CN114516781B - Preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene - Google Patents
Preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene Download PDFInfo
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- CN114516781B CN114516781B CN202210263217.6A CN202210263217A CN114516781B CN 114516781 B CN114516781 B CN 114516781B CN 202210263217 A CN202210263217 A CN 202210263217A CN 114516781 B CN114516781 B CN 114516781B
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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
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
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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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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Abstract
The application relates to the technical field of fluorine chemical engineering, in particular to a preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene, which comprises the following steps: (1) Adding perfluorooctyl iodide and an initiator into a reaction kettle, introducing ethylene gas, maintaining a certain pressure, cooling after the reaction is finished, and purifying after obtaining perfluorooctyl ethyl iodide; (2) Mixing and stirring the purified perfluorooctyl ethyl iodide, inorganic base, methanol and a phase transfer catalyst, and then heating and refluxing to react to obtain perfluorooctyl ethylene. The preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene has the advantages of mild reaction conditions, simple operation process, short reaction time, easy separation of products, and capability of preparing products with high purity and high yield, thereby reducing the cost and being beneficial to realizing industrial production.
Description
Technical Field
The application relates to the technical field of fluorine chemical engineering, in particular to a preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene.
Background
The disclosure of this background section is only intended to increase the understanding of the general background of the application and is not necessarily to be construed as an admission or any form of suggestion that this information forms the prior art already known to those of ordinary skill in the art.
Perfluorooctyl ethylene is an important intermediate for preparing perfluorocarboxylic acid surfactants and perfluoroalkyl polymers, and is widely applied to industries such as metal, fire protection, rubber and the like because of the fact that F atom radius is small and polarizability is low, so that C-F bonds have higher bond energy, and the compound with perfluoroalkyl structure can obviously improve hydrophobic oleophobicity, antifouling property, leveling property and the like of the surface of an object. Perfluoro compounds possess excellent properties under extreme conditions not possessed by hydrocarbons in which the perfluoroalkyl group has a C number of carbon atoms 8 -C 12 The compounds of (2) most readily exhibit the above properties.
The inventor discovers that in the existing synthesis scheme, perfluorooctyl ethyl iodide reacts with an inorganic alkali solution or an organic alkali solution, and then the perfluorooctyl ethylene is obtained by layering and washing after stirring and refluxing, the reaction time is long, and the yield and purity of the product are low.
Disclosure of Invention
Aiming at the problems in the prior art, the application aims to provide a preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene, which has the advantages of mild reaction conditions, simple operation process, short reaction time, easy separation of products, and capability of preparing products with high purity and high yield, thereby reducing cost and being beneficial to realizing industrial production.
In order to achieve the above object, the technical scheme of the present application is as follows:
in an embodiment of the present application, there is provided a method for producing perfluorooctyl ethyl iodide and perfluorooctyl ethylene, comprising the steps of:
(1) Adding perfluorooctyl iodide and an initiator into a reaction kettle, introducing ethylene gas, maintaining a certain pressure, cooling after the reaction is finished, and purifying after obtaining perfluorooctyl ethyl iodide;
(2) Mixing and stirring the purified perfluorooctyl ethyl iodide, inorganic base, methanol and a phase transfer catalyst, and then heating and refluxing to react to obtain perfluorooctyl ethylene.
According to the method for synthesizing perfluorooctyl ethyl iodide and perfluorooctyl ethylene, perfluorooctyl iodide, an initiator and ethylene gas are added into a reaction kettle to react to generate perfluorooctyl ethyl iodide, and then dichloromethane is used for purifying the product; mixing perfluorooctyl ethyl iodide, inorganic base, methanol and a phase transfer catalyst, heating and stirring, cooling the reaction liquid to room temperature after the reaction is finished, and standing for layering; separating the lower crude product, washing for multiple times to obtain the product perfluorooctyl ethylene, and purifying with simple process. The method has the advantages of mild reaction conditions, short reaction time, low requirements on the production process, easy separation of products, and capability of preparing products with high purity and high yield, thereby reducing the production cost and being beneficial to realizing industrial production.
