A high-boiling hydrofluoroolefin compound, a preparation method and application thereof

Abstract

The embodiment of the present application provides a high-boiling hydrogen fluoride alkene ether compound and a preparation method and application thereof, relates to the field of fluorine chemical industry and heat management technology. The hydrogen fluoride alkene ether compound provided by the embodiment of the present application has a structure shown in formula I. The hydrogen fluoride alkene ether compound provided by the embodiment of the present application has excellent environmental protection (ODP value is 0, and GWP value is less than 100) and high boiling point (> 150 DEG C), thereby having a wide adaptive temperature range. Moreover, the hydrogen fluoride alkene ether compound has excellent material compatibility, has no corrosiveness to various metals, high polymer materials and glass ceramic materials; has low low-temperature viscosity; has excellent insulation performance and good high-temperature resistance. The hydrogen fluoride alkene ether compound is used as a temperature control working medium, has high efficient temperature control stability advantages, and can achieve the purpose of energy saving and consumption reduction. The embodiment of the present application provides a preparation method of the hydrogen fluoride alkene ether compound, raw materials are easy to obtain, the process is simple, the yield is high, and excellent cost advantages are achieved.

Description

Technical Field

[0001] This application relates to the fields of fluorochemicals and thermal management technology, and in particular to a high-boiling-point hydrofluoroolefin compound, its preparation method, and its application. Background Technology

[0002] Fluorine fluid is a liquid with unique properties. Applications of fluorine fluid include: (1) Industrial applications: Fluorine fluid is mainly used as a heat transfer medium in high-temperature and high-pressure equipment, such as in oil and gas extraction, nuclear power plants, aerospace, and automotive engines; (2) Electronic applications: In the electronics field, fluorine fluid is used in thermostats, heaters, and other thermal control equipment in semiconductor manufacturing processes, as well as cooling systems in high-precision instruments. The main chemical properties of fluorine fluid are: (1) Non-flammability: Fluorine fluid has an extremely high flash point or no flash point, making it non-flammable and suitable for environments requiring fire protection; (2) Chemical corrosion resistance: It can resist corrosion from various chemicals and is suitable for various corrosive environments; (3) Radiation resistance: It can remain stable in radiation environments and is suitable for high-radiation environments such as nuclear facilities; (4) Long lifespan: Due to its stable chemical properties, fluorine fluid has a long service life, reducing the frequency of replacement and maintenance.

[0003] With the continuous development of industry and electronics, the demand for high-performance heat transfer media is constantly increasing. Fluorine fluids, due to their excellent thermal conductivity, chemical stability, and wide applicability, have a very broad market prospect as temperature control working fluids. However, the GWP (Global Warming Potential) value of fluorine fluids is still relatively high, which has an adverse impact on the environment. In addition, the boiling point of fluorine fluids is currently low, generally below 150°C, which limits their application range. Summary of the Invention

[0004] In view of this, the purpose of this application is to provide a high-boiling-point hydrofluoroolefin ether compound, its preparation method, and its application. The hydrofluoroolefin ether compound provided in this application has excellent environmental friendliness (GWP value less than 100), a high boiling point (>150℃), and a wide temperature range, making it an advantageous working fluid for temperature control.

[0005] To achieve the above-mentioned objectives, this application provides the following technical solutions:

[0006] This application provides a high-boiling-point hydrofluoroolefin ether compound having the structure shown in Formula I:

[0007]

[0008] In Formula I, Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, and Rfh is an alkyl or fluoroalkyl group.

[0009] In one specific embodiment of this application, the alkyl group is -CH3 or CH3CH2-, and the fluoroalkyl group is CHF2CH2-, CF3CH2-, CF3CH2CH2-, -CH(CF3)2 or CF3CHFCF2CH2-.

[0010] The high-boiling-point hydrofluoroolefin ether compounds provided in this application possess excellent environmental friendliness (ODP value of 0, GWP value less than 100) and high boiling point (>150℃), thus exhibiting a wide operating temperature range. Furthermore, these hydrofluoroolefin ether compounds demonstrate excellent material compatibility, showing no corrosiveness to various metals, polymers, or glass / ceramic materials; they exhibit low viscosity at low temperatures; and they possess excellent insulation properties and good high-temperature resistance. Using these hydrofluoroolefin ether compounds as temperature control working fluids offers highly efficient temperature control and stability, achieving energy conservation and consumption reduction.

[0011] This application provides a method for preparing the high-boiling-point hydrofluoroolefin ether compounds described in the above technical solutions, including the following steps:

[0012] The high-boiling-point hydrofluoroolefin ether compound was obtained by mixing hexafluoropropylene trimer, alcohol compound, basic catalyst and polar solvent and carrying out elimination substitution reaction.

[0013] The hexafluoropropylene trimer has the structure shown in Formula II; the alcohol compound has the structure shown in Formula III, and is an alcohol or a fluorinated alcohol.

[0014] Rfh-OH formula III.

[0015] In one specific embodiment of this application, the alcohol is methanol or ethanol; the fluorinated alcohol is 2,2-difluoroethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoropropanol, hexafluoroisopropanol or hexafluorobutanol.

[0016] In one specific embodiment of this application, when the alcohol compound is an alcohol, the molar ratio of the alcohol compound to the hexafluoropropylene trimer is 5 to 10:1; when the alcohol compound is a fluorinated alcohol, the molar ratio of the alcohol compound to the hexafluoropropylene trimer is 1:5 to 10.

[0017] As one specific embodiment of this application, the alkaline catalyst is an inorganic alkaline composite catalyst or an organic alkaline catalyst.

[0018] The inorganic alkaline composite catalyst comprises an inorganic alkaline compound and a quaternary ammonium salt, wherein the inorganic alkaline compound is KF or KOH, and the quaternary ammonium salt is an alkyl ammonium chloride or an alkyl ammonium bromide, and the molar ratio of the inorganic alkaline compound to the quaternary ammonium salt is 1:0.01 to 0.1;

[0019] The organic basic catalyst is one or more of pyridine, 4-dimethylaminopyridine, and triethylamine.

[0020] In one specific embodiment of this application, the molar ratio of the alcohol compound to the compound with the smallest molar amount in the hexafluoropropylene trimer and the inorganic alkaline compound in the inorganic alkaline composite catalyst is 1:1 to 1.5; the molar ratio of the alcohol compound to the compound with the smallest molar amount in the hexafluoropropylene trimer and the organic alkaline catalyst is 1:0.01 to 0.1.

[0021] In one specific embodiment of this application, the elimination substitution reaction is carried out at a temperature of 100–150°C for 8–24 hours.

