Hydrofluoroalkene ether compound as well as preparation method and application thereof

Abstract

The embodiment of the invention belongs to the technical field of temperature control working media, and particularly relates to a hydrofluoroalkene ether compound and a preparation method and application thereof. The hydrofluoroalkene ether compound provided by the embodiment of the invention has a structure as shown in a formula I: # imgabs0 #, in the formula I, Rfa and Rfb are-CF3, and Rfc is-CF2CF3; and Rfh is alkyl or fluoroalkyl. The hydrofluoroalkene ether compound provided by the invention has excellent high and low temperature resistance and insulating property, has better oxidation resistance compared with silicone oil and mineral oil, has excellent material compatibility, and has no corrosion to various metals, high polymer materials and glass ceramic materials; the liquid is wide in applicable temperature range, and can be used as a high-temperature or low-temperature temperature control liquid in a range of-80 to 150 DEG C; most importantly, the GWP of the hydrofluoroalkene ether compound provided by the invention is less than 100, and the hydrofluoroalkene ether compound is environment-friendly.

Description

Technical Field

[0001] The embodiments of the present application belong to the technical field of temperature control fluids, and specifically relate to a hydrofluoroolefin ether compound and a preparation method and application thereof. Background Art

[0002] Fluorine-containing fluid is a liquid with unique properties. It is widely used as a heat transfer medium in ultra-low temperature, high temperature and high pressure environments and as an inert protective medium in chemical reactions. Its main features include excellent insulation, non-flammability, chemical corrosion resistance, oxidation resistance, radiation resistance and long life. The non-flammability is as follows: fluorine-containing fluid has an extremely high flash point or no flash point, is non-flammable, and is suitable for environments that require fire protection; chemical corrosion resistance is as follows: fluorine-containing fluid can resist corrosion from a variety of chemical substances and is suitable for various corrosive environments; radiation resistance is as follows: fluorine-containing fluid can remain stable in radiation environments and is suitable for high radiation environments such as nuclear facilities; long life is as follows: due to the stable chemical properties of fluorine-containing fluids, the service life is long, reducing the frequency of replacement and maintenance.

[0003] With the continuous development of the industrial and electronic industries, the demand for high-performance thermal conductive media is increasing. Fluorinated fluids are widely used in the industrial and electronic industries due to their excellent thermal conductivity and chemical stability. For example, industrial applications: heat transfer media in high-temperature and high-pressure equipment, such as oil and gas extraction, nuclear power plants, aerospace and automotive engines; electronic industry applications in semiconductor production processes such as thermostats, heaters and other thermal control equipment, as well as cooling systems in high-precision instruments.

[0004] However, most of the existing fluorinated fluids used as heat transfer media have high global warming potentials (GWPs), are strong greenhouse effect substances, and are difficult to achieve environmental friendliness. Summary of the invention

[0005] In view of this, the embodiments of the present application provide a hydrofluoroolefin ether compound and a preparation method and application thereof. The hydrofluoroolefin ether compound provided in the present application has insulation, non-flammability and environmental protection, and its GWP is less than 100, and it is environmentally friendly when used as a temperature control medium.

[0006] In order to solve the above technical problems, a hydrofluoroolefin ether compound provided in an embodiment of the present application has a structure as shown in Formula I:

[0007]

[0008] Among them, Rfa and Rfb are both -CF3, and Rfc is -CF2CF3;

[0009] Rfh is alkyl or fluoroalkyl.

[0010] As a specific embodiment of the present application, the alkyl group includes a methyl group;

[0011] The fluoroalkyl group includes -CH2CHF2, -CH2CF3, -CH2CH2CF3, -CH2CF2CHF2, -CH(CF3)2, -CH2CF2CHFCF3 or -CH2(CF2)3CHF2.

[0012] The hydrofluoroolefin ether compounds provided in the present application have excellent high and low temperature resistance and insulation properties, have better antioxidant properties compared with silicone oils and mineral oils, have excellent material compatibility, and are non-corrosive to various metals, polymer materials, and glass and ceramic materials; and have a wide applicable temperature range, and can be used as high-temperature or low-temperature temperature control liquids in the range of -80 to 150°C; most importantly, the GWP of the hydrofluoroolefin ether compounds provided in the present application is less than 100, and is environmentally friendly.

[0013] The present application also provides a method for preparing the hydrofluoroolefin ether compound described in the above technical solution, comprising the following steps:

[0014] Mixing compound 1, compound 2, a catalyst and a polar solvent to carry out elimination substitution reaction to obtain the hydrofluoroolefin ether compound;

[0015] The compound 1 has a structure shown in formula a, and the compound 2 has a structure shown in formula b:

[0016] Rfh-OH formula b;

[0017] Wherein, Rfh is an alkyl group or a fluoroalkyl group;

[0018] The catalyst comprises an inorganic alkaline composite catalyst or an organic alkaline catalyst; the inorganic alkaline composite catalyst is an inorganic alkaline compound and an alkyl ammonium halide; the organic alkaline catalyst comprises pyridine, 4-dimethylaminopyridine or triethylamine.

[0019] As a specific embodiment of the present application, the compound 2 includes methanol, difluoroethanol, trifluoroethanol, trifluoropropanol, tetrafluoropropanol, hexafluoroisopropanol, hexafluorobutanol or octafluoropentanol.

[0020] As a specific embodiment of the present application, when compound 2 is methanol, the molar ratio of compound 1 to methanol is 1:5-10;

[0021] When compound 2 is difluoroethanol, trifluoroethanol, trifluoropropanol, tetrafluoropropanol, hexafluoroisopropanol, hexafluorobutanol or octafluoropentanol, the molar ratio of compound 1 to compound 2 is 5 to 10:1.

[0022] As a specific embodiment of the present application, the inorganic alkaline compound includes potassium fluoride or potassium hydroxide; the alkyl ammonium halide compound includes alkyl ammonium chloride or alkyl ammonium bromide;

[0023] The molar ratio of the inorganic alkaline compound to the alkyl ammonium halide is 1:0.01-0.1.

[0024] As a specific embodiment of the present application, the polar solvent includes water, acetonitrile, dichloromethane, methyl tert-butyl ether, 1,2-dichloroethane, tetrahydrofuran or dioxane;

[0025] The temperature of the elimination substitution reaction is 25 to 80° C. and the time is 4 to 12 hours.

[0026] The raw materials used in the preparation method provided in the present application are easily available, the preparation process is simple, and the production cost of the hydrofluoroolefin ether compound is reduced.

[0027] The embodiments of the present application also provide the use of the hydrofluoroolefin ether compound described in the above technical solution or the hydrofluoroolefin ether compound prepared by the preparation method described in the above technical solution as a temperature control working fluid.

[0028] As a specific embodiment of the present application, the fields in which the hydrofluoroolefin ether compound is used as a temperature control fluid include direct contact immersion thermal management of batteries, new energy charging equipment, temperature control devices during semiconductor manufacturing and testing, or immersion liquid cooling systems in server data centers.

