KR102476557B1 - Method for Preparing Perfluorodialkylether and Apparatus for Preparing Perfluorodialkylether - Google Patents

Abstract

The present invention comprises the steps of (A) preparing a perfluorodialkyl ether from a compound represented by Formula 1 continuously supplied from the outside in the presence of a metal fluoride; and (B) separating the perfluorodialkyl ether and continuously discharging the perfluorodialkyl ether to the outside. a reaction unit for producing rhodialkyl ether; a reactant supply unit for supplying the compound represented by Chemical Formula 1 to the reaction unit; a discharge unit for discharging the perfluorodialkyl ether from an upper portion of the reaction unit; A first pump for continuously supplying the compound represented by Formula 1 to the reaction unit through the reactant supply unit; and a second pump for continuously discharging the perfluorodialkyl ether to the outside of the reaction unit through the discharge unit.

Description

Method for preparing perfluorodialkyl ether and apparatus for preparing perfluorodialkyl ether {Method for Preparing Perfluorodialkylether and Apparatus for Preparing Perfluorodialkylether}

The present invention relates to a method for producing perfluorodialkyl ether and an apparatus for producing perfluorodialkyl ether.

SF ₆ gas, called sulfur hexafluoride, is a colorless, odorless, flame retardant gas that is not only less toxic, but also has a property of combining with free electrons that form heavy ions with low mobility. It has a high dielectric strength (about 3 times that of air), high thermal barrier ability (about 10 times that of air) and high heat transfer characteristics (about 2 times that of air), making it very difficult to unfold, so it is suitable for use in the electrical, electronic industry and light metal industry. It is widely used as insulating gas, etching gas, and molten metal protection gas in the semiconductor industry.

This SF ₆ gas is non-toxic, has never been reported for its potential for acute or chronic ecotoxicity, and has very low solubility in water, posing no risk to surface water, groundwater or soil. In particular, because bioaccumulation does not occur, SF ₆ gas is neither harmful to the ecosystem nor considered a carcinogen or mutagen.

However, SF ₆ gas is harmless to the human body, but is known as a gas that promotes global warming along with CO ₂ , HFCs, and PFCs _. This 3,200 year level is so long that recycling of SF ₆ gas without emission into the atmosphere has become very environmentally important.

In addition, recently, as it has been found that chemically stable SF ₆ gas is decomposed into various fluorides and/or sulfides under specific circumstances, interest in the effects of decomposition products of SF ₆ gas on the environment and human body has also increased.

Various researches and developments are being conducted to replace the SF ₆ gas as described above, and among various methods, research to introduce a material capable of replacing the SF ₆ gas is continuously being conducted.

In order to solve the above problems, the present invention is to provide perfluorodialkyl ether as an alternative gas for SF ₆ gas. In particular, perfluorodialkyl ether can be continuously produced by continuously supplying fluorine-containing acyl fluoride in the presence of a metal fluoride catalyst, and in addition, perfluorodialkyl ether with high conversion rate and high purity is obtained.

According to one embodiment of the present invention, (A) preparing a perfluorodialkyl ether from a compound represented by Formula 1 continuously supplied from the outside in the presence of a metal fluoride; and (B) separating the perfluorodialkyl ether and continuously discharging the perfluorodialkyl ether to the outside.

[Formula 1]

In Formula 1, n is an integer from 1 to 3.

In addition, according to another embodiment of the present invention, a reaction unit for preparing a perfluorodialkyl ether from the compound represented by the formula (1) in the presence of metal fluoride; a reactant supply unit for supplying the compound represented by Chemical Formula 1 to the reaction unit; a discharge unit for discharging the perfluorodialkyl ether from an upper portion of the reaction unit; a first pump for continuously supplying the compound represented by Chemical Formula 1 to the reaction unit through the reactant supply unit; and a second pump for continuously discharging the perfluorodialkyl ether to the outside of the reaction unit through the discharge unit.

In the present invention, in the production of perfluorodialkyl ether, as the fluorine-containing acyl fluoride represented by Formula 1 is continuously supplied in the presence of metal fluoride, perfluorodialkyl ether is obtained with high conversion rate and high purity in one single reactor. There is an effect that can be produced continuously.

