decoloring and filtering by using active oxygen to obtain phenyltrimethylsilane.
Example 4
A method for preparing phenyltrimethylsilane from organosilicon byproducts, comprising the steps of:
s1, pumping the phenyl trichlorosilane high-boiling substance into a batching kettle A by a pump, adding methyl trichlorosilane, wherein the mass ratio of the phenyl trichlorosilane high-boiling substance to the methyl trichlorosilane is 1:0.4, and stirring for 9min to obtain a first mixed material.
S2, adding byproducts in the synthesis of the methyl monomer into a batching kettle B, wherein the mass ratio of the phenyltrichlorosilane high-boiling residues to the byproducts in the synthesis of the methyl monomer is 1:2.8, adding 4wt% of catalyst of the phenyltrichlorosilane high-boiling residues and 4wt% of CuCl powder of the phenyltrichlorosilane high-boiling residues, wherein the catalyst is N-butylpyridine chloroaluminate acid and aluminum trichloride with the mass of 1:1, and stirring for 8min to mix uniformly to obtain a second mixed material.
S3, pressurizing the tubular reactor to 1.5Mpa, heating to 550 ℃, horizontally pumping the second mixed material into the tubular reactor, and vertically pumping the first mixed material into the tubular reactor to generate a phenyltrimethylsilane-containing product.
S4, removing low-boiling substances from the obtained product at 110 ℃ under reduced pressure of-0.08 Mpa, recovering unreacted low-boiling byproducts and methyltrichlorosilane, and then decoloring and filtering by using active oxygen to obtain phenyltrimethylsilane.
Example 5
A method for preparing phenyltrimethylsilane from organosilicon byproducts, comprising the steps of:
s1, pumping the phenyl trichlorosilane high-boiling substance into a batching kettle A by a pump, adding methyl trichlorosilane, wherein the mass ratio of the phenyl trichlorosilane high-boiling substance to the methyl trichlorosilane is 1:0.5, and stirring for 10min to obtain a first mixed material.
S2, adding byproducts in the synthesis of the methyl monomer into a batching kettle B, wherein the mass ratio of the phenyltrichlorosilane high-boiling substance to the byproducts in the synthesis of the methyl monomer is 1:3, adding a catalyst with the weight percent of 5% of the phenyltrichlorosilane high-boiling substance and 5% of CuCl powder with the weight percent of the phenyltrichlorosilane high-boiling substance, wherein the catalyst is triethylamine chloroaluminate acid hydrochloride and 1-methyl-3-butylimidazole chloroaluminate acid with the mass ratio of 1:1, and stirring for 10min to mix uniformly to obtain a second mixed material.
S3, pressurizing the tubular reactor to 2.0Mpa, heating to 660 ℃, horizontally pumping the second mixed material into the tubular reactor, and vertically pumping the first mixed material into the tubular reactor to generate a phenyltrimethylsilane-containing product.
S4, removing low-boiling substances from the obtained product at 120 ℃ under reduced pressure of-0.075 Mpa, recovering unreacted low-boiling byproducts and methyltrichlorosilane, and then decolorizing and filtering by using active oxygen to obtain phenyltrimethylsilane.
Comparative example 1
A method for preparing phenyltrimethylsilane from organosilicon byproducts, comprising the steps of:
s1, pumping the phenyl trichlorosilane high-boiling substance into a batching kettle A by a pump, adding methyl trichlorosilane, wherein the mass ratio of the phenyl trichlorosilane high-boiling substance to the methyl trichlorosilane is 1:0.05, and stirring for 5min to obtain a first mixed material.
Otherwise, the same as in example 1 was conducted.
Comparative example 2
S2, adding byproducts in the synthesis of the methyl monomer into a batching kettle B, wherein the mass ratio of the phenyltrichlorosilane high-boiling substance to the byproducts in the synthesis of the methyl monomer is 1:1, adding 0.5wt% of catalyst of the phenyltrichlorosilane high-boiling substance and 0.5wt% of CuCl powder of the phenyltrichlorosilane high-boiling substance, wherein the catalyst is triethylamine chloroaluminate hydrochloride, and stirring for 5min to mix uniformly to obtain a second mixed material.
Otherwise, the same as in example 1 was conducted.