[0022] The preparation method of the high-boiling-point hydrofluoroolefin ether compound provided in this application embodiment uses readily available raw materials, has a simple process, high yield, and excellent cost advantages. Furthermore, by controlling the feed ratio of raw materials, this application embodiment reduces the generation of by-products, and excess raw materials can be recycled, achieving a target product yield of up to 87.14%, effectively reducing production costs.

[0023] This embodiment provides the application of the high-boiling-point hydrofluoroolefin ether compounds described in the above technical solutions or the high-boiling-point hydrofluoroolefin ether compounds prepared by the above technical solutions as temperature control working fluids in temperature control systems.

[0024] This 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 a hydrofluoroolefin ether compound as described in the above technical solution or a hydrofluoroolefin ether compound prepared by the preparation method described in the above technical solution. Attached Figure Description

[0025] Figure 1 This is a schematic diagram of a single-phase immersion liquid cooling system for servers or data centers using hydrofluoroolefin ether compounds as the liquid cooling medium, provided in this application. In the diagram, 1 is a sealed shell, 11 is the space inside the sealed shell, 2 is a heat source, and 3 is the liquid cooling medium. Detailed Implementation

[0026] This application provides a high-boiling-point hydrofluoroolefin ether compound having the structure shown in Formula I:

[0027]

[0028] In Formula I, Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, and Rfh is an alkyl or fluoroalkyl group.

[0029] As one specific embodiment of this application, the alkyl group can be -CH3 or CH3CH2-, and the fluoroalkyl group can be CHF2CH2-, CF3CH2-, CF3CH2CH2-, -CH(CF3)2 or CF3CHFCF2CH2-.

[0030] As a specific embodiment of this application, the high-boiling-point hydrofluoroolefin compound is a compound with any of the following structures:

[0031] Structure 1: Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, Rfh = -CH3;

[0032] Structure 2: Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, Rfh = CH3CH2-;

[0033] Structure 3: Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, Rfh = CHF2CH2-;

[0034] Structure 4: Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, Rfh = CF3CH2-;

[0035] Structure 5: Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, Rfh = CF3CH2CH2-;

[0036] Structure 6: Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, Rfh = -CH(CF3)2;

[0037] Structure 7: Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, Rfh = CF3CHFCF2CH2-.

[0038] The hydrofluoroolefin ether compounds provided in this application have a boiling point of 152–211°C, classifying them as high-boiling-point hydrofluoroolefin ether compounds. They exhibit excellent environmental performance, with an ODP value of 0 and a GWP value of <100. They have no flash point and demonstrate excellent high-temperature resistance and insulation properties, with a breakdown voltage >25kV and a volume resistivity >10. 10 Ω·cm, compared with silicone oil or mineral oil, it has better antioxidant properties.

[0039] ODP (Ozone Depletion Potential), also known as ozone depletion potential, is the ratio of the change in total ozone volume caused by a certain gas in the atmosphere to the change in total ozone volume caused by a unit mass of trichlorofluoromethane in the atmosphere. This ratio is used to measure the destructive potential of chemical substances to the stratospheric ozone layer. The hydrofluoroolefin compounds provided in this application do not contain chlorine or bromine, and their degradation process does not pose a risk of ozone layer depletion.

[0040] The Global Warming Potential (GWP) is an indicator used to measure the potential impact of greenhouse gases on global warming. Based on the radiative properties of well-mixed greenhouse gases, it compares the impact of different greenhouse gases on global warming. GWP uses carbon dioxide as a benchmark, comparing the greenhouse effect of other greenhouse gases to that of carbon dioxide. A higher GWP value indicates a stronger greenhouse effect and a greater potential contribution to global warming. The IPCC defines GWP as the ratio of the integral of the radiative forcing caused by a transient pulse emission of 1 kg of chemical substance x over a certain time period to the integral of the radiative forcing caused by the emission of an equivalent amount of reference gas (CO2) under the same conditions over the same time period. The calculation formula is as follows:

[0041]

[0042] x(t)=e -t / τ ;

[0043]

[0044] Where TH represents the time range (e.g., 20, 100, and 500 years), and 100 years is used in this application; t represents time; RF x and RF r Represent the radiative forcing of compound x and reference gas CO2, respectively; a x and a r Let represent the corresponding radiative efficiency; x(t) and r(t) represent the time response functions of compound x and the reference gas, respectively; τ is the atmospheric lifetime in years (a); the atmospheric response function r(t) of the reference compound CO2 is the formula recently published by the IPCC in 2007, with parameters a0, a2, ... i and τ i It is a constant published by the IPCC.

[0045] This application provides a method for preparing the high-boiling-point hydrofluoroolefin ether compounds described in the above technical solutions, including the following steps:

[0046] The high-boiling-point hydrofluoroolefin ether compound was obtained by mixing hexafluoropropylene trimer, alcohol compound, basic catalyst and polar solvent and carrying out elimination substitution reaction.

[0047] The hexafluoropropylene trimer has the structure shown in Formula II; the alcohol compound has the structure shown in Formula III, and is an alcohol or a fluorinated alcohol.

[0048] Rfh-OH formula III.

[0049] Unless otherwise specified, all raw materials involved in the embodiments of this application are commercially available products well known in the art.

[0050] In the embodiments of this application, the alcohol compound is an alcohol or a fluorinated alcohol. As a specific embodiment of this application, the alcohol can be methanol or ethanol, and the fluorinated alcohol can be 2,2-difluoroethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoropropanol, hexafluoroisopropanol (i.e., 1,1,1,3,3,3-hexafluoro-2-propanol) or hexafluorobutanol (i.e., 2,2,3,4,4,4-hexafluoro-1-butanol).

[0051] As a specific embodiment of this application, when the alcohol compound is an alcohol, such as when preparing compounds of structure 1 and structure 2 (methanol is used to prepare structure 1 and ethanol is used to prepare structure 2), the molar ratio of the alcohol compound to the hexafluoropropylene trimer (represented as T2 in the example) can be approximately 5 to 10:1, specifically 5:1, 8:1 or 10:1. The molar amount of hexafluoropropylene trimer is small, the purpose of which is to allow an excess of inexpensive methanol or ethanol, thereby promoting the conversion rate of the hexafluoropropylene trimer, which is a relatively expensive raw material compared to methanol and ethanol, and effectively reducing production costs. The excess inexpensive raw material methanol or ethanol can be recovered and reused by distillation during the purification process after the reaction.

[0052] As a specific embodiment of this application, when the alcohol compound is a fluorinated alcohol, such as when preparing compounds of structures 3 to 7 (the fluorinated alcohols used to prepare structures 3 to 7 are, in order, 2,2-difluoroethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoropropanol, hexafluoroisopropanol, and hexafluorobutanol), the molar ratio of the alcohol compound to the hexafluoropropylene trimer can be approximately 1:5 to 10, specifically 1:5, 1:8, or 1:10. The molar amount of the fluorinated alcohol is small, the purpose of which is to allow an excess of the relatively inexpensive hexafluoropropylene trimer raw material to promote the conversion rate of the high-priced fluorinated alcohol, which can effectively reduce production costs. The excess inexpensive raw material hexafluoropropylene trimer can be recovered and reused by distillation during the purification process after the reaction.