In addition, the manufactured perfluorodialkyl ether has no problem of global warming as an alternative gas to SF ₆ gas, and can be provided as an insulating gas, etching gas, or cleaning gas in various industrial fields, so its utilization is very high.

1 is a diagram schematically illustrating an apparatus for producing a perfluorodialkyl ether according to an embodiment of the present invention.
2 is a diagram schematically illustrating an apparatus for producing a perfluorodialkyl ether according to another embodiment of the present invention.
3 is a diagram schematically illustrating a reaction mechanism and a process of discharging products in a continuous reactor according to Example 1 of the present invention.
4 is a graph showing the gas chromatography results of perfluoromethylethyl ether prepared in Example 1 according to Experimental Example 4 of the present invention.
5 is a graph showing the results of ¹⁹ F-nuclear magnetic resonance analysis of perfluoromethylethyl ether prepared in Example 1 according to Experimental Example 4 of the present invention.

Hereinafter, the present invention will be described in detail.

1. Method for producing perfluorodialkyl ether

The present invention provides a method for preparing a perfluorodialkyl ether.

A method for preparing a perfluorodialkyl ether according to an embodiment of the present invention includes (A) preparing a perfluorodialkyl ether from a compound represented by Formula 1 continuously supplied from the outside in the presence of a metal fluoride; and (B) separating the perfluorodialkyl ether and continuously discharging it to the outside.

[Formula 1]

In Formula 1, n is an integer from 1 to 3.

Specifically, the compound represented by Chemical Formula 1 may include at least one selected from compounds represented by Chemical Formulas 1-1 to 1-4 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

The compound represented by Formula 1 may include the compound represented by Formula 1-1.

The metal fluoride is not particularly limited as long as it corresponds to a Lewis acid that can be used in the production of perfluorodialkyl ether, and for example, antimony fluoride (SbF ₅ ), aluminum trifluoride (AlF ₃ ), trifluoride It may include at least one selected from the group consisting of cobalt fluoride (CoF ₃ ) and combinations thereof.

In the step (A), the compound represented by Formula 1 may be continuously supplied from the outside at a flow rate of 0.5 parts by weight / minute to 5 parts by weight / minute based on 100 parts by weight of the metal fluoride, specifically, In the step (A), the compound represented by Formula 1 was added at a flow rate of 0.5 parts by weight / min to 4 parts by weight / min, 0.5 parts by weight / min to 3 parts by weight / min, based on 100 parts by weight of the metal fluoride, It may be continuously supplied from the outside at a flow rate of 0.7 parts by weight/minute to 2.5 parts by weight/minute. When the flow rate of the compound represented by Chemical Formula 1 with respect to 100 weight of the metal fluoride satisfies the above range, the conversion rate of the product, perfluorodialkyl ether, can be significantly increased.

In addition, the step (A) may be performed at -15 ° C to 10 ° C, specifically -12 ° C to 8 ° C, -10 ° C to 5 ° C, -8 ° C to 5 ° C, More specifically, it may be performed at -5 °C to 5 °C. When the temperature of the step (A) satisfies the above range, the reaction time may be shortened and the conversion rate of perfluorodialkyl ether may be increased. When the temperature of the step (A) is less than -15 ° C, the conversion rate may decrease as the reaction temperature decreases, and when the temperature exceeds 10 ° C, the conversion rate may decrease rapidly. may remain in a state of reaction.

The internal pressure of the steps (A) and (B) may be adjusted to 0.2 bar or more as a gauge pressure, and specifically, may be adjusted to 0.4 bar or more. When the internal pressure is less than 0.2 bar as a gauge pressure, the concentration of the unreacted compound represented by Chemical Formula 1 increases as the internal pressure decreases, and thus the conversion rate may decrease.

In the step (B), the alkyl of the perfluorodialkyl ether may include an alkyl group having 1 to 3 carbon atoms. The two alkyl groups of the perfluorodialkyl ether may be the same as or different from each other.

In the step (B), the perfluorodialkyl ether may be represented by Formula 2 below.