The specific embodiment of the application has the following beneficial effects:
the preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene has the advantages of mild reaction conditions, simple operation process, short reaction time, easy separation of products, and capability of preparing products with high purity and high yield, thereby reducing the cost and being beneficial to realizing industrial production;
the addition of the phase transfer catalyst can increase the contact area of two phases, so that the purity and the yield of the product are improved;
the supernatant liquid can be subjected to reduced pressure distillation or rotary distillation during liquid separation to obtain corresponding solvent and phase catalyst, and the corresponding solvent and phase catalyst can be recycled;
the temperature and the reactant dosage in different ranges are tested to determine the most favorable conditions, the reaction speed is high, the reaction degree is thorough, the cost can be reduced, and the method is favorable for industrial production.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the application.
FIG. 1 is a graph of perfluorooctyl ethyl iodide purity of the product of example 1 as measured by gas chromatography-mass spectrometry;
FIG. 2 is a graph of perfluorooctyl ethylene purity as measured by gas chromatography-mass spectrometry for the product of example 1;
FIG. 3 is a graph of perfluorooctyl ethylene purity as measured by gas chromatography-mass spectrometry for the product of example 2;
FIG. 4 is a graph of perfluorooctyl ethylene purity as measured by gas chromatography-mass spectrometry for the product of example 3;
FIG. 5 is an infrared spectrum of perfluorooctyl ethyl iodide synthesized in example 1;
FIG. 6 is a spectrum of perfluorooctyl ethyl hydrogen iodide synthesized in example 1;
FIG. 7 is a spectrum of perfluorooctyl ethyl fluoride synthesized in example 1;
FIG. 8 is a spectrum of perfluorooctyl ethyl hydrogen synthesized in example 1;
FIG. 9 is a graph of perfluorooctyl ethyl iodide purity of the product of comparative example 1 as measured by gas chromatography-mass spectrometry;
FIG. 10 is a graph of perfluorooctyl ethylene purity as measured by gas chromatography-mass spectrometry for the product of comparative example 2;
FIG. 11 is a schematic illustration of the reaction process of examples 1-3 of the present application.
Detailed Description
It should be noted that the following detailed description is illustrative and is intended to provide further explanation of the application. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the present application. As used herein, the singular is also intended to include the plural unless the context clearly indicates otherwise, and furthermore, it is to be understood that the terms "comprises" and/or "comprising" when used in this specification are taken to specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof.
In one embodiment of the application, a method for preparing perfluorooctyl ethyl iodide and perfluorooctyl ethylene is provided, comprising the following steps:
(1) Adding perfluorooctyl iodide and an initiator into a reaction kettle, introducing ethylene gas, maintaining a certain pressure, cooling after the reaction is finished, and purifying after obtaining perfluorooctyl ethyl iodide;
(2) Mixing and stirring the purified perfluorooctyl ethyl iodide, inorganic base, methanol and a phase transfer catalyst, and then heating and refluxing to react to obtain perfluorooctyl ethylene.
The reaction process is shown in figure 11.
In one or more embodiments, in step (1), the initiator is di-tert-butyl peroxide;
in one or more embodiments, in step (1), the reaction pressure is maintained at 0.5 to 1.0MPa, preferably 0.5MPa;
in one or more embodiments, in step (1), the reaction time is from 1.5 to 3.0 hours, preferably 2.0 hours;
in one or more embodiments, in step (1), the reaction temperature is from 90 to 130 ℃, preferably 115 ℃.
In one or more embodiments, in step (1), the temperature is cooled to 30-70 ℃, preferably 50 ℃;
in one or more embodiments, the reaction vessel in step (1) is provided with a mechanical agitation, condenser and heating system;
in one or more embodiments, after cooling at the temperature in the step (1), adding a purifying solvent into the perfluorooctyl ethyl iodide, and performing reduced pressure distillation or rotary evaporation after filtering to obtain perfluorooctyl ethyl iodide with higher purity;
preferably, the purification solvent is selected from dichloromethane, petroleum ether, ethyl acetate or acetone, preferably dichloromethane.
In one or more embodiments, after the reaction is finished after the heating reflux in the step (2), the reaction solution is cooled to room temperature and is kept stand for layering; separating the crude product at the lower layer, washing for multiple times to obtain the product perfluorooctyl ethylene, and removing other impurities by vacuum distillation or rotary distillation to obtain the perfluorooctyl ethylene with higher purity.