[0053] As one specific embodiment of this application, the alkaline catalyst can be an inorganic alkaline composite catalyst or an organic alkaline catalyst.

[0054] In one specific embodiment of this application, the inorganic basic composite catalyst may include an inorganic basic compound and a quaternary ammonium salt. In another specific embodiment, the inorganic basic compound may be KF or KOH; when preparing compounds of structures 1, 3, 4, and 6, the inorganic basic compound may be KOH; when preparing compounds of structures 2, 5, and 7, the inorganic basic compound may be KF. In yet another specific embodiment, the quaternary ammonium salt may be alkyl ammonium chloride or alkyl ammonium bromide (i.e., the inorganic basic composite catalyst is KF + alkyl ammonium chloride, KF + alkyl ammonium bromide, KOH + alkyl ammonium chloride, KOH + alkyl ammonium bromide), wherein the alkyl ammonium chloride and alkyl ammonium bromide act as phase transfer catalysts, increasing the solubility of organic matter in the solvent, which is more conducive to the reaction. In one specific embodiment of this application, the alkyl ammonium chloride may be one or more of benzyltrimethylammonium chloride, trimethyloctadecylammonium chloride, trimethylhexadecylammonium chloride, trimethyltetradecylammonium chloride, and benzyldimethylhexadecylammonium chloride; the alkyl ammonium bromide may be one or more of benzyltrimethylammonium bromide, trimethyloctadecylammonium bromide, trimethylhexadecylammonium bromide, trimethyltetradecylammonium bromide, and benzyldimethylhexadecylammonium bromide. In another specific embodiment of this application, the molar ratio of the inorganic basic compound to the quaternary ammonium salt may be approximately 1:0.01 to 0.1, specifically 1:0.01, 1:0.02, 1:0.03, 1:0.04, 1:0.05, 1:0.06, 1:0.07, 1:0.08, 1:0.09, or 1:0.1.

[0055] As one specific embodiment of this application, the organic basic catalyst may be one or more of pyridine, 4-dimethylaminopyridine and triethylamine.

[0056] As a specific embodiment of this application, the molar ratio of the alcohol compound to the compound with a small molar amount in the hexafluoropropylene trimer and the inorganic basic compound in the inorganic basic composite catalyst can be approximately 1:1 to 1.5, specifically 1:1, 1:1.2, 1:1.3 or 1:1.5; the molar ratio of the alcohol compound to the compound with a small molar amount in the hexafluoropropylene trimer and the organic basic catalyst can be approximately 1:0.01 to 0.1, specifically 1:0.01, 1:0.05 or 1:0.1.

[0057] As a specific embodiment of this application, when the alkaline catalyst is an inorganic alkaline composite catalyst, the composition and raw material molar ratio of the inorganic alkaline composite catalyst for preparing compounds of structures 1 to 7 can be as follows:

[0058] When preparing compound 1, the ratio of hexafluoropropylene trimer:KOH:benzyltrimethylammonium chloride is 1:1:0.01; or, hexafluoropropylene trimer:KOH:trimethyloctadecylammonium bromide is 1:1.2:0.05; or, hexafluoropropylene trimer:KOH:benzyldimethylhexadecylammonium chloride is 1:1.5:0.1.

[0059] When preparing compound 2, the ratio of hexafluoropropylene dimer:KF:benzyltrimethylammonium chloride is 1:1:0.01; or, hexafluoropropylene trimer:KF:trimethyloctadecylammonium bromide is 1:1.3:0.05; or, hexafluoropropylene trimer:KF:benzyldimethylhexadecylammonium chloride is 1:1.5:0.1.

[0060] When preparing compound structure 3, the ratio of 2,2-difluoroethanol:KOH:benzyltrimethylammonium chloride is 1:1:0.01; or, 2,2-difluoroethanol:KOH:trimethyloctadecylammonium bromide is 1:1.2:0.05; or, 2,2-difluoroethanol:KOH:benzyldimethylhexadecylammonium chloride is 1:1.5:0.1.

[0061] When preparing compound 4, the ratio of 2,2,2-trifluoroethanol:KOH:benzyltrimethylammonium chloride is 1:1:0.01; or, 2,2,2-trifluoroethanol:KOH:trimethyloctadecylammonium bromide is 1:1.2:0.05; or, 2,2,2-trifluoroethanol:KOH:benzyldimethylhexadecylammonium chloride is 1:1.5:0.1.

[0062] When preparing compound structure 5, the ratio of 3,3,3-trifluoropropanol:KF:benzyltrimethylammonium chloride is 1:1:0.01; or, 3,3,3-trifluoropropanol:KF:trimethyloctadecylammonium bromide is 1:1.3:0.05; or, 3,3,3-trifluoropropanol:KF:benzyldimethylhexadecylammonium chloride is 1:1.5:0.1.

[0063] When preparing compound 6, the ratio of hexafluoroisopropanol:KOH:benzyltrimethylammonium chloride is 1:1:0.01; or, hexafluoroisopropanol:KOH:trimethyloctadecylammonium bromide is 1:1.2:0.05; or, hexafluoroisopropanol:KOH:benzyldimethylhexadecylammonium chloride is 1:1.5:0.1.

[0064] When preparing compound 7, the ratio of hexafluorobutanol:KF:benzyltrimethylammonium chloride is 1:1:0.01; or, hexafluorobutanol:KF:trimethyloctadecylammonium bromide is 1:1.3:0.05; or, hexafluorobutanol:KF:benzyldimethylhexadecylammonium chloride is 1:1.5:0.1.

[0065] As a specific embodiment of this application, when the basic catalyst is an organic basic catalyst, the molar ratio of the organic basic catalyst and raw materials for preparing compounds of structures 1 to 7 is as follows:

[0066] When preparing compound 1, the ratio of hexafluoropropylene trimer to 4-dimethylaminopyridine is 1:0.01; or, the ratio of hexafluoropropylene trimer to 4-dimethylaminopyridine is 1:0.05; or, the ratio of hexafluoropropylene trimer to 4-dimethylaminopyridine is 1:0.1.

[0067] When preparing compound 2, the ratio of hexafluoropropylene trimer to triethylamine is 1:0.01; or, the ratio of hexafluoropropylene trimer to triethylamine is 1:0.05; or, the ratio of hexafluoropropylene trimer to triethylamine is 1:0.1.

