CN112209960A - Preparation of N, N-bis (trimethylsilyl) allylamine - Google Patents
Preparation of N, N-bis (trimethylsilyl) allylamine Download PDFInfo
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- CN112209960A CN112209960A CN201910629946.7A CN201910629946A CN112209960A CN 112209960 A CN112209960 A CN 112209960A CN 201910629946 A CN201910629946 A CN 201910629946A CN 112209960 A CN112209960 A CN 112209960A
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- trimethylsilyl
- bis
- allylamine
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- organic
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- CVNCFZIIZGNVFD-UHFFFAOYSA-N n,n-bis(trimethylsilyl)prop-2-en-1-amine Chemical compound C[Si](C)(C)N([Si](C)(C)C)CC=C CVNCFZIIZGNVFD-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012074 organic phase Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000000706 filtrate Substances 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 11
- 239000008367 deionised water Substances 0.000 claims abstract description 10
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 10
- 239000012535 impurity Substances 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000006482 condensation reaction Methods 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 150000007530 organic bases Chemical class 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 3
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 abstract description 6
- 238000005260 corrosion Methods 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
- 239000012295 chemical reaction liquid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 1
- NNQDMQVWOWCVEM-UHFFFAOYSA-N 1-bromoprop-1-ene Chemical compound CC=CBr NNQDMQVWOWCVEM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 231100000481 chemical toxicant Toxicity 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000005051 trimethylchlorosilane 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C07F7/20—Purification, separation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention discloses a preparation method of N, N-bis (trimethylsilyl) allylamine, which comprises the following steps: firstly, dropwise adding an organic alkali solution into allyl bromide to carry out condensation reaction, removing the organic solvent by rotary evaporation after the reaction is finished, and filtering to remove generated metal salt to obtain a filtrate; and secondly, adding deionized water into the filtrate for low-temperature water washing to remove metal salts and other water-soluble impurities, standing and separating the liquid, separating an organic phase, rectifying the organic phase, and collecting the finished product of the N, N-bis (trimethylsilyl) allylamine. The invention has the advantages that: firstly, the reaction safety coefficient is greatly improved, and the corrosion to equipment is effectively reduced. And secondly, effectively removing by-products or impurities generated in the preparation process, thereby effectively improving the purity and yield of the product.
Description
Technical Field
The invention relates to the technical field of preparation of additives in lithium battery electrolyte, in particular to a preparation method of N, N-bis (trimethylsilyl) allylamine.
Background
N, N-bis (trimethylsilyl) allylamine is a key intermediate useful in the preparation of modified polyimides. Meanwhile, due to the unique molecular structure, N, N-bis (trimethylsilyl) allylamine is used as a novel additive of lithium ion electrolyte, so that the lithium ion electrolyte is easier to form a film, has the characteristics of reducing hydrofluoric acid and improving safety, and is a very promising additive of lithium ion electrolyte under the trend that electric automobiles are increasingly popularized.
The currently known methods for synthesizing N, N-bis (trimethylsilyl) allylamine include the following: the mono-hexamethyldisilazane reacts with chloropropene or bromopropene, and the reaction can generate hydrogen chloride and hydrogen bromide, so that equipment is corroded, and the reaction temperature is high, so that the use is dangerous. Reacting allyl amine and trimethylchlorosilane or allyl amine and hexamethyldisilazane; currently, allylamine is in the list of highly toxic chemicals, and thus the risks and hazards of using allylamine as a starting material are greater.
Disclosure of Invention
The purpose of the invention is: provides a preparation method of N, N-bis (trimethylsilyl) allylamine, which greatly reduces the preparation risk, effectively improves the safety and has high product purity.
In order to achieve the purpose, the invention adopts the technical scheme that: preparation of N, N-bis (trimethylsilyl) allylamine comprising the steps of: firstly, dropwise adding an organic alkali solution into allyl bromide to carry out condensation reaction, removing the organic solvent by rotary evaporation after the reaction is finished, and filtering to remove generated metal salt to obtain a filtrate; and secondly, adding deionized water into the filtrate for low-temperature water washing to remove metal salts and other water-soluble impurities, standing and separating the liquid, separating an organic phase, rectifying the organic phase, and collecting the organic phase to obtain the finished product of the N, N-bis (trimethylsilyl) allylamine.
Further, the preparation of the N, N-bis (trimethylsilyl) allylamine, wherein the organic base solution comprises one of a lithium bis (trimethylsilyl) amide solution, a sodium bis (trimethylsilyl) amide solution and a potassium bis (trimethylsilyl) amide solution, and the reaction scheme is shown as follows;
wherein R represents Li, Na or K, the molar ratio of allyl bromide to organic base is 1.1-1.3, the reaction temperature is-10-20 ℃, and the reaction time of the organic base and the allyl bromide is 0.5-2 hours.
Further, in the above preparation of N, N-bis (trimethylsilyl) allylamine, the organic base solution is preferably a lithium bis (trimethylsilyl) amide solution.
