CN106397761B - Process for fluorinating acid end groups of perfluoropolyethers - Google Patents
Process for fluorinating acid end groups of perfluoropolyethers Download PDFInfo
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- CN106397761B CN106397761B CN201610802875.2A CN201610802875A CN106397761B CN 106397761 B CN106397761 B CN 106397761B CN 201610802875 A CN201610802875 A CN 201610802875A CN 106397761 B CN106397761 B CN 106397761B
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- perfluoropolyether
- gas
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- liquid contact
- acid
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- 239000010702 perfluoropolyether Substances 0.000 title claims abstract description 58
- 239000002253 acid Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 239000012025 fluorinating agent Substances 0.000 claims abstract description 27
- 239000000945 filler Substances 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 18
- 239000011737 fluorine Substances 0.000 claims abstract description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 14
- 239000006227 byproduct Substances 0.000 claims abstract description 5
- 229910001220 stainless steel Inorganic materials 0.000 claims abstract description 5
- 239000010935 stainless steel Substances 0.000 claims abstract description 5
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 claims description 4
- WZJQNLGQTOCWDS-UHFFFAOYSA-K cobalt(iii) fluoride Chemical compound F[Co](F)F WZJQNLGQTOCWDS-UHFFFAOYSA-K 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000002474 experimental method Methods 0.000 claims description 2
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical group FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 claims description 2
- 238000007664 blowing Methods 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910000975 Carbon steel Inorganic materials 0.000 abstract description 3
- 239000010962 carbon steel Substances 0.000 abstract description 3
- 238000010924 continuous production Methods 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 abstract description 2
- 239000007789 gas Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- YPDSOAPSWYHANB-UHFFFAOYSA-N [N].[F] Chemical compound [N].[F] YPDSOAPSWYHANB-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- USPWUOFNOTUBAD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F USPWUOFNOTUBAD-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910018503 SF6 Inorganic materials 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 1
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/323—Polymers modified by chemical after-treatment with inorganic compounds containing halogens
- C08G65/3233—Molecular halogen
- C08G65/3236—Fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/326—Polymers modified by chemical after-treatment with inorganic compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/328—Polymers modified by chemical after-treatment with inorganic compounds containing other elements
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- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of fluorine chemical synthesis, and particularly relates to a method for fluorinating a perfluoropolyether acid end group, which takes perfluoropolyether acid and a fluorinating agent as raw materials and is synthesized in a gas-liquid contact reaction tube taking a filler passivated by fluorine gas as a filler, wherein the filler is one or a mixture of carbon steel, stainless steel 304 and stainless steel 316. The perfluoropolyether acid or the solution thereof is sprayed from top to bottom on the top of the gas-liquid contact reaction tube, and the fluorinating agent gas continuously contacts with the perfluoropolyether through a filler gap in the gas-liquid contact reaction tube from bottom to top, so that the gas-liquid contact maximization is achieved, the utilization rate of the fluorinating agent is realized to the maximum degree, and the full and complete fluorination reaction of the perfluoropolyether is realized. In addition, the method carries out continuous fluorination on the perfluoropolyether, solves the problem that the fluorination needs to be carried out in one kettle and one kettle in the prior art, and simplifies the operation procedure. The method has the advantages of less fluorinated perfluoropolyether byproducts, simple operation, continuous production, safe and stable reaction and suitability for industrial large-scale production and application.
Description
Technical Field
The invention belongs to the field of fluorine chemical synthesis, and particularly relates to a method for fluorinating acid end groups of perfluoropolyether.
Background
Perfluoropolyethers and perfluoropolyether esters have extremely wide application in advanced scientific fields such as military industry, aerospace industry and nuclear industry due to excellent extreme high temperature resistance, large working temperature range, excellent oxidation resistance and chemical corrosion resistance, wide material compatibility, excellent electrical insulation performance, excellent film forming performance, excellent bearing performance and lubricating performance.
Either hexafluoropropylene oxide represented by DuPont is used as a raw material to prepare perfluoropolyether acid through anionic polymerization or a photo-oxidation method represented by Suwei is used to prepare the perfluoropolyether acid, the generated perfluoropolyether acid end group contains active acyl fluoride, and the end group needs to be stabilized in order to improve the stability of the perfluoropolyether. The thermal stability of the end group hydrogenation product is low, the stability of the end group fluorinated perfluoropolyether acid is optimal, and the method is an important technology for industrially preparing the perfluoropolyether.