[0068] When preparing compound structure 3, the ratio of 2,2-difluoroethanol to triethylamine is 1:0.01; or, 2,2-difluoroethanol to triethylamine is 1:0.05; or, 2,2-difluoroethanol to triethylamine is 1:0.1.

[0069] When preparing compound structure 7, the ratio of hexafluorobutanol to 4-dimethylaminopyridine is 1:0.01; or, hexafluorobutanol to 4-dimethylaminopyridine is 1:0.05; or, hexafluorobutanol to 4-dimethylaminopyridine is 1:0.1.

[0070] As a specific embodiment of this application, the polar solvent can be one or more of water, acetonitrile, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and diethylene glycol dimethyl ether; the volume ratio of the polar solvent to the total volume of hexafluoropropylene trimer and alcohol compound can be approximately 1 to 1.5:1, specifically 1:1, 1.2:1, or 1.5:1.

[0071] In one specific embodiment of this application, the method for mixing the hexafluoropropylene trimer, alcohol compound, alkaline catalyst, and polar solvent can be as follows: mixing the alkaline catalyst and polar solvent, adding the hexafluoropropylene trimer to obtain a mixture; and adding the alcohol compound dropwise to the mixture using a dropping funnel. In one specific embodiment of this application, the alcohol compound can be added dropwise over 60 minutes.

[0072] As one specific embodiment of this application, the temperature of the elimination substitution reaction can be approximately 100 to 150°C, specifically 100, 110, 120, 130, 140 or 150°C, and the time can be approximately 8 to 24 hours, specifically 8, 10, 12, 20 or 24 hours.

[0073] In the embodiments of this application, the reaction formulas involved in the elimination substitution reaction are as follows (where Rfh is: -CH3, -CH2CH3, -CH2CHF2, -CH2CF3, -CH2CH2CF3, -CH(CF3)2 or -CH2CF2CHFCF3):

[0074]

[0075] As one specific embodiment of this application, after the elimination substitution reaction, the resulting reaction solution can be further post-processed.

[0076] As a specific embodiment of this application, when the alkaline catalyst is an inorganic alkaline composite catalyst and the polar solvent is water, the post-processing method can be as follows: distilling the reaction solution to distill off all liquid substances, i.e., fractions; separating the fractions again (layer separation or distillation separation) to obtain an organic phase containing the target product; washing the organic phase containing the target product with water and separating and filtering to obtain a crude product of hydrofluoroolefin ethers; and purifying the crude product of hydrofluoroolefin ethers by distillation to obtain a high-purity hydrofluoroolefin ether compound.

[0077] In one specific embodiment of this application, when the alkaline catalyst is an inorganic alkaline composite catalyst and the polar solvent is an organic solvent, the post-treatment method can be as follows: distilling the reaction solution to distill off all liquid substances and obtain a liquid fraction; further purifying the liquid fraction by distillation to distill off excess raw material (hexafluoropropylene trimer or alcohol compound) and solvent, obtaining a bottom liquid; washing the bottom liquid with water and separating and filtering to obtain a crude product of hydrofluoroolefin ether compound; further purifying the crude product by distillation to obtain a high-purity hydrofluoroolefin ether compound. In another specific embodiment of this application, the excess raw material (hexafluoropropylene trimer or alcohol compound) and solvent distilled off can be recovered and reused; the water washing can be performed three times.

[0078] As a specific embodiment of this application, when the alkaline catalyst is an organic alkaline catalyst, the post-processing method may be: distilling the reaction solution to distill off excess raw materials and solvents to obtain a bottom liquid; washing the bottom liquid with water and separating and filtering it to obtain a crude product of hydrofluoroolefin ether compounds; and purifying the crude product by distillation to obtain high-purity hydrofluoroolefin ether compounds.

[0079] The preparation method provided in this application uses readily available raw materials, has a simple process, and offers excellent cost advantages, providing more options for market applications.

[0080] This application provides the application of the high-boiling-point hydrofluoroolefin ether compounds described in the above technical solutions or the high-boiling-point hydrofluoroolefin ether compounds prepared by the above technical solutions as temperature control working fluids in temperature control systems.

[0081] As one specific embodiment of this application, the temperature control system may include a battery direct contact immersion thermal management system, a new energy charging equipment, a temperature control device in semiconductor manufacturing and testing processes, or a server data center immersion liquid cooling system.

[0082] The hydrofluoroolefin ether compound provided in this application possesses excellent properties, a wide temperature range (-60℃ to 200℃), and can be selected for suitable applications as a high- or low-temperature temperature control fluid. It has no flash point, is non-flammable, and even has fire-extinguishing properties, posing no fire hazard. It exhibits excellent insulation properties, offering significant advantages in applications requiring insulation. It also demonstrates good material compatibility, showing no corrosiveness to various metals, polymers, or glass and ceramic materials. As a specific embodiment of this application, the hydrofluoroolefin ether compound can be used as a fluid medium in low-temperature thermostatic baths, low-temperature circulating pumps, industrial refrigeration units, high- and low-temperature integrated machines, or high-temperature circulating pumps. Alternatively, it can be used as a temperature control fluid for semiconductor testing, a coolant for liquid-cooled charging piles, a temperature control fluid for lithium battery energy storage, and a high-temperature heat transfer medium. The hydrofluoroolefin ether compound, acting as a heat transfer fluid or a cold transfer fluid, is used to transport heat or cold media via a liquid transfer pump, or to facilitate heat exchange between heat or cold media via a liquid circulation pump, thereby achieving precise temperature control.

[0083] This 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 a hydrofluoroolefin ether compound as described in the above technical solution or a hydrofluoroolefin ether compound prepared by the preparation method described in the above technical solution.

[0084] As one specific embodiment of this application, the heat source may include a CPU, graphics card, memory chip, power transformer, capacitor, resistor, inductor, diode, transistor, or cable; when the heat source is a CPU, graphics card, memory chip, power transformer, capacitor, resistor, inductor, diode, or transistor, the immersion liquid cooling system may be a server data center immersion liquid cooling system; when the heat source is a cable, the immersion liquid cooling system may be a charging gun cable immersion liquid cooling system in new energy charging equipment.

[0085] To further illustrate this application, the high-boiling-point hydrofluoroene ether compounds, their preparation methods, and applications provided in this application are described in detail below with examples, but these should not be construed as limiting the scope of protection of this application.