[Formula 2]

In Formula 2, n is an integer from 1 to 3.

Specifically, the perfluorodialkyl ether may include at least one selected from compounds represented by Chemical Formulas 2-1 to 2-4 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

Preferably, the perfluorodialkyl ether may include a compound represented by Chemical Formula 2-1.

In the method for producing perfluorodialkyl ether, perfluorodialkyl ether is prepared by continuously supplying the compound represented by Formula 1 from the outside in the presence of metal fluoride in step (A), and the resulting perfluorodialkyl ether It may be performed continuously, including the step of separating and continuously discharging to the outside.

When the compound represented by Formula 1 is continuously supplied, the metal fluoride may be a filtrate remaining after separating and discharging perfluorodialkyl ether in step (B).

The step (B) may be to separate the perfluorodialkyl ether by gas-liquid separation.

In the method for producing the perfluorodialkyl ether, the compound represented by Chemical Formula 1 and the metal fluoride may exist in a liquid state under reaction conditions. On the other hand, since the perfluorodialkyl ether can exist in a gaseous form under reaction conditions, when a reaction occurs in the reactor to produce perfluorodialkyl ether, the liquid phase as a reactant and the gaseous phase as a product are separated from each other, resulting in gas-liquid separation. By this, perfluorodialkyl ether can be separated.

In the step (A), carbon monoxide may be generated as a by-product in addition to perfluorodialkyl ether. Therefore, when the perfluorodialkyl ether is separated by the gas-liquid separation, carbon monoxide gas can also be gas-liquid separated from the liquid phase reactant together with the perfluorodialkyl ether to be separated.

When the steps (A) and (B) are performed continuously, the filtrate containing the remaining metal fluoride remaining in the reactor can be reused without separate treatment and separation, thereby obtaining the compound represented by Formula 1 Since perfluorodialkyl ether can be produced at a high conversion rate only by continuously supplying it from the outside, perfluorodialkyl ether can be economically produced without introducing an additional reaction device.

In addition, after the reaction is over, the residual metal fluoride remaining in the reactor may be separately separated and subjected to a process of removing components other than the metal fluoride, or the separated metal fluoride may be stored separately and then reused.

The method for preparing a perfluorodialkyl ether comprising steps (A) and (B) may be carried out as a continuous process, and as described above, step (A) in one continuous reactor in the presence of the metal fluoride And as the cycle of step (B) is performed continuously, perfluorodialkyl ether can be produced.

Separating the perfluorodialkyl ether and continuously discharging the separated perfluorodialkyl ether to the outside in the step (B) may further include separating the separated perfluorodialkyl ether from carbon monoxide.

Gas-liquid separation separates gaseous perfluorodialkyl ether and carbon monoxide from liquid reactants and discharges them simultaneously, and the perfluorodialkyl ether can be separated from carbon monoxide by cooling the discharged gas. In addition, a step of temporarily storing the perfluorodialkyl ether separated from the carbon monoxide may be included.

The method for preparing the perfluorodialkyl ether may further include distilling the perfluorodialkyl ether separated in step (B).

The distilling may include distilling the perfluorodialkyl ether separated from carbon monoxide.

The perfluorodialkyl ether obtained by distillation as described above is obtained as a high-purity perfluorodialkyl ether, and can be used according to the purpose of use after going through a step of storing in a separate storage unit.

2. Apparatus for producing perfluorodialkyl ether

The present invention provides an apparatus for producing perfluorodialkyl ether.

An apparatus for producing a perfluorodialkyl ether according to an embodiment of the present invention includes a reaction unit 110 for producing a perfluorodialkyl ether from a compound represented by Formula 1 in the presence of a metal fluoride; a reactant supply unit 120 for supplying the compound represented by Chemical Formula 1 to the reaction unit 110; a discharge unit 130 for discharging the perfluorodialkyl ether from an upper portion of the reaction unit 110; A first pump 140 for continuously supplying the compound represented by Chemical Formula 1 to the reaction unit 110 through the reactant supply unit 120; and a second pump 150 for continuously discharging the perfluorodialkyl ether to the outside of the reaction unit 110 through the discharge unit 130 .

