CN114573637B - Preparation method of trimethylsiloxy pentafluoroethyl triphosphazene - Google Patents
Preparation method of trimethylsiloxy pentafluoroethyl triphosphazene Download PDFInfo
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- CN114573637B CN114573637B CN202011398779.9A CN202011398779A CN114573637B CN 114573637 B CN114573637 B CN 114573637B CN 202011398779 A CN202011398779 A CN 202011398779A CN 114573637 B CN114573637 B CN 114573637B
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- trimethylsiloxy
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- hexamethyldisiloxane
- preparation
- pentafluoroethyl
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- -1 trimethylsiloxy pentafluoroethyl triphosphazene Chemical compound 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims abstract description 14
- 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 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 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
- 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
- 238000000034 method Methods 0.000 claims description 6
- 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
- 150000002825 nitriles Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 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
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 208000012839 conversion disease Diseases 0.000 abstract description 4
- 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 abstract 1
- 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- LQIZMOLWEQTWCW-UHFFFAOYSA-N C[Si](O)(C)C.[Li] Chemical compound C[Si](O)(C)C.[Li] LQIZMOLWEQTWCW-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- COTHYYYVPUZALV-UHFFFAOYSA-N hydroxy(trimethyl)silane;potassium Chemical compound [K].C[Si](C)(C)O COTHYYYVPUZALV-UHFFFAOYSA-N 0.000 description 2
- VHQSQWCOIYFCCJ-UHFFFAOYSA-N hydroxy(trimethyl)silane;sodium Chemical compound [Na].C[Si](C)(C)O VHQSQWCOIYFCCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 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 pentafluoro cyclotriphosphazene, which is characterized by comprising the following steps of: comprising the following steps: and reacting hexafluorocyclotriphosphazene with hexamethyldisiloxane in the presence of benzenesulfonic acid catalyst at 40-90 ℃ to obtain trimethylsiloxyl pentafluoroetriphosphazene. The invention has the advantages that: the reaction route is very simple, the reaction condition is simple and easy to control, and the reaction conversion rate is high and can reach more than 95 percent especially under the temperature condition of 70-90 ℃. 2. The hexamethyldisiloxane as a reaction raw material has low price and sufficient market supply, which is greatly beneficial to the production of the trimethylsiloxy pentafluoroethylcyclotriphosphazene, greatly reduces the production cost, and further can effectively reduce the cost of the lithium ion battery.
Description
Technical Field
The invention relates to the technical field of compound synthesis, in particular to a method for synthesizing silicon-containing cyclic phosphazenes.
Background
The cyclic phosphazene compound is a novel inorganic-organic hybrid having a skeleton in which phosphorus and nitrogen atoms are alternately arranged. The special structure gives the cyclic phosphazene compound excellent properties. The organic silicon flame retardant is a novel, efficient, low-toxicity and environment-friendly halogen-free flame retardant.
The trimethyl siloxy pentafluoroethylene triphosphate is a flame retardant combining cyclic phosphazene and organic silicon, contains P, N, F, si flame retardant elements in molecules, has synergistic effect, and can improve flame retardant efficiency while reducing the consumption of the flame retardant in lithium ion battery electrolyte.
Patent application CN107915759a relates to a method for synthesizing trimethylsiloxy pentafluoroethylphosphazene by reacting raw materials of potassium trimethylsilanol, sodium trimethylsilanol or lithium trimethylsilanol with hexafluorocyclotriphosphazene, and the obtained material is used as a flame retardant for lithium ion battery electrolyte, so that an excellent flame retardant effect is obtained. However, the raw material of the potassium (sodium and lithium) trimethylsilanol is not a commonly and easily available raw material, and the production scale is often limited because the raw material yield is limited during industrial production; 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 pentafluoroethylphosphazene is easy to obtain the reaction raw materials, simple in reaction route and high in conversion rate.
In order to solve the problems, the invention adopts the following technical scheme: the preparation method of the trimethylsiloxy pentafluoroethyl triphosphazene comprises the following steps: and reacting hexafluorocyclotriphosphazene with hexamethyldisiloxane in the presence of benzenesulfonic acid catalyst at 40-90 ℃ to obtain trimethylsiloxyl pentafluoroetriphosphazene.
Further, the preparation method of the trimethylsiloxy pentafluoroethyl cyclotriphosphazene, wherein the benzenesulfonic acid catalyst is at least one selected from p-toluenesulfonic acid, p-nitrobenzenesulfonic acid and m-hydroxybenzenesulfonic acid.
Further, the preparation method of the trimethylsiloxy pentafluoroethyl triphosphazene comprises the step of preparing the trimethylsiloxy pentafluoroethyl triphosphazene, wherein the mass of the catalyst is 0.1-1% of that of hexamethyldisiloxane.
Further, in the above-mentioned process for producing trimethylsiloxy pentafluoroethyl triphosphazene, the reaction temperature is preferably controlled to be 70℃to 90 ℃.
Further, the preparation method of the trimethylsiloxy pentafluoroethylphosphazene comprises the step of preparing the trimethylsiloxy pentafluoroethylphosphazene, wherein the molar ratio of the hexafluorocyclotriphosphazene to the hexamethyldisiloxane is 1:1-1:5.