[0029] An embodiment of the present application also provides an immersion liquid cooling system, including a liquid cooling medium and a heat source immersed in the liquid cooling medium; the liquid cooling medium is the hydrofluoroolefin ether compound described in the above technical solution or the hydrofluoroolefin ether compound prepared by the preparation method described in the above technical solution. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1 This is a structural schematic diagram of a single-phase immersion liquid cooling system for a server or data center using the hydrofluoroolefin ether compounds provided in the present application as liquid cooling media; wherein 1 is a sealed shell, 11 is a space within the sealed shell, 2 is a heat source, and 3 is a liquid cooling media. DETAILED DESCRIPTION

[0031] The present application provides a hydrofluoroolefin ether compound having a structure as shown in Formula I:

[0032]

[0033] Among them, Rfa and Rfb are both -CF3, and Rfc is -CF2CF3;

[0034] Rfh is alkyl or fluoroalkyl.

[0035] As a specific embodiment of the present application, the alkyl group includes a methyl group; the fluoroalkyl group includes -CH2CHF2, -CH2CF3, -CH2CH2CF3, -CH2CF2CHF2, -CH(CF3)2, -CH2CF2CHFCF3 or -CH2(CF2)3CHF2.

[0036] As a specific embodiment of the present application, the hydrofluoroolefin ether compound has any one of structures 1 to 8:

[0037] Structure 1: Rfa and Rfb are both -CF3, Rfc is -CF2CF3, and Rfh is -CH3;

[0038] Structure 2: Rfa and Rfb are both -CF3, Rfc is -CF2CF3, and Rfh is -CH2CHF2;

[0039] Structure 3: Rfa and Rfb are both -CF3, Rfc is -CF2CF3, and Rfh is -CH2CF3;

[0040] Structure 4: Rfa and Rfb are both -CF3, Rfc is -CF2CF3, and Rfh is -CH2CH2CF3;

[0041] Structure 5: Rfa and Rfb are both -CF3, Rfc is -CF2CF3, and Rfh is -CH2CF2CHF2;

[0042] Structure 6: Rfa and Rfb are both -CF3, Rfc is -CF2CF3, and Rfh is -CH(CF3)2;

[0043] Structure 7: Rfa and Rfb are both -CF3, Rfc is -CF2CF3, and Rfh is -CH2CF2CHFCF3;

[0044] Structure 8: Rfa and Rfb are both -CF3, Rfc is -CF2CF3, and Rfh is -CH2(CF2)3CHF2.

[0045] As a specific embodiment of the present application, the hydrofluoroolefin ether compound having any of structures 1 to 8 has no flash point, a breakdown voltage of more than 25KV, and a volume resistivity of more than 10 10 Ω·cm, ODP value is 0, GWP value is <100, the boiling point of structure 1 is 96℃, the boiling point of structure 2 is 105℃, the boiling point of structure 3 is 110℃, the boiling point of structure 4 is 128℃, the boiling point of structure 5 is 133℃, the boiling point of structure 6 is 118℃, the boiling point of structure 7 is 153℃, and the boiling point of structure 8 is 176℃.

[0046] The present application also provides a method for preparing the hydrofluoroolefin ether compound described in the above technical solution, comprising the following steps:

[0047] Mixing compound 1, compound 2, a catalyst and a polar solvent to carry out elimination substitution reaction to obtain the hydrofluoroolefin ether compound;

[0048] The compound 1 has a structure shown in formula a, and the compound 2 has a structure shown in formula b:

[0049] Rfh-OH formula b;

[0050] Wherein, Rfh is an alkyl group or a fluoroalkyl group.

[0051] As a specific implementation of the present application, the mixing comprises the following steps:

[0052] The catalyst and the polar solvent are first mixed to obtain a first mixed solution;

[0053] Compound 1 and the first mixed solution are mixed for the second time, and then compound 2 is added dropwise.

[0054] The present application first mixes the catalyst and the polar solvent to obtain a first mixed solution. As a specific embodiment of the present application, the catalyst includes an inorganic alkaline composite catalyst or an organic alkaline catalyst; the inorganic alkaline composite catalyst is an inorganic alkaline compound and an alkyl ammonium halide; the organic alkaline catalyst includes pyridine, 4-dimethylaminopyridine or triethylamine. As a specific embodiment of the present application, the inorganic alkaline compound may include potassium fluoride (KF) or potassium hydroxide (KOH); the alkyl ammonium halide compound may include alkyl ammonium chloride or alkyl ammonium bromide; the inorganic alkaline composite catalyst may specifically be a mixture of KF and alkyl ammonium chloride, a mixture of KF and alkyl ammonium bromide, a mixture of KOH and alkyl ammonium chloride, a mixture of KOH and alkyl ammonium bromide. As a specific embodiment of the present application, the alkylammonium chloride may include one or more of benzyltrimethylammonium chloride, trimethyloctadecylammonium chloride, trimethylhexadecylammonium chloride, trimethyltetradecylammonium chloride, and benzyldimethylhexadecylammonium chloride; the alkylammonium bromide may include one or more of benzyltrimethylammonium bromide, trimethyloctadecylammonium bromide, trimethylhexadecylammonium bromide, trimethyltetradecylammonium bromide, and benzyldimethylhexadecylammonium bromide. In the present application, the alkylammonium chloride or alkyl bromide acts as a phase transfer catalyst, increases the solubility of compound 1 and compound 2 in polar solvents, and is more conducive to the reaction.

[0055] As a specific embodiment of the present application, the molar ratio of the inorganic alkaline compound to the alkyl ammonium halide may be approximately 1:0.01 to 0.1. As a specific embodiment of the present application, the inorganic alkaline composite catalyst may be specifically a mixture of KOH and benzyltrimethylammonium chloride in a molar ratio of 1:0.01, a mixture of KOH and trimethyloctadecylammonium bromide in a molar ratio of 1:0.05, a mixture of KOH and benzyldimethylhexadecylammonium chloride in a molar ratio of 1:0.1, a mixture of KF and benzyltrimethylammonium chloride in a molar ratio of 1:0.01, a mixture of KF and trimethyloctadecylammonium bromide in a molar ratio of 1:0.05, a mixture of KF and benzyldimethylhexadecylammonium chloride in a molar ratio of 1:0.1,

[0056] As a specific embodiment of the present application, the polar solvent may include water, acetonitrile, dichloromethane (DCM), methyl tert-butyl ether (MTBE), 1,2-dichloroethane, tetrahydrofuran or dioxane; the water may be deionized water. As a specific embodiment of the present application, the volume ratio of the total volume of the compound 1, compound 2 and the catalyst to the polar solvent may be approximately 1:1.5 to 2, and may be specifically 1:1.5, 1:1.8 or 1:2.

[0057] As a specific embodiment of the present application, the first mixing can be carried out under stirring conditions, the stirring temperature can be room temperature, the room temperature can be approximately 20-35°C, and can also be approximately 25-30°C; the stirring time can be approximately 1-2h; the present application has no special requirements for the stirring speed, as long as it can be mixed evenly.

[0058] After obtaining the first mixed solution, the present application performs a second mixing of compound 1 and the first mixed solution and then drops compound 2. As a specific embodiment of the present application, the compound 2 may include methanol, difluoroethanol, trifluoroethanol, trifluoropropanol, tetrafluoropropanol, hexafluoroisopropanol, hexafluorobutanol or octafluoropentanol.

[0059] As a specific embodiment of the present application, when compound 2 is methanol, the molar ratio of compound 1 to methanol can be about 1:5-10; the present application makes cheap methanol excessive, promotes the conversion rate of high-priced raw material hexafluoropropylene dimer, and can effectively reduce production costs. The excess cheap raw material methanol can be recovered and reused by distillation during the purification process.