[0086] Example 1

[0087] (1) Preparation of compound with structure 1 [((CF3)2CF)2C=C(-OCH3)CF3]

[0088] In a 5L 316 stainless steel reactor equipped with a dropping device, solvent water and an inorganic alkaline composite catalyst (KOH + alkylammonium) were added as substrates and stirred at room temperature for 1 hour. Then, 900g of hexafluoropropylene trimer (represented by T2, structure as shown in Formula II, the same below) was added. Methanol was then added dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction conditions were controlled at 100–150℃, and the reaction was continued with stirring for 8–24 hours. After the reaction was completed, the reaction solution was directly distilled to distill off all liquid substances. The bottom solid was the inorganic alkaline composite catalyst, which could be recycled. The distilled fraction consisted of two layers. The lower organic phase was the product phase, which was washed three times with water, separated, filtered, and the crude product of compound 1 was collected. The upper aqueous phase was an excess of the raw material methanol-water solution, which could be distilled to recover the raw material methanol. The crude product received was analyzed by gas chromatography (GC) to determine the content of the target product (compound of structure 1) and to calculate the yield of the target product (compound of structure 1). The crude product was purified by distillation to obtain a high-purity target product (compound of structure 1), and its gas chromatographic purity was measured. The reaction conditions and reaction results of Example 1 (1) are shown in Table 1.

[0089] Table 1 Reaction conditions and results of Example 1(1)

[0090]

[0091]

[0092] (2) Preparation of compound with structure 1 [((CF3)2CF)2C=C(-OCH3)CF3]

[0093] In a 5L 316 stainless steel reactor equipped with a dropping device, acetonitrile solvent and an inorganic alkaline composite catalyst (KF + alkylammonium) as substrate were added. The mixture was stirred at room temperature for 1 hour, then 900g of hexafluoropropylene trimer (T2) was added. Methanol was then added dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction conditions were controlled at 100–150℃, and the reaction was continued with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled to distill off all liquid substances. The bottom solid was the inorganic alkaline composite catalyst, which could be recycled. All the distilled liquid fractions were purified by further distillation. The first fraction was the excess methanol-acetonitrile solvent layer, which could be recycled. The bottom liquid was the product layer, which was washed three times with water, filtered again, and the lower organic phase, i.e., the crude product of compound 1, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound 1) and calculate the yield of the target product (compound 1). The crude product was purified by distillation to obtain a high-purity target product (compound of structure 1), and its purity was measured by gas chromatography. The reaction conditions and results of Example 1(2) are shown in Table 2.

[0094] Table 2 Reaction conditions and results of Example 1(2)

[0095]

[0096] Example 2

[0097] (1) Preparation of compound 2 with structure [((CF3)2CF)2C=C(-OCH2CH3)CF3]

[0098] In a 5L 316 stainless steel reactor equipped with a dropping device, solvent water and an inorganic alkaline composite catalyst (KOH + alkylammonium) were added as substrates. The mixture was stirred at room temperature for 1 hour, then 900g of hexafluoropropylene trimer (T2) was added. Ethanol was then added dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction conditions were controlled at 100–150℃, and the reaction was continued with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled, and all liquid substances were distilled off. The bottom solid was the inorganic alkaline composite catalyst, which could be recycled. The distilled fraction consisted of two layers: the lower organic phase was the product phase, which was washed three times with water, filtered again, and the crude product of structure 2 was collected; the upper aqueous phase was an excess of the raw material ethanol-water solution, which could be distilled to recover the raw material ethanol. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (structure 2 compound) and calculate the yield of the target product (structure 2 compound). The crude product was purified by distillation to obtain a high-purity target product (compound of structure 2), and its purity was measured by gas chromatography. The reaction conditions and results of Example 2(1) are shown in Table 3.

[0099] Table 3 Reaction conditions and results of Example 2(1)

[0100]

[0101] (2) Preparation of compound 2 with structure [((CF3)2CF)2C=C(-OCH2CH3)CF3]

[0102] In a 5L 316 stainless steel reactor equipped with a dropping device, acetonitrile solvent and an inorganic alkaline composite catalyst (KF + alkylammonium) as substrate were added. The mixture was stirred and mixed at room temperature for 1 hour. Then, 900g of hexafluoropropylene trimer (T2) was added, followed by the addition of ethanol dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction conditions were maintained at 100–150℃ and the reaction was continued with stirring for 8–24 hours. After the reaction was completed, the reaction solution was directly distilled to remove all liquid substances. The bottom solid was the inorganic alkaline composite catalyst, which could be recycled. All distilled liquid fractions were further purified by distillation. The first fraction was the excess ethanol-acetonitrile solvent layer, which could be recycled. The bottom liquid was the product layer. The product layer was washed three times with water, filtered again, and the lower organic phase, i.e., the crude product of compound 2, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound 2) and calculate the yield of the target product (compound 2). The crude product was purified by distillation to obtain a high-purity target product (compound of structure 2), and its purity was measured by gas chromatography. The reaction conditions and results of Example 2(2) are shown in Table 4.

[0103] Table 4. Reaction conditions and results of Example 2(2)

[0104]

[0105]

[0106] Example 3

[0107] Preparation of compound 3 [((CF3)2CF)2C=C(-OCH2CHF2)CF3]

[0108] In a 20L 316 stainless steel reactor equipped with a dropping device, solvent water and an inorganic alkaline composite catalyst (KOH + alkylammonium) were added as substrates. The mixture was stirred at room temperature for 1 hour, and then hexafluoropropylene trimer (T2) was added in an amount 5–10 times the molar amount of the fluorinated alcohol. 2,2-Difluoroethanol (164g) was then added dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction was continued at 100–150℃ with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled to remove all liquid substances. The bottom solid was the inorganic alkaline composite catalyst, which could be recycled. All the distilled liquid fractions were further purified by distillation. The first fraction was the excess raw material hexafluoropropylene trimer (T2)-water solvent layer, which could be recycled after separation. The bottom liquid was the product layer, which was washed three times with water, filtered again, and the lower organic phase, i.e., the crude product of compound 3, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound of structure 3) and calculate its yield. The crude product was purified by distillation to obtain a high-purity target product (compound of structure 3), and its gas chromatographic purity was determined. The reaction conditions and results of Example 3 are shown in Table 5.

[0109] Table 5. Reaction conditions and results of Example 3

[0110]

[0111] Example 4

[0112] Preparation of compound 4, [((CF3)2CF)2C=C(-OCH2CF3)CF3]

[0113] In a 20L 316 stainless steel reactor equipped with a dropping device, solvent water and an inorganic alkaline composite catalyst (KOH + alkylammonium) were added as substrates. The mixture was stirred at room temperature for 1 hour, and then hexafluoropropylene trimer (T2) was added in an amount 5–10 times the molar amount of the fluorinated alcohol. 2,2,2-trifluoroethanol (200g) was then added dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction was continued at 100–150℃ with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled to remove all liquid substances. The bottom solid was the inorganic alkaline composite catalyst, which could be recycled. All distilled liquid fractions were further purified by distillation. The first fraction was the excess raw material hexafluoropropylene trimer (T2)-water solvent layer, which could be recycled after separation. The bottom liquid was the product layer, which was washed three times with water, separated and filtered again, and the lower organic phase, i.e., the crude product of structure 4, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound of structure 4) and calculate its yield. The crude product was purified by distillation to obtain a high-purity target product (compound of structure 4), and its gas chromatographic purity was determined. The reaction conditions and results of Example 4 are shown in Table 6.