In one or more embodiments, in step (2), the inorganic base is selected from potassium hydroxide, sodium methoxide or sodium ethoxide, preferably potassium hydroxide.
In one or more embodiments, in step (2), the phase transfer catalyst is selected from tetrabutylammonium bromide, tetrabutylammonium chloride, polyethylene glycol 2000 or polyethylene glycol 4000, preferably tetrabutylammonium bromide.
In one or more embodiments, in step (2), the reaction time of the heat reflux is 1.0 to 5.0 hours, preferably 1.5 hours.
In one or more embodiments, in step (2), the reaction temperature is from 30 to 100 ℃, preferably 40 ℃.
The application is further illustrated and described below in connection with specific examples.
Example 1
A preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene comprises the following steps:
(1) 20g (0.0364 mol) of perfluorooctyl iodide with the purity of 99.5 percent and 0.05g of initiator di-tert-butyl peroxide are added into a 200ml reaction kettle with a mechanical stirring system, a condenser and a heating system, ethylene gas is introduced, the pressure is increased to 0.5MPa after air is exhausted, the pressure is maintained to be 0.5-0.8MPa in the reaction process, the rotating speed is 600r/min, the reaction is carried out for 2 hours at 115 ℃, the temperature is cooled to 50 ℃, the product perfluorooctyl ethyl iodide crude product is collected, the product is cooled and added into dichloromethane to dissolve the product, insoluble impurities are filtered and removed, the dichloromethane is removed by rotary evaporation to obtain 20.3g of the product, the purity is 99.84 percent and the yield is 97 percent after detection by a gas chromatograph.
(2) 1.0g (0.0178 mol) of potassium hydroxide, 10ml (0.246 mol) of methanol, 0.10g of tetrabutylammonium bromide and 5g (0.0087 mol) of perfluorooctyl ethyl iodide are added into a single-neck flask, then are uniformly mixed and stirred, the rotating speed is 200r/min, the mixture reacts for 2.0h at 40 ℃, the mixture is cooled and stood, the product at the lower layer of the separated liquid is obtained into perfluorooctyl ethylene crude product, deionized water is used for cleaning 3 to 4 times, 3.48g of perfluorooctyl ethylene is obtained after the separation, the purity is 98.42% after the detection by a gas chromatograph-mass spectrometer, and the yield is 88%.
Example 2
A preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene comprises the following steps:
(1) The same procedure was followed for perfluorooctyl ethylene iodine synthesis as in example one.
(2) 1.5g (0.0267 mol) potassium hydroxide, 10ml (0.246 mol) methanol, 0.05g tetrabutylammonium bromide and 5g (0.0087 mol) perfluorooctyl ethyl iodide are added into a single-neck flask, then are uniformly mixed and stirred, the rotating speed is 200r/min, the mixture reacts for 2 hours at 50 ℃, the mixture is cooled and kept stand, the product at the lower layer of the separated liquid is obtained into perfluorooctyl ethylene crude product, deionized water is used for cleaning 3-4 times, 3.38g perfluorooctyl ethylene is obtained after liquid separation and rotary evaporation, the purity is 96.68 percent after detection by a gas chromatograph, and the yield is 84 percent.
Example 3
A preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene comprises the following steps:
(1) The same procedure was followed for perfluorooctyl ethylene iodine synthesis as in example one.
(2) 1.5g (0.0267 mol) potassium hydroxide, 10ml (0.246 mol) methanol, 0.10g tetrabutylammonium bromide and 5g (0.0087 mol) perfluorooctyl ethyl iodide are added into a single-neck flask, then are uniformly mixed and stirred, the rotating speed is 200r/min, the mixture reacts for 1.5h at 60 ℃, the mixture is cooled and kept stand, the product at the lower layer of the separated liquid is obtained into perfluorooctyl ethylene crude product, deionized water is used for cleaning 3-4 times, 3.29g perfluorooctyl ethylene is obtained after the separated liquid is subjected to rotary evaporation, and the purity is 95.73% and the yield is 81% after the detection by a gas chromatograph.
