CN114682190A - Method and equipment for selective fluorination reaction by taking fluorine gas as fluoro reagent - Google Patents
Method and equipment for selective fluorination reaction by taking fluorine gas as fluoro reagent Download PDFInfo
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- CN114682190A CN114682190A CN202011578541.4A CN202011578541A CN114682190A CN 114682190 A CN114682190 A CN 114682190A CN 202011578541 A CN202011578541 A CN 202011578541A CN 114682190 A CN114682190 A CN 114682190A
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- 238000003682 fluorination reaction Methods 0.000 title claims abstract description 91
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 46
- 239000011737 fluorine Substances 0.000 title claims abstract description 46
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 9
- 125000001153 fluoro group Chemical group F* 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 238000006467 substitution reaction Methods 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000000524 functional group Chemical group 0.000 claims abstract description 13
- 238000010521 absorption reaction Methods 0.000 claims abstract description 9
- 239000007789 gas Substances 0.000 claims description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 239000012025 fluorinating agent Substances 0.000 claims description 6
- 239000010453 quartz Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 229920006026 co-polymeric resin Polymers 0.000 claims description 2
- 229920001973 fluoroelastomer Polymers 0.000 claims description 2
- -1 perfluoro compound Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 239000011347 resin Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YPDSOAPSWYHANB-UHFFFAOYSA-N [N].[F] Chemical compound [N].[F] YPDSOAPSWYHANB-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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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
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/128—Infrared light
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- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method and equipment for carrying out selective fluorination reaction by taking fluorine gas as a fluorination reagent, wherein the method comprises the following steps: carrying out fluorination substitution reaction on a fluorination reagent and a fluorinated compound, and applying electromagnetic waves with specific frequency in the reaction process to obtain a product; wherein the frequency of the electromagnetic wave is selected according to the absorption frequency of the functional group at the desired fluorinated position to infrared rays. The method provided by the invention can improve the selectivity of substitution reaction during fluorination on the premise of reducing the concentration of fluorine gas and the reaction temperature and pressure, so that the fluorination efficiency is improved, the carbon chain skeleton of the fluoride is not damaged, and the fluorination is more efficient and stable.
Description
Technical Field
The invention relates to the technical field of fluorination reaction, in particular to a method and equipment for carrying out selective fluorination reaction by taking fluorine gas as a fluorination reagent.
Background
With the continuous research on the utilization of fluorine gas at home and abroad, fluorine gas fluorination is beginning to be applied to various fields such as surface fluorination of rubber, fluorination of fluorinated fine chemicals, fluorination end-capping technology of perfluorinated compounds, and the like.
Because the energy released by C-F bond generated by reaction is far higher than the breaking energy of C-C bond or C-H bond, and the homolytic energy of fluorine gas is very low, the direct reaction of fluorine gas and organic matter is often carried out in an explosive manner, and an uncontrollable chain reaction is easily initiated even under low temperature and no light, therefore, the direct fluorination reaction needs to control high reaction heat to obtain perfluorination or selective fluorination product, and the conventional means is to control the fluorination degree by heating, controlling the concentration of fluorine gas, increasing the reaction system, and the like.
For perfluorinated products, the general procedure is to select a suitable solvent for the reaction in the liquid phase, and to dilute the fluorine gas with an inert gas; or a slow stepwise increase of the fluorine gas concentration. However, in the selective fluorination reaction, it is necessary to perform a specific fluorination substitution of some functional groups, and if the activation energy for fluorination is ensured, the backbone carbon chain of the fluorinated compound is broken, but the activation energy is lowered and the fluorination substitution cannot be performed, so that there are disadvantages that the fluorination efficiency is low and the fluorination is incomplete when the selective fluorination reaction is performed.
Disclosure of Invention
The invention aims to provide a method and equipment for carrying out selective fluorination reaction by using fluorine gas as a fluorinating reagent. The method provided by the invention can improve the selectivity of the substitution reaction during the fluorination on the premise of reducing the concentration of fluorine gas and the reaction temperature and pressure, thereby improving the fluorination efficiency without damaging the carbon chain skeleton of the fluoride and ensuring more efficient and stable fluorination.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a process for selective fluorination using fluorine gas as a fluorinating agent, said process comprising:
carrying out fluorination substitution reaction on a fluorination reagent and a fluorinated compound, and applying electromagnetic waves with specific frequency in the reaction process to obtain a product;
wherein the frequency of the electromagnetic wave is selected according to the absorption frequency of the functional group at the desired fluorinated position to infrared rays.