Comparative example 3
And S3, heating the tubular reactor to 150 ℃, horizontally pumping the second mixed material into the tubular reactor, vertically pumping the first mixed material into the tubular reactor, and reacting the mixed materials under normal pressure to generate a phenyltrimethylsilane-containing product.
Otherwise, the same as in example 1 was conducted.
Testing
The phenyltrimethylsilane content and the phenyltrimethylsilane yield of the products of examples 1 to 5 and comparative example were measured, and the phenyltrimethylsilane content was analyzed by a chromatograph, and the yield = phenyltrimethylsilane actual yield/phenyltrimethylsilane theoretical yield, and the results are shown in table 1:
TABLE 1
| Project | Content/% | Yield/% |
| Example 1 | 75 | 81 |
| Example 2 | 79 | 83 |
| Example 3 | 84 | 85 |
| Example 4 | 85 | 86 |
| Example 5 | 83 | 84 |
| Comparative example 1 | 57 | 67 |
| Comparative example 2 | 49 | 61 |
| Comparative example 3 | 43 | 58 |
As can be seen from Table 1, the phenyltrimethylsilane content in the products obtained in examples 1 to 5 is 75 to 85%, the yield is 81 to 86%, and as can be seen from comparison with comparative examples 1 to 3, the phenyltrimethylsilane content in the products obtained in examples 1 to 5 and the phenyltrimethylsilane yield are far greater than those in comparative example 1 (the raw material ratio in step S1 is different from that in example 1), comparative example 2 (the raw material ratio in step S2 is different from that in example 1) and comparative example 3 (the process condition in step S3 is different from that in example 1), and therefore, the invention is characterized in that the content and yield of the phenyltrimethylsilane obtained are high by selecting the proper raw material ratio and the specific process condition.
The above is merely exemplary embodiments of the present invention, and the scope of the present invention is not limited in any way. All technical schemes formed by adopting equivalent exchange or equivalent substitution fall within the protection scope of the invention.
Claims (3)
1. The preparation method of the phenyl trimethylsilane is characterized by comprising the following steps of:
s1, pumping high-boiling-point substances of phenyl trichlorosilane into a batching kettle A by using a pump, adding methyl trichlorosilane, and stirring and uniformly mixing to obtain a first mixed material;
s2, adding byproducts in the synthesis of the methyl monomers into a batching kettle B, adding a catalyst and CuCl powder, and uniformly stirring to obtain a second mixed material;
s3, pressurizing and heating the tubular reactor, pumping the second mixed material into the tubular reactor, and then pumping the first mixed material into the tubular reactor, wherein the first mixed material and the second mixed material react to generate a product;
s4, removing low-boiling-point substances in the product, recovering unreacted byproducts and methyltrichlorosilane, and decoloring and filtering the product to obtain phenyltrimethylsilane;
in the first mixed material, the mass ratio of the phenyl trichlorosilane high-boiling-point substance to the methyl trichlorosilane is 1:0.2-0.5;
in the second mixed material, the byproducts in the synthesis of the methyl monomer comprise 55-65wt% of CH 4Si;
the mass ratio of the phenyl trichlorosilane high-boiling-point substance to the byproduct in the synthesis of the methyl monomer is 1:2-3;
in the step S4, the low-boiling-point substances of the product are removed under the conditions of 80-120 ℃ and reduced pressure of-0.095 to-0.075 Mpa, unreacted byproducts and methyltrichlorosilane are recovered, and then active oxygen is used for decoloration and filtration to obtain phenyltrimethylsilane;
the catalyst is one or more of triethylamine chloroaluminate, 1-methyl-3-butyl imidazole chloroaluminate, N-butyl pyridine chloroaluminate and aluminum trichloride, and the addition amount of the catalyst is 1-5 wt% of phenyl trichlorosilane high-boiling residues;
in the step S3, the pressure in the tubular reactor is 0.2-2.0 Mpa, and the temperature is 280-660 ℃.
2. The method for preparing phenyltrimethylsilane according to claim 1, wherein the amount of the CuCl powder added is 1-5 wt% of the phenyltrichlorosilane high boiling point substance.
3. The method for preparing phenyltrimethylsilane according to claim 1, wherein in the step S3, the second mixed material is horizontally fed into the tubular reactor, and the feeding direction of the first mixed material and the second mixed material is 90 °.
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