Further, the aforementioned preparation of N, N-bis (trimethylsilyl) allylamine, wherein, in the first step, the molar ratio of allyl bromide to organic base is preferably 1.2: 1.
Further, in the aforementioned preparation of N, N-bis (trimethylsilyl) allylamine, the reaction time of the organic base with allyl bromide in the first step is preferably 1 hour.
Further, in the aforementioned preparation of N, N-bis (trimethylsilyl) allylamine, the reaction temperature of the organic base with allyl bromide in the first step is preferably 10 ℃ to 15 ℃.
Further, in the preparation of the N, N-bis (trimethylsilyl) allylamine, in the first step, the organic solvent of the organic base solution comprises one or more of dichloromethane, 1,2 dichloroethane, toluene, chloroform, N-hexane, cyclohexane, tetrahydrofuran, and the like, and preferably N-hexane or tetrahydrofuran.
Further, the preparation of the aforementioned N, N-bis (trimethylsilyl) allylamine, wherein, in the second step, the low-temperature water washing step is: adding deionized water at the temperature of-10-0 ℃, stirring and washing the organic phase, wherein the washing time is 5-15 min; the adding amount of the deionized water is 50-150 percent of the mass of the filtrate, and the preference is 100 percent.
Further, in the preparation of the aforementioned N, N-bis (trimethylsilyl) allylamine, the low-temperature water washing time is preferably 10 min.
Further, in the preparation of the aforementioned N, N-bis (trimethylsilyl) allylamine, in the second step, the rectification is a reduced pressure rectification, and the pressure is preferably-0.1 MPa.
The invention has the advantages that: firstly, the reaction safety coefficient is greatly improved, and the corrosion to equipment is effectively reduced. And secondly, effectively removing by-products or impurities generated in the preparation process, thereby effectively improving the purity and yield of the product.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
Example 1.
145.2g of allyl bromide is added into a three-neck flask provided with a condenser, a thermometer, a stirrer and a nitrogen protection device, nitrogen protection is slowly introduced, the flask is placed in a bath kettle with flowing water, 898g of tetrahydrofuran solution containing 167g of lithium bis (trimethylsilyl) amide solute is added dropwise for 0.5 hour, then stirring is continued for 0.5 hour at 10-15 ℃, the total reaction time is 1 hour, and stirring is stopped to obtain reaction liquid.
And (3) carrying out negative pressure rotary evaporation on the reaction liquid in the previous step to remove the solvent, so that salt dissolved in the solvent is separated out, and obtaining 313g of reaction liquid containing byproduct salt. Suction filtration was carried out to obtain 104.4g of wet residue and 208.6g of filtrate.
And (3) putting the filtrate into refrigerating fluid, adding 208.6g of deionized water when the kettle temperature is reduced to-8 ℃, stirring for 10min, and standing for liquid separation to obtain 205g of organic phase and 212g of water phase.
And putting the organic phase into a three-neck flask again, rectifying under the pressure of-0.1 MPa, collecting the fraction at 40-50 ℃, namely the finished product of the N, N-bis (trimethylsilyl) allylamine, wherein the purity is 99.22% by GC (gas chromatography) detection, the molar yield is 87.56% by calculation according to 176g of the finished product.
Example 2.
133.1g of allyl bromide is added into a three-neck flask provided with a condenser, a thermometer, a stirrer and a nitrogen protection device, nitrogen protection is slowly introduced, the flask is placed in a bath kettle with flowing water, 860g of n-hexane solution containing 183g of bis (trimethylsilyl) sodium amide solute is added dropwise for 0.5 hour, then stirring is continued for 1.5 hours at 15-20 ℃, the total reaction time is 2 hours, and stirring is stopped.
And (3) carrying out negative pressure rotary evaporation on the reaction liquid in the previous step to remove the solvent, so that salt dissolved in the solvent is separated out, and obtaining 326g of reaction liquid containing byproduct salt. Suction filtration gave 129g of wet residue and 197g of filtrate.
And (3) putting the filtrate into refrigerating fluid, adding 210g of deionized water when the kettle temperature is reduced to-5 ℃, stirring for 8min, and standing for liquid separation to obtain 196g of an organic phase and 211g of a water phase.
And putting the organic phase into a three-neck flask again, rectifying under the pressure of-0.1 MPa, collecting the fraction at 40-50 ℃, namely the finished product of the N, N-bis (trimethylsilyl) allylamine, wherein the purity is 99.17% by GC detection, and the calculated molar yield is 85.07% by 171g of the finished product.
Example 3.
157.3g of allyl bromide is added into a three-neck flask provided with a condenser, a thermometer, a stirrer and a nitrogen protection device, nitrogen protection is slowly introduced, the flask is placed in a bath kettle with flowing water, 1000g of n-hexane solution containing 199g of bis (trimethylsilyl) amino potassium solute is added dropwise for 0.5 hour, then stirring is continued for 1 hour at 15-20 ℃, the total reaction time is 1.5 hours, and the stirring is stopped.