[0114] Table 6. Reaction conditions and results of Example 4

[0115]

[0116] Example 5

[0117] Preparation of compound 5 with structure [((CF3)2CF)2C=C(-OCH2CH2CF3)CF3]

[0118] In a 20L 316 stainless steel reactor equipped with a dropping device, acetonitrile solvent and an inorganic alkaline composite catalyst (KF + alkylammonium) as substrate were added and stirred at room temperature for 1 hour. Then, hexafluoropropylene trimer (T2) was added in an amount 5–10 times the molar amount of the fluorinated alcohol. Next, 228g of 3,3,3-trifluoropropanol was added dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction was continued at 100–150℃ with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled, and all liquid substances were distilled off. The bottom solid was the inorganic alkaline composite catalyst, which could be recycled. All the distilled liquid substances were then purified by further distillation. The first fraction to emerge was the hexafluoropropylene trimer (T2)-acetonitrile solvent layer, from which excess hexafluoropropylene trimer (T2) and acetonitrile solvent could be recovered and reused. The bottom liquid was the product layer. The product layer was washed three times with water, then separated and filtered again. The lower organic phase, i.e., the crude product of structure 5, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound 5) and calculate its yield. The crude product was purified by distillation to obtain a high-purity target product (compound 5), and its gas chromatographic purity was determined. The reaction conditions and results of Example 5 are shown in Table 7.

[0119] Table 7. Reaction conditions and results of Example 5

[0120]

[0121] Example 6

[0122] Preparation of compound 6 with structure [((CF3)2CF)2C=C(-OCH(CF3)2)CF3]

[0123] In a 20L 316 stainless steel reactor equipped with a dropping device, solvent water and an inorganic alkaline composite catalyst (KOH + alkylammonium) were added as substrates. The mixture was stirred at room temperature for 1 hour. Then, hexafluoropropylene trimer (T2) was added in an amount 5–10 times the molar amount of the fluorinated alcohol. Next, 1,1,1,3,3,3-hexafluoro-2-propanol (i.e., hexafluoroisopropanol, 336g) was added dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction conditions were controlled at 100–150℃, and the reaction was continued with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled, and all liquid substances were distilled off. The bottom solid was the inorganic alkaline composite catalyst, which could be recycled. All the distilled liquid substances were then purified by further distillation. The first fraction, hexafluoropropylene trimer (T2)-water solvent layer, could be recovered and reused if excess hexafluoropropylene trimer (T2) was extracted. The bottom liquid is the product layer. The product layer is washed three times with water, then separated and filtered again. The lower organic phase, i.e., the crude product of compound 6 (structure 6), is collected. The crude product is analyzed by gas chromatography (GC) to determine the content of the target product (compound 6) and calculate its yield. The crude product is then purified by distillation to obtain a high-purity target product (compound 6), whose gas chromatographic purity is determined.

[0124] The reaction conditions and results of Example 6 are shown in Table 8.

[0125] Table 8. Reaction conditions and results of Example 6

[0126]

[0127] Example 7

[0128] Preparation of compound 7 [((CF3)2CF)2C=C(-OCH2CF2CHFCF3)CF3]

[0129] In a 20L 316 stainless steel reactor equipped with a dropping device, acetonitrile solvent and an inorganic alkaline composite catalyst (KF + alkylammonium) as substrate were added and stirred at room temperature for 1 hour. Then, hexafluoropropylene trimer (T2) was added in an amount 5–10 times the molar amount of the fluorinated alcohol. Next, 364g of 2,2,3,4,4,4-hexafluoro-1-butanol was added dropwise to the substrate using a dropping funnel, with the addition completed over 60 minutes at a controlled dropping rate. After the addition was complete, the reaction conditions were maintained at 100–150℃ with continued stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled, and all liquid substances were distilled off. The bottom solid was the inorganic alkaline composite catalyst, which can be recycled and reused. All distilled liquid substances were purified by further distillation. The first fraction, hexafluoropropylene trimer (T2)-acetonitrile solvent layer, was collected to recover excess hexafluoropropylene trimer (T2) and acetonitrile for reuse. The bottom liquid was the product layer, which was washed three times with water, filtered again, and the lower organic phase, i.e., the crude product of structure 7, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound 7) and calculate its yield. Further purification of the crude product by distillation yielded the high-purity target product (compound 7), and its GC purity was determined. The reaction conditions and results of Example 7 are shown in Table 9.

[0130] Table 9. Reaction conditions and results of Example 7

[0131]

[0132] Example 8

[0133] Preparation of compound 1 [((CF3)2CF)2C=C(-OCH3)CF3]

[0134] In a 5L 316 stainless steel reactor equipped with a dropping device, solvent and an organic base catalyst (4-dimethylaminopyridine) were added as the substrate. The mixture was stirred and mixed at room temperature for 1 hour. Then, 900g of hexafluoropropylene trimer (T2) was added, followed by the addition of methanol dropwise using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction was continued at 100–150°C with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled to remove excess methanol and solvent for recycling. The organic phase of the substrate was the product phase. The product phase was washed three times with water, separated and filtered again, and the target product, i.e., the crude product of structure 1, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound 1) and calculate the yield of the target product (compound 1). The crude product phase was purified by distillation to obtain a high-purity target product (compound 1), and its GC purity was measured. The reaction conditions and results of Example 8 are shown in Table 10.

[0135] Table 10. Reaction conditions and results of Example 8

[0136]

[0137] Example 9

[0138] Preparation of compound 2 [((CF3)2CF)2C=C(-OCH2CH3)CF3]

[0139] In a 5L 316 stainless steel reactor equipped with a dropping device, acetonitrile solvent and triethylamine organic base catalyst were added as substrates. The mixture was stirred and mixed at room temperature for 1 hour. Then, 900g of hexafluoropropylene trimer (T2) was added, followed by the addition of ethanol dropwise to the substrate using a dropping funnel, with the dropping rate controlled to complete the addition within 60 minutes. After the addition was complete, the reaction conditions were maintained at 100–150℃, and the reaction was continued with stirring for 8–24 hours. After the reaction was completed, the reaction solution was directly distilled to recover excess ethanol and acetonitrile solvent. The organic phase of the substrate was the product phase. The product phase was washed three times with water, separated and filtered again, and the target product, namely the crude product of structure 2 compound, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (structure 2 compound) and calculate the yield of the target product (structure 2 compound). The crude product was purified by distillation to obtain a high-purity target product (structure 2 compound), and its gas chromatographic purity was measured. The reaction conditions and results of Example 9 are shown in Table 11.

