CN109704935B - Method for preparing perfluoro-3-methyl-2-butanone - Google Patents
Method for preparing perfluoro-3-methyl-2-butanone Download PDFInfo
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Abstract
The invention discloses a method for preparing perfluoro-3-methyl-2-butanone by reacting hexafluoropropylene and trifluoroacetyl fluoride under the action of a liquid phase catalyst, wherein the liquid phase catalyst comprises a main catalyst, an auxiliary agent and an organic solvent, the main catalyst is selected from metal fluoride and/or metal fluorohydride, the auxiliary catalyst is selected from C6-C9 perfluoroolefin, the auxiliary agent is selected from crown ether and/or crown ether-like, and the organic solvent is selected from polar aprotic solvents. The preparation method provided by the invention can realize one-step reaction, and has the advantages of high reaction speed and high product yield.
Description
Technical Field
The invention relates to a preparation method of fluoroketone, in particular to a preparation method of perfluoro-3-methyl-2-butanone.
Background
Perfluoro-3-methyl-2-butanone is a perfluoroketone compound, has ODP of 0 and GWP of 1, is an environment-friendly compound, and has certain application potential in the fields of fire extinguishing, smelting, refrigeration and the like. In addition, the perfluoro-3-methyl-2-butanone has excellent insulating property, so that the perfluoro-3-methyl-2-butanone has application potential in the field of insulation.
As for the production method of perfluoro-3-methyl-2-butanone, there are those produced by liquid phase reaction and those produced by gas-solid phase reaction in the prior art, and the following reports are given:
(1) document j.fluorine.chem.,89, (1998)5 discloses a process for preparing perfluoro-3-methyl-2-butanone by liquid phase reaction of trifluoroacetyl halide and heptafluoroiodopropane in benzonitrile as a solvent under the action of hexaethylphosphonium phosphite to obtain perfluoro-3-methyl-2-butanone. The yield of the method is only 55 percent, and the feeding is required to be carried out at the low temperature of-196 ℃;
(2) U.S. Pat. No. 4,794,79 discloses a process for the preparation of perfluoro-3-methyl-2-butanone by reacting hexafluoropropylene with trifluoroacetic anhydride for 16 hours in the presence of equal molar equivalents of potassium fluoride and the solvent diethylene glycol dimethyl ether. The yield of the method can reach 60%, but the reaction rate is slow and the reaction time is long;
(3) document j.am.chem.soc.,84,4285,1962 discloses a method for preparing perfluoro-3-methyl-2-butanone, which comprises reacting trifluoroacetyl fluoride and hexafluoropropylene by stepwise temperature rise using potassium bifluoride as a catalyst and acetonitrile as a solvent to obtain perfluoro-3-methyl-2-butanone, wherein the yield is 75% after 9 hours of reaction. In the method, if solvents such as acetonitrile and the like are not used, the yield is 65 percent after the reaction is carried out for 14 hours in a sectional gradual heating mode. The method has the problems of high reaction temperature, difficult treatment of the solid catalyst and the like no matter the method does not use an organic solvent except long reaction time;
(4) literature Zhurnal Prikladnoi Khimi, 2013,86 and 1269 discloses a preparation method of perfluoro-3-methyl-2-butanone, wherein cesium fluoride adsorbed on BAU-A-2 activated carbon is used as a solid-phase catalyst, hemutexafluoropropylene omutexide is firstly prepared on the solid-phase catalyst to obtain trifluoroacetyl fluoride, and then the trifluoroacetyl fluoride and hemutexafluoropropylene are further synthesized into the perfluoro-3-methyl-2-butanone under the action of the solid-phase catalyst. In this method, the solid phase catalyst is difficult to prepare.
Therefore, there is a need for further improvement of the process for producing perfluoro-3-methyl-2-butanone.
Disclosure of Invention
The invention aims to provide a method for preparing perfluoro-3-methyl-2-butanone by using a specific liquid-phase catalyst to realize one-step preparation of perfluoro-3-methyl-2-butanone.
