CN114984885B - Equipment and process for producing perfluoro polyether peroxide - Google Patents

Equipment and process for producing perfluoro polyether peroxide Download PDF

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CN114984885B
CN114984885B CN202210775562.8A CN202210775562A CN114984885B CN 114984885 B CN114984885 B CN 114984885B CN 202210775562 A CN202210775562 A CN 202210775562A CN 114984885 B CN114984885 B CN 114984885B
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oxygen
gas
reactor
equipment
reaction
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CN114984885A (en
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吴庆
王树华
王宗令
李宏峰
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Zhejiang Juhua Technology Center Co Ltd
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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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/087—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electric or magnetic energy
    • B01J19/088—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electric or magnetic energy giving rise to electric discharges
    • 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
    • B01J3/00—Processes of utilising sub-atmospheric or super-atmospheric pressure to effect chemical or physical change of matter; Apparatus therefor
    • B01J3/04—Pressure vessels, e.g. autoclaves
    • 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
    • C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
    • C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
    • C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
    • 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
    • Y02P20/10—Process efficiency

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to the technical field of fluorine chemical industry, and provides equipment and a process for producing perfluoropolyether peroxide, wherein the equipment comprises gas phase pressurizing equipment, liquid phase pressurizing equipment, a reactor and gas-liquid separating equipment which are mutually independent; the bottom of the reactor is connected with a stirring shaft through a mechanical seal, one section of the stirring shaft extending out of the reactor is contacted with a spring and an electric brush, and one section extending into the reactor is connected with a first flat electrode. The invention also discloses a production process of the perfluoropolyether peroxide, which can continuously generate oxygen plasma and various free radicals, and the oxygen containing the oxygen plasma is fully mixed with hexafluoropropylene quickly, so that the oxygen and hexafluoropropylene are fully sheared and mixed, and the perfluoropolyether peroxide is obtained by high-efficiency polymerization.