According to the invention, aiming at the characteristic that different functional groups in the compound have different absorption frequencies for infrared spectrum, in the process of carrying out selective fluorination reaction, electromagnetic waves with different frequencies are applied according to the absorption frequency of the functional group at the required fluorination position for infrared, so that the reaction efficiency of the selective fluorination reaction can be improved, and the mode can also ensure that the skeleton carbon chain of the fluorinated compound cannot be damaged.
The selective fluorination reaction of the present invention refers to a fluorination substitution reaction for certain specific functional groups.
In a preferred embodiment of the present invention, the frequency of the electromagnetic wave is an absorption frequency of the functional group at the desired fluorinated position to infrared.
The method for improving the efficiency can improve the fluorination selectivity and simultaneously avoid substitution reaction on other functional groups and carbon chain breakage; the method of the invention can not only control the fluorinated substituted functional group, but also greatly reduce the occurrence of fluorination side reaction.
In a preferred embodiment of the present invention, the fluorinated substitution reaction is a fluorinated capping reaction.
In a preferred embodiment of the present invention, the fluorinated substitution reaction is a fluorinated capping reaction of a perfluoro compound.
The method of the present invention is preferably applicable to fluorination of most terminal groups such as hydroxyl, carbonyl, chloride, cyano, etc., since the group undergoing selective fluorination is a terminal group.
The fluorinated compound of the present invention is selected from any one or a combination of at least two of a copolymer resin of tetrafluoroethylene and hexafluoropropylene, another fluororesin or a fluororubber.
The frequency range of the electromagnetic wave is selected from 1014～1012Hz, e.g. 1013Hz。
The method can also reduce the fluorination reaction temperature, and the fluorination substitution reaction temperature is 60-90 ℃, such as 70 ℃, 80 ℃ and the like.
The reaction pressure of the fluorination substitution reaction of the present invention is 0.5 to 0.6MPa, for example, 0.55 MPa.
In a second aspect, the present invention provides an apparatus for carrying out selective fluorination reactions, which apparatus can carry out the process of the first aspect;
wherein the equipment comprises an electromagnetic wave generating device and a fluorination reaction device.
The fluorination reaction device, namely the fluorination chamber, is preferably made of high-density transparent quartz, can resist corrosion of high-concentration fluorine gas, ensures the penetrability of electromagnetic waves, does not influence the action of the electromagnetic waves, can select different reaction chambers aiming at different forms of fluorinated compounds, and has no difference in material and slight difference in structure; the detachable cylinder of both ends open-type can be selected for use to the solid chamber of fluorinating, and the liquid phase chamber of fluorinating can be inclosed container formula chamber, and the accessible pipeline directly lets in the liquid phase with fluorine nitrogen gas mixture.
The electromagnetic wave generating device of the invention can select an infrared generating device which can emit at the frequency of 1014～1010Hz electromagnetic wave with adjustable frequency and power of more than or equal to 600W.
The electromagnetic wave generating device can adjust infrared light with different frequencies according to the characteristic that different functional groups in the compound have different absorption frequencies of infrared light spectrum, and the compound is heated and activated by aiming at the functional groups of different substances.
In the present invention, the material of the fluorination reaction apparatus is preferably selected from transparent quartz.
The equipment of the invention also comprises a metering device and/or a tail gas treatment device.
Since it is generally necessary to add a part of inert gas to prevent the reaction from being too violent in the fluorination reaction using fluorine gas at present, the metering device is preferably a fluorine/nitrogen metering device in the present invention. Through the metering device who sets up, measurement that can be more accurate lets in the volume.
In order to avoid the pollution of the unreacted fluorine gas to the environment, the tail gas treatment device is respectively provided with sulfur and alkaline solution. In the tail gas treatment process, the first step is 130 ℃ sulfur, the second step is a KOH aqueous solution with the concentration of about 12%, the unreacted fluorine gas can be completely absorbed by two steps of absorption, and the content of the fluorine gas in the tail gas reaches the emission standard of less than 1 ppm.