The invention adopts the following technical scheme:
a method for preparing perfluoro-3-methyl-2-butanone is characterized in that: under the action of a liquid phase catalyst, hexafluoropropylene and trifluoroacetyl fluoride react to obtain perfluoro-3-methyl-2-butanone;
the liquid phase catalyst comprises a main catalyst, an auxiliary agent and an organic solvent, wherein the main catalyst is selected from metal fluoride and/or metal fluorohydride, the auxiliary catalyst is selected from C6-C9 perfluoroolefin, the auxiliary agent is selected from crown ether and/or crown ether-like, and the organic solvent is selected from polar aprotic solvents.
Some terms of the invention are explained below:
(1) crown ether-like refers to ether compounds capable of combining with metal ions to form structures similar to those of crown ether complexed with metal ions);
(2) the sulfone solvent contains (-SO)2-) groups or (-SO-) sulfoxide groups.
The preparation method provided by the invention uses a liquid phase catalyst which comprises a main catalyst, a cocatalyst, an auxiliary agent and an organic solvent.
The main catalyst can be metal fluoride, metal hydrofluoride, or the mixture of metal fluoride and metal hydrofluoride.
Preferably, the procatalyst is selected from at least one of an alkali metal fluoride, an alkali metal fluorohydride, an alkaline earth metal fluoride and an alkaline earth metal fluorohydride.
Further preferably, the main catalyst is at least one selected from the group consisting of potassium fluoride, potassium bifluoride, cesium fluoride, sodium fluoride, lithium fluoride, and magnesium fluoride.
Most preferably, the procatalyst is selected from at least one of potassium fluoride, potassium bifluoride and lithium fluoride.
The catalyst promoter may be perfluoropentene, perfluoroheptene, or the mixture of perfluoropentene and perfluoroheptene.
Preferably, the co-catalyst is selected from at least one of perfluoro-2-methyl-2-pentene, perfluoro-4-methyl-2-pentene, perfluoro-3, 4-dimethyl-2-pentene, perfluoro-3-isopropyl-4-methyl-2-pentene, perfluoro-2, 4-dimethyl-3-heptene, perfluoro-2, 4-dimethyl-3-ethyl-2-pentene and perfluoro-2, 3, 4-trimethyl-2-pentene.
It is further preferred that the co-catalyst is selected from at least one of perfluoro-4-methyl-2-pentene, perfluoro-2-methyl-2-pentene, perfluoro-3-isopropyl-4-methyl-2-pentene, perfluoro-2, 4-dimethyl-3-heptene and perfluoro-2, 4-dimethyl-3-ethyl-2-pentene.
Most preferably, the co-catalyst is selected from at least one of perfluoro-4-methyl-2-pentene, perfluoro-2-methyl-2-pentene, perfluoro-3-isopropyl-4-methyl-2-pentene, perfluoro-2, 4-dimethyl-3-heptene and perfluoro-2, 4-dimethyl-3-ethyl-2-pentene.
Wherein the assistant can be crown ether, crown ether-like, or mixture of crown ether and crown ether-like.
Preferably, the auxiliary agent is at least one selected from C8-C12 crown ether, cyclodextrin and polyethylene glycol with the average molecular weight of less than or equal to 1000.
Further preferably, the auxiliary agent is at least one selected from 18 crown 6 ether, dibenzo 18 crown 6 ether, 15 crown 5 ether, 12 crown 4 ether, beta-cyclodextrin, gamma-cyclodextrin, polyethylene glycol 400, polyethylene glycol 600 and polyethylene glycol 1000.
Most preferably, the adjuvant is selected from at least one of 18 crown 6 ether, 15 crown 5 ether, beta-cyclodextrin and polyethylene glycol 400.
The polyethylene glycol 400 is a polyethylene glycol having an average molecular weight of 400.
The polyethylene glycol 600 is a polyethylene glycol having an average molecular weight of 600.
The polyethylene glycol 1000 is a polyethylene glycol having an average molecular weight of 1000.
Wherein the organic solvent is selected from polar aprotic solvents.