Description

Equipment and process for producing perfluoro polyether peroxide
Technical Field
The invention relates to the technical field of fluorine chemical industry, in particular to equipment and a process for producing perfluoropolyether peroxide.
Background
Perfluoropolyether (Perfluom Polyethers, PFPE) is a polymer having only C, F, O three elements in the molecule and is liquid at room temperature. The PFPE molecule has stronger C-F bond to replace C-H bond in hydrocarbon, and the PFPE has higher chemical stability and oxidation stability and good chemical inertness and insulation property due to the existence of C-O and C-C strong covalent bonds and the characteristic of neutrality of the PFPE molecule. Such perfluoropolyethers have a wide range of potential uses, for example, when the end groups are fluorinated to form stable-CF 3 Groups which can be used as perfluoropolyether oils; when the end group is hydrolyzed to form-COOH, the-COOH can be used as an emulsifier, and can be widely applied to oil fields, coatings, fluorine-containing polymer emulsifiers and the like.
CN108440748A discloses a method for synthesizing high molecular weight perfluoropolyether peroxide with acyl fluoride group, which is to directly synthesize the perfluoropolyether peroxide with acyl fluoride group from oxygen and perfluoro monomer by using initiator and auxiliary agent, wherein the auxiliary agent is one or more than two of ozone, oxydifluoride, dichloro oxide or peroxide.
In the prior art, ozone is adopted to initiate the oxidation polymerization of oxygen and hexafluoropropylene, so that the efficiency is low, the yield of the product is low, and the energy consumption is low.
Disclosure of Invention
Through long-term practice, oxygen plasmas and various free radicals synthesized by using a DBD technology are used as new initiators for synthesizing the perfluoropolyether peroxide by oxidation polymerization of oxygen and hexafluoropropylene. If the polymerization degree of the oxidative polymerization can be simply and easily regulated and controlled by simply changing the power, the voltage and the like of the oxygen plasma generator, the regulation and control of the molecular weight of the product can be realized. However, the existence time of the oxygen plasma is very short, the oxygen plasma is easy to quench and finally generate ozone, and the ozone can trigger oxygen and hexafluoropropylene to perform oxidative polymerization, so that the efficiency is low, the ozone concentration is required to reach more than 3% of the oxygen or oxygen-enriched gas concentration, and the product generation amount is small; the energy consumption is huge during large-scale industrial production, and the input-output ratio is low.
The invention aims to provide a perfluoropolyether peroxide production device to realize full shearing and mixing of oxygen and hexafluoropropylene and obtain the perfluoropolyether peroxide by high-efficiency polymerization. The perfluoropolyether peroxide production equipment comprises gas phase pressurizing equipment, liquid phase pressurizing equipment, a reactor and gas-liquid separation equipment which are mutually independent; the bottom of the reactor is connected with a stirring shaft through a mechanical seal, one section of the stirring shaft extending out of the reactor is contacted with a spring and an electric brush, and one section extending into the reactor is connected with a first flat electrode.
Preferably, the stirring shaft is hollow, the side is provided with an opening, and the opening is connected with the static sealing air inlet device, so that pure oxygen or rich oxygen can be introduced.
Preferably, the bottom of the stirring shaft is also connected in an insulating manner.
Preferably, high-voltage electric discharge can be introduced between the first plate electrode and the second plate electrode, and when pure oxygen or oxygen-enriched gas enters the stirring shaft through the static sealing air inlet device, oxygen plasma and free radical initiator are generated through discharge, and the free radical initiator only contains C, O, F elements.
Preferably, part of the pure oxygen or oxygen-enriched gas is carried by the reaction and enters the gas-liquid separation equipment at the top of the reactor, wherein the reaction tail gas after the separation of the gas-liquid separation equipment is supplemented with part of the pure oxygen to become oxygen-enriched gas after passing through the gas-phase pressurizing equipment, and then enters the reactor again through the static sealing air inlet device; the reaction liquid separated by the gas-liquid separation device is returned to the reactor after passing through the liquid phase pressurizing device.
Preferably, the pure oxygen is oxygen with the oxygen content of more than 98%; the oxygen-enriched gas is oxygen with the oxygen content of more than 70 percent.
The invention further provides a process for producing the perfluoropolyether peroxide, hexafluoropropylene is condensed into a reactor through gas-liquid separation equipment, stirring is started, pure oxygen or oxygen-enriched gas is introduced, when the gas-liquid phase reaches saturation, high-voltage electricity is introduced between a first flat plate electrode and a second flat plate electrode, at the moment, an initiator starts to be continuously generated between the electrodes, oxidation polymerization reaction of oxygen and hexafluoropropylene is initiated, and after the reaction is finished, the products are separated.
Preferably, the reaction temperature is-100-20 ℃ and the reaction pressure is 100-1000 KPa.
Further preferably, the reaction temperature is-70 to-40 ℃ and the reaction pressure is 400 to 800KPa.
Preferably, the aeration rate of pure oxygen and oxygen-enriched gas is 1000-4500NL/h.
Further preferably, the oxidative polymerization reactor is jacketed, and a refrigerant can be introduced into the jacket to maintain the required reaction temperature.
The invention also provides a perfluoropolyether peroxide prepared by the process, which has the molecular formula of: CF (compact flash) 3 O-(CF(CF 3 )CF 2 O)m-(CF 2 O)n-(CFO(CF 3 ))p-COF。
The perfluoropolyether peroxide production equipment provided by the invention can realize continuous generation of oxygen plasma and various free radicals, and can be used for fully mixing oxygen containing the oxygen plasma with hexafluoropropylene quickly, so that the problem of poor ozone initiation effect generated by quenching the oxygen plasma is solved. Meanwhile, through the reaction equipment, all reaction tail gas is fully utilized, almost no waste gas is generated, the atom economy is high, the material utilization rate is high, and the yield is high. In addition, a process for continuous oxidative polymerization of oxygen and hexafluoropropylene is provided, and the process realizes large-scale production of a single kettle.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention, illustrate and explain the invention and are not to be construed as limiting the invention. In the drawings:
FIG. 1 is a schematic diagram of an apparatus;
FIG. 2 is a schematic diagram of the reaction;
FIG. 3 shows the products obtained in the examples of the present invention 19 F spectrogram.
Reference numerals illustrate:
1 spring, 2 electric brush, 3 stirring shaft, 4 static sealing air inlet device, 5 mechanical seal, 6 gas phase pressurizing device, 7 liquid phase pressurizing device, 8 reactor, 9 gas-liquid separating device, 10 first plate electrode, 11 second plate electrode, 12 insulating connection
