CN114315761A - Continuous preparation method of hexafluoropropylene tripolymer epoxide - Google Patents
Continuous preparation method of hexafluoropropylene tripolymer epoxide Download PDFInfo
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- CN114315761A CN114315761A CN202111385450.3A CN202111385450A CN114315761A CN 114315761 A CN114315761 A CN 114315761A CN 202111385450 A CN202111385450 A CN 202111385450A CN 114315761 A CN114315761 A CN 114315761A
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- hexafluoropropylene
- epoxide
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- hexafluoropropylene trimer
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Abstract
The invention discloses a continuous preparation method of hexafluoropropylene tripolymer epoxide, which comprises the steps of continuously introducing hexafluoropropylene tripolymer and oxidant into a microchannel reactor for reaction in the presence of a phase transfer catalyst, wherein the reaction temperature is 10-60 ℃, the retention time is 0.5-3 min, collecting reaction products, standing for layering, rectifying and drying to obtain a hexafluoropropylene tripolymer epoxide product. The invention has the advantages of simple process, convenient operation, safety, environmental protection and high production efficiency.
Description
Technical Field
The invention belongs to the field of fluorine chemical industry, and particularly relates to a continuous preparation method of hexafluoropropylene tripolymer epoxide.
Background
Along with the development of electronic equipment, the number of high-heat-density servers in a data room is gradually increased, the scale of the data room is also increasingly huge, the traditional air cooling air heat dissipation mode cannot meet the heat dissipation requirement of the high-heat-density data room, a large amount of energy is wasted, the liquid cooling technology has higher heat dissipation efficiency and lower energy consumption, and compared with air cooling, the liquid cooling technology can greatly reduce the energy consumption of a data center, so that the cost is reduced.
Common liquid cooling agents include water, alcohols, mineral oils, fluorocarbon compounds and the like, wherein the fluorocarbon compounds are applied to the liquid cooling direction of the data center due to the inert characteristics of insulation and non-combustion. Hexafluoropropylene trimer epoxide as a new fluorine-containing inert solvent is concerned to be applied in the direction of liquid coolant, and the preparation method thereof is a hotspot of research.
Use of 50% H as reported in CN103702988A2O2Process for the epoxidation of hexafluoropropene trimer by adding 50% H dropwise to a mixture of acetonitrile solvent, HFP trimer and potassium hydroxide solution2O2And reacting to generate a hexafluoropropylene tripolymer epoxide crude product, and washing and rectifying the crude product to obtain the hexafluoropropylene tripolymer epoxide with the purity of more than or equal to 99 percent. The process adopts an intermittent dropwise adding method for preparation, has long reaction time and poor reaction temperature controllability, can cause product decomposition due to long contact time of the obtained epoxide and hydroxyl ions in a solution, uses a large amount of organic solvent acetonitrile, and increases the difficulty in treating three wastes
For example, US5789606A discloses a method for epoxidizing hexafluoropropylene trimer using tertiary amine-N-oxide as oxidant, adding hexafluoropropylene trimer into dimethyl formaldehyde (DMF) and trimethylamine-N-oxide dihydrate solution under stirring, washing and separating after the reaction to obtain hexafluoropropylene trimer epoxide, the method has relatively simple process, suitable raw material price, reaction selectivity of more than 85%, but reaction yield is low, only about 70%, and in addition, a large amount of tertiary amine by-product impurities exist in the product after the reaction is finished, which is not beneficial to separation and purification of the product, is easy to pollute environment, and increases process cost.
For another example, CN112812747A discloses a method for oxidizing hexafluoropropylene trimer by using sodium hypochlorite solution, in which hexafluoropropylene trimer is slowly dropped into the mixed solution of sodium hypochlorite and acetonitrile, and reacted at 20-40 ℃ for 3h, and the reaction product is left to stand and delaminate to obtain crude hexafluoropropylene trimer epoxide, with the yield of 89%. The method adopts an intermittent dripping method for preparation, has long reaction time and poor reaction temperature controllability, and is not beneficial to industrial scale-up production.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a continuous preparation method of hexafluoropropylene trimer epoxide, which has the advantages of simple process, convenient operation, safety, environmental protection and high production efficiency.
In order to solve the technical problems, the invention adopts the technical scheme that: a continuous preparation method of hexafluoropropylene tripolymer epoxide is provided, hexafluoropropylene tripolymer and oxidant are continuously introduced into a microchannel reactor to react in the presence of a phase transfer catalyst, the reaction temperature is 10-60 ℃, the retention time is 0.5-3 min, reaction products are collected, and hexafluoropropylene tripolymer epoxide products are obtained through standing, layering, rectifying and drying.