[0060] As a specific embodiment of the present application, when compound 2 is difluoroethanol, trifluoroethanol, trifluoropropanol, tetrafluoropropanol, hexafluoroisopropanol, hexafluorobutanol or octafluoropentanol, the molar ratio of compound 1 to compound 2 can be about 5 to 10:1. Excessive raw materials can promote the conversion rate of high-priced fluorinated alcohols and effectively reduce production costs. Excessive cheap raw materials hexafluoropropylene dimer can be recovered and reused by distillation during the purification process.

[0061] When compound 2 is methanol and the catalyst is an inorganic alkaline composite catalyst, the molar ratio of compound 1 to the alkaline compound in the inorganic alkaline composite catalyst can be approximately 1:1 to 1.6, specifically 1:1, 1:1.2 or 1:1.5. When compound 2 is methanol and the catalyst is an organic alkaline catalyst, the molar ratio of compound 1 to the organic alkaline catalyst can be approximately 1:0.01 to 0.1, specifically 1:0.01, 1:0.05 or 1:0.1. When compound 2 is difluoroethanol, trifluoroethanol, trifluoropropanol, tetrafluoropropanol, hexafluoroisopropanol, hexafluorobutanol or octafluoropentanol, and the catalyst is an inorganic alkaline composite catalyst, the molar ratio of compound 2 to the alkaline compound in the inorganic alkaline composite catalyst can be approximately 1:1 to 1.6, specifically 1:1, 1:1.2 or 1:1.5. When compound 2 is difluoroethanol, trifluoroethanol, trifluoropropanol, tetrafluoropropanol, hexafluoroisopropanol, hexafluorobutanol or octafluoropentanol, and the catalyst is an organic basic catalyst, the molar ratio of compound 2 to the organic basic catalyst can be approximately 1:0.01 to 0.1, specifically 1:0.01, 1:0.05 or 1:0.1.

[0062] As a specific embodiment of the present application, when the catalyst is an inorganic alkaline composite catalyst, the amount of the catalyst can be limited in the following manner when preparing the hydrofluoroolefin ether compounds of structures 1 to 8:

[0063] In some specific embodiments, the method for limiting the amount of catalyst used when preparing the compound of structure 1 can be: ① The molar ratio of KOH and benzyltrimethylammonium chloride is 1:1:0.01,② The molar ratio of KOH and trimethyloctadecylammonium bromide is 1:1.2:0.05, ③ The molar ratio of KOH and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1,④ The molar ratio of KF and benzyltrimethylammonium chloride is 1:1:0.01; ⑤ The molar ratio of KF and trimethyloctadecylammonium bromide is 1:1.2:0.05;⑥ The molar ratio of KF and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1;

[0064] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 2 can be limited as follows: ① the molar ratio of difluoroethanol, KF and benzyltrimethylammonium chloride is 1:1:0.01; ② the molar ratio of difluoroethanol, KF and trimethyloctadecylammonium bromide is 1:1.2:0.05; ③ the molar ratio of difluoroethanol, KF and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1;

[0065] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 3 can be limited as follows: ① the molar ratio of trifluoroethanol, KOH and benzyltrimethylammonium chloride is 1:1:0.01; ② the molar ratio of trifluoroethanol, KOH and trimethyloctadecylammonium bromide is 1:1.2:0.05; ③ the molar ratio of trifluoroethanol, KOH and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1;

[0066] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 4 can be limited as follows: ① the molar ratio of trifluoropropanol, KF and benzyltrimethylammonium chloride is 1:1:0.01; ② the molar ratio of trifluoropropanol, KF and trimethyloctadecylammonium bromide is 1:1.3:0.05; ③ the molar ratio of trifluoropropanol, KF and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1;

[0067] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 5 can be limited as follows: ① the molar ratio of tetrafluoropropanol, KOH and benzyltrimethylammonium chloride is 1:1:0.01; ② the molar ratio of tetrafluoropropanol, KOH and trimethyloctadecylammonium bromide is 1:1.3:0.05; ③ the molar ratio of tetrafluoropropanol, KOH and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1;

[0068] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 6 can be limited as follows: ① the molar ratio of hexafluoroisopropanol, KOH and benzyltrimethylammonium chloride is 1:1:0.01; ② the molar ratio of hexafluoroisopropanol, KOH and trimethyloctadecylammonium bromide is 1:1.2:0.05; ③ the molar ratio of hexafluoroisopropanol, KOH and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1;

[0069] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 7 can be limited as follows: ① the molar ratio of hexafluorobutanol, KF and benzyltrimethylammonium chloride is 1:1:0.01; ② the molar ratio of hexafluorobutanol, KF and trimethyloctadecylammonium bromide is 1:1.3:0.05; ③ the molar ratio of hexafluorobutanol, KF and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1;

[0070] In some specific embodiments, the amount of catalyst used in preparing the compound of structure 8 can be limited as follows: ① the molar ratio of octafluoropentanol, KF and benzyltrimethylammonium chloride is 1:1:0.01; ② the molar ratio of octafluoropentanol, KF and trimethyloctadecylammonium bromide is 1:1.3:0.05; ③ the molar ratio of octafluoropentanol, KOH and benzyldimethylhexadecylammonium chloride is 1:1.5:0.1.

[0071] As a specific embodiment of the present application, when the catalyst is an organic alkaline catalyst, the amount of the catalyst used in preparing the hydrofluoroolefin ether compounds of structures 1 to 8 can be limited in the following manner:

[0072] In some specific embodiments, the method for limiting the amount of catalyst used when preparing the compound of structure 1 can be: ① The molar ratio of triethylamine is 1:0.01;② The molar ratio of triethylamine is 1:0.05; ③ The molar ratio of triethylamine is 1:0.1;

[0073] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 2 can be limited in the following manner: ① the molar ratio of difluoroethanol to triethylamine is 1:0.01; ② the molar ratio of difluoroethanol to triethylamine is 1:0.05; ③ the molar ratio of difluoroethanol to triethylamine is 1:0.1;

[0074] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 5 can be limited as follows: ① the molar ratio of tetrafluoropropanol to pyridine is 1:0.01; ② the molar ratio of tetrafluoropropanol to pyridine is 1:0.05; ③ the molar ratio of tetrafluoropropanol to pyridine is 1:0.1;

[0075] In some specific embodiments, the amount of the catalyst used in preparing the compound of structure 7 can be limited as follows: ① the molar ratio of hexafluorobutanol to 4-dimethylaminopyridine is 1:0.01; ② the molar ratio of hexafluorobutanol to 4-dimethylaminopyridine is 1:0.05; ③ the molar ratio of hexafluorobutanol to 4-dimethylaminopyridine is 1:0.1;

[0076] In some specific embodiments, the amount of catalyst used in preparing the compound of structure 8 can be limited as follows: ① the molar ratio of octafluoropentanol to 4-dimethylaminopyridine is 1:0.01; ② the molar ratio of octafluoropentanol to 4-dimethylaminopyridine is 1:0.05; ③ the molar ratio of octafluoropentanol to 4-dimethylaminopyridine is 1:0.1.

[0077] As a specific embodiment of the present application, the temperature of the elimination substitution reaction can be about 25 to 80°C, or about 30 to 70°C, or about 40 to 60°C; the time of the elimination substitution reaction can be about 4 to 12 hours, or about 6 to 10 hours. The present application can select appropriate reaction conditions according to the different alcohols and catalyst systems selected.