Preferably, the polar aprotic solvent is selected from at least one of amide, dimethyl ether and sulfone-based solvents.
Further preferably, the polar aprotic solvent is selected from at least one of acetonitrile, glyme, diethylene glycol methyl ether, dimethylformamide, dimethyl sulfoxide, dimethylacetamide, N-methylpyrrolidone, and sulfolane.
Most preferably, the polar aprotic solvent is selected from at least one of acetonitrile, glyme, sulfolane and N-methylpyrrolidone.
The liquid phase catalyst provided by the invention has the advantages that the proportion of the four components of the main catalyst, the cocatalyst, the auxiliary agent and the organic solvent is satisfied, so that the reaction can be smoothly carried out.
Preferably, the molar ratio of the main catalyst to the cocatalyst to the auxiliary agent to the organic solvent is 1.0: 0.1-1.0: 1.0-3.0: 5.0-15.0.
More preferably, the molar ratio of the main catalyst to the cocatalyst to the auxiliary agent to the organic solvent is 1: 0.2-0.8: 1.0-2.0: 7.0-12.0.
According to the preparation method provided by the invention, the dosage of the catalyst is enough to ensure that the reaction is smoothly carried out.
Preferably, the mass ratio of the liquid-phase catalyst to the hexafluoropropylene is 1.0: 1.0-8.0.
More preferably, the mass ratio of the liquid phase catalyst to the hexafluoropropylene is 1.0: 1.0-3.0.
According to the preparation method provided by the invention, the molar ratio of the raw materials of hexafluoropropylene and trifluoroacetyl fluoride meets the requirement of smooth reaction.
Preferably, the molar ratio of the hexafluoropropylene to the trifluoroacetyl fluoride is 1.0: 1.0-5.0.
More preferably, the molar ratio of the hexafluoropropylene to the trifluoroacetyl fluoride is 1.0: 1.0-2.5.
According to the preparation method provided by the invention, the reaction temperature is satisfied, so that the reaction can be smoothly carried out.
Preferably, the reaction temperature is 40-110 ℃.
More preferably, the reaction temperature is 50 to 100 ℃.
Compared with the prior art, the preparation method provided by the invention has the following advantages:
(1) by creatively using the liquid phase catalyst, one-step reaction can not be realized, and the product yield can be obviously improved by 20-40 percent compared with the prior art;
(2) the reaction condition is mild, the reaction can be carried out at a lower reaction temperature, the reaction speed is high, and the method is suitable for industrial large-scale production.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to limit the invention to these embodiments. It will be appreciated by those skilled in the art that the present invention encompasses all alternatives, modifications and equivalents as may be included within the scope of the claims.
Example 1 preparation of catalyst Cat1
Respectively adding 1.2g of potassium fluoride, 5.3g of octadecanoyl hexaether and 18.9g of diethylene glycol dimethyl ether into a three-neck flask provided with a reflux condenser tube, a constant-pressure dropping funnel and a magnetic stirrer, setting the temperature at 50 ℃, starting stirring and heating, slowly dropping 2.8g of perfluoro-4-methyl-2-pentene, continuing stirring for 1 hour after the addition is finished, and stopping stirring and cooling to room temperature to obtain a liquid-phase catalyst Cat 1.
Example 2 preparation of catalyst Cat2
1.2g of potassium fluoride, 5.3g of octadecanoyl hexaether and 18.9g of diethylene glycol dimethyl ether are respectively added into a three-neck flask provided with a reflux condenser tube, a constant-pressure dropping funnel and a magnetic stirrer, the temperature is set at 50 ℃, stirring and heating are started, stirring is carried out for 1 hour, and the stirring is stopped and the temperature is reduced to the room temperature, thus obtaining the liquid-phase catalyst Cat 2.
Example 3 preparation of catalyst Cat3
Respectively adding 1.2g of potassium fluoride and 18.9g of diethylene glycol dimethyl ether into a three-neck flask provided with a reflux condenser tube, a constant-pressure dropping funnel and a magnetic stirrer, setting the temperature at 50 ℃, starting stirring and heating, slowly dropwise adding 2.8g of perfluoro-4-methyl-2-pentene, continuing stirring for 1 hour after the addition is finished, and stopping stirring and cooling to room temperature to obtain a liquid-phase catalyst Cat 3.