Currently, perfluoropolyether acid end group fluorination techniques fall into two categories. First, by fluorinating agent AlF3、SbF5The catalyst used in the method is expensive, and the separation of metal elements introduced into the product is difficult, and the quality of the product can be seriously influenced; secondly, the fluorine gas and nitrogen mixed gas directly fluorinates the perfluoropolyether acid, the method has low utilization rate of the fluorinating agent, the molar ratio of the fluorine-containing gas to the perfluoropolyether is more than 10 generally, the method is mostly intermittent reaction, the equipment utilization rate is low, the reaction cost is greatly increased, and the method is not beneficial to industrial production. Therefore, the search for a more convenient and faster method for fluorinating perfluoropolyether is an urgent need in the perfluoropolyether industry chain.
Patent publication CN103111253A discloses a reactor in which fluorine gas is circulated through stirring paddles to contact the material to increase the utilization of the fluorinating agent. The hollow stirring rod and the hollow porous stirring paddle can enable the fluorinating agent gas at the upper end of the liquid level of the material to return to the hollow stirring paddle through the hollow stirring rod, and then the fluorinating agent gas is dispersed in the material again through the air holes of the hollow stirring paddle, so that the gas-liquid contact maximization is achieved, and the higher utilization rate of the fluorinating agent is obtained. However, the method cannot carry out continuous fluorination reaction, and the reaction equipment is complex and relatively high in maintenance cost.
Disclosure of Invention
The invention aims to overcome the defects of intermittent synthesis, low utilization rate of fluorinating agent gas and low fluorination conversion rate in the prior art, and provides a method for fluorinating perfluoropolyether.
The technical scheme adopted for realizing the purpose of the invention is as follows: a method for fluorinating the end group of perfluoropolyether acid takes perfluoropolyether acid and a fluorinating agent as raw materials and synthesizes the perfluoropolyether acid and the fluorinating agent in a gas-liquid contact reaction tube which takes filler passivated by fluorine gas as a filler, wherein the filler is one of carbon steel, stainless steel 304 and stainless steel 316. The gas-liquid contact reaction tube can be a device which is commonly used in the prior art and is used for carrying out catalytic reaction on gas and liquid.
Preferably, the filler is filled with a catalyst CoF3, and the mass content of CoF3 is 5-10%.
The synthesis adopts the following steps: heating a gas-liquid contact reaction tube filled with catalyst filler to 60-260 ℃; the perfluoropolyether acid is sprayed into the filler from the top of the gas-liquid contact reaction tube; meanwhile, the fluorinating agent gas is introduced into the bottom of the gas-liquid contact reaction tube.
The gas-liquid catalysis pipe filled with the catalyst filler is heated to 60-160 ℃.
The fluorinating agent is one of a mixture of fluorine gas and nitrogen gas, sulfur tetrafluoride, sulfur hexafluoride or boron trifluoride; the fluorinating agent generates fluorine gas and the perfluoropolyether with the molar ratio of 20: 1-1.2: 1.
the perfluoropolyether acid is diluted in advance by using a solvent, and the mass concentration of the diluted perfluoropolyether acid is not less than 20%; the solvent is a fluorine-containing solvent with the boiling point of 60-160 ℃.
Preferably, the ratio of the molar amount of fluorine gas generated by the fluorinating agent to the molar amount of the perfluoropolyether is 6: 1-2: 1.
the fluorine-containing solvent is one or a mixture of several of perfluorooctane, perfluoromethylbenzene, hexafluorobenzene, FC-75 or hexafluoropropylene oxide oligomer fluoride K6.
The weight average molecular weight Mw of the perfluoropolyether acid is 1000-20000 g/mol.
The introduction speed of the fluorinating agent is 2-4L/min.