[0078] As a specific implementation of the present application, the equation for the elimination substitution reaction is:

[0079]

[0080] When performing the elimination substitution reaction in the present application, a pressure-resistant reactor or a glass reaction bottle (with a condensation reflux device) can be selected. When a glass reaction bottle is used, condensation water below 20° C. can be used for condensation reflux. Selecting appropriate condensation reflux conditions can save energy and reduce consumption, and can also prevent the reaction raw materials from volatilizing out of the reaction system before the reaction is complete, which can promote the reaction conversion rate.

[0081] The present application reduces the generation of by-products by controlling the feed ratio of raw materials, and the excess raw materials can be recycled, so that the yield of the target product can reach up to 95.5%, effectively reducing the production cost.

[0082] As a specific embodiment of the present application, when the catalyst is an inorganic alkaline composite catalyst and the polar solvent is water, the elimination substitution reaction may further include:

[0083] Distilling the system after the elimination substitution reaction to obtain a distillate and a solid;

[0084] The distillate is allowed to stand for separation to obtain a mixed solution of excess reactants and polar solvents and a crude hydrofluoroolefin ether compound;

[0085] Mixing the crude hydrofluoroolefin ether compound with water and washing the separated liquid to obtain a hydrofluoroolefin ether compound;

[0086] The mixed solution of the excess reactant and the polar solvent is separated to obtain the excess reactant and the polar solvent respectively.

[0087] The present application has no special requirements for the distillation, and the conventional method in the art can be used. In the present application, the solid obtained by distillation is a catalyst, and the present application first separates and removes the catalyst through distillation.

[0088] As a specific implementation of the present application, the steps of mixing the crude hydrofluoroolefin ether compound with water and then washing and separating the liquids may be repeated, and the number of repetitions may be about 2 to 3 times.

[0089] As a specific embodiment of the present application, when the catalyst is an inorganic alkaline composite catalyst and the polar solvent is a polar solvent other than water, the elimination substitution reaction may further include:

[0090] Distilling the system after the elimination substitution reaction to obtain a distillate and a solid;

[0091] The distillate is subjected to rectification to obtain a mixed solution of excess reactants and polar solvents and a crude hydrofluoroolefin ether compound;

[0092] Mixing the crude hydrofluoroolefin ether compound with water and washing the separated liquid to obtain a hydrofluoroolefin ether compound;

[0093] The mixed solution of the excess reactant and the polar solvent is separated to obtain the excess reactant and the polar solvent respectively.

[0094] The present application has no special requirements for the rectification and distillation, and conventional methods in the art can be used. In the present application, the solid obtained by distillation is a catalyst, and the present application first separates and removes the catalyst through distillation.

[0095] As a specific implementation of the present application, the steps of mixing the crude hydrofluoroolefin ether compound with water and then washing and separating the liquids may be repeated, and the number of repetitions may be about 2 to 3 times.

[0096] The present application has no special requirements on the method of separating the mixture of excess reactants and polar solvents, and conventional methods in the art can be used.

[0097] As a specific embodiment of the present application, when the catalyst is an organic alkaline catalyst, the elimination substitution reaction may further include:

[0098] The system after the elimination substitution reaction is distilled to obtain a mixed solution of excess reactants and polar solvents and a mixed solution of hydrofluoroolefin ether compounds and organic alkaline catalysts;

[0099] The crude hydrofluoroolefin ether compound and the organic alkaline catalyst are mixed with water, and then washed and separated to obtain the hydrofluoroolefin ether compound;

[0100] The mixed solution of the excess reactant and the polar solvent is separated to obtain the excess reactant and the polar solvent respectively.

[0101] The present application has no special requirements for the distillation, and conventional methods in the art may be used.

[0102] As a specific implementation of the present application, the steps of mixing the mixed solution of the hydrofluoroolefin ether compound and the organic alkaline catalyst with water and then washing and separating the mixture may be repeated about 2 to 3 times.

[0103] The present application has no special requirements on the method of separating the mixture of excess reactants and polar solvents, and conventional methods in the art can be used.

[0104] The present application also provides the use of the hydrofluoroolefin ether compound described in the above technical solution or the hydrofluoroolefin ether compound prepared by the preparation method described in the above technical solution as a temperature control medium. As a specific implementation scheme of the present application, the fields where the hydrofluoroolefin ether compound is used as a temperature control medium include direct contact immersion thermal management of batteries, new energy charging equipment, temperature control devices in semiconductor manufacturing and testing processes, or immersion liquid cooling systems in server data centers.

[0105] An embodiment of the present application also provides an immersion liquid cooling system, including a liquid cooling medium and a heat source immersed in the liquid cooling medium; the liquid cooling medium is the hydrofluoroolefin ether compound described in the above technical solution or the hydrofluoroolefin ether compound prepared by the preparation method described in the above technical solution.

[0106] As a specific implementation of the present application, the heat source may include a CPU, a graphics card, a memory chip, a power transformer, a capacitor, a resistor, an inductor, a diode, a transistor or a cable; when the heat source is a CPU, a graphics card, a memory chip, a power transformer, a capacitor, a resistor, an inductor, a diode or a transistor, the immersion liquid cooling system may be an immersion liquid cooling system for a server data center; when the heat source is a cable, the immersion liquid cooling system may be an immersion liquid cooling system for a charging gun line in a new energy charging device.

[0107] In order to further illustrate the present application, the technical solutions provided by the present application are described in detail below in combination with embodiments, but they should not be construed as limiting the protection scope of the present application.

[0108] In the embodiment, there is The hexafluoropropylene dimer of this structure is referred to as D2.

[0109] Example 1

[0110] Preparation of compound (CF3)2C=C(OCH3)CF2CF3 of structure 1

[0111] In a 10L 316 stainless steel reactor equipped with a dripping device, deionized water and an inorganic alkaline composite catalyst (KOH and alkyl ammonium halide) were added, stirred and mixed at room temperature (30°C) for 1h, and then hexafluoropropylene dimer was added. 1500g, then use a dropping funnel to drop methanol into the mixed solution, control the dropping rate to 60min to complete the dropping. After the dropping is completed, control the reaction conditions: continue stirring at 25-80℃ to eliminate the substitution reaction for 4-12h; directly distill after the elimination substitution reaction is completed, distill out all liquid substances, the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; the distilled fraction is divided into two layers, the lower organic phase is the product phase, the product phase is washed with water three times, and the liquid is separated again to collect the target product (recorded as a crude product): structure 1 compound; the upper aqueous phase is a mixed solution phase of excess raw material methanol and water, and the raw material methanol can be distilled and recovered.

[0112] The crude product was analyzed by gas chromatography (GC), and the content of the target product (compound of structure 1) is shown in Table 1. The yield of the target product (compound of structure 1) was calculated. The collected crude product was subjected to rectification and purification to obtain a high-purity target product (compound of structure 1), and the gas chromatography purity is shown in Table 1.

