CN114669311B - Composite catalyst and preparation method and application thereof - Google Patents
Composite catalyst and preparation method and application thereof Download PDFInfo
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/138—Halogens; Compounds thereof with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/32—Manganese, technetium or rhenium
- B01J23/34—Manganese
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/132—Halogens; Compounds thereof with chromium, molybdenum, tungsten or polonium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/22—Halogenating
- B01J37/26—Fluorinating
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
- C07C17/281—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons of only one compound
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- 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
Abstract
The invention discloses a composite catalyst and a preparation method and application thereof, wherein the preparation method of the composite catalyst comprises the following steps: mixing at least two salt solutions containing active elements to obtain a mixed solution, regulating the pH value of the mixed solution to 9.8-10.2, filtering to obtain a precipitate, washing the precipitate, drying, and then compacting and forming to obtain a catalyst precursor; the active element is selected from one of Fe, ni, cr, al, pd, ni, zn and Mn; and gradually activating the catalyst precursor by introducing hexafluoropropylene and protective gas to prepare the composite catalyst. The composite catalyst is used for preparing hexafluoropropylene dimer and trimer by catalysis, and has good stability and can be recycled.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a composite catalyst, a preparation method and application thereof.
Background
Hexafluoropropylene dimer and trimer are electronic fluorinated liquids, a versatile nonflammable liquid, with excellent dielectric properties, a broad boiling point range, superior material compatibility and thermal stability, low Global Warming Potential (GWP) and zero Ozone Depletion Potential (ODP), excellent environmental performance characteristics.
The preparation method of hexafluoropropylene dimer/trimer mainly comprises a gas phase method and a liquid phase method; the liquid phase method generally dissolves the catalyst and the additive in the polar aprotic solvent, and then hexafluoropropylene is introduced to carry out oligomerization reaction; the liquid phase method is widely used for various catalysts, but some catalysts are easy to absorb water to reduce the catalytic efficiency; the byproducts of the catalytic reaction are extremely toxic substances, which causes great threat to the personal safety and environment of experimental staff. Therefore, a new catalyst needs to be sought.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a composite catalyst, and a preparation method and application thereof. The composite catalyst is used for catalyzing oligomerization of hexafluoropropylene to synthesize hexafluoropropylene dimer and trimer. The preparation method has the advantages of low raw material cost, good catalyst stability and repeated recycling.
The aim of the invention is achieved by the following technical scheme:
a method for preparing a composite catalyst, comprising the steps of:
(1) Mixing at least two salt solutions containing active elements to obtain a mixed solution, regulating the pH value of the mixed solution to 9.8-10.2, filtering to obtain a precipitate, washing the precipitate, drying, and then compacting and forming to obtain a catalyst precursor; the active element is selected from one of Fe, ni, cr, al, pd, ni, zn and Mn;
(2) Heating the catalyst precursor to 400-410 ℃ under the protection gas, preserving heat for 9.5-11 h at the temperature, and then cooling to 200-210 ℃; firstly, introducing protective gas at the rate of 95-105 ml/min, and introducing hexafluoropropylene to activate the catalyst precursor at the rate of 15-25 ml/min for 9.5-10 h; then, introducing protective gas at the rate of 95-105 ml/min and hexafluoropropylene to activate the catalyst precursor at the rate of 45-55 ml/min for 9.5-10 h; then introducing protective gas at the rate of 45-55 ml/min and hexafluoropropylene to activate the catalyst precursor at the rate of 95-105 ml/min for 9.5-10 h; finally, introducing hexafluoropropylene to activate the catalyst precursor for 9.5-10 h at the rate of 95-105 ml/min, heating to 350-360 ℃, and then introducing hexafluoropropylene to activate the catalyst precursor for 9.5-10 h at the rate of 95-105 ml/min, thus completing the gradual activation of the catalyst and preparing the composite catalyst.
Preferably, the method for adjusting the pH of the mixed solution in the step (1) is as follows: 30wt% ammonia was added to adjust the pH.