Detailed Description
The following describes specific embodiments of the present invention in detail with reference to the drawings. It should be understood that the detailed description and specific examples, while indicating and illustrating the invention, are not intended to limit the invention.
In order that those skilled in the art will better understand the present invention, a technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in which it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the present invention without making any inventive effort, shall fall within the scope of the present invention.
In order to solve a series of problems of low efficiency, low yield of product production, low energy consumption and the like in the prior art that ozone is adopted to initiate oxygen and hexafluoropropylene to perform oxidative polymerization. The invention provides a perfluoropolyether peroxide production device, as shown in figure 1, which comprises a gas phase pressurizing device 6, a liquid phase pressurizing device 7, a reactor 8 and a gas-liquid separating device 9 which are mutually independent; the bottom of the reactor 8 is connected with the stirring shaft 3 through the mechanical seal 5, one end of the stirring shaft 3 extending out of the reactor 8 is contacted with the spring 1 and the electric brush 2, and the other end extending into the reactor is connected with the first flat plate electrode 10.
The perfluoropolyether peroxide production equipment can realize continuous oxygen plasma and various free radical generation, and can fully mix oxygen containing the oxygen plasma with hexafluoropropylene rapidly, so that the problem of poor ozone initiation effect generated by oxygen plasma quenching is solved. Meanwhile, through the reaction equipment, all reaction tail gas is fully utilized, almost no waste gas is generated, the atom economy is high, the material utilization rate is high, and the yield is high.
In order to be able to supply pure oxygen or oxygen-enriched air from the static seal air inlet 4 more continuously, the stirring shaft 3 is preferably hollow, with openings on the sides, which are connected to the static seal air inlet 4 and can supply pure oxygen or oxygen-enriched air.
In order to generate oxygen plasma or free radical initiator by high-voltage discharge, in the preferred case of the invention, high-voltage electric discharge can be introduced between the first plate electrode 10 and the second plate electrode 11, and when pure oxygen or oxygen-enriched gas enters the stirring shaft 3 through the static sealing air inlet device 4, then the oxygen plasma and the free radical initiator are generated by discharge, and the free radical initiator only contains C, O, F elements.
In order to better obtain enough pure oxygen to become rich oxygen, and the unreacted oxygen enters into circulation for use, so that the benefit is improved and the waste is reduced, in the preferred case of the invention, the pure oxygen or the rich oxygen carries a part of reaction to enter into the gas-liquid separation equipment 9 at the top of the reactor, wherein the reaction tail gas separated by the gas-liquid separation equipment 9 is supplemented with a part of pure oxygen to become rich oxygen after passing through the gas-phase pressurizing equipment 6, and then enters into the reactor 8 again through the static sealing air inlet device 4; the reaction liquid separated by the gas-liquid separation device 9 is returned to the reactor by the liquid phase pressurizing device 7.
In order to enable the high-voltage electric arc between the first plate electrode 10 and the second plate electrode 11 to better enable oxygen to generate oxygen plasma required by oxygen, the pure oxygen is preferably oxygen with the oxygen content of more than 98%; the oxygen-enriched gas is oxygen with the oxygen content of more than 70 percent.
As shown in figure 2, a cooling medium is introduced into a jacket of a heat exchange section of the reactor, a stirring shaft drives a flat plate electrode to rotate, pure oxygen or oxygen-enriched gas is introduced into the reactor through a static sealing air inlet device, and the pure oxygen and the oxygen-enriched gas are fully mixed with liquid hexafluoropropylene under the action of the shearing force of the flat plate electrode to form a gas-liquid mixture with extremely high dispersity. Due to the action of shearing force, the flat plate electrode continuously sucks liquid hexafluoropropylene from the middle to be sheared and mixed with gas, and the gas-liquid mixture is thrown out from the edge of the flat plate electrode and passes through the heat exchange section to reach the top of the reactor.
In order that those skilled in the art will better understand the present invention, a technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in which it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the present invention without making any inventive effort, shall fall within the scope of the present invention.
Example 1
700kg of hexafluoropropylene was condensed into a 500L reactor and stirring was started at a stirring speed of 400 rpm. Ensuring that the ventilation rate of pure oxygen or oxygen-enriched gas is 2000NL/h, after ventilation for 10min, mixing gas and liquid phases to reach saturation, introducing high-voltage electricity between an electrode connected with a stirring shaft and an electrode in a reactor, at the moment, continuously generating oxygen plasma and various free radical (only containing C, O, F elements) initiators between the electrodes, and initiating oxidation polymerization reaction of oxygen and hexafluoropropylene. After 24 hours, 480kg of the perfluoropolyether peroxide was isolated, and GPC measurement was performed using a Viscotek GPC gel permeation chromatograph to obtain a molecular weight product having an average molecular weight of about 3500.
The product was analyzed as follows, with the following test results:
(1) The product was analyzed by iodine (cf. GB/T32102-2015) to determine an active oxygen content of 1.2%.
(3) By nuclear magnetism 19 The F spectrum (600 MHz) determines the structure as:
CF 3 O-(CF(CF 3 )CF 2 O)m-(CF 2 O)n-(CFO(CF 3 ))p-COF。
in FIG. 3 19 The characteristic peak at-146 ppm chemical shift in the F-NMR spectrum is represented by- (CF) 3 )CF 2 The characteristic peak at-131 ppm of chemical shift of the-CF-group in O) is represented by- (CFO (CF) 3 ) The characteristic peak at chemical shift of-55 ppm in the-CF-group is represented by- (CF) 2 -CF in O) 2 The signal at a chemical shift of-57 ppm represents CF 3 CF in O 3 The characteristic peak at-81 to-82 ppm of chemical shift of-group represents- (CF) 3 )CF 2 CF in O) 3 -and CF 2 -a group.
The preparation of examples 2-10 was identical to example 1, except that the following reaction conditions were changed, as detailed in Table 1:
table 1: reaction conditions of examples 2 to 10
After the reaction, the reaction passes through nuclear magnetism 19 The structure of the F spectrum was determined to be consistent with that of the product obtained in example 1, and other measurement results were as follows.
Table 2: test results of examples 2 to 10
As can be seen from the test results of Table 2, the quality of the product obtained by using the equipment is in the order of hundred kilograms, and the reaction efficiency is greatly improved.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (3)