In a preferred embodiment of the present invention, the phase transfer catalyst is at least one of diethylene glycol dimethyl ether and 18-crown-6.
In a preferred embodiment of the present invention, the amount of the phase transfer catalyst is 2 to 5% by mass of the hexafluoropropylene trimer.
In a preferred embodiment of the present invention, the oxidant is sodium hypochlorite or hydrogen peroxide.
In a preferred embodiment of the present invention, the feed molar ratio of the hexafluoropropylene trimer to the oxidant is 1: 1.2-1.4.
In a preferred embodiment of the present invention, the reaction temperature is 20 to 50 ℃.
In a preferred embodiment of the present invention, the residence time is 1 to 2 min.
According to the invention, hexafluoropropylene tripolymer is used as a raw material, a microchannel reactor is adopted, the process is optimized, especially diethylene glycol dimethyl ether and/or 18-crown ether-6 are/is used as a phase transfer catalyst to prepare hexafluoropropylene tripolymer epoxide, the contact time with an oxidant is increased, the reaction speed is improved, the continuous reaction is realized, no organic solvent is required to be added, and the method has the advantages of simple process, convenience in operation, short reaction time and high production efficiency.
The hexafluoropropylene tripolymer epoxide prepared by the invention mainly has three isomers, and the structural formula is as follows:
the microchannel reactor is a miniaturized chemical reaction system with unit reaction interface size in micron level. Because of its small size, large specific surface area and regular micro-channel, it shows extraordinary capacity in the aspects of mass transfer and heat transfer, etc., and is obviously superior to the traditional reactor, and the micromixing is the mixing on the molecular scale, and it has important influence on the quick reaction processes of combustion, polymerization, organic synthesis, precipitation, crystallization, etc.
The number of the mixed reaction modules of the microchannel reactor can be selected according to the actual production condition. The microchannel reactor can be made of common special glass, ceramics, silicon carbide, 316 stainless steel or hastelloy and the like.
The microchannel structure of the microchannel reactor can be a straight-flow tubular structure, a reinforced mixed T-shaped structure, a spherical baffle structure and the like, and the reinforced mixed T-shaped structure is preferred.
Compared with the prior art, the invention has the following advantages:
1. the microchannel reactor adopted by the invention can enhance the heat transfer and mass transfer performance, keep the reaction temperature constant, has simple operation and stable and controllable reaction process, effectively improves the safety of the reaction process, and improves the operation elasticity because the number of the mixed reaction modules of the microchannel reactor can be selected according to the actual production condition.
2. The invention realizes continuous reaction, shortens the reaction time from dozens of minutes to even hours to several minutes, and obviously improves the reaction efficiency.
3. The yield is high, the cost is low, the yield is more than 89%, no organic solvent is needed to be added in the reaction process, and the standing layered inorganic phase containing the phase transfer catalyst can be recycled, so that the discharge of three wastes is further reduced, and the generation cost is reduced.
Detailed Description
The present invention will be described in further detail with reference to examples, but the present invention is not limited to the following examples.
The starting materials and the apparatus used in the examples according to the invention and in the comparative examples are commercially available, some of which are illustrated below:
micro-channel reactor: shandong Haimai mechanical manufacturing, Inc., model RMHS2010, reactor mix reactor 10 modules.
Tubular static mixing reactor: SK type, pipe diameter
Example 1
Adding diethylene glycol dimethyl ether into hexafluoropropylene trimer according to the mass ratio of the diethylene glycol dimethyl ether to the hexafluoropropylene trimer of 3 percent, uniformly mixing, then setting the flow rates of the hexafluoropropylene trimer containing the diethylene glycol dimethyl ether and 12wt percent (wt percent and mass percent) of sodium hypochlorite solution according to the molar ratio of the hexafluoropropylene trimer to the sodium hypochlorite of 1:1.2 and the retention time of the materials in a reactor of 2min, respectively entering a microchannel reactor for reaction through a metering pump, controlling the reaction temperature to be 20 ℃, collecting reactants at an outlet of the microchannel reactor, standing for layering, separating out a lower layer organic phase to obtain a hexafluoropropylene trimer epoxide crude product, rectifying the crude product, and drying to obtain the hexafluoropropylene trimer epoxide product. A sample was taken for analysis and the hexafluoropropylene trimer epoxide yield was 89.12%.