Preferably, the pH of the mixed solution in the step (1) is adjusted to 10.
Preferably, the concentration of the salt solution containing the active element in the step (1) is 30-35 wt%.
Preferably, in the step (2), the heating to 400-410 ℃ is performed in the following manner: raising the temperature to 400-410 ℃ at a speed of 1-1.2 ℃/min.
Preferably, in the step (2), the catalyst precursor is heated to 400-410 ℃ under the protection gas and is kept at the temperature for 10 hours.
Preferably, in the step (2), firstly, shielding gas is introduced at a rate of 100ml/min, and hexafluoropropylene is introduced at a rate of 20ml/min to activate the catalyst precursor for 10 hours; then, shielding gas is introduced at the rate of 100ml/min, and hexafluoropropylene is introduced at the rate of 50ml/min to activate the catalyst precursor for 10h; then, introducing protective gas at the rate of 50ml/min and hexafluoropropylene to activate the catalyst precursor at the rate of 100ml/min for 10 hours; finally, introducing hexafluoropropylene to activate the catalyst precursor for 10 hours at the rate of 100ml/min, heating to 350 ℃, and then introducing hexafluoropropylene to activate the catalyst precursor for 10 hours at the rate of 100ml/min, thus completing the gradual activation of the catalyst.
The composite catalyst prepared by the preparation method of the composite catalyst.
The application of the composite catalyst in preparing hexafluoropropylene dimer and trimer by catalysis.
Preferably, the application comprises the steps of: hexafluoropropylene (CAS: 116-15-4, CF) 3 CF=CF 2 ) And (3) heating and reacting under the atmosphere of the compound catalyst and protective gas to obtain hexafluoropropylene dimer (CAS: 13429-24-8) and hexafluoropropylene trimer (CAS: 6792-31-0)
Preferably, the shielding gas is nitrogen or an inert gas, more preferably nitrogen.
Preferably, the mole ratio of hexafluoropropylene to nitrogen is 1:0.1 to 5.
Preferably, the temperature of the heating reaction is 100-400 ℃.
Preferably, the space velocity of the compound catalyst is 500-10000 h < -1 >.
Compared with the prior art, the invention has the beneficial effects that:
1. the composite catalyst prepared by the invention has the advantages of low raw materials cost and convenient sources.
2. The catalyst has good stability and can be recycled.
3. The gas phase catalytic product is directly separated, and compared with the liquid phase reaction, the separation and purification of the product are simple.
4. The synthesis process is safe and suitable for industrial production.
Detailed Description
The present invention will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
Example 1
CrCl with a molar ratio of 60:20:20 (referring to the molar ratio of active elements) 3 Solution, al (NO) 3 ) 3 Solution and Zn (NO) 3 ) 2 Solution (CrCl) 3 ,Al(NO 3 ) 3 And Zn (NO) 3 ) 2 The concentrations of the solutions were 32 wt%) were mixed, 30wt% aqueous ammonia was added dropwise to the mixed solution, and ph=10.0 was adjusted. Filtering the precipitate, washing with deionized water, drying, and compression molding to obtain a fluorinated catalyst precursor Cr-Al-Zn;
50ml of the catalyst Cr-Al-Zn precursor was fed into a fixed bed reactor, which was heated with an open tube furnace. The catalyst was first heated to 400℃at 1℃per minute under nitrogen (flow rate 100 ml/min) and then dried at this temperature for 10 hours, and then the temperature was reduced to 200 ℃. This completes the drying process of the catalyst.
The reactor was heated to 200℃and the catalyst was activated by passing nitrogen (at a rate of 100 ml/min) and hexafluoropropylene (at a rate of 20 ml/min) for 10 hours; the catalyst was activated by passing nitrogen (flow rate 100 ml/min) and hexafluoropropylene (flow rate 50 ml/min) for 10 hours; the catalyst was activated by passing nitrogen (flow rate 50 ml/min) and hexafluoropropylene (flow rate 100 ml/min) for 10 hours; activating the catalyst by passing pure hexafluoropropylene (flow rate is 100 ml/min) for 10 hours; the temperature was raised to 350℃and finally the catalyst was activated by passing pure hexafluoropropylene (flow rate 100 ml/min) for 10 hours. Thus, the activation process of the Cr-Al-Zn catalyst was completed.