And (3) carrying out negative pressure rotary evaporation on the reaction liquid in the previous step to remove the solvent, so that salt dissolved in the solvent is separated out, and 382g of reaction liquid containing the byproduct salt is obtained. Suction filtration gave 155g of wet residue and 227g of filtrate.
And (3) putting the filtrate into refrigerating fluid, adding 200g of deionized water into the refrigerating fluid when the kettle temperature is reduced to-6 ℃, stirring for 6min, and standing for liquid separation to obtain 212g of an organic phase and 215g of a water phase.
And putting the organic phase into a three-neck flask again, rectifying under the pressure of-0.1 MPa, collecting the fraction at 40-50 ℃, namely the finished product of the N, N-bis (trimethylsilyl) allylamine, wherein the purity is 99.11% by GC detection, and the calculated molar yield is 84.08% when the finished product is 169 g.
From the above embodiments it is possible to obtain: firstly, the reaction safety coefficient is greatly improved, and the corrosion to equipment is effectively reduced. And secondly, effectively removing by-products or impurities generated in the preparation process, thereby effectively improving the purity and yield of the product.
Claims (10)
- Preparation of N, N-bis (trimethylsilyl) allylamine characterized by: the method comprises the following steps: firstly, dropwise adding an organic alkali solution into allyl bromide to carry out condensation reaction, removing the organic solvent by rotary evaporation after the reaction is finished, and filtering to remove generated metal salt to obtain a filtrate; and secondly, adding deionized water into the filtrate for low-temperature water washing to remove metal salts and other water-soluble impurities, standing and separating the liquid, separating an organic phase, rectifying the organic phase, and collecting the organic phase to obtain the finished product of the N, N-bis (trimethylsilyl) allylamine.
- 2. The preparation of N, N-bis (trimethylsilyl) allylamine of claim 1, wherein: the organic alkali solution comprises one of a lithium bis (trimethylsilyl) amide solution, a sodium bis (trimethylsilyl) amide solution and a potassium bis (trimethylsilyl) amide solution, and the reaction is schematically represented by the formula;
wherein R represents Li, Na or K, the molar ratio of allyl bromide to organic base is 1.1-1.3, the reaction temperature is-10-20 ℃, and the reaction time of the organic base and the allyl bromide is 0.5-2 hours. - 3. The preparation of N, N-bis (trimethylsilyl) allylamine of claim 2, wherein: the organic base solution is preferably a lithium bis (trimethylsilyl) amide solution.
- 4. The preparation of N, N-bis (trimethylsilyl) allylamine according to claim 2 or 3, characterized in that: in the first step, the molar ratio of allyl bromide to organic base is preferably 1.2: 1.
- 5. The preparation of N, N-bis (trimethylsilyl) allylamine according to claim 2 or 3, characterized in that: in the first step, the reaction time of the organic base with allyl bromide is preferably 1 hour.
- 6. The preparation of N, N-bis (trimethylsilyl) allylamine according to claim 2 or 3, characterized in that: in the first step, the reaction temperature of the organic base with allyl bromide is preferably 10 ℃ to 15 ℃.
- 7. The preparation of N, N-bis (trimethylsilyl) allylamine according to claim 2 or 3, characterized in that: in the first step, the organic solvent of the organic alkali solution comprises one or more of dichloromethane, 1,2 dichloroethane, toluene, chloroform, n-hexane, cyclohexane, tetrahydrofuran, and the like, preferably n-hexane or tetrahydrofuran.
- 8. The preparation of N, N-bis (trimethylsilyl) allylamine of claim 1 or 2 or 3, characterized in that: in the second step, the low-temperature water washing step is as follows: adding deionized water at the temperature of-10-0 ℃, stirring and washing the organic phase, wherein the washing time is 5-15 min; the adding amount of the deionized water is 50-150 percent of the mass of the filtrate, and the preference is 100 percent.
- 9. The preparation of an N, N-bis (trimethylsilyl) allylamine of claim 8, wherein: the low-temperature water washing time is preferably 10 min.
- 10. The preparation of N, N-bis (trimethylsilyl) allylamine of claim 1 or 2 or 3, characterized in that: in the second step, the rectification is reduced pressure rectification, and the pressure is preferably-0.1 MPa.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910629946.7A CN112209960A (en) | 2019-07-12 | 2019-07-12 | Preparation of N, N-bis (trimethylsilyl) allylamine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113717307A (en) * | 2021-09-26 | 2021-11-30 | 烟台明远创意生活科技股份有限公司 | Polymer microsphere and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102933613A (en) * | 2009-12-21 | 2013-02-13 | 思迪隆欧洲有限公司 | Modified polymer compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102933613A (en) * | 2009-12-21 | 2013-02-13 | 思迪隆欧洲有限公司 | Modified polymer compositions |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113717307A (en) * | 2021-09-26 | 2021-11-30 | 烟台明远创意生活科技股份有限公司 | Polymer microsphere and preparation method and application thereof |
| CN113717307B (en) * | 2021-09-26 | 2023-08-15 | 烟台明远创意生活科技股份有限公司 | Polymer microsphere and preparation method and application thereof |
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Application publication date: 20210112 |