1. The equipment for producing the perfluoropolyether peroxide is characterized by comprising a gas phase pressurizing device (6), a liquid phase pressurizing device (7), a reactor (8) and a gas-liquid separating device (9) which are independent of each other; the bottom of the reactor (8) is connected with a stirring shaft (3) through a mechanical seal (5), one end of the stirring shaft (3) extending out of the reactor (8) is contacted with a spring (1) and an electric brush (2), and one end extending into the reactor is connected with a first flat electrode (10); the stirring shaft (3) is hollow, the side edge of the stirring shaft is provided with an opening, and the opening is connected with the static sealing air inlet device (4) and can be filled with pure oxygen or rich oxygen; high-voltage electric discharge can be introduced between the first plate electrode (10) and the second plate electrode (11), when pure oxygen or oxygen-enriched gas enters the stirring shaft (3) through the static sealing air inlet device (4), oxygen plasma and a free radical initiator are generated through discharge, and the free radical initiator only contains C, O, F elements; a part of reaction liquid carried by the reaction tail gas enters a gas-liquid separation device (9) at the top of the reactor, wherein after the gas-liquid separation device (9) separates, part of pure oxygen is supplemented into oxygen-enriched gas after the reaction tail gas passes through a gas-phase pressurizing device (6), and the oxygen-enriched gas enters the reactor (8) again through a static sealing air inlet device (4); the reaction liquid separated by the gas-liquid separation equipment (9) returns to the reactor after passing through the liquid phase pressurizing equipment (7); the pure oxygen is oxygen with the oxygen content of more than 98 percent; the oxygen-enriched gas is oxygen with the oxygen content of more than 70%; condensing hexafluoropropylene into a reactor through gas-liquid separation equipment, starting stirring, introducing pure oxygen or oxygen-enriched gas, introducing high-voltage electricity between a first plate electrode and a second plate electrode when the gas-liquid phase is saturated, at the moment, starting to continuously generate oxygen plasma and free radical initiator between the electrodes, initiating the oxidative polymerization reaction of the oxygen and hexafluoropropylene, and separating to obtain a product after the reaction is finished.
2. The perfluoropolyether peroxide production equipment according to claim 1, wherein the reaction temperature is-70 to-40 ℃ and the reaction pressure is 400 to 800kpa.
3. The perfluoropolyether peroxide production apparatus of claim 1 wherein the aeration rate of the pure oxygen and the oxygen-enriched gas is from 1000 to 4500NL/h.
CN202210775562.8A 2022-07-01 2022-07-01 Equipment and process for producing perfluoro polyether peroxide Active CN114984885B (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114621427A (en) * 2020-12-11 2022-06-14 成都晨光博达新材料股份有限公司 Production process for preparing perfluoropolyether with peroxide by photo-oxidative polymerization

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114621427A (en) * 2020-12-11 2022-06-14 成都晨光博达新材料股份有限公司 Production process for preparing perfluoropolyether with peroxide by photo-oxidative polymerization

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
李凯等.《低温等离子体表面修饰技术在催化剂材料制备中的应用》.冶金工业出版社,2017,第158-160页. *

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