[Formula 1]

In Formula 1, n is an integer from 1 to 3.

The reaction unit 110 may include a reactor in which the metal fluoride and the compound represented by Formula 1 react, and the reaction unit 110 may include a continuous reaction unit, so long as it is a continuous reaction unit. It is not limited and may include a conventionally used tubular reactor.

The reaction unit 110 may further include a stirring unit, and the stirring unit may further include a stirring motor, a stirring rod, a stirrer, and the like. The stirring unit may use a commonly used stirring device.

The apparatus for producing perfluorodialkyl ether may further include a temperature controller 200 for controlling the temperature of the reaction unit 110 . The temperature of the reactor 110 may be maintained at -15 °C to 10 °C through the temperature controller 200 . When the temperature of the reaction unit 110 is maintained within the above range, the reaction time may be shortened and the conversion rate of perfluorodialkyl ether may be increased.

The temperature controller 200 may include a constant temperature jacket. The constant temperature jacket is a member for maintaining a constant temperature of the reaction unit 110, and may further include a constant temperature water supply unit and/or a constant temperature water discharge unit, but is not limited thereto.

The reactant supply unit 120 is a member for injecting the compound represented by Chemical Formula 1 into the reaction unit 110 . When the compound represented by Chemical Formula 1 is introduced into the reaction unit 110 through the reactant supply unit 120, a first pump 140 may be further included to continuously supply the compound at a constant flow rate. The first pump 140 is organically connected to the reactant supply unit 120 to supply the compound represented by Chemical Formula 1 from the reactant supply unit 120 to the reaction unit 110 at a constant flow rate. Specifically, the first pump 140 is adjusted to continuously supply the compound represented by Formula 1 from the outside at a flow rate of 0.5 parts by weight / minute to 5 parts by weight / minute based on 100 parts by weight of the metal fluoride. Specifically, the compound represented by Formula 1 with respect to 100 parts by weight of the metal fluoride at a flow rate of 0.5 parts by weight / min to 4 parts by weight / min, a flow rate of 0.5 parts by weight / min to 3 parts by weight / min, It can be adjusted to supply continuously from the outside at a flow rate of 0.7 parts by weight/minute to 2.5 parts by weight/minute. When the flow rate of the compound represented by Chemical Formula 1 with respect to 100 weight of the metal fluoride satisfies the above range, the conversion rate of the product, perfluorodialkyl ether, can be significantly increased.

The apparatus for producing perfluorodialkyl ether may further include a metal fluoride supply unit 160 for injecting the metal fluoride into the reaction unit 110 .

The discharge part 130 is for discharging the perfluorodialkyl ether generated in the reaction part 110 to the outside, and the discharge part 130 is connected to the upper part of the reaction part 110 so that the reaction part A second pump 150 may be further included to continuously discharge perfluorodialkyl ether from the top of 110 to the outside.

When perfluorodialkyl ether is generated in the reaction unit 110, carbon monoxide is produced as a by-product in addition to perfluorodialkyl ether, and gaseous perfluorodialkyl ether and carbon monoxide gas together with reactants are generated in the reaction unit 110. exists. At this time, the carbon monoxide gas may also be continuously discharged to the outside of the reaction unit 110 through the discharge unit 130 through the second pump 150 .

By continuously discharging the perfluorodialkyl ether generated in the reaction unit 110 to the outside and continuously supplying the compound represented by Chemical Formula 1 to the reaction unit 110, the reaction unit 110 metal fluoride. Perfluorodialkyl ether can be continuously prepared from the compound represented by Formula 1 in the presence of

At this time, the perfluorodialkyl ether exists in a gaseous state under the reaction conditions, so that reactants and products can be separated by gas-liquid separation inside the reaction unit 110, and accordingly, the discharge unit 130 is specifically It may be connected to the reaction unit 110 by being located above the liquid level where the liquid compound of Chemical Formula 1 and metal fluoride contained in the reaction unit 110 exist.