Compared with the prior art, the invention has the beneficial effects that:
in order to solve the problems in the process of fluorinating the perfluoropolyether acid, the invention provides a method for fluorinating the perfluoropolyether acid with the end group. The perfluoropolyether acid or the solution thereof is sprayed from top to bottom on the top of the gas-liquid contact reaction tube, and the fluorinating agent gas continuously contacts with the perfluoropolyether through a filler gap in the gas-liquid contact reaction tube from bottom to top, so that the gas-liquid contact maximization is achieved, the utilization rate of the fluorinating agent is realized to the maximum degree, and the full and complete fluorination reaction of the perfluoropolyether is realized. In addition, the method carries out continuous fluorination on the perfluoropolyether, solves the problem that the fluorination needs to be carried out in one kettle and one kettle in the prior art, and simplifies the operation procedure. The method has the advantages of less fluorinated perfluoropolyether byproducts, simple operation, continuous production, safe and stable reaction and suitability for industrial large-scale production and application.
Detailed Description
In order to make the technical solutions of the present invention better understood by those skilled in the art, the present invention will be further described in detail with reference to the following preferred embodiments.
Example 1:
filling a gas-liquid contact reaction tube with the inner diameter of 15cm and the height of 200cm with a filler passivated by fluorine gas and with the particle size of 3mm, wherein the filler in the embodiment is carbon steel, controlling the temperature to be 60 ℃, and carrying out fluorinated perfluoropolyether acid reaction by taking fluorine nitrogen with the fluorine gas content of 20% as a fluorinating agent. Hexafluorobenzene is used as a solvent, and a perfluoropolyether acid solution with the mass concentration of 50% and the weight-average molecular weight of 8000g/mol is used as a reaction solution. The fluorination experiment was carried out while controlling the molar amount of fluorine in the fluorine-nitrogen gas to 20:1 based on the amount of perfluoropolyether. The fluorinating agent was blown into the gas inlet at the bottom of the reaction tube at a rate of 2L/min, and the perfluoropolyether content of the product collected in the product-collecting bottle at the lower end of the reaction tube was 89%, and no other by-product was found.
Other examples are similar to example 1, and the operating conditions are shown in Table 1.
In conclusion, the perfluoropolyether acid or the solution thereof is sprayed from top to bottom on the reaction column, and the fluorinating agent gas continuously passes through the filler gap in the reaction tube from bottom to top to be fully contacted with the perfluoropolyether acid, so that the gas-liquid contact is maximized, the utilization rate of the fluorinating agent is realized to the maximum extent, and the full and complete fluorination reaction of the perfluoropolyether is realized. In addition, the method carries out continuous fluorination on the perfluoropolyether, solves the problem that the fluorination needs to be carried out in one kettle and one kettle in the prior art, and simplifies the operation procedure. The method has the advantages of less fluorinated perfluoropolyether byproducts, simple operation, continuous production, safe and stable reaction and suitability for industrial large-scale production and application.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (1)
1. A method for fluorinating the acid end group of perfluoropolyether is characterized in that perfluoropolyether acid and a fluorinating agent are taken as raw materials and synthesized in a gas-liquid contact reaction tube which takes filler passivated by fluorine gas as a filler, wherein the filler is stainless steel 316; the filler is filled with a catalyst CoF3, and the content of CoF3 is 8% by mass; the gas-liquid contact reaction tube filled with the catalyst filler is heated to 60 ℃; the fluorinating agent is sulfur tetrafluoride; the perfluoropolyether acid is diluted in advance by using a solvent hexafluorobenzene, and the mass concentration of the diluted perfluoropolyether acid is 50%; the weight average molecular weight Mw of the perfluoropolyether acid is 8000 g/mol;