Heating the reactor to 150 ℃, and uniformly mixing hexafluoropropylene (purity is 95 percent; flow rate is 100 ml/min) and nitrogen (flow rate is 10 ml/min) together in a mixing cavity by adopting a mass flowmeter; thereafter, the mixture was passed through a reactor containing 50ml of a catalyst (space velocity of the catalyst: 8000 h-1) until a buffer bottle, a washing bottle, a concentrated alkali absorber, a cooling collector. After the end of the experiment, the product was mainly distributed in the cooling collector. The collected product was subjected to GC analysis. GC results showed that the product collected contained 25% hexafluoropropylene dimer and 10% hexafluoropropylene trimer.
Example 2
Fe (NO) with a molar ratio of 90:10 (referring to the molar ratio of active elements) 3 ) 3 Solution and Zn (NO) 3 ) 2 Solution (Fe (NO) 3 ) 3 The concentration of the solution was 35wt%; zn (NO) 3 ) 2 The concentration of the solution was 30 wt%) was mixed, 30wt% aqueous ammonia was added dropwise to the mixed solution, and ph=10.0 was adjusted. Filtering the precipitate, washing with deionized water, drying, and compression molding to obtain a fluorinated catalyst precursor Fe-Zn;
50ml of the Fe-Zn precursor catalyst was fed into a fixed bed reactor, which was heated with an open tube furnace. The catalyst was first heated to 400℃at 1℃per minute under nitrogen (flow rate 100 ml/min) and dried at this temperature for 10 hours, and then cooled to 200 ℃. This completes the drying process of the catalyst.
The reactor was heated to 200℃and the catalyst was activated by passing nitrogen (at a rate of 100 ml/min) and hexafluoropropylene (at a rate of 20 ml/min) for 10 hours; the catalyst was activated by passing nitrogen (flow rate 100 ml/min) and hexafluoropropylene (flow rate 50 ml/min) for 10 hours; the catalyst was activated by passing nitrogen (flow rate 50 ml/min) and hexafluoropropylene (flow rate 100 ml/min) for 10 hours; activating the catalyst by passing pure hexafluoropropylene (flow rate is 100 ml/min) for 10 hours; the temperature was raised to 350℃and finally the catalyst was activated by passing pure hexafluoropropylene (flow rate 100 ml/min) for 10 hours. This completes the activation process of the Fe-Zn catalyst.
The reactor was heated to 250℃and hexafluoropropylene (purity 95%;100 ml/min) was mixed with nitrogen (flow rate 10 ml/min) using a mass flow meter into a mixing chamber. Thereafter, the mixture was passed through a reactor containing 50ml of a catalyst (space velocity of the catalyst: 5000 h-1) until a buffer bottle, a washing bottle, a concentrated alkali absorber, a cooling collector. After the end of the experiment, the product was mainly distributed in the cooling collector. The collected product was subjected to GC analysis. GC results showed that the product collected contained 44% hexafluoropropylene dimer and 20% hexafluoropropylene trimer.
Example 3
The molar ratio is 90:5:5 (refer to the molar ratio of active elements) Cr (NO) 3 Solution, al (NO) 3 ) 3 Solution (Cr (NO) 3 Solution and Mn (NO) 3 ) 2 Solution (Cr (NO) 3 The concentration of the solution was 31wt%; al (NO) 3 ) 3 The concentration of the solution was 32wt%, mn (NO 3 ) 2 The concentration of the solution was 35 wt%) was mixed, 30wt% aqueous ammonia was added dropwise to the mixed solution, and ph=10.0 was adjusted. Filtering the precipitate, washing with deionized water, drying, and compression molding to obtain a fluorinated catalyst precursor Cr-Al-Mn;
50ml of the catalyst Cr-Al-Mn precursor was fed into a fixed bed reactor, which was heated with an open tube furnace. The catalyst was first heated to 400℃at 1℃per minute under nitrogen (flow rate 100 ml/min) and dried at this temperature for 10 hours, and then the temperature was reduced to 200 ℃. This completes the drying process of the catalyst.