Further, in the preparation method of the trimethylsiloxy pentafluoroethyl triphosphazene, the molar ratio of the hexafluoro cyclotriphosphazene to the hexamethyldisiloxane is preferably 1:2-1:5.
Further, the preparation method of the trimethylsiloxy pentafluoroethyl triphosphazene, wherein the reaction time is 1-12 hours.
The beneficial effects of the invention are as follows: 1. the reaction route is very simple, the reaction condition is simple and easy to control, and the reaction conversion rate is high and can reach more than 95 percent especially under the temperature condition of 70-90 ℃. 2. The hexamethyldisiloxane as a reaction raw material has low price and sufficient market supply, which is greatly beneficial to the production of the trimethylsiloxy pentafluoroethylcyclotriphosphazene, greatly reduces the production cost, and further can effectively reduce the cost of the lithium ion battery.
Detailed Description
The preparation method of trimethylsiloxy pentafluoroethyl cyclotriphosphazene according to the present invention is described in further detail by means of specific examples.
The abbreviation of hexafluorocyclotriphosphazene is PNF; the abbreviation of hexamethyldisiloxane is MM; the abbreviation of p-toluenesulfonic acid is TsOH; the p-nitrobenzenesulfonic acid is abbreviated as pNBA and the m-hydroxybenzenesulfonic acid is abbreviated as mPA.
Example 1: 300g of hexafluorocyclotriphosphazene, 590g of hexamethyldisiloxane and 0.6g of p-toluenesulfonic acid are added into a 2000mL three-neck flask with a stirring pipe, a condensing pipe and a thermometer, the temperature is raised to 80 ℃, the reaction is completed after 4 hours of reaction, 379g of trimethylsiloxy pentafluoroetriphosphazene is obtained after concentration and rectification, and the reaction conversion rate is 98.7%.
Examples 2 to 8: the reaction equipment and the reaction steps are the same as in example 1, and the ratio of reactants, the types of the catalysts, the quality of the catalysts, the reaction temperature and the reaction time are changed compared with those in example 1. This is more intuitively illustrated by the list below. The reactions of examples 1 to 8 are specifically shown in Table 1.
Table 1:
the above examples show that the preparation method of trimethylsiloxy pentafluoroethyl cyclotriphosphazene has very simple reaction route and simple and easily controlled reaction conditions, and particularly has high reaction conversion rate of more than 95 percent under the temperature condition of 70-90 ℃.
More important is: the price of the potassium trimethylsilanol in the background technology is about 5000 yuan/kg, the price of the sodium trimethylsilanol is about 8000 yuan/kg, the price of the lithium trimethylsilanol is about 6000 yuan/kg, the price is very high, the supply quantity is small, most of the materials are small-package reagents, and the production is very unfavorable, so that the preparation cost of the trimethylsiloxy pentafluoroethyl triphosphazene is high. By adopting the preparation method of the trimethylsiloxy pentafluoroethylcyclotriphosphazene, the price of the reaction raw material hexamethyldisiloxane 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 pentafluoroethylcyclotriphosphazene, greatly reduces the production cost, and further can effectively reduce the cost of the lithium ion battery.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (5)
1. The preparation method of the trimethylsiloxy pentafluoroethyl triphosphazene is characterized by comprising the following steps: comprising the following steps: reacting hexafluorocyclotriphosphazene with hexamethyldisiloxane in the presence of benzenesulfonic acid catalyst at 70-90 ℃ to obtain trimethylsiloxyl pentafluoroetriphosphazene; the benzenesulfonic acid catalyst is at least one selected from p-toluenesulfonic acid, p-nitrobenzenesulfonic acid and m-hydroxybenzenesulfonic acid.
2. The method for preparing trimethylsiloxy pentafluoroethyl triphosphazene according to claim 1, characterized in that: the mass of the catalyst is 0.1-1% of that of hexamethyldisiloxane.
3. The method for producing trimethylsiloxy pentafluoroetylphosphoric nitrile according to claim 1 or 2, characterized by: the molar ratio of the hexafluorocyclotriphosphazene to the hexamethyldisiloxane is 1:1-1:5.
4. A process for the preparation of trimethylsiloxy pentafluoroethyl triphosphazene as claimed in claim 3, wherein: the molar ratio of the hexafluorocyclotriphosphazene to the hexamethyldisiloxane is 1:2-1:5.
5. The method for producing trimethylsiloxy pentafluoroetylphosphoric nitrile according to claim 1 or 2, characterized by: the reaction time is 1-12 hours.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011398779.9A CN114573637B (en) | 2020-12-02 | 2020-12-02 | Preparation method of trimethylsiloxy pentafluoroethyl triphosphazene |
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|---|---|---|---|
| CN202011398779.9A CN114573637B (en) | 2020-12-02 | 2020-12-02 | Preparation method of trimethylsiloxy pentafluoroethyl triphosphazene |
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| CN114573637B true CN114573637B (en) | 2023-11-17 |
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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 |
-
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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