the synthesis adopts the following steps: filling a fluorine gas passivated filler with the grain diameter of 3mm in a gas-liquid contact reaction tube with the inner diameter of 15cm and the height of 200cm, and carrying out fluorinated perfluoropolyether acid reaction; the perfluoropolyether acid solution dissolved in the perfluorinated solvent is sprayed into the filler from the top of the gas-liquid contact reaction tube; simultaneously blowing a fluorinating agent into a gas inlet at the reaction bottom of the catalytic tube at the speed of 4L/min, and controlling the molar ratio of fluorine gas generated by the fluorinating agent to perfluoropolyether to be 6:1 to carry out fluorination experiment; the product perfluoropolyether content collected in the product collection bottle at the lower end of the reaction tube was 98%, and no by-product was produced.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610802875.2A CN106397761B (en) | 2016-09-06 | 2016-09-06 | Process for fluorinating acid end groups of perfluoropolyethers |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610802875.2A CN106397761B (en) | 2016-09-06 | 2016-09-06 | Process for fluorinating acid end groups of perfluoropolyethers |
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| CN106397761A CN106397761A (en) | 2017-02-15 |
| CN106397761B true CN106397761B (en) | 2021-06-18 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110054768B (en) * | 2019-05-30 | 2022-01-04 | 上海欧勒奋生物科技有限公司 | Method for improving heterogeneous contact efficiency |
| CN110183643B (en) * | 2019-05-30 | 2021-12-14 | 上海欧勒奋生物科技有限公司 | Fluorination system of unstable terminal group of perfluoropolyether |
| CN110467723B (en) * | 2019-08-06 | 2021-11-30 | 湖北卓熙氟化股份有限公司 | Preparation method of end-capped perfluoropolyether oil |
| CN115246928A (en) * | 2022-06-30 | 2022-10-28 | 成都晨光博达新材料股份有限公司 | Perfluoropolyether oil and preparation process and device thereof |
| CN116426024B (en) * | 2023-06-14 | 2023-08-18 | 上海森桓新材料科技有限公司 | Method for passivating end group of fluorine elastomer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1104930A (en) * | 1993-10-04 | 1995-07-12 | 美国3M公司 | Fluorination in tubular reactor system |
| CN1684934A (en) * | 2002-09-25 | 2005-10-19 | 纳幕尔杜邦公司 | Process for preparing fluorocarboxylic acids |
| CN103111253A (en) * | 2013-03-14 | 2013-05-22 | 湖南有色郴州氟化学有限公司 | Method and equipment for perfluor polyether fluorination |
| CN103145971A (en) * | 2013-03-07 | 2013-06-12 | 湖南有色郴州氟化学有限公司 | Synthetic method of perfluoropolyether |
| CN104672442A (en) * | 2013-12-02 | 2015-06-03 | 浙江省化工研究院有限公司 | Preparation method of hexafluoropropylene oxide oligomer |
| CN105188904A (en) * | 2013-01-11 | 2015-12-23 | 巴斯夫欧洲公司 | Device and method for the continuous reaction of liquids with gases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6908601B2 (en) * | 2002-02-08 | 2005-06-21 | The Boc Group, Inc. | Method for the production of nitrogen trifluoride |
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- 2016-09-06 CN CN201610802875.2A patent/CN106397761B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1104930A (en) * | 1993-10-04 | 1995-07-12 | 美国3M公司 | Fluorination in tubular reactor system |
| CN1684934A (en) * | 2002-09-25 | 2005-10-19 | 纳幕尔杜邦公司 | Process for preparing fluorocarboxylic acids |
| CN105188904A (en) * | 2013-01-11 | 2015-12-23 | 巴斯夫欧洲公司 | Device and method for the continuous reaction of liquids with gases |
| CN103145971A (en) * | 2013-03-07 | 2013-06-12 | 湖南有色郴州氟化学有限公司 | Synthetic method of perfluoropolyether |
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Effective date of registration: 20221014 Address after: 300000 Tianjin Binhai New Area Economic and Technological Development Zone (Nangang Industrial Zone) No.29 factory building No.10 Patentee after: TIANJIN CHANGLU CHEMICAL NEW MATERIAL Co.,Ltd. Patentee after: TIANJIN CHANGLU NEW MATERIAL RESEARCH INSTITUTE CO.,LTD. Address before: 300000 Building 9, ligangyuan, Shuanggang Industrial Zone, Shuanggang Town, Jinnan District, Tianjin Patentee before: TIANJIN CHANGLU NEW MATERIAL RESEARCH INSTITUTE CO.,LTD. |
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Effective date of registration: 20231122 Address after: No. 60 Cangsheng Street, Economic and Technological Development Zone (Nangang Industrial Zone), Binhai New Area, Tianjin, 300452 Patentee after: TIANJIN CHANGLU CHEMICAL NEW MATERIAL Co.,Ltd. Address before: 300000 Tianjin Binhai New Area Economic and Technological Development Zone (Nangang Industrial Zone) No.29 factory building No.10 Patentee before: TIANJIN CHANGLU CHEMICAL NEW MATERIAL Co.,Ltd. Patentee before: TIANJIN CHANGLU NEW MATERIAL RESEARCH INSTITUTE CO.,LTD. |
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