CN114573637A - Preparation method of trimethylsiloxy pentafluorocyclotriphosphazene - Google Patents
Preparation method of trimethylsiloxy pentafluorocyclotriphosphazene Download PDFInfo
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- CN114573637A CN114573637A CN202011398779.9A CN202011398779A CN114573637A CN 114573637 A CN114573637 A CN 114573637A CN 202011398779 A CN202011398779 A CN 202011398779A CN 114573637 A CN114573637 A CN 114573637A
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- Prior art keywords
- trimethylsiloxy
- pentafluorocyclotriphosphazene
- reaction
- hexamethyldisiloxane
- preparation
- 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.)
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- USVZHJXLJYLEBS-UHFFFAOYSA-N C[Si](C)(C)OP1(F)=NP(F)(F)=NP(F)(F)=N1 Chemical compound C[Si](C)(C)OP1(F)=NP(F)(F)=NP(F)(F)=N1 USVZHJXLJYLEBS-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000003377 acid catalyst Substances 0.000 claims abstract description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims abstract description 5
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 trimethylsiloxy pentachlorocyclotriphosphazene Chemical compound 0.000 claims abstract description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 4
- SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 claims description 3
- ZCLXQTGLKVQKFD-UHFFFAOYSA-N 3-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1 ZCLXQTGLKVQKFD-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 8
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract description 5
- 229910001416 lithium ion Inorganic materials 0.000 abstract description 5
- 208000012839 conversion disease Diseases 0.000 abstract description 4
- 239000003063 flame retardant Substances 0.000 description 8
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
- DKQPXAWBVGCNHG-UHFFFAOYSA-N 2,2,4,4,6,6-hexafluoro-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound FP1(F)=NP(F)(F)=NP(F)(F)=N1 DKQPXAWBVGCNHG-UHFFFAOYSA-N 0.000 description 4
- OXOZHAWWRPCVGL-UHFFFAOYSA-N lithium;trimethyl(oxido)silane Chemical compound [Li+].C[Si](C)(C)[O-] OXOZHAWWRPCVGL-UHFFFAOYSA-N 0.000 description 3
- LBKJNHPKYFYCLL-UHFFFAOYSA-N potassium;trimethyl(oxido)silane Chemical compound [K+].C[Si](C)(C)[O-] LBKJNHPKYFYCLL-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- HSNUIYJWTSJUMS-UHFFFAOYSA-N sodium;trimethyl(oxido)silane Chemical compound [Na+].C[Si](C)(C)[O-] HSNUIYJWTSJUMS-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PEJQKHLWXHKKGS-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octachloro-1,3,5,7-tetraza-2$l^{5},4$l^{5},6$l^{5},8$l^{5}-tetraphosphacycloocta-1,3,5,7-tetraene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 PEJQKHLWXHKKGS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention discloses a preparation method of trimethylsiloxy pentafluorocyclotriphosphazene, which is characterized by comprising the following steps: the method comprises the following steps: reacting hexachlorocyclotriphosphazene with hexamethyldisiloxane in the presence of benzenesulfonic acid catalyst at 40-90 ℃ to obtain trimethylsiloxy pentachlorocyclotriphosphazene. The invention has the advantages that: the reaction route is very simple, the reaction conditions are simple and easy to control, and particularly, the reaction conversion rate is high and can reach more than 95% under the temperature condition of 70-90 ℃. And the hexamethyldisiloxane as the reaction raw material is low in price and sufficient in market supply, so that the production of trimethylsiloxy pentafluorocyclotriphosphazene is greatly facilitated, the production cost is greatly reduced, and the cost of the lithium ion battery can be effectively reduced.
Description
Technical Field
The invention relates to the technical field of compound synthesis, in particular to a synthetic method of silicon-containing cyclic phosphazenes.
Background
Cyclic phosphazene compounds are a new type of inorganic-organic hybrid, which has a backbone with alternating phosphorus and nitrogen atoms. The special structure endows the cyclic phosphazene compound with excellent performance. The organic silicon flame retardant is a novel, high-efficiency, low-toxicity and environment-friendly halogen-free flame retardant.