Examples 4 to 6 preparation of catalysts Cat4 to Cat6
The kinds and the feeding amount of the metal fluorine salt are changed, and the rest of the operation conditions are consistent with those of the example 1, so that the catalysts Cat 4-Cat 6 are obtained.
TABLE 1 catalysts Cat 4-Cat 6
| Examples | Catalyst and process for preparing same | Metal fluoro salt species | Metal villiaumite input/g |
| 4 | Cat4 | Potassium bifluoride | 1.6 |
| 5 | Cat5 | Sodium fluoride | 0.9 |
| 6 | Cat6 | Lithium fluoride | 0.5 |
Example 7 preparation of perfluoro-3-methyl-2-butanone
28.0g of catalyst Cat1 was added to the autoclave, which was then sealed and purged with nitrogen. 60.0g of hexafluoropropylene and 47.0g of trifluoroacetyl fluoride were added, and the reaction was carried out at 60 ℃ for 3 hours. Stopping the reaction, cooling to room temperature, opening the reaction kettle, pouring the liquid phase into a separating funnel, and taking the lower layer fluorine phase. The yield of perfluoro-3-methyl-2-butanone is 95.1% by GC detection.
Examples 8 to 12 preparation of perfluoro-3-methyl-2-butanone
Perfluoro-3-methyl-2-butanone was obtained by changing the kind and amount of catalyst and operating conditions in accordance with example 7.
The yields of perfluoro-3-methyl-2-butanone in examples 8 to 12 are shown in Table 2.
Table 2, product yields in examples 7 to 12
| Examples | Catalyst numbering | Catalyst input/g | Perfluoro-3-methyl-2-butanone yield/%) |
| 7 | Cat1 | 27.1 | 95.1 |
| 8 | Cat2 | 24.3 | 40.6 |
| 9 | Cat3 | 21.8 | 40.5 |
| 10 | Cat4 | 27.5 | 85.5 |
| 11 | Cat5 | 26.8 | 85.0 |
| 12 | Cat6 | 26.5 | 85.2 |
Examples 13 to 21 preparation of catalysts Cat7 to Cat15
Catalysts Cat7 to Cat15 were obtained by changing the kinds of auxiliary agents and co-catalysts in accordance with the operating conditions of example 1, as shown in Table 3 below.
TABLE 3 catalysts Cat 7-Cat 15
Examples 22 to 30 preparation of perfluoro-3-methyl-2-butanone
By changing the kind of the catalyst, which was in accordance with the operating conditions of example 7, perfluoro-3-methyl-2-butanone was produced. The yields of perfluoro-3-methyl-2-butanone in examples 22 to 30 are shown in Table 4.
Table 4, product yields in examples 22 to 30
| Examples | Catalyst numbering | Catalyst input/g | Perfluoro-3-methyl-2-butanone yield/%) |
| 22 | Cat7 | 26.3 | 89.2 |
| 23 | Cat8 | 44.5 | 88.6 |
| 24 | Cat9 | 29.8 | 90.3 |
| 25 | Cat10 | 27.5 | 95.2 |
| 26 | Cat11 | 27.1 | 91.5 |
| 27 | Cat12 | 27.5 | 92.3 |
| 28 | Cat13 | 27.5 | 90.6 |
| 29 | Cat14 | 27.5 | 90.6 |
| 30 | Cat15 | 27.3 | 95.3 |
Examples 31 to 38 preparation of catalysts Cat16 to Cat23
The remaining operating conditions were identical to those of example 1, with the solvent being varied, to give catalysts Cat 16-Cat 23, as shown in Table 5 below.