Comparative example 1
(1) 20g (0.0364 mol) of perfluorooctyl iodide with the purity of 99.5 percent is added into a 200ml reaction kettle with a mechanical stirring system, a condenser and a heating system, ethylene gas is introduced, air is exhausted and pressurized to 0.5MPa, the pressure is maintained at 0.5-0.8MPa in the reaction process, the rotating speed is 600r/min, the reaction is carried out for 2 hours at 115 ℃, the reaction is cooled to 50 ℃, the product perfluorooctyl ethyl iodide crude product is collected, the dichloromethane dissolved product is added after the product is cooled, insoluble impurities are removed by filtration, 16.43g of dichloromethane is removed by rotary evaporation, and the purity is 82.39 percent and the yield is 65 percent after the detection by a gas chromatograph.
Comparative example 2
(1) The same procedure was followed for perfluorooctyl ethylene iodine synthesis as in example one.
(2) 1.0g (0.0267 mol) of potassium hydroxide, 10ml (0.246 mol) of methanol and 5g (0.0087 mol) of perfluorooctyl ethyl iodide are added into a single-neck flask, then the mixture is uniformly mixed and stirred, the rotating speed is 200r/min, the mixture is reacted for 2.0h at 40 ℃, the mixture is cooled and kept stand, the product at the lower layer of the mixture is separated to obtain a perfluorooctyl ethylene crude product, the perfluorooctyl ethylene crude product is washed 3 to 4 times by water, 3.14g of perfluorooctyl ethylene is obtained after separation by rotary evaporation, the purity is 76.7% and the yield is 62% after detection by a gas chromatograph.
The above description is only of the preferred embodiments of the present application and is not intended to limit the present application, but various modifications and variations can be made to the present application by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the protection scope of the present application.
Claims (7)
1. The preparation method of perfluorooctyl ethyl iodide and perfluorooctyl ethylene is characterized by comprising the following steps of:
(1) Adding perfluorooctyl iodide and an initiator into a reaction kettle, introducing ethylene gas, maintaining a certain pressure, cooling after the reaction is finished, and purifying after obtaining perfluorooctyl ethyl iodide;
(2) Mixing and stirring the purified perfluorooctyl ethyl iodide, inorganic base, methanol and a phase transfer catalyst, and then heating and refluxing to react to obtain perfluorooctyl ethylene;
in the step (1), the initiator is di-tert-butyl peroxide; the reaction pressure is maintained between 0.5 and 1.0 MPa; the reaction temperature is 90-130 ℃, and the reaction time is 1.5-3.0 h; cooling to 30-70deg.C;
after the reaction is finished after the heating reflux in the step (2), cooling the reaction liquid to room temperature, standing and layering; separating the lower crude product, washing for 3-4 times to obtain perfluorooctyl ethylene, and removing other impurities by vacuum distillation or rotary distillation to obtain perfluorooctyl ethylene;
in the step (2), the reaction temperature of heating reflux is 30-100 ℃; the reaction time is 1.0-5.0 h;
in the step (2), the inorganic base is potassium hydroxide; the phase transfer catalyst is tetrabutylammonium bromide.
2. The process for producing perfluorooctyl ethyl iodide and perfluorooctyl ethylene according to claim 1, wherein the reaction pressure is maintained at 0.5MPa in the step (1).
3. The method for producing perfluorooctyl ethyl iodide and perfluorooctyl ethylene according to claim 1, wherein in step (1), the reaction temperature is 115 ℃; the reaction time was 2.0. 2.0 h.
4. The process for the preparation of perfluorooctyl ethyl iodide and perfluorooctyl ethylene according to claim 1 wherein in step (1) the temperature is cooled to 50 ℃.
5. The method for producing perfluorooctyl ethyl iodide and perfluorooctyl ethylene according to claim 1, wherein the perfluorooctyl ethyl iodide is obtained by adding a purification solvent to perfluorooctyl ethyl iodide after cooling at the temperature in step (1), filtering, and distilling under reduced pressure or rotary-evaporating;
the purification solvent is selected from dichloromethane, petroleum ether, ethyl acetate or acetone.
6. The method for producing perfluorooctyl ethyl iodide and perfluorooctyl ethylene according to claim 5, wherein the purifying solvent is methylene chloride.
7. The method for producing perfluorooctyl ethyl iodide and perfluorooctyl ethylene according to claim 1, wherein the reaction temperature of the heated reflux is 40 ℃; the reaction time was 1.5. 1.5h.
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