The reactor was heated to 200℃and the catalyst was activated by passing nitrogen (at a rate of 100 ml/min) and hexafluoropropylene (at a rate of 20 ml/min) for 10 hours; the catalyst was activated by passing nitrogen (flow rate 100 ml/min) and hexafluoropropylene (flow rate 50 ml/min) for 10 hours; the catalyst was activated by passing nitrogen (flow rate 50 ml/min) and hexafluoropropylene (flow rate 100 ml/min) for 10 hours; activating the catalyst by passing pure hexafluoropropylene (flow rate is 100 ml/min) for 10 hours; the temperature was raised to 350℃and finally the catalyst was activated by passing pure hexafluoropropylene (flow rate 100 ml/min) for 10 hours. Thus, the activation process of the Cr-Al-Mn catalyst was completed.
The reactor was heated to 330℃and hexafluoropropylene (purity 95%; flow rate 100 ml/min) was mixed with nitrogen (flow rate 10 ml/min) using a mass flow meter into a mixing chamber. Thereafter, the mixture was passed through a reactor containing 50ml of the catalyst (space velocity of the catalyst: 1000 h-1) until a buffer bottle, a water wash bottle, a concentrated alkali absorber, a cooling collector. After the end of the experiment, the product was mainly distributed in the cooling collector. The collected product was subjected to GC analysis. GC results showed that the product collected contained 53% hexafluoropropylene dimer and 31% hexafluoropropylene trimer.
The above-described embodiments of the present invention do not limit the scope of the present invention. Any other corresponding changes and modifications made in accordance with the technical idea of the present invention shall be included in the scope of the claims of the present invention.
Claims (10)
1. A method for preparing a composite catalyst, comprising the steps of:
(1) Mixing at least two salt solutions containing active elements to obtain a mixed solution, regulating the pH value of the mixed solution to 9.8-10.2, filtering to obtain a precipitate, washing, drying and pressing the precipitate to obtain a catalyst precursor; the active element is selected from one of Fe, ni, cr, al, pd, zn and Mn;
(2) Heating the catalyst precursor to 400-410 ℃ under the protection gas, preserving heat for 9.5-11 h at the temperature, and then cooling to 200-210 ℃; firstly, introducing protective gas at the rate of 95-105 ml/min, and introducing hexafluoropropylene to activate the catalyst precursor at the rate of 15-25 ml/min for 9.5-10 h; then, introducing protective gas at the rate of 95-105 ml/min and hexafluoropropylene to activate the catalyst precursor at the rate of 45-55 ml/min for 9.5-10 h; then introducing protective gas at the rate of 45-55 ml/min and hexafluoropropylene to activate the catalyst precursor at the rate of 95-105 ml/min for 9.5-10 h; finally, introducing hexafluoropropylene to activate the catalyst precursor for 9.5-10 h at the rate of 95-105 ml/min, heating to 350-360 ℃, and then introducing hexafluoropropylene to activate the catalyst precursor for 9.5-10 h at the rate of 95-105 ml/min, thus completing the gradual activation of the catalyst and preparing the composite catalyst.
2. The method for preparing a composite catalyst according to claim 1, wherein the means for adjusting the pH of the mixed solution in step (1) is as follows: adding 30wt% ammonia water to adjust the pH;
the mode of heating to 400-410 ℃ in the step (2) is as follows: raising the temperature to 400-410 ℃ at a speed of 1-1.2 ℃/min.
3. The method for preparing a composite catalyst according to claim 1 or 2, wherein the step (1) is performed by adjusting the pH of the mixed solution to 10;
the concentration of the salt solution containing the active elements in the step (1) is 30-35 wt%.