The trimethylsiloxy pentafluorocyclotriphosphazene is a flame retardant combining cyclic phosphazene and organosilicon, contains P, N, F, Si four flame retardant elements in the molecule, has a synergistic effect, and can improve the flame retardant efficiency while reducing the dosage of the flame retardant in the lithium ion battery electrolyte.
Patent application CN107915759A relates to synthesis of trimethylsiloxy pentafluorocyclotriphosphazene by reaction of potassium trimethylsilanolate, sodium trimethylsilanolate or lithium trimethylsilanolate as raw materials with hexafluorocyclotriphosphazene, and the trimethylsiloxy pentafluorocyclotriphosphazene is used as a flame retardant for lithium ion battery electrolyte, so that excellent flame retardant effect is obtained. However, the raw material potassium trimethylsilanolate (sodium, lithium) is not a commonly available raw material, and is limited by the yield of the raw material in industrial production, so the production scale is often limited; and the method has low conversion rate and complex reaction route.
Disclosure of Invention
The technical problems to be solved by the invention are as follows: the preparation method of the trimethylsiloxy pentafluorocyclotriphosphazene has the advantages of easily obtained reaction raw materials, simple reaction route and high conversion rate.
In order to solve the problems, the invention adopts the technical scheme that: a preparation method of trimethylsiloxy pentafluorocyclotriphosphazene comprises the following steps: reacting hexachlorocyclotriphosphazene with hexamethyldisiloxane in the presence of benzenesulfonic acid catalyst at 40-90 ℃ to obtain trimethylsiloxy pentachlorocyclotriphosphazene.
Further, in the preparation method of trimethylsiloxy pentafluorocyclotriphosphazene, the benzenesulfonic acid catalyst is at least one selected from p-toluenesulfonic acid, p-nitrobenzenesulfonic acid and m-hydroxybenzenesulfonic acid.
Further, in the preparation method of trimethylsiloxy pentafluorocyclotriphosphazene, the mass of the catalyst is 0.1-1% of the mass of hexamethyldisiloxane.
Further, in the method for preparing trimethylsiloxy pentafluorocyclotriphosphazene, the reaction temperature is preferably controlled to 70 to 90 ℃.
Further, the preparation method of the trimethylsiloxy pentafluorocyclotriphosphazene comprises the step of preparing the hexafluorocyclotriphosphazene and the hexamethyldisiloxane in a molar ratio of 1: 1-1: 5.
Further, in the method for preparing trimethylsiloxy pentafluorocyclotriphosphazene, the molar ratio of hexafluorocyclotriphosphazene to hexamethyldisiloxane is preferably 1:2 to 1: 5.
Further, the reaction time of the preparation method of trimethylsiloxy pentafluorocyclotriphosphazene is 1-12 hours.
The invention has the beneficial effects that: firstly, the reaction route is very simple, the reaction conditions are simple and easy to control, and particularly, the reaction conversion rate is high and can reach more than 95% under the temperature condition of 70-90 ℃. And the hexamethyldisiloxane as the reaction raw material is low in price and sufficient in market supply, so that the production of trimethylsiloxy pentafluorocyclotriphosphazene is greatly facilitated, the production cost is greatly reduced, and the cost of the lithium ion battery can be effectively reduced.
Detailed Description
The preparation of trimethylsiloxypentafluorocyclotriphosphazene according to the invention is described in more detail below with reference to specific examples.
The phosphonitrilic chloride hexaflouride is referred to as PNF for short; hexamethyldisiloxane abbreviated as MM; TsOH for p-toluenesulfonic acid; pNBA for p-nitrobenzenesulfonic acid and mPA for m-hydroxybenzenesulfonic acid.
Example 1: 300g of hexafluorocyclotriphosphazene, 590g of hexamethyldisiloxane and 0.6g of p-toluenesulfonic acid are added into a 2000mL three-neck flask provided with a stirring pipe, a condensing pipe and a thermometer, the temperature is raised to 80 ℃, reaction is finished after 4 hours, the temperature is reduced, reaction is finished, and the trimethylsiloxy pentafluorocyclotriphosphazene is obtained by concentration and rectification, wherein the reaction conversion rate is 98.7%.
Examples 2 to 8: the reaction equipment and the reaction steps were the same as in example 1, and the proportions of the reactants, the types of catalysts, the masses of the catalysts, the reaction temperatures and the reaction times were changed from those in example 1. This is more intuitively explained below by means of a list. The reactions of examples 1 to 8 are shown in Table 1.