[0113] Table 1 Parameters of the relevant schemes of Example 1

[0114]

[0115] Example 2

[0116] Preparation of compound (CF3)2C=C(OCH3)CF2CF3 of structure 1

[0117] In a 10L 316 stainless steel reactor equipped with a dripping device, add acetonitrile solvent and inorganic alkaline composite catalyst (KF and alkyl ammonium halide), stir and mix at room temperature (30°C) for 1h, and then add hexafluoropropylene dimer 1500g, then methanol is added dropwise to the mixed solution with a dropping funnel, and the dropping rate is controlled to be 60min. After the dropwise addition is completed, the reaction conditions are controlled: 25℃~80℃ continue to stir and eliminate the substitution reaction for 4~12h; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; the distilled fraction is distilled and purified again, and the first fraction is the raw material methanol-acetonitrile solvent layer, which can be recycled and reused; the bottom liquid is the product layer, the product layer is washed with water three times, and the liquid is separated again, and the lower organic phase-target product (recorded as crude product) is collected: structure 1 compound. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 1 compound) is shown in Table 2. Calculate the yield of the target product (structure 1 compound). The crude product is distilled and purified to obtain a high-purity target product (structure 1 compound), and the gas chromatographic purity is shown in Table 2.

[0118] Table 2 Parameters of the relevant schemes of Example 2

[0119]

[0120] Example 3

[0121] Preparation of structure 3 compound (CF3)2C=C(OCH2CF3)CF2CF3

[0122] In a 10L 316 stainless steel reactor equipped with a dripping device, add solvent water, inorganic alkaline composite catalyst (KOH and alkyl ammonium halide), stir and mix at room temperature (30°C) for 1h, and then add hexafluoropropylene dimer The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 2,2,2-trifluoroethanol (200g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60min. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 25℃ to 80℃ to eliminate the substitution reaction for 4 to 12h; after the catalysis is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; all the distilled liquid substances are distilled and purified again, and the first fraction is hexafluoropropylene dimer -Water solvent layer, can recover and extract excess hexafluoropropylene dimer Reuse; the bottom liquid is the product layer, the product layer is washed with water three times, separated again, and the lower organic phase - the target product (recorded as a crude product): structure 3 compound is collected. The crude product obtained is analyzed by gas chromatography (GC), and the content of the target product (structure 3 compound) is shown in Table 3. The yield of the target product (structure 3 compound) is calculated. The product phase is distilled and purified to obtain a high-purity target product (structure 3 compound), and the gas chromatography purity is shown in Table 3.

[0123] Table 3 Parameters of the relevant schemes of Example 3

[0124]

[0125] Example 4

[0126] Preparation of compound (CF3)2C=C(OCH2CF2H)CF2CF3 of structure 2

[0127] In a 10L 316 stainless steel reactor equipped with a dripping device, solvent dichloromethane (DCM) and inorganic alkaline composite catalyst (KF and alkyl ammonium halide) were added, stirred and mixed at room temperature (30°C) for 1h, and then hexafluoropropylene dimer was added. The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 2,2-difluoroethanol (164 g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60 minutes. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 25°C to 80°C to eliminate the substitution reaction for 4 to 12 hours; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; all the distilled liquid substances are distilled and purified again, and the first fraction is hexafluoropropylene dimer -DCM solvent layer, can be used to recover and extract excess hexafluoropropylene dimer and solvent DCM for reuse; the bottom liquid is the product layer, the product layer is washed with water three times, separated again, and the lower organic phase - the target product (recorded as a crude product): structure 2 compound is collected. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 2 compound) is shown in Table 4. The yield of the target product (structure 2 compound) is calculated. The product phase is distilled and purified to obtain a high-purity target product (structure 2 compound), and the gas chromatography purity is shown in Table 4.

[0128] Table 4 Parameters of the relevant schemes of Example 4

[0129]

[0130] Example 5

[0131] Preparation of structure 4 compound (CF3)2C=C(OCH2CH2CF3)CF2CF3

[0132] In a 10L 316 stainless steel reactor equipped with a dripping device, add acetonitrile solvent and inorganic alkaline composite catalyst (KF and alkyl ammonium halide), stir and mix at room temperature (30°C) for 1h, and then add hexafluoropropylene dimer The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 3,3,3-trifluoropropanol (228 g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60 minutes. After the dropwise addition is completed, the reaction conditions are controlled: 25°C to 80°C and the catalytic stirring is continued for 4 to 12 hours; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; all the distilled liquid substances are distilled and purified again, and the first fraction is hexafluoropropylene dimer -Acetonitrile solvent layer, can be used to recover and extract excess hexafluoropropylene dimer and the solvent acetonitrile for reuse; the bottom liquid is the product layer, the product layer is washed with water three times, separated again, and the lower organic phase - the target product (recorded as a crude product): structure 4 compound is collected. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 4 compound) is shown in Table 5. The yield of the target product (structure 4 compound) is calculated. The product phase is distilled and purified to obtain a high-purity target product (structure 4 compound), and the gas chromatography purity is shown in Table 5.

[0133] Table 5 Parameters of the relevant schemes of Example 5

[0134]

[0135] Example 6

[0136] Preparation of structure 5 compound (CF3)2C=C(OCH2CF2CF2H)CF2CF3

[0137] In a 10L 316 stainless steel reactor equipped with a dripping device, add solvent water, inorganic alkaline composite catalyst (KOH and alkyl ammonium halide), stir and mix at room temperature (30°C) for 1h, and then add hexafluoropropylene dimer The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 2,2,3,3-tetrafluoropropanol (264g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60min. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 25℃ to 80℃ to eliminate the substitution reaction for 4 to 12h; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; all the distilled liquid substances are distilled and purified again, and the first fraction is hexafluoropropylene dimer -Water solvent layer, can recover and extract excess hexafluoropropylene dimer Reuse; the bottom liquid is the product layer, the product layer is washed with water three times, separated again, and the lower organic phase - the target product (recorded as a crude product): structure 5 compound is collected. The crude product obtained is analyzed by gas chromatography (GC), and the content of the target product (structure 5 compound) is shown in Table 6. The yield of the target product (structure 5 compound) is calculated. The product phase is distilled and purified to obtain a high-purity target product (structure 5 compound), and the gas chromatography purity is shown in Table 6.

[0138] Table 6 Parameters of the relevant schemes of Example 6

[0139]

[0140] Example 7

[0141] Preparation of structure 6 compound (CF3)2C=C(OCH(CF3)2)CF2CF3

[0142] In a 10L 316 stainless steel reactor equipped with a dripping device, add solvent water, inorganic alkaline composite catalyst (KOH and alkyl ammonium halide), stir and mix at room temperature (30°C) for 1h, and then add hexafluoropropylene dimer The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 1,1,1,3,3,3-hexafluoro-2-propanol (336g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60min. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 25℃~80℃ to eliminate the substitution reaction for 4 to 12h; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; all the distilled liquid substances are distilled and purified again, and the first fraction is hexafluoropropylene dimer -Water solvent layer, can recover and extract excess hexafluoropropylene dimer Reuse; the bottom liquid is the product layer, the product layer is washed with water three times, separated again, and the lower organic phase - the target product (recorded as a crude product): structure 6 compound is collected. The crude product obtained is analyzed by gas chromatography (GC), and the content of the target product (structure 6 compound) is shown in Table 7. The yield of the target product (structure 6 compound) is calculated. The product phase is distilled and purified to obtain a high-purity target product (structure 6 compound), and the gas chromatography purity is shown in Table 7.