[0140] Table 11 Reaction conditions and results of Example 9

[0141]

[0142] Example 10

[0143] Preparation of compound 3 [((CF3)2CF)2C=C(-OCH2CHF2)CF3]

[0144] In a 20L 316 stainless steel reactor equipped with a dropping device, solvent and an organic base catalyst (triethylamine) were added as the substrate. The mixture was stirred at room temperature for 1 hour, then hexafluoropropylene trimer (T2) was added in an amount 5–10 times the molar amount of the fluorinated alcohol. 164g of 2,2-difluoroethanol was then added dropwise to the substrate using a dropping funnel, with the addition completed over 60 minutes at a controlled dropping rate. After the addition was complete, the reaction was continued at 100–150℃ with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled to recover excess hexafluoropropylene trimer (T2) and solvent. The organic phase of the substrate was the product phase. The product phase was washed three times with water, separated, and filtered again to collect the target product, i.e., the crude product of structure 3. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (structure 3 compound) and calculate the yield of the target product (structure 3 compound). The crude product was purified by distillation to obtain the target product (compound of structure 3) with high purity, and its purity was determined by gas chromatography. The reaction conditions and results of Example 10 are shown in Table 12.

[0145] Table 12 Reaction conditions and results of Example 10

[0146]

[0147] Example 11

[0148] Preparation of compound 7 [((CF3)2CF)2C=C(-OCH2CF2CHFCF3)CF3]

[0149] In a 20L 316 stainless steel reactor equipped with a dropping device, 3L of acetonitrile solvent and an organic base catalyst (4-dimethylaminopyridine) as the substrate were added. The mixture was stirred and mixed at room temperature for 1 hour. Then, hexafluoropropylene trimer (T2) was added in an amount 5–10 times the molar amount of the fluorinated alcohol. 2,2,3,4,4,4-hexafluoro-1-butanol (364g) was then added dropwise to the substrate using a dropping funnel, with the addition completed over 60 minutes at a controlled dropping rate. After the addition was complete, the reaction was continued at 100–150℃ with stirring for 8–24 hours. After the reaction was complete, the reaction solution was directly distilled to recover excess hexafluoropropylene trimer (T2) and acetonitrile solvent. The organic phase of the bottom liquid was the product phase. The product phase was washed three times with water, filtered again, and the target product, namely the crude product of compound structure 7, was collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound of structure 7) and calculate the yield of the target product (compound of structure 7). The crude product was purified by distillation to obtain a high-purity target product (compound of structure 7), and its gas chromatographic purity was determined. The reaction conditions and results of Example 11 are shown in Table 13.

[0150] Table 13 Reaction conditions and results of Example 11

[0151]

[0152]

[0153] In the above embodiments, the compounds of structures 1 to 7 were selected from the products with the highest purity after distillation and purification for physical property testing and compatibility testing, respectively.

[0154] (I) Physical property testing

[0155] Boiling point test: according to national standard GB / T616-2006 "General Method for Determination of Boiling Point of Chemical Reagents"; flash point test: according to national standard GB / T261-2021 "Flash Point-Pinsky-Martin Closed Cup Method"; breakdown voltage test: according to national standard GB / T1408.1-2006 "Test Method for Electrical Strength of Insulating Materials"; volume resistivity test: according to national standard GB / T5654-2007 "Measurement of Relative Permittivity, Dielectric Loss Factor and DC Resistivity of Liquid Insulating Materials"; thermal conductivity: according to the "Transient Hot Wire Method", referring to standard ASTM D7896; specific heat capacity: calculated according to the specific heat capacity definition formula: Q = Cp·m·δt (where Cp represents specific heat capacity, Q represents the heat absorbed or released, m represents the mass of the substance, and δt represents the temperature change); kinematic viscosity: according to national standard GB / T 265-88 "Determination of Kinematic Viscosity of Petroleum Products". Test results are shown in Table 14.

[0156] Table 14 Physical property data of compounds with structures 1 to 7

[0157] physical properties boiling point density Specific heat capacity kinematic viscosity thermal conductivity Flash point Breakdown voltage Dielectric constant Volume resistivity ODP GWP Serial Number ℃ <![CDATA[g / cm 3 ]]> J / (℃·g) cSt-25℃ W / mk ℃ KV / Ω·cm / / Structure 1 152 1.72 1.13 2.83 0.066 none 31.2 4.4 <![CDATA[6.7×10 11 ]]> 0 ＜100 Structure 2 167 1.71 1.12 2.22 0.067 none 33.2 4.5 <![CDATA[6.8×10 11 ]]> 0 ＜100 Structure 3 165 1.75 1.11 2.53 0.068 none 32.5 4.1 <![CDATA[3.4×10 12 ]]> 0 ＜100 Structure 4 161 1.77 1.15 2.55 0.071 none 33.5 3.6 <![CDATA[5.2×10 12 ]]> 0 ＜100 Structure 5 188 1.78 1.1 4.52 0.071 none 29.7 3.9 <![CDATA[6.6×10 12 ]]> 0 ＜100 Structure 6 168 1.83 1.21 4.25 0.07 none 28.8 3.4 <![CDATA[4.2×10 12 ]]> 0 ＜100 Structure 7 192 1.81 1.23 5.7 0.067 none 28.6 3.7 <![CDATA[4.4×10 12 ]]> 0 ＜100

[0158] As can be seen from the data in Table 14, compounds of structures 1 to 7 have excellent environmental protection properties, high boiling points, low viscosity at low temperatures, and good insulation properties, which fully meet the requirements of temperature-controlled liquid working fluids.

[0159] (II) Compatibility Testing

[0160] Compatibility testing was divided into room temperature compatibility testing and high temperature compatibility testing. The testing method was as follows: 50 mL of the purified compounds of structures 1 to 7 were measured and placed in 100 mL stainless steel hydrothermal reactors, respectively. Then, materials of various types were added, and room temperature immersion experiments were conducted for 25℃-168 h and high temperature immersion experiments were conducted for 100℃-168 h. The compatibility test results are shown in Tables 15 and 16.

[0161] Table 15. Room temperature compatibility test results (25℃-168h) of compounds with structures 1 to 7.

[0162]

[0163]

[0164] Table 16. High-temperature compatibility test results (100℃-168h) of compounds with structures 1 to 7.

[0165]

[0166] As can be seen from the data in Tables 15-16, compounds of structures 1 to 7 have excellent material compatibility, exhibit slight swelling of silicone rubber seals, and slight swelling of fluororubber seals, indicating slightly poor compatibility.