TABLE 5 catalysts Cat 16-Cat 23
| Examples | Catalyst and process for preparing same | Kind of solvent | Solvent input/g |
| 31 | Cat16 | Acetonitrile | 15.8 |
| 32 | Cat17 | Tetraethylene glycol dimethyl ether | 20.18 |
| 33 | Cat18 | Dimethyl sulfoxide | 22 |
| 34 | Cat19 | Dimethyl formamide | 18.96 |
| 35 | Cat20 | Sulfolane | 25.22 |
| 36 | Cat21 | N-methyl pyrrolidone | 20.56 |
| 37 | Cat22 | Sulfolane + diethylene glycol dimethyl ether | 12.6+9.5 |
| 38 | Cat23 | Acetonitrile + sulfolane | 7.9+12.6 |
Examples 39 to 46 preparation of perfluoro-3-methyl-2-butanone
By changing the kind of the catalyst, which was in accordance with the operating conditions of example 7, perfluoro-3-methyl-2-butanone was produced. The yields of perfluoro-3-methyl-2-butanone in examples 39 to 460 are shown in Table 6.
Table 6, product yields in examples 39 to 46
| Examples | Catalyst numbering | Catalyst input/g | Perfluoro-3-methyl-2-butanone yield/%) |
| 39 | Cat16 | 24 | 85.9 |
| 40 | Cat17 | 28.4 | 88.9 |
| 41 | Cat18 | 30.2 | 87.4 |
| 42 | Cat19 | 27.2 | 86.5 |
| 43 | Cat20 | 33.5 | 90.6 |
| 44 | Cat21 | 28.8 | 87.8 |
| 45 | Cat22 | 21.1 | 95.0 |
| 46 | Cat23 | 19.5 | 94.7 |
Examples 47 to 49 preparation of perfluoro-3-methyl-2-butanone
By changing the reaction temperature, which was the same as that in example 7, perfluoro-3-methyl-2-butanone was produced. The yields of perfluoro-3-methyl-2-butanone in examples 39 to 460 are shown in Table 7.
Table 7, product yields in examples 47 to 49
| Examples | Catalyst and process for preparing same | Temperature/. degree.C | Perfluoro-3-methyl-2-butanone yield/%) |
| 47 | Cat1 | 40 | 80.0 |
| 48 | Cat1 | 80 | 95.1 |
| 49 | Cat1 | 100 | 95.0 |
EXAMPLE 50 perfluoro-3-methyl-2-butanone preparation
42.0g of catalyst Cat1 was added to the autoclave, which was then sealed and purged with nitrogen. 60.0g of hexafluoropropylene and 47.0g of trifluoroacetyl fluoride are added, the temperature is raised to 60 ℃, the reaction is stopped after 3 hours of reaction, the temperature is reduced to room temperature, the reaction kettle is opened, the liquid phase is poured into a separating funnel, and the lower layer fluorine phase is taken out. The yield of perfluoro-3-methyl-2-butanone by GC detection is 94.9%.
EXAMPLE 51 perfluoro-3-methyl-2-butanone preparation
14.0g of catalyst Cat1 was added to the autoclave, which was then sealed and purged with nitrogen. 60.0g of hexafluoropropylene and 47.0g of trifluoroacetyl fluoride are added, the temperature is raised to 60 ℃, the reaction is stopped after 3 hours of reaction, the temperature is reduced to room temperature, the reaction kettle is opened, the liquid phase is poured into a separating funnel, and the lower layer fluorine phase is taken out. The yield of perfluoro-3-methyl-2-butanone is 85.6 percent by GC detection.
Example 52 catalyst cycling Performance
The catalyst Cat1 obtained after completion of the reaction in example 7 was used as a catalyst in example 52, and the remaining operating conditions were the same as in example 7. The catalyst is recycled once, and after the reaction is stopped, the yield of the perfluoro-3-methyl-2 butanone is 95.0 percent through GC detection.
Examples 53 to 56, catalyst circulation Performance
The catalyst was recycled in the same manner as in example 52, and the results are shown in Table 8.