4. The method for preparing a composite catalyst according to claim 1, wherein the catalyst precursor in the step (2) is heated to 400-410 ℃ under the protection gas and is kept at the temperature for 10 hours; and (3) the protective gas in the step (2) is nitrogen.
5. The method for preparing a composite catalyst according to claim 1, wherein in the step (2), the protecting gas is introduced at a rate of 100ml/min, and the hexafluoropropylene is introduced at a rate of 20ml/min to activate the catalyst precursor for 10 hours; then, shielding gas is introduced at the rate of 100ml/min, and hexafluoropropylene is introduced at the rate of 50ml/min to activate the catalyst precursor for 10h; then, introducing protective gas at the rate of 50ml/min and hexafluoropropylene to activate the catalyst precursor at the rate of 100ml/min for 10 hours; finally, introducing hexafluoropropylene to activate the catalyst precursor for 10 hours at the rate of 100ml/min, heating to 350 ℃, and then introducing hexafluoropropylene to activate the catalyst precursor for 10 hours at the rate of 100ml/min, thus completing the gradual activation of the catalyst.
6. A composite catalyst prepared by the method for preparing a composite catalyst according to any one of claims 1 to 5.
7. Use of the composite catalyst according to claim 6 for the catalytic preparation of hexafluoropropylene dimers and trimers.
8. The use according to claim 7, characterized by the steps of: and heating hexafluoropropylene in the presence of the composite catalyst and protective gas to react, thus obtaining hexafluoropropylene dimer and hexafluoropropylene trimer.
9. The use according to claim 8, wherein the shielding gas is nitrogen or an inert gas; the mol ratio of hexafluoropropylene to nitrogen is 1:0.1 to 5.
10. The use according to claim 8 or 9, wherein the temperature of the heating reaction is 100-400 ℃; the space velocity of the compound catalyst is 500-10000 h < -1 >.
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5616429A (en) * | 1979-07-19 | 1981-02-17 | Daikin Ind Ltd | Preparation of hexafluoropropene oligomer |
US5254774A (en) * | 1992-12-28 | 1993-10-19 | Minnesota Mining And Manufacturing Company | Preparation of hexafluoropropene oligomers |
CN104549155A (en) * | 2015-01-23 | 2015-04-29 | 中国科学院生态环境研究中心 | Biological activated carbon composite material and application thereof |
CN108155368A (en) * | 2017-12-29 | 2018-06-12 | 武汉船用电力推进装置研究所(中国船舶重工集团公司第七二研究所) | A kind of preparation method of carbon coating lithium manganese phosphate nanometer rods |
CN112830863A (en) * | 2021-01-04 | 2021-05-25 | 山东华夏神舟新材料有限公司 | Method for continuously and controllably preparing hexafluoropropylene dimer/trimer |
-
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- 2022-03-17 CN CN202210264244.5A patent/CN114669311B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5616429A (en) * | 1979-07-19 | 1981-02-17 | Daikin Ind Ltd | Preparation of hexafluoropropene oligomer |
US5254774A (en) * | 1992-12-28 | 1993-10-19 | Minnesota Mining And Manufacturing Company | Preparation of hexafluoropropene oligomers |
CN104549155A (en) * | 2015-01-23 | 2015-04-29 | 中国科学院生态环境研究中心 | Biological activated carbon composite material and application thereof |
CN108155368A (en) * | 2017-12-29 | 2018-06-12 | 武汉船用电力推进装置研究所(中国船舶重工集团公司第七二研究所) | A kind of preparation method of carbon coating lithium manganese phosphate nanometer rods |
CN112830863A (en) * | 2021-01-04 | 2021-05-25 | 山东华夏神舟新材料有限公司 | Method for continuously and controllably preparing hexafluoropropylene dimer/trimer |
Non-Patent Citations (1)
Title |
---|
PVDF及其共聚物膜的耐碱性能研究;叶灿等;《 膜科学与技术》;72-79 * |
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