[0167] The application scenarios for high-boiling-point hydrofluoroolefin ether compounds used in temperature control are as follows:

[0168] Application Scenario 1: Battery direct contact immersion thermal management

[0169] The high-boiling-point hydrofluoroolefin ether compounds provided in this application can be used as thermal management systems in electrochemical batteries (such as lithium-ion batteries). In energy storage systems, the energy storage cells are directly immersed in coolant, completely isolating them from air, moisture, etc., to control the operating temperature of the energy storage battery system and achieve thermal management, while also preventing catastrophic failures due to thermal runaway under certain conditions. Thermal runaway is a series of internal exothermic reactions triggered by heat; excessive heat can be generated from overcharging, overheating, or internal electrical short circuits.

[0170] Application Scenario 2: New Energy Charging Equipment Scenario

[0171] The high-boiling-point hydrofluoroolefin ether 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 units (CDUs)). In high-power liquid-cooled charging guns, a large amount of heat is generated due to the large current (e.g., 600A and above), so an electronic pump is needed to drive the flow of the liquid working fluid. When the liquid working fluid passes through the cable (which generates heat due to carrying a large current during operation), it carries away the heat from the cable and charging connector, returning to the storage tank (which stores coolant), and then dissipates the heat through the radiator driven by the electronic pump.

[0172] Application Scenario 3: Chiller scenario for temperature control devices in semiconductor manufacturing and testing

[0173] Chillers, temperature control devices used in semiconductor manufacturing and testing processes, typically employ a compressor-based refrigeration and heating cycle to achieve precise temperature control. They monitor the temperature of the object being cooled or heated in real time using sensors and feed the temperature signal back to the control system. The control system automatically adjusts the cooling or heating power based on the set temperature value and the actual temperature feedback to maintain temperature stability. In refrigeration mode, the compressor in the chiller compresses the refrigerant into a high-temperature, high-pressure gas, which then dissipates heat through a condenser, turning the refrigerant into a high-pressure liquid. This high-pressure liquid is then depressurized by an expansion valve, becoming a low-pressure liquid, and enters the evaporator to evaporate and absorb heat, thereby lowering the temperature of the object being cooled. In heating mode, the chiller uses an electric heater or other heating methods to raise the temperature of the object being heated. Depending on the specific temperature requirements, the temperature control device should be able to cover a wide range from extremely low temperatures to high temperatures, such as -92 to 250°C, to meet the manufacturing and testing requirements of different chips. Depending on the specific temperature requirements, any one of the compounds with a specific boiling point from the structures shown in structures 1 to 7 provided in this application can be output from the chiller device as a temperature control medium.

[0174] Application Scenario 4: Immersion Liquid Cooling System for Server Data Centers

[0175] The hydrofluoroolefin compounds provided in this application can be used in single-phase immersion liquid cooling systems for servers or data centers. The cooling liquid working fluid exchanges heat with the computer's hardware heat sources via a pump, thereby transferring heat away from the server. The liquid working fluid used for single-phase immersion cooling of servers typically has a high boiling point exceeding approximately 75°C to reduce evaporation losses. The liquid working fluid is added in an amount that at least completely submerges all heat sources, and the liquid working fluid is in direct contact with the electronic components within the heat sources. Figure 1 This is a schematic diagram of a single-phase immersion liquid cooling system for a server or data center, where 1 is a sealed housing, 11 is the space inside the sealed housing, 2 is a heat source, and 3 is the liquid cooling medium; the heat source 2 may include a CPU, graphics card, memory chip, power transformer, capacitor, resistor, inductor, diode or transistor.

[0176] The above description is merely a preferred embodiment of this application and does not constitute any limitation on this application. It should be noted that those skilled in the art can make various improvements and modifications without departing from the principles of this application, and these improvements and modifications should also be considered within the scope of protection of this application.

Claims

1. A high-boiling-point hydrofluoroolefin compound, characterized in that, It has the structure shown in Equation I: In Formula I, Rfa = Rfb = -CF(CF3)2, Rfc = -CF3, and Rfh is a fluoroalkyl group, wherein the fluoroalkyl group is CF3CH2CH2- or CF3CHFCF2CH2-.

2. The method for preparing the high-boiling-point hydrofluoroolefin ether compound according to claim 1, characterized in that, Includes the following steps: The high-boiling-point hydrofluoroolefin ether compound was obtained by mixing hexafluoropropylene trimer, alcohol compound, basic catalyst and polar solvent and carrying out elimination substitution reaction. The hexafluoropropylene trimer has the structure shown in Formula II; the alcohol compound has the structure shown in Formula III and is a fluorinated alcohol, wherein the fluorinated alcohol is 3,3,3-trifluoropropanol or hexafluorobutanol. Rfh-OH formula III.

3. The preparation method according to claim 2, characterized in that, When the alcohol compound is a fluorinated alcohol, the molar ratio of the alcohol compound to the hexafluoropropylene trimer is 1:5 to 10.

4. The preparation method according to claim 2, characterized in that, The alkaline catalyst is an inorganic alkaline composite catalyst or an organic alkaline catalyst; The inorganic alkaline composite catalyst comprises an inorganic alkaline compound and a quaternary ammonium salt, wherein the inorganic alkaline compound is KF or KOH, and the quaternary ammonium salt is an alkyl ammonium chloride or an alkyl ammonium bromide, and the molar ratio of the inorganic alkaline compound to the quaternary ammonium salt is 1:0.01 to 0.1; The organic basic catalyst is one or more of pyridine, 4-dimethylaminopyridine, and triethylamine.

5. The preparation method according to claim 4, characterized in that, The molar ratio of the alcohol compound to the compound with the smallest molar amount in the hexafluoropropylene trimer and the inorganic basic compound in the inorganic basic composite catalyst is 1:1 to 1.5; the molar ratio of the alcohol compound to the compound with the smallest molar amount in the hexafluoropropylene trimer and the organic basic catalyst is 1:0.01 to 0.

1.

6. The preparation method according to claim 2, characterized in that, The elimination substitution reaction is carried out at a temperature of 100–150°C for 8–24 hours.

7. The application of the high-boiling-point hydrofluoroene ether compound of claim 1 or the high-boiling-point hydrofluoroene ether compound prepared by any one of claims 2 to 6 as a temperature control working fluid in a temperature control system.

8. An immersion liquid cooling system, characterized in that, Includes a liquid cooling medium and a heat source immersed in the liquid cooling medium; The liquid cooling medium is the high-boiling-point hydrofluoroolefin ether compound of claim 1 or the high-boiling-point hydrofluoroolefin ether compound prepared by the preparation method of any one of claims 2 to 6.

Images