Example 2
Adding diethylene glycol dimethyl ether into hexafluoropropylene trimer according to the mass of the diethylene glycol dimethyl ether being 3 percent of that of the hexafluoropropylene trimer, uniformly mixing, then setting the flow rates of the hexafluoropropylene trimer containing the diethylene glycol dimethyl ether and 12 weight percent of sodium hypochlorite solution according to the molar ratio of the hexafluoropropylene trimer to the sodium hypochlorite being 1:1.2 and the retention time of the materials in a reactor being 2min, respectively entering a microchannel reactor for reaction through a metering pump, controlling the reaction temperature to be 30 ℃, collecting reactants at an outlet of the microchannel reactor, standing for layering, separating out a lower layer organic phase to obtain a hexafluoropropylene trimer epoxide crude product, rectifying and drying the crude product to obtain the hexafluoropropylene trimer epoxide product. A sample was taken for analysis and the hexafluoropropylene trimer epoxide yield was 93.12%.
Example 3
Adding 18-crown ether-6 into hexafluoropropylene trimer according to the dosage of 18-crown ether-6 being 4 percent of the mass of the hexafluoropropylene trimer, uniformly mixing, then setting the flow rates of the hexafluoropropylene trimer containing 18-crown ether-6 and 12 percent by weight of sodium hypochlorite solution according to the molar ratio of the hexafluoropropylene trimer to the sodium hypochlorite being 1:1.2 and the retention time of the materials in a reactor being 2min, respectively entering a microchannel reactor for reaction through a metering pump, controlling the reaction temperature to be 50 ℃, collecting the reactant at the outlet of the microchannel reactor, standing for layering, separating out the lower layer organic phase to obtain a hexafluoropropylene trimer epoxide crude product, rectifying and drying the crude product to obtain the hexafluoropropylene trimer epoxide product. Sampling analysis, hexafluoropropylene trimer epoxide yield of 90.17%.
Example 4
Adding diethylene glycol dimethyl ether into hexafluoropropylene trimer according to the mass of the diethylene glycol dimethyl ether being 3 percent of that of the hexafluoropropylene trimer, uniformly mixing, then setting the flow rates of the hexafluoropropylene trimer containing the diethylene glycol dimethyl ether and 12wt percent of sodium hypochlorite solution according to the molar ratio of the hexafluoropropylene trimer to the sodium hypochlorite being 1:1.3 and the retention time of the materials in a reactor being 1min, respectively entering a microchannel reactor for reaction through a metering pump, controlling the reaction temperature to be 30 ℃, collecting reactants at an outlet of the microchannel reactor, standing for layering, separating out a lower layer organic phase to obtain a hexafluoropropylene trimer epoxide crude product, rectifying and drying the crude product to obtain the hexafluoropropylene trimer epoxide product. A sample was taken for analysis and the hexafluoropropylene trimer epoxide yield was 91.56%.
Example 5
Adding 18-crown ether-6 into hexafluoropropylene trimer according to the dosage of 18-crown ether-6 being 3 percent of the mass of the hexafluoropropylene trimer, uniformly mixing, then setting the flow rates of the hexafluoropropylene trimer containing 18-crown ether-6 and 12 percent by weight of sodium hypochlorite solution according to the molar ratio of the hexafluoropropylene trimer to the sodium hypochlorite being 1:1.4 and the retention time of the materials in a reactor being 1min, respectively entering a microchannel reactor for reaction through a metering pump, controlling the reaction temperature to be 30 ℃, collecting the reactant at the outlet of the microchannel reactor, standing for layering, separating out the lower layer organic phase to obtain a hexafluoropropylene trimer epoxide crude product, rectifying and drying the crude product to obtain the hexafluoropropylene trimer epoxide product. A sample was taken for analysis and the hexafluoropropylene trimer epoxide yield was 89.56%.
Example 6
Adding 18-crown ether-6 into hexafluoropropylene tripolymer according to the dosage of 18-crown ether-6 being 5 percent of the mass of the hexafluoropropylene tripolymer, uniformly mixing, then setting the hexafluoropropylene tripolymer containing 18-crown ether-6 and 30wt percent of hydrogen peroxide water flow according to the molar ratio of the hexafluoropropylene tripolymer to hydrogen peroxide being 1:1.3 and the retention time of the materials in a reactor being 1.5min, respectively entering a microchannel reactor for reaction through a metering pump, controlling the reaction temperature to be 30 ℃, collecting reactants at the outlet of the microchannel reactor, standing for layering, separating out a lower layer organic phase to obtain a hexafluoropropylene tripolymer epoxide crude product, rectifying and drying the crude product to obtain the hexafluoropropylene tripolymer epoxide product. A sample was taken for analysis and the hexafluoropropylene trimer epoxide yield was 90.13%.