As a specific embodiment of the invention, the equipment comprises a fluorine/nitrogen metering device, an electromagnetic wave generating device, a fluorination reaction device made of transparent quartz and a tail gas treatment device;
during the selective fluorination reaction, fluorine gas is introduced into the fluorination reaction device through the metering device to perform the selective fluorination reaction with the fluorinated compound, in the reaction process, the electromagnetic wave generating device applies electromagnetic waves with specific frequency to improve the efficiency of the selective fluorination reaction, and then the unreacted fluorine gas enters the tail gas treatment device to be treated.
Compared with the prior art, the invention has the following beneficial effects:
the method provided by the invention can improve the reaction efficiency of the selective fluorination reaction, and the method can also ensure that the skeleton carbon chain of the fluorinated compound cannot be damaged; meanwhile, the method provided by the invention can reduce the occurrence of side fluorination reaction, and can reduce the reaction temperature, pressure and the like of the fluorination reaction.
Drawings
FIG. 1 is a schematic structural view of a reaction apparatus provided in example 1 of the present invention;
wherein, 1-fluorine/nitrogen metering device; 2-an infrared generating device; 3-fluorinating a chamber; 4-tail gas treatment device.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
The present example provides an apparatus for performing selective fluorination and a method for performing selective fluorination using fluorine gas as the fluorinating agent.
As shown in fig. 1, the apparatus includes a fluorine/nitrogen metering device 1, an infrared generation device 2, a fluorination chamber 3, and an exhaust gas treatment device 4.
The fluorination chamber 3 is made of high-density transparent quartz, and the tail gas treatment device comprises sulfur with the temperature of 130 ℃ and KOH solution with the concentration of 12 percent.
The method for carrying out selective fluorination reaction by taking fluorine gas as a fluorination reagent comprises the following steps:
fluorine gas and nitrogen gas are introduced into a fluorination chamber 3 through a fluorine/nitrogen metering device 1, in the reaction process, electromagnetic waves with specific frequency are applied to the reaction through an infrared generating device 2, the reaction result can obtain a product, and the incompletely reacted tail gas enters a tail gas treatment device for treatment.
Example 2
This example provides a method for selective fluorination using fluorine as the fluorinating agent.
20g F46Resin powder (polymerized resin of tetrafluoroethylene and hexafluoropropylene) was placed in a fluorination chamber, fluorine gas and nitrogen gas were mixed at a ratio of 1:4, and then introduced into the fluorination chamber at a flow rate of 500L/h through a fluorine/nitrogen metering device, and the frequency of an infrared generator was adjusted to 4X 1013Hz, controlling the reaction temperature at 80 ℃ and the pressure at 0.6MPa for fluorination reaction, ending the reaction when the molar ratio of the introduced fluorine gas to the end group is 16:1, discharging the product after the reaction is ended, and treating the incompletely reacted tail gas in a tail gas treatment device,19g of product were obtained.
Comparative example 1
This comparative example provides a process for selective fluorination using fluorine as the fluorinating agent. The difference from example 2 is that in this comparative example, 4X 10 is not applied13Electromagnetic waves of Hz.
Comparative example 2
The comparative example provides a process for selective fluorination using fluorine as the fluorinating agent as follows:
20g F46Resin powder (polymerized resin of tetrafluoroethylene and hexafluoropropylene) is placed in a fluorination chamber, fluorine gas and nitrogen gas are mixed at a flow rate of 2:3, then fluorine gas and nitrogen gas are introduced into the fluorination chamber through a fluorine/nitrogen metering device at a flow rate of 500L/h, the fluorination reaction is carried out under the conditions that the reaction temperature is controlled at 200 ℃ and the pressure is 1.5MPa, the reaction is finished when the molar ratio of the introduced fluorine gas to the terminal groups is 20:1, a product is discharged after the reaction is finished, and the tail gas which is not completely reacted enters a tail gas treatment device for treatment to obtain 17.2g of the product.
The statistical results relating to example 2 and comparative examples 1-2 are shown in table 1:
TABLE 1
The product obtained in example 2 is obviously superior to the product obtained in comparative examples 1-2 in appearance, and has good film-forming transparency, less impurities and no foaming, so that the fluorination efficiency of the product obtained in example 2 is high, and the product yield is high.