[0143] Table 7 Parameters of the relevant schemes of Example 7

[0144]

[0145] Example 8

[0146] Preparation of structure 7 compound (CF3)2C=C(OCH2CF2CHFCF3)CF2CF3

[0147] In a 10L 316 stainless steel reactor equipped with a dripping device, add acetonitrile solvent and inorganic alkaline composite catalyst (KF and alkyl ammonium halide), stir and mix at room temperature (30°C) for 1h, and then add hexafluoropropylene dimer The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 2,2,3,4,4,4-hexafluoro-1-butanol (364g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60min. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 50℃ to 80℃ to eliminate the substitution reaction for 8 to 12h; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; all the distilled liquid substances are distilled and purified again, and the first fraction is hexafluoropropylene dimer -Acetonitrile solvent layer, can be used to recover and extract excess hexafluoropropylene dimer and the solvent acetonitrile for reuse; the bottom liquid is the product layer, the product layer is washed with water three times, separated again, and the lower organic phase - the target product (recorded as the crude product): structure 7 compound is collected. The crude product obtained is analyzed by gas chromatography (GC), and the content of the target product (structure 7 compound) is shown in Table 8. The yield of the target product (structure 7 compound) is calculated. The product phase is distilled and purified to obtain a high-purity target product (structure 7 compound), and the gas chromatography purity is shown in Table 8.

[0148] Table 8 Parameters of the relevant schemes of Example 8

[0149]

[0150] Example 9

[0151] Preparation of structure 8 compound (CF3)2C=C(OCH2CF2CF2CF2CHF2)CF2CF3

[0152] In a 10L 316 stainless steel reactor equipped with a dripping device, add acetonitrile solvent and inorganic alkaline composite catalyst (KF and alkyl ammonium halide), stir and mix at room temperature (30°C) for 1h, and then add hexafluoropropylene dimer The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (464g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60min. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 50℃ to 80℃ to eliminate the substitution reaction for 8 to 12h; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused; all the distilled liquid substances are distilled and purified again, and the first fraction is hexafluoropropylene dimer -Acetonitrile solvent layer, can be used to recover and extract excess hexafluoropropylene dimer and the solvent acetonitrile for reuse; the bottom liquid is the product layer, the product layer is washed with water three times, separated again, and the lower organic phase - the target product (recorded as the crude product): the compound of structure 8 is collected. The crude product obtained is analyzed by gas chromatography (GC), and the content of the target product (compound of structure 8) is shown in Table 9. The yield of the target product (compound of structure 8) is calculated. The product phase is distilled and purified to obtain a high-purity target product (compound of structure 8), and the gas chromatography purity is shown in Table 9.

[0153] Table 9 Parameters of the relevant schemes of Example 9

[0154]

[0155] Example 10

[0156] Preparation of compound (CF3)2C=C(OCH3)CF2CF3 of structure 1

[0157] In a 10L 316 stainless steel reactor equipped with a dripping device, methyl tert-butyl ether (MTBE) solvent and 4-dimethylaminopyridine as an organic alkaline catalyst were added, stirred and mixed at room temperature (30°C) for 1h, and then hexafluoropropylene dimer was added. 1500g, then use a dropping funnel to drop methanol into the substrate, control the dropping rate to 60min to complete the dropping. After the dropwise addition is completed, control the reaction conditions: continue stirring at 25℃~80℃ to eliminate the substitution reaction for 4~12h; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out the excess methanol and solvent MTBE for recycling; the bottom liquid organic phase is the product phase, the product phase is washed with water three times, separated again, and the target product (recorded as crude product) is collected: structure 1 compound. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 1 compound) is shown in Table 10. Calculate the yield of the target product (structure 1 compound). The organic product phase is distilled and purified to obtain a high-purity target product (structure 1 compound), and the gas chromatographic purity is shown in Table 10.

[0158] Table 10 Parameters of the relevant schemes of Example 10

[0159]

[0160] Embodiment 11

[0161] Preparation of compound (CF3)2C=C(OCH3)CF2CF3 of structure 1

[0162] In a 10L 316 stainless steel reactor equipped with a dripping device, dichloromethane (DCM) solvent and triethylamine as an organic alkaline catalyst were added as a substrate, stirred and mixed at room temperature (30°C) for 1h, and then hexafluoropropylene dimer was added. 1500g, then methanol is added dropwise to the substrate using a dropping funnel, and the dropping rate is controlled to be 60min. After the dropwise addition is completed, the reaction conditions are controlled: 25℃~80℃ continue to stir and eliminate the substitution reaction for 4~12h; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out the excess methanol and solvent DCM for recycling; the bottom liquid organic phase is the product phase, the product phase is washed with water three times, and the liquid is separated again to collect the target product (recorded as crude product): structure 1 compound. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 1 compound) is shown in Table 11. Calculate the yield of the target product (structure 1 compound). The organic product phase is distilled and purified to obtain a high-purity target product (structure 1 compound), and the gas chromatographic purity is shown in Table 11.

[0163] Table 11 Parameters of the relevant schemes of Example 11

[0164]

[0165] Example 12

[0166] Preparation of compound (CF3)2C=C(OCH2CHF2)CF2CF3 of structure 2

[0167] In a 10L 316 stainless steel reactor equipped with a dripping device, dichloromethane (DCM) solvent and triethylamine as an organic alkaline catalyst were added as a substrate, stirred and mixed at room temperature (30°C) for 1h, and then hexafluoropropylene dimer was added. The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 164 g of 2,2-difluoroethanol is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60 minutes. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 25°C to 80°C to eliminate the substitution reaction for 4 to 12 hours; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out the excess hexafluoropropylene dimer and solvent DCM for recycling; the bottom liquid organic phase is the product phase, the product phase is washed with water three times, separated again, and the target product (recorded as crude product) is collected: structure 2 compound. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 2 compound) is shown in Table 12. The yield of the target product (structure 2 compound) is calculated. The organic product phase is distilled and purified to obtain a high-purity target product (structure 2 compound), and the gas chromatography purity is shown in Table 12.

[0168] Table 12 Parameters of the relevant schemes of Example 12

[0169]

[0170] Example 13

[0171] Preparation of structure 5 compound (CF3)2C=C(OCH2CF2CF2H)CF2CF3

[0172] In a 10L 316 stainless steel reactor equipped with a dripping device, 3L of dichloroethane (DCM) solvent and pyridine as an organic alkaline catalyst were added, stirred and mixed at room temperature (30°C) for 1h, and then hexafluoropropylene dimer was added. The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 264 g of 2,2,3,3-tetrafluoro-1-propanol is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60 minutes. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 25°C to 80°C to eliminate the substitution reaction for 4 to 12 hours; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out the excess hexafluoropropylene dimer and solvent dichloroethane for recycling; the bottom liquid organic phase is the product phase, the product phase is washed with water three times, separated again, and the target product (recorded as crude product) is collected: structure 5 compound. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 5 compound) is shown in Table 13. The yield of the target product (structure 5 compound) is calculated. The organic product phase is distilled and purified to obtain a high-purity target product (structure 5 compound), and the gas chromatography purity is shown in Table 13.

[0173] Table 13 Parameters of the relevant schemes of Example 13

[0174]

[0175] Embodiment 14

[0176] Preparation of structure 7 compound (CF3)2C=C(OCH2CF2CHFCF3)CF2CF3

[0177] In a 10L 316 stainless steel reactor equipped with a dripping device, 3L of acetonitrile solvent and 4-dimethylaminopyridine as an organic alkaline catalyst were added, stirred and mixed at room temperature (30°C) for 1h, and then hexafluoropropylene dimer was added. The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 2,2,3,4,4,4-hexafluoro-1-butanol (364 g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60 minutes. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 50°C to 80°C to eliminate the substitution reaction for 8 to 12 hours; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out the excess hexafluoropropylene dimer and solvent acetonitrile for recycling; the bottom liquid organic phase is the product phase, the product phase is washed with water three times, separated again, and the target product (recorded as crude product) is collected: structure 7 compound. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 7 compound) is shown in Table 14. The yield of the target product (structure 7 compound) is calculated. The organic product phase is distilled and purified to obtain a high-purity target product (structure 7 compound), and the gas chromatography purity is shown in Table 14.