Example 7
Adding diethylene glycol dimethyl ether into hexafluoropropylene trimer according to the mass of the diethylene glycol dimethyl ether being 5 percent of that of the hexafluoropropylene trimer, uniformly mixing, setting the flow rates of the hexafluoropropylene trimer containing the diethylene glycol dimethyl ether and 30wt percent of hydrogen peroxide according to the molar ratio of the hexafluoropropylene trimer to the hydrogen peroxide being 1:1.3 and the retention time of materials in a reactor being 1.5min, respectively entering a microchannel reactor for reaction through a metering pump, controlling the reaction temperature to be 20 ℃, collecting reactants at an outlet of the microchannel reactor, standing for layering, separating out a lower layer organic phase to obtain a hexafluoropropylene trimer epoxide crude product, rectifying and drying the crude product to obtain the hexafluoropropylene trimer epoxide product. A sample was taken for analysis and the hexafluoropropylene trimer epoxide yield was 89.67%.
Comparative example 1
Adding diethylene glycol dimethyl ether with the amount of 3 wt% of hexafluoropropylene tripolymer into the hexafluoropropylene tripolymer, uniformly mixing, setting the flow rates of the hexafluoropropylene tripolymer containing the diethylene glycol dimethyl ether and the sodium hypochlorite according to the molar ratio of the hexafluoropropylene tripolymer to the sodium hypochlorite of 1:1.2 and the retention time of materials in a reactor of 2min, respectively entering a tubular static mixing reactor through a metering pump for reaction, controlling the reaction temperature to be 30 ℃, collecting reactants at an outlet of the tubular static mixing reactor, standing for layering to obtain a crude hexafluoropropylene tripolymer epoxide product, and sampling and analyzing to obtain the hexafluoropropylene tripolymer epoxide with the yield of 55.66%.
Comparative example 2
Adding diethylene glycol dimethyl ether with the amount of 5 wt% of hexafluoropropylene tripolymer into the hexafluoropropylene tripolymer, uniformly mixing, setting the flow rates of the hexafluoropropylene tripolymer containing the diethylene glycol dimethyl ether and 30 wt% of hydrogen peroxide according to the molar ratio of the hexafluoropropylene tripolymer to the hydrogen peroxide of 1:1.3 and the retention time of materials in a reactor of 1.5min, respectively entering a tubular static mixing reactor for reaction through a metering pump, controlling the reaction temperature to be 20 ℃, collecting reactants at an outlet of the tubular static mixing reactor, standing and layering to obtain a crude epoxide product of the hexafluoropropylene tripolymer, and sampling and analyzing to obtain the epoxide yield of the hexafluoropropylene tripolymer of 34.24%.
And (3) testing physical and chemical properties:
samples of the hexafluoropropylene trimer epoxide product prepared in example 1 were taken for testing of physicochemical properties, wherein:
the boiling point test is executed according to the general method for measuring the boiling point of the GB/T616-206 chemical reagent;
the density test is carried out according to the test method of testing the liquid density, the relative density and the API gravity by a GB/T29617-2013 digital densimeter;
the viscosity test is carried out according to the measurement of the liquid viscosity of GB/T22235-;
the dielectric strength test is executed according to the technical requirements and the test method of the cooling liquid of the liquid cooling system of the data center T/CCSA 274-2019;
the dielectric loss test is carried out according to GB/T5654-2007 measurement of relative permittivity, dielectric loss factor and direct current resistivity of liquid insulating materials.
The results of the basic physicochemical property tests are as follows:
the data in the table show that the physical and chemical property data of the hexafluoropropylene tripolymer epoxide prepared by the invention meet the requirement of serving as a data center coolant and have the potential of serving as a liquid refrigerant.
Claims (7)
1. A continuous preparation method of hexafluoropropylene tripolymer epoxide is characterized in that hexafluoropropylene tripolymer and oxidant are continuously introduced into a microchannel reactor to react in the presence of a phase transfer catalyst, the reaction temperature is 10-60 ℃, the retention time is 0.5-3 min, reaction products are collected, and hexafluoropropylene tripolymer epoxide products are obtained through standing, layering, rectification and drying.