In addition, the apparatus for producing perfluorodialkyl ether may further include a pressure control unit for measuring and/or adjusting the pressure of the reaction unit 110 . The pressure inside the reaction unit 110 may be adjusted to 0.2 bar or more as a gauge pressure through the pressure controller, and specifically, it may be adjusted to 0.4 bar or more. In particular, when the internal pressure of the reaction unit 110 is less than 0.2 bar as a gauge pressure, the concentration of the unreacted compound represented by Chemical Formula 1 increases as the internal pressure decreases, and thus the conversion rate may decrease.

In addition, after the reaction, the remaining metal fluoride remaining inside the reactor may be separated from the reaction unit 110 and subjected to a process of removing components other than metal fluoride, and the separated metal fluoride may be stored separately and then reused. .

The apparatus for producing perfluorodialkyl ether may further include a cooling unit 220 for separating the perfluorodialkyl ether separated through the discharge unit 130 from carbon monoxide. By gas-liquid separation in the reaction unit 110, gaseous perfluorodialkyl ether and carbon monoxide are separated from liquid reactants and simultaneously discharged through the discharge unit 130 and supplied to the cooling unit 220, the cooling unit ( 220), the perfluorodialkyl ether is cooled through the step of cooling the discharged gas, and carbon monoxide can be separated into a gas. The cooling unit 220 may be used without limitation as long as it is a member for cooling gas.

The apparatus for producing perfluorodialkyl ether may include a first storage unit 221 for temporarily storing the perfluorodialkyl ether separated from the cooling unit 220 .

The perfluorodialkyl ether manufacturing apparatus distills the perfluorodialkyl ether separated in the cooling unit 220 or the perfluorodialkyl ether stored in the first storage unit 221 to obtain high-purity perfluorodialkyl ether. A distillation unit 230 for obtaining ether may be further included. The distillation unit 230 may be used without limitation as long as it is a member for distilling and separating liquid into gas.

In addition, the apparatus for producing perfluorodialkyl ether may further include a second storage unit 240 for storing the high-purity perfluorodialkyl ether obtained through the distillation unit 230 . As described above, the perfluorodialkyl ether stored in the second storage unit 240 may be used according to the purpose of use.

Hereinafter, the present invention will be described in more detail through examples. However, these examples are only for helping the understanding of the present invention, and the scope of the present invention is not limited to these examples in any sense.

<Example 1>

1) 1,200 g (5.537 moles) of anhydrous antimony pentafluoride (SbF ₅ ) was added to a 0.7 L tubular reactor with a constant temperature jacket, and the internal temperature of the reactor was maintained at about 0 ° C using a heating circulator. Then, the multi-turbine-attached stirring bar was stirred at a speed of about 200 rpm using a mechanical stirrer.

2) 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride (CF ₃ OCF) was added to the reactor of step 1) (CF ₃ )C(=O)F) was introduced at a flow rate of about 25.0 g/min (0.108 moles/min) using a metering pump. Perfluoromethylethyl ether and carbon monoxide generated through the reaction were continuously discharged through the outlet while maintaining the reactor internal pressure (gauge pressure) of 0.4 bar.

3) Perfluoromethylethyl ether (CF ₃ OCF ₂ CF ₃ ) and carbon monoxide (CO) discharged in step 2) are removed by using a cooler maintained at -50 ° C to obtain perfluoromethylethyl ether from which carbon monoxide is separated. 1 Stored in storage.

4) The perfluoromethylethyl ether in the first reservoir of step 3) was sent to the distillation column through the feed pump and subjected to a high-purity distillation process, and the obtained high-purity perfluoromethylethyl ether was stored in the second reservoir.

<Example 2>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 8.7 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 3>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 10.4 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 4>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 12.5 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 5>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 30.0 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 6>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 37.5 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 7>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 50.0 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 8>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 62.5 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 9>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 75.0 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 10>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 87.5 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 11>

In Example 1, the same as in Example 1, except that the input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was changed to about 100.0 g / min. Perfluoromethylethyl ether was prepared by carrying out the method.

<Example 12>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the reaction temperature was changed to about -12 °C.

<Example 13>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the reaction temperature was changed to about -8 °C.