According to the embodiment and the performance test, the method provided by the invention can improve the selectivity of the substitution reaction during the fluorination on the premise of reducing the concentration of fluorine gas and the reaction temperature and pressure, so that the fluorination efficiency is improved, the carbon chain skeleton of the fluoride is not damaged, the fluorination is more efficient and stable, and the product yield is higher.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A method for selective fluorination using fluorine gas as a fluorinating agent, comprising:
carrying out fluorination substitution reaction on a fluorination reagent and a fluorinated compound, and applying electromagnetic waves with specific frequency in the reaction process to obtain a product;
wherein the frequency of the electromagnetic wave is selected according to the absorption frequency of the functional group at the desired fluorinated position to infrared rays.
2. The method of claim 1, wherein the electromagnetic wave has a frequency that is the frequency of absorption of infrared by the functional group at the desired fluorinated site.
3. The method of claim 1 or 2, wherein the fluorinated substitution reaction is a fluorinated capping reaction;
preferably, the fluorinated substitution reaction is a fluorinated capping reaction of a perfluoro compound.
4. The method according to any one of claims 1 to 3, wherein the fluorinated compound is selected from any one of or a combination of at least two of a copolymer resin of tetrafluoroethylene and hexafluoropropylene, another fluororesin, or a fluororubber.
5. The method according to any one of claims 1 to 4, wherein the frequency range of the electromagnetic wave is selected from 1012～1014Hz。
6. The method according to any one of claims 1 to 5, wherein the reaction temperature of the fluorinated substitution reaction is 60 to 90 ℃;
and/or the reaction pressure of the fluorination substitution reaction is 0.5-0.6 MPa.
7. An apparatus for carrying out selective fluorination reactions, wherein the apparatus is capable of carrying out the process of any one of claims 1 to 6;
wherein the equipment comprises an electromagnetic wave generating device and a fluorination reaction device.
8. The apparatus of claim 7, wherein the material of the fluorination reaction apparatus is selected from the group consisting of transparent quartz.
9. The plant according to claim 7 or 8, characterized in that it further comprises a metering device and/or a tail gas treatment device;
preferably, the metering device is a fluorine/nitrogen metering device;
preferably, the tail gas treatment device is provided with sulfur and an alkaline solution respectively.
10. The apparatus according to any one of claims 7 to 9, characterized in that the apparatus comprises a fluorine/nitrogen metering device, an electromagnetic wave generating device, a fluorination reaction device made of transparent quartz, and an off-gas treatment device;
the fluorine gas is introduced into the fluorination reaction device through the metering device to perform selective fluorination reaction with the fluorinated compound, in the reaction process, the electromagnetic wave generating device applies electromagnetic waves with specific frequency to improve the efficiency of the selective fluorination reaction, and then the unreacted fluorine gas enters the tail gas treatment device to be treated.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202011578541.4A CN114682190A (en) | 2020-12-28 | 2020-12-28 | Method and equipment for selective fluorination reaction by taking fluorine gas as fluoro reagent |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202011578541.4A CN114682190A (en) | 2020-12-28 | 2020-12-28 | Method and equipment for selective fluorination reaction by taking fluorine gas as fluoro reagent |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB774103A (en) * | 1952-09-15 | 1957-05-08 | Robert Neville Haszeldine | Halogenated organic compounds |
| US5274049A (en) * | 1991-07-19 | 1993-12-28 | William S. Shamban | Fluorination of articles molded from elastomers |
| CN105801377A (en) * | 2016-04-14 | 2016-07-27 | 山东飞源科技有限公司 | Process for preparing fluorophenol with photocatalysis method |
| CN106132971A (en) * | 2014-03-31 | 2016-11-16 | 3M创新有限公司 | Fluoro-alkyl organosilicon |
-
2020
- 2020-12-28 CN CN202011578541.4A patent/CN114682190A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB774103A (en) * | 1952-09-15 | 1957-05-08 | Robert Neville Haszeldine | Halogenated organic compounds |
| US5274049A (en) * | 1991-07-19 | 1993-12-28 | William S. Shamban | Fluorination of articles molded from elastomers |
| CN106132971A (en) * | 2014-03-31 | 2016-11-16 | 3M创新有限公司 | Fluoro-alkyl organosilicon |
| CN105801377A (en) * | 2016-04-14 | 2016-07-27 | 山东飞源科技有限公司 | Process for preparing fluorophenol with photocatalysis method |
Non-Patent Citations (2)
| Title |
|---|
| 于永忠;: "激光选择性激发化学反应", 火炸药学报 * |
| 姚介兴;史济良;: "红外光化学", 有机化学 * |
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