2. The continuous production method of a hexafluoropropylene trimer epoxide according to claim 1, wherein said phase transfer catalyst is at least one of diethylene glycol dimethyl ether and 18-crown-6.
3. The continuous production method of a hexafluoropropylene trimer epoxide according to claim 1, wherein the amount of said phase transfer catalyst is 2-5% by mass of hexafluoropropylene trimer.
4. The continuous preparation method of hexafluoropropylene trimer epoxide according to claim 1, wherein said oxidant is sodium hypochlorite or hydrogen peroxide.
5. The continuous production method of a hexafluoropropylene trimer epoxide according to claim 1, wherein the feed molar ratio of hexafluoropropylene trimer to oxidant is 1: 1.2-1.4.
6. The continuous production method of a hexafluoropropylene trimer epoxide according to claim 1, wherein the reaction temperature is 20-50 ℃.
7. The continuous production method of a hexafluoropropylene trimer epoxide as claimed in claim 1, wherein said retention time is 1-2 min.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116162072A (en) * | 2023-02-27 | 2023-05-26 | 浙江诺亚氟化工有限公司 | Hexafluoropropylene trimer epoxide with specific structure and preparation method thereof |
| CN116162072B (en) * | 2023-02-27 | 2024-05-03 | 浙江诺亚氟化工有限公司 | Hexafluoropropylene trimer epoxide with specific structure and preparation method thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102356072A (en) * | 2009-03-17 | 2012-02-15 | 大金工业株式会社 | Method for producing hexafluoropropylene oxide |
| CN103880783A (en) * | 2012-12-20 | 2014-06-25 | 中国科学院大连化学物理研究所 | Method for preparing epoxypropane by catalyzing propylene epoxidation with phase-transfer catalyst under reaction control |
| CN106831653A (en) * | 2015-12-04 | 2017-06-13 | 中国科学院大连化学物理研究所 | A kind of preparation method of HFPO |
| CN108840843A (en) * | 2018-06-28 | 2018-11-20 | 贵州微化科技有限公司 | A kind of method of micro passage reaction preparation epoxy monomer |
| CN112047904A (en) * | 2020-09-11 | 2020-12-08 | 中国天辰工程有限公司 | Method for preparing cyclohexene oxide by using microchannel reactor |
| CN112812747A (en) * | 2021-01-25 | 2021-05-18 | 浙江诺亚氟化工有限公司 | Fully-immersed single-phase liquid coolant suitable for IT equipment and application thereof |
| CN113548943A (en) * | 2020-04-26 | 2021-10-26 | 浙江蓝天环保高科技股份有限公司 | Continuous preparation method of hexafluoropropylene tripolymer |
-
2021
- 2021-11-22 CN CN202111385450.3A patent/CN114315761A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102356072A (en) * | 2009-03-17 | 2012-02-15 | 大金工业株式会社 | Method for producing hexafluoropropylene oxide |
| CN103880783A (en) * | 2012-12-20 | 2014-06-25 | 中国科学院大连化学物理研究所 | Method for preparing epoxypropane by catalyzing propylene epoxidation with phase-transfer catalyst under reaction control |
| CN106831653A (en) * | 2015-12-04 | 2017-06-13 | 中国科学院大连化学物理研究所 | A kind of preparation method of HFPO |
| CN108840843A (en) * | 2018-06-28 | 2018-11-20 | 贵州微化科技有限公司 | A kind of method of micro passage reaction preparation epoxy monomer |
| CN113548943A (en) * | 2020-04-26 | 2021-10-26 | 浙江蓝天环保高科技股份有限公司 | Continuous preparation method of hexafluoropropylene tripolymer |
| CN112047904A (en) * | 2020-09-11 | 2020-12-08 | 中国天辰工程有限公司 | Method for preparing cyclohexene oxide by using microchannel reactor |
| CN112812747A (en) * | 2021-01-25 | 2021-05-18 | 浙江诺亚氟化工有限公司 | Fully-immersed single-phase liquid coolant suitable for IT equipment and application thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116162072A (en) * | 2023-02-27 | 2023-05-26 | 浙江诺亚氟化工有限公司 | Hexafluoropropylene trimer epoxide with specific structure and preparation method thereof |
| CN116162072B (en) * | 2023-02-27 | 2024-05-03 | 浙江诺亚氟化工有限公司 | Hexafluoropropylene trimer epoxide with specific structure and preparation method thereof |
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