[0178] Table 14 Parameters of the relevant schemes of Example 14

[0179]

[0180] Embodiment 15

[0181] Preparation of structure 8 compound (CF3)2C=C(OCH2CF2CF2CF2CHF2)CF2CF3

[0182] In a 10L 316 stainless steel reactor equipped with a dripping device, 3L of acetonitrile solvent and 4-dimethylaminopyridine as an organic alkaline catalyst were added, stirred and mixed at room temperature (30°C) for 1h, and then hexafluoropropylene dimer was added. The amount of addition is 5 to 10 times the molar amount of the fluorinated alcohol, and then 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (464 g) is added to the substrate using a dropping funnel, and the dropping rate is controlled to be 60 minutes. After the dropwise addition is completed, the reaction conditions are controlled: stirring is continued at 50°C to 80°C to eliminate the substitution reaction for 8 to 12 hours; after the elimination substitution reaction is completed, the reaction liquid is directly distilled to distill out the excess hexafluoropropylene dimer and solvent acetonitrile for recycling; the bottom liquid organic phase is the product phase, the product phase is washed with water three times, separated again, and the target product (recorded as crude product) is collected: structure 8 compound. The crude product received is analyzed by gas chromatography (GC), and the content of the target product (structure 8 compound) is shown in Table 15. The yield of the target product (structure 8 compound) is calculated. The organic product phase is distilled and purified to obtain a high-purity target product (structure 8 compound), and the gas chromatography purity is shown in Table 15.

[0183] Table 15 Parameters of the relevant schemes of Example 15

[0184]

[0185]

[0186] The product with the highest purity among the target products (compounds of structures 1 to 8) after distillation and purification in the above Examples 1 to 15 was dried and then subjected to physical property tests, and the results are listed in Table 16. The boiling point test was carried out in accordance with the national standard, GB / T616-2006 "General method for determination of boiling point of chemical reagents"; the flash point test was carried out in accordance with the national standard, GB / T261-2021 "Flash point-Pinsky-Martin closed cup method"; the breakdown voltage test was carried out in accordance with the national standard: GB / T1408.1-2006 "Electrical strength test method for insulating materials"; the volume resistivity test was carried out in accordance with the national standard: GB / T5654-2007 "Measurement of relative permittivity, dielectric loss factor and DC resistivity of liquid insulating materials". Thermal conductivity is measured in accordance with the Transient Hot Wire Method, with reference to standard ASTM D7896. Specific heat capacity is measured and calculated in accordance with the definition formula for specific heat capacity: Q = Cp·m·δt, where Cp represents specific heat capacity, Q represents the amount of heat absorbed or released, m represents the mass of the substance, and δt represents the temperature change. Kinematic viscosity is measured in accordance with national standard GB / T 265-88 Determination of kinematic viscosity of petroleum products.

[0187] Definition: ODP value (Ozone Depletion Potential), also known as ozone depletion potential or ozone depletion potential value, refers to the ratio of the total amount of ozone change caused by a certain gas in the atmosphere to the total amount of ozone change caused by a unit mass of trichlorofluoromethane in the atmosphere. This ratio is used to measure the ability of chemical substances to destroy the stratospheric ozone layer. The compounds of structure 1 to structure 8 of the present application do not contain chlorine or bromine elements, and there is no risk of depletion of the ozone layer during degradation.

[0188] Definition: GWP value, Global Warming Potential (GWP) is an indicator used to measure the potential impact of greenhouse gases on global warming. It is based on the radiation characteristics of fully mixed greenhouse gases and is used to compare the impact of different greenhouse gases on global warming. GWP takes carbon dioxide as a benchmark and compares the greenhouse effect of other greenhouse gases with the greenhouse effect of carbon dioxide. The higher the GWP value, the stronger the greenhouse effect of the gas and the greater its potential contribution to global warming. IPCC defines GWP (Global Warming Potential) as the ratio of the integral of the radiative forcing caused by the instantaneous pulse emission of 1kg of chemical substance x within a certain time range to the integral of the radiative forcing caused by the emission of the same amount of reference gas (CO2) under the same conditions within the same time range, that is:

[0189]

[0190] x(t)=e -t / τ ;

[0191]

[0192] Where TH is the time horizon (e.g., 20, 100, and 500 years), 100 years is taken in this study; t represents time;

[0193] RFx and RFr represent the radiative forcing of compound x and reference gas CO2, respectively; a x and a r They represent the corresponding radiation efficiency respectively; x(t) and r(t) represent the time response function of compound x and reference gas respectively; τ is the atmospheric lifetime, unit is a; the atmospheric response function r(t) of reference compound CO2 is the latest formula published by IPCC in 2007, with parameters a0, a i , τi is a constant published by IPCC.

[0194] Table 16 Physical properties of compounds of structures 1 to 8 prepared in Examples 1 to 15

[0195]

[0196] It can be seen from Table 16 that the boiling points of compounds of structures 1 to 8 are 96 to 176°C, all have no flash point, breakdown voltage>25KV, and volume resistivity>10 10 Ω·cm, ODP value is 0, GWP value is <100; it has excellent properties, adapts to a wide temperature range, has no flash point and is not easy to burn, and even has a fire extinguishing effect, without any fire hazards; it has excellent insulation performance and good material compatibility, and has natural advantages in some scenarios requiring insulation.

[0197] Compounds of structures 1 to 8 can be used as low-temperature constant temperature bath fluid media, low-temperature circulating pump fluid media, industrial refrigeration machine fluid media, high-temperature integrated machine fluid media, high-temperature circulating pump fluid media, semiconductor test temperature control liquid, liquid-cooled charging pile coolant, lithium battery energy storage temperature control liquid, high-temperature thermal conductive medium and other scenarios.

[0198] Example 16

[0199] In the above Examples 1 to 15, the compounds of structures 1 to 8 were selected from the highest purity after distillation and purification for material compatibility testing. The testing method is: 50 mL of the compounds of structures 1 to 8 after distillation and purification were measured and placed in a stainless steel hydrothermal reactor with a volume of 100 mL, and then various types of materials were added to perform room temperature immersion tests at 25°C / 168h and high temperature immersion tests at 100°C / 168h. The criteria for judging compatibility are as follows:

[0200] ☆-Excellent compatibility, almost no change in appearance, quality and volume;

[0201] ○-Good compatibility, no change in appearance, quality and volume changes ≤1%;

[0202] □-Basically compatible, no change in appearance, and changes in mass and volume within 1-3%;

[0203] △-Incompatible, the appearance has changed significantly, and the mass or volume has also changed, and the mass or volume change is greater than 3%;

[0204] ×-Not carried out, the material itself cannot withstand high temperature of 100℃ for a long time.

[0205] Compatibility test data are shown in Table 17 and Table 18

[0206] Table 17 Compatibility test results of room temperature immersion test 25℃ / 168h

[0207]

[0208] Table 18 Compatibility test results of high temperature immersion test 100℃ / 168h

[0209]

[0210]

[0211] From the data recorded in Tables 17 to 18, it can be seen that the compounds of structures 1 to 8 have excellent material compatibility, have a slight swelling effect on silicone rubber seals, and have slightly poor compatibility with fluororubber seals.