Table 1:
the above examples show that the preparation method of trimethylsiloxy pentafluorocyclotriphosphazene has a very simple reaction route and simple and easily controllable reaction conditions, and particularly has a high reaction conversion rate of over 95% at a temperature of 70-90 ℃.
More importantly: the price of potassium trimethylsilanolate mentioned in the background art is about 5000 yuan/kg, the price of sodium trimethylsilanolate is about 8000 yuan/kg, the price of lithium trimethylsilanolate is about 6000 yuan/kg, the price is very high, the supply amount is small, most of the lithium trimethylsilanolate is a reagent in small packages, and the production is very unfavorable, so the preparation cost of the trimethylsiloxy pentafluorocyclotriphosphazene is high. By adopting the preparation method of the trimethylsiloxy pentafluorocyclotriphosphazene, the price of the hexamethyldisiloxane as the reaction raw material is about 50 yuan/kg, and the market supply is sufficient, so that the preparation method is greatly beneficial to the production of the trimethylsiloxy pentafluorocyclotriphosphazene, greatly reduces the production cost, and further can effectively reduce the cost of the lithium ion battery.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (7)
1. The preparation method of trimethylsiloxy pentafluorocyclotriphosphazene is characterized by comprising the following steps: the method comprises the following steps: reacting hexachlorocyclotriphosphazene with hexamethyldisiloxane in the presence of benzenesulfonic acid catalyst at 40-90 ℃ to obtain trimethylsiloxy pentachlorocyclotriphosphazene.
2. The method of preparing trimethylsiloxy pentafluorocyclotriphosphazene according to claim 1, wherein: the benzene sulfonic acid catalyst is at least one of p-toluenesulfonic acid, p-nitrobenzenesulfonic acid and m-hydroxybenzenesulfonic acid.
3. The method for producing trimethylsiloxy pentafluorocyclotriphosphazene according to claim 1 or 2, characterized in that: the mass of the catalyst is 0.1-1% of that of hexamethyldisiloxane.
4. The method for producing trimethylsiloxy pentafluorocyclotriphosphazene according to claim 1 or 2, characterized in that: the reaction temperature is preferably controlled to 70 ℃ to 90 ℃.
5. The method for producing trimethylsiloxy pentafluorocyclotriphosphazene according to claim 1 or 2, characterized in that: the molar ratio of the hexachlorocyclotriphosphazene to the hexamethyldisiloxane is 1:1 to 1: 5.
6. The method of preparing trimethylsiloxy pentafluorocyclotriphosphazene according to claim 5, wherein: the molar ratio of the hexachlorocyclotriphosphazene to the hexamethyldisiloxane is 1:2 to 1: 5.
7. The method for producing trimethylsiloxy pentafluorocyclotriphosphazene according to claim 1 or 2, characterized in that: the reaction time is 1-12 hours.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107302108A (en) * | 2017-06-02 | 2017-10-27 | 山东大学 | A kind of phosphonitrile of efficient flame-retarding agent siloxy fluoro ring three and its synthetic method |
CN107337694A (en) * | 2016-05-03 | 2017-11-10 | 广东广山新材料股份有限公司 | A kind of phosphazene compound with silanol, fire retardant, composition epoxy resin and composite metal substrate |
CN107915759A (en) * | 2017-11-08 | 2018-04-17 | 山东泽世新材料科技有限公司 | A kind of three phosphonitrile of efficient flame-retarding agent siloxy fluoro ring and its synthetic method |
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2020
- 2020-12-02 CN CN202011398779.9A patent/CN114573637B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107337694A (en) * | 2016-05-03 | 2017-11-10 | 广东广山新材料股份有限公司 | A kind of phosphazene compound with silanol, fire retardant, composition epoxy resin and composite metal substrate |
CN107302108A (en) * | 2017-06-02 | 2017-10-27 | 山东大学 | A kind of phosphonitrile of efficient flame-retarding agent siloxy fluoro ring three and its synthetic method |
CN107915759A (en) * | 2017-11-08 | 2018-04-17 | 山东泽世新材料科技有限公司 | A kind of three phosphonitrile of efficient flame-retarding agent siloxy fluoro ring and its synthetic method |
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