<Example 14>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the reaction temperature was changed to about -5 °C.

<Example 15>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the reaction temperature was changed to about 5 °C.

<Example 16>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the reaction temperature was changed to about 8 °C.

<Example 17>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the reaction temperature was changed to about 10 °C.

<Example 18>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the reaction temperature was changed to about 15 °C.

<Example 19>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the pressure inside the reactor was changed to about 0 bar.

<Example 20>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the pressure inside the reactor was changed to about 0.1 bar.

<Example 21>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the pressure inside the reactor was changed to about 0.2 bar.

<Example 22>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the pressure inside the reactor was changed to about 0.3 bar.

<Example 23>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the pressure inside the reactor was changed to about 0.5 bar.

<Example 24>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the pressure inside the reactor was changed to about 0.6 bar.

<Example 25>

In Example 1, perfluoromethylethyl ether was prepared in the same manner as in Example 1, except that the pressure inside the reactor was changed to about 0.8 bar.

<Experimental Example 1> Conversion rate of perfluoromethylethyl ether according to flow rate

Conversion rates of perfluoromethylethyl ether synthesized in Examples 1 to 11 were confirmed through quantitative gas chromatography (GC) analysis, and are shown in Table 1 below.

division Feed rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride (g/min) Input flow rate of 2,3,3,3-tetrafluoro-2-trifluoromethoxypropionyl fluoride (g/min)/antimony fluoride (g) Conversion rate of perfluoromethylethyl ether (%) Example 1 25.0 0.0208 94.9 Example 2 8.7 0.0073 95.0 Example 3 10.4 0.0087 95.0 Example 4 12.5 0.0104 94.9 Example 5 30.0 0.0250 94.1 Example 6 37.5 0.0313 93.6 Example 7 50.0 0.0417 92.1 Example 8 62.5 0.0521 84.4 Example 9 75.0 0.0625 75.3 Example 10 87.5 0.0729 63.7 Example 11 100.0 0.0833 52.1

As shown in Table 1, the input flow rate (g) of 2,3,3,3-tetrafluoro-2-trifluoromethoxypropionyl fluoride compared to the weight (g) of antimony fluoride introduced into the reactor /min) decreased, the conversion rate of perfluoromethylethyl ether showed a tendency to increase. In particular, the input flow rate (g/min) of 2,3,3,3-tetrafluoro-2-trifluoromethoxypropionyl fluoride relative to the weight (g) of antimony pentafluoride is about 94.9 at a weight ratio of about 0.0208 or less. It was confirmed that a high conversion rate of % or more and a constant value were exhibited.

<Experimental Example 2> Conversion rate of perfluoromethyl ethyl ether according to reaction temperature

The conversion rate of perfluoromethylethyl ether prepared in Examples 1 and 12 to 18 was confirmed through the same analysis method as in Experimental Example 1, and is shown in Table 2 below.

division Reaction temperature (℃) Conversion rate of perfluoromethyl ethyl ether (%) Example 1 0 94.9 Example 12 -12 91.9 Example 13 -8 94.1 Example 14 -5 94.9 Example 15 5 94.4 Example 16 8 90.2 Example 17 10 83.4 Example 18 15 72.1

As shown in Table 2, when the internal temperature of the reactor was -15 ° C to 10 ° C, a conversion rate of about 83% or more was exhibited. When the temperature inside the reactor was -12 °C to 8 °C, a conversion rate of about 90% or more was exhibited. In addition, when the internal temperature of the reactor was -8 ° C to 5 ° C, a conversion rate of about 94% or more was exhibited. In particular, at a reaction temperature of 15 DEG C, 27.9% of unreacted 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride was confirmed.

<Experimental Example 3> Conversion rate of perfluoromethylethyl ether according to the pressure inside the reactor

The conversion rate of perfluoromethylethyl ether prepared in Example 1 and Examples 19 to 25 was confirmed through the same analysis method as in Experimental Example 1, and is shown in Table 3 below.

division Pressure inside the reactor (gauge pressure) (bar) Conversion rate of perfluoromethyl ethyl ether (%) Example 1 0.4 94.9 Example 19 0.0 87.8 Example 20 0.1 89.9 Example 21 0.2 91.7 Example 22 0.3 93.2 Example 23 0.5 94.9 Example 24 0.6 94.8 Example 25 0.8 94.9

As shown in Table 3, a high conversion rate of 91% or more was exhibited when the pressure inside the reactor was 0.2 bar or more.