Table 8, product yields in examples 52 to 56
| Examples | Catalyst and process for preparing same | Number of catalyst cycles | Perfluoro-3-methyl-2-butanone yield/%) |
| 52 | Cat1 | 1 | 95.0 |
| 53 | Cat1 | 2 | 94.5 |
| 54 | Cat1 | 3 | 95.1 |
| 55 | Cat1 | 4 | 94.6 |
| 56 | Cat1 | 5 | 94.5 |
Comparative example 1 preparation of perfluoro-3-methyl-2-butanone
The liquid phase catalyst was not prepared in advance.
1.2g of potassium fluoride, 5.3g of octadecanohexa-ether, 18.9g of diethylene glycol dimethyl ether and 2.8g of perfluoro-4-methyl-2-pentene were added to the autoclave, and the autoclave was sealed. 60.0g of hexafluoropropylene and 47.0g of trifluoroacetyl fluoride are added, the temperature is raised to 60 ℃, the reaction is stopped after 3 hours of reaction, the temperature is reduced to room temperature, the reaction kettle is opened, the liquid phase is poured into a separating funnel, and the lower layer fluorine phase is taken out. The yield of perfluoro-3-methyl-2-butanone is 75.0% by GC detection.
Claims (5)
1. A method for preparing perfluoro-3-methyl-2-butanone is characterized in that: under the action of a liquid phase catalyst, hexafluoropropylene and trifluoroacetyl fluoride react to obtain perfluoro-3-methyl-2-butanone;
the liquid phase catalyst comprises a main catalyst, a cocatalyst, an auxiliary agent and an organic solvent, and is prepared by the following steps: mixing a main catalyst, an auxiliary agent and an organic solvent, setting the temperature at 50 ℃, starting stirring and heating, slowly dripping an auxiliary catalyst, continuing stirring for 1 hour after the auxiliary catalyst is added, stopping stirring, and cooling to room temperature to obtain the liquid-phase catalyst, wherein the organic solvent is a polar aprotic solvent;
the main catalyst is at least one of potassium fluoride, potassium bifluoride and lithium fluoride; the cocatalyst is selected from at least one of perfluoro-4-methyl-2-pentene, perfluoro-2-methyl-2-pentene, perfluoro-3-isopropyl-4-methyl-2-pentene, perfluoro-2, 4-dimethyl-3-heptene and perfluoro-2, 4-dimethyl-3-ethyl-2-pentene; the auxiliary agent is at least one of 18 crown 6 ether, 15 crown 5 ether, beta-cyclodextrin and polyethylene glycol 400; the polar aprotic solvent is selected from at least one of acetonitrile, glyme, sulfolane and N-methylpyrrolidone; the molar ratio of the main catalyst to the cocatalyst to the auxiliary agent to the organic solvent is 1.0: 0.1-1.0: 1.0-3.0: 5.0-15.0;
after the liquid phase catalyst is prepared, the liquid phase catalyst is used for preparing perfluoro-3-methyl-2-butanone;
the molar ratio of the hexafluoropropylene to the trifluoroacetyl fluoride is 1.0: 1.0-5.0; the mass ratio of the liquid-phase catalyst to the hexafluoropropylene is 1.0: 1.0-8.0, and the reaction temperature is 40-110 ℃.
2. The process for producing perfluoro-3-methyl-2-butanone according to claim 1, wherein: the molar ratio of the main catalyst to the cocatalyst to the auxiliary agent to the organic solvent is 1.0: 0.2-0.8: 1.0-2.0: 7.0-12.0.
3. The process for producing perfluoro-3-methyl-2-butanone according to claim 1, wherein: the molar ratio of the hexafluoropropylene to the trifluoroacetyl fluoride is 1.0: 1.0-2.5.
4. The process for producing perfluoro-3-methyl-2-butanone according to claim 1, wherein: the mass ratio of the liquid-phase catalyst to the hexafluoropropylene is 1.0: 1.0-3.0.
5. The process for producing perfluoro-3-methyl-2-butanone according to claim 1, wherein: the reaction temperature is 50-100 ℃.
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| CN106316809A (en) * | 2016-07-22 | 2017-01-11 | 北京天康达科技发展有限公司 | Method of preparing pentafluoroethyl isopropyl ketone |
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