[0212] The application scenarios of the hydrofluoroolefin temperature control fluid provided in this application are as follows:

[0213] Application scenario 1: Battery direct contact immersion thermal management

[0214] The hydrofluoroolefin compounds provided in the present application can be used as a thermal management system in an electrochemical cell (e.g., a lithium-ion battery). In an energy storage system, the energy storage cell is directly immersed in a coolant to completely isolate the cell from air, moisture, etc., so as to control the operating temperature of the energy storage battery system and achieve thermal management, and at the same time to prevent catastrophic failures of thermal runaway under certain conditions. Thermal runaway is a series of internal exothermic reactions triggered by heat, and the generation of excess heat can come from overcharging, overheating, or from an internal electrical short circuit.

[0215] Application scenario 2: New energy charging equipment scenario

[0216] The hydrofluoroolefin compounds provided in this application can be used as thermal management liquid working fluids in new energy charging equipment (such as charging guns and their coolant distribution devices (CDU)). In high-power liquid-cooled charging guns, since large currents (such as 600A and above) generate a lot of heat, it is necessary to drive the flow of liquid working fluids through electronic pumps. When the liquid working fluid passes through the cable (the cable will heat up due to the large current it carries when working), it takes away the heat of the cable and the charging connector, returns to the liquid storage tank (storing the coolant), and then drives the electronic pump through the radiator to dissipate the heat.

[0217] Application scenario 3: Chiller scenario for temperature control device in semiconductor manufacturing and testing process

[0218] The temperature control device Chiller in the semiconductor manufacturing and testing process usually uses a compressor refrigeration and heating cycle to achieve precise temperature control; it monitors the temperature of the object to be cooled or heated in real time through a sensor, and feeds back the temperature signal to the control system. The control system automatically adjusts the refrigeration or heating power according to the set temperature value and the actual temperature value fed back to maintain the temperature stability. In the refrigeration mode, the compressor in the Chiller compresses the refrigerant into a high-temperature and high-pressure gas, and then dissipates the heat through the condenser, turning the refrigerant into a high-pressure liquid. The high-pressure liquid is reduced in pressure by the expansion valve and becomes a low-pressure liquid, which enters the evaporator to evaporate and absorb heat, thereby reducing the temperature of the object to be cooled. In the heating mode, the Chiller increases the temperature of the heated object through an electric heater or other heating methods. According to different temperature requirements, the temperature control equipment should be able to cover a wide range from extremely low temperature to high temperature, such as -92 to 250°C, to meet the manufacturing and testing requirements of different chips. According to the specific requirements of different temperatures, any one of the structural compounds shown in structures 1 to 8 provided by this application with a specific boiling point can be output from the Chiller device as a temperature control medium.

[0219] Application scenario 4: Server data center immersion liquid cooling system

[0220] The hydrofluoroolefin ether compounds provided in the present application can be used as a single-phase immersion liquid cooling system for servers or data centers. The cooling liquid exchanges heat with the hardware heat source of the computer through the transportation flow of the pump, thereby transferring heat away from the server. The liquid working fluid used for single-phase immersion cooling of servers usually has a higher boiling point of more than about 75°C to reduce evaporation losses. The amount of liquid working fluid added is at least enough to completely immerse all heat sources, and the liquid working fluid is in direct contact with the electronic components in the heat source. Figure 1 It is a structural schematic diagram of a single-phase immersion liquid cooling system for a server or data center, wherein 1 is a sealed shell, 11 is a space inside the sealed shell, 2 is a heat source, and 3 is a liquid cooling medium; the heat source 2 may include a CPU, a graphics card, a memory chip, a power transformer, a capacitor, a resistor, an inductor, a diode or a transistor.

[0221] Although the above-mentioned embodiment provides a detailed description of the present application, it is only a part of the embodiments of the present application, not all of the embodiments. People can also obtain other embodiments based on this embodiment without creativity, and these embodiments all fall within the scope of protection of the present application.

Claims

1. A hydrofluoroolefin ether compound, characterized in that: Having the structure shown in Formula I: Among them, Rfa and Rfb are both -CF3, and Rfc is -CF2CF3; Rfh is alkyl or fluoroalkyl.

2. The hydrofluoroolefin ether compound according to claim 1, characterized in that: The alkyl group includes a methyl group; The fluoroalkyl group includes -CH2CHF2, -CH2CF3, -CH2CH2CF3, -CH2CF2CHF2, -CH(CF3)2, -CH2CF2CHFCF3 or -CH2(CF2)3CHF2.

3. The method for preparing the hydrofluoroolefin ether compound according to claim 1 or 2, characterized in that: The following steps are involved: Mixing compound 1, compound 2, a catalyst and a polar solvent, and performing elimination substitution reaction to obtain the hydrofluoroolefin ether compound; The compound 1 has a structure shown in formula a, and the compound 2 has a structure shown in formula b: Rfh-OH formula b; Wherein, Rfh is an alkyl group or a fluoroalkyl group; The catalyst comprises an inorganic alkaline composite catalyst or an organic alkaline catalyst; the inorganic alkaline composite catalyst is an inorganic alkaline compound and an alkyl ammonium halide; the organic alkaline catalyst comprises pyridine, 4-dimethylaminopyridine or triethylamine.

4. The preparation method according to claim 3, characterized in that: The compound 2 includes methanol, difluoroethanol, trifluoroethanol, trifluoropropanol, tetrafluoropropanol, hexafluoroisopropanol, hexafluorobutanol or octafluoropentanol.

5. The preparation method according to claim 4, characterized in that: When compound 2 is methanol, the molar ratio of compound 1 to methanol is 1:5-10; When compound 2 is difluoroethanol, trifluoroethanol, trifluoropropanol, tetrafluoropropanol, hexafluoroisopropanol, hexafluorobutanol or octafluoropentanol, the molar ratio of compound 1 to compound 2 is 5 to 10:

1.

6. The preparation method according to claim 3, characterized in that: The inorganic alkaline compound includes potassium fluoride or potassium hydroxide; the alkyl ammonium halide includes alkyl ammonium chloride or alkyl ammonium bromide; The molar ratio of the inorganic alkaline compound to the alkyl ammonium halide is 1:0.01-0.

1.

7. The preparation method according to claim 3, characterized in that: The polar solvent includes water, acetonitrile, dichloromethane, methyl tert-butyl ether, 1,2-dichloroethane, tetrahydrofuran or dioxane; the temperature of the elimination substitution reaction is 25 to 80° C., and the time is 4 to 12 hours.

8. Use of the hydrofluoroolefin ether compound according to claim 1 or 2 or the hydrofluoroolefin ether compound prepared by the preparation method according to any one of claims 3 to 7 as a temperature control medium.

9. The use according to claim 8, characterized in that: The fields where the hydrofluoroolefin ether compounds are used as temperature control fluids include direct contact immersion thermal management of batteries, new energy charging equipment, temperature control devices during semiconductor manufacturing and testing, or immersion liquid cooling systems in server data centers.

10. An immersion liquid cooling system, characterized in that: It includes a liquid cooling medium and a heat source immersed in the liquid cooling medium; The liquid cooling medium is the hydrofluoroolefin ether compound according to claim 1 or 2 or the hydrofluoroolefin ether compound prepared by the preparation method according to any one of claims 3 to 7.

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