When the pressure inside the reactor was 0.4 bar or more, a high conversion rate of 94% or more was exhibited. On the other hand, when the internal pressure of the reactor was less than 0.2 bar, the concentration of unreacted 2,3,3,3-tetrafluoro-2-trifluoromethoxy propionyl fluoride increased as the internal pressure decreased, and the internal pressure of the reactor was 0 Bar showed a relatively low conversion rate of about 87.8%.

<Experimental Example 4> Purity of perfluoromethylethyl ether

Table 4 shows the purity of perfluoromethylethyl ether synthesized in Examples 1 to 3 through distillation.

division Purity (%) of perfluoromethylethyl ether after distillation Example 1 99.1 Example 2 99.0 Example 3 99.1

110: reaction unit
120: reactant supply unit
130: discharge unit
140: first pump
150: second pump
200: temperature controller
210: stirring unit
220: cooling unit
221: first storage unit
230: distillation unit
240: second storage unit

Claims (12)

(A) preparing a perfluorodialkyl ether represented by the following Chemical Formula 2 from a compound represented by the following Chemical Formula 1 continuously supplied from the outside in the presence of a metal fluoride as a Lewis acid; and
(B) separating the perfluorodialkyl ether and continuously discharging it to the outside;
A method for producing a perfluorodialkyl ether comprising:
[Formula 1]

In Formula 1, n is an integer from 1 to 3.
[Formula 2]

In Formula 2, n is an integer from 1 to 3 The method of claim 1,
Wherein step (B) is to separate the perfluorodialkyl ether by gas-liquid separation. delete The method of claim 1,
The method of producing a perfluorodialkyl ether, wherein the metal fluoride includes at least one selected from the group consisting of antimony fluoride, aluminum trifluoride, cobalt trifluoride, and combinations thereof. The method of claim 1,
In the step (A), the compound represented by Formula 1 is continuously supplied from the outside at a flow rate of 0.5 parts by weight / min to 5 parts by weight / min based on 100 parts by weight of the metal fluoride, perfluorodialkyl ether manufacturing method. The method of claim 1,
The step (A) is carried out at -15 ℃ to 10 ℃, a method for producing a perfluorodialkyl ether. The method of claim 1,
Steps (A) and (B) are methods for producing perfluorodialkyl ethers in which the internal pressure is adjusted to 0.2 bar or more as a gauge pressure. a reaction unit for producing a perfluorodialkyl ether represented by the following Chemical Formula 2 from a compound represented by the following Chemical Formula 1 in the presence of a metal fluoride as a Lewis acid;
a reactant supply unit for supplying the compound represented by Chemical Formula 1 to the reaction unit;
a discharge unit for discharging the perfluorodialkyl ether from an upper portion of the reaction unit;
a first pump for continuously supplying the compound represented by Chemical Formula 1 to the reaction unit through the reactant supply unit; and
a second pump for continuously discharging the perfluorodialkyl ether to the outside of the reaction unit through the discharge unit;
Apparatus for producing a perfluorodialkyl ether comprising:
[Formula 1]

In Formula 1, n is an integer from 1 to 3.
[Formula 2]

In Formula 2, n is an integer from 1 to 3 The method of claim 8,
Further comprising a metal fluoride supply unit for injecting the metal fluoride into the reaction unit, the apparatus for producing a perfluorodialkyl ether. The method of claim 8,
The apparatus for producing a perfluorodialkyl ether further comprising a temperature control unit for controlling the temperature of the reaction unit. The method of claim 10,
The apparatus for producing a perfluorodialkyl ether, wherein the temperature controller includes a constant temperature jacket. The method of claim 8,
The apparatus for producing a perfluorodialkyl ether further comprising a pressure control unit for adjusting the pressure of the reaction unit.

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