High-boiling-point hydrofluoroalkene ether compound as well as preparation method and application thereof

Abstract

The embodiment of the invention provides a high-boiling-point hydrofluoroalkene ether compound as well as a preparation method and application thereof, and relates to the technical field of fluorine chemical industry and thermal management. The hydrofluoroalkene ether compound provided by the embodiment of the invention has a structure as shown in a formula I. The hydrofluoroalkene ether compound provided by the embodiment of the invention has excellent environmental friendliness (the ODP value is 0, and the GWP value is less than 100) and high boiling point (more than 150 DEG C), so that the hydrofluoroalkene ether compound has a wide adaptive temperature range; moreover, the hydrofluoroalkene ether compound is excellent in material compatibility and has no corrosion to various metals, high polymer materials and glass ceramic materials; the low-temperature viscosity is small; the insulation performance is excellent, and the high-temperature resistance is good. The hydrofluoroalkene ether compound is used as a temperature control working medium, has the advantages of high efficiency and stable temperature control, and can achieve the purposes of energy conservation and consumption reduction. The preparation method of the hydrofluoroalkene ether compound provided by the embodiment of the invention has the advantages of easily available raw materials, simple process, high yield and excellent cost advantage.

Description

Technical Field

[0001] The embodiments of the present application relate to the field of fluorine chemical industry and thermal management technology, and in particular to a high-boiling-point hydrofluoroolefin ether compound and a preparation method and application thereof. Background Art

[0002] Fluorine fluid is a liquid with unique properties. The application areas of fluorine fluid are: (1) Industrial application: Fluorine fluid is mainly used as heat transfer medium in high-temperature and high-pressure equipment in the industrial field, such as oil and gas extraction, nuclear power plants, aerospace and automobile engines; (2) Electronic application: In the electronics field, fluorine fluid is used in thermostats, heaters and other thermal control equipment in the semiconductor production process, as well as cooling systems in high-precision instruments. The main chemical properties of fluorine fluid: (1) Non-flammability: Fluorine fluid has an extremely high flash point or no flash point, is not flammable, and is suitable for environments that require fire protection; (2) Chemical corrosion resistance: It can resist corrosion from a variety of 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 life: 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 the industrial and electronic industries, the demand for high-performance thermal conductive media continues to increase. Fluorine fluids have a very broad market prospect as temperature control fluids due to their excellent thermal conductivity, chemical stability and wide applicability. However, the GWP value (global warming potential) of fluorine fluids is still relatively high, which has an adverse impact on the environment. In addition, the boiling point of fluorine fluids is relatively low, generally below 150°C, which limits their scope of application. Summary of the invention

[0004] In view of this, the purpose of the embodiments of the present application is to provide a high-boiling-point hydrofluoroolefin ether compound and its preparation method and application. The hydrofluoroolefin ether compound provided in the present application has excellent environmental protection (GWP value is less than 100), high boiling point (> 150°C), wide temperature range, and outstanding advantages as a temperature control working fluid.

[0005] In order to achieve the above-mentioned invention object, the present application provides the following technical solutions:

[0006] The present application provides a high boiling point hydrofluoroolefin ether compound having a structure shown in Formula I:

[0007]

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

[0009] As a specific implementation of the present 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 the embodiments of the present application have excellent environmental protection (ODP value is 0, GWP value is less than 100) and high boiling point (>150°C), thus having a wide temperature range; and the hydrofluoroolefin ether compounds have excellent material compatibility, are non-corrosive to various metals, polymer materials, and glass ceramic materials; have low low temperature viscosity; have excellent insulation properties and good high temperature resistance. The hydrofluoroolefin ether compounds are used as temperature control working fluids, which have the advantages of efficient temperature control and stability, and can achieve the purpose of energy saving and consumption reduction.

[0011] The present application provides a method for preparing the high-boiling-point hydrofluoroolefin ether compound described in the above technical solution, comprising the following steps:

[0012] The hexafluoropropylene trimer, an alcohol compound, an alkaline catalyst and a polar solvent are mixed to carry out an elimination substitution reaction to obtain the high-boiling-point hydrofluoroolefin ether compound;

[0013] The hexafluoropropylene trimer has a structure shown in Formula II; the alcohol compound has a structure shown in Formula III and is an alcohol or a fluorine-containing alcohol;

[0014] Rfh-OH formula III.

[0015] As a specific implementation of the present application, the alcohol is methanol or ethanol; the fluorine-containing alcohol is 2,2-difluoroethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoropropanol, hexafluoroisopropanol or hexafluorobutanol.

[0016] As a specific implementation of the present application, when the alcohol compound is alcohol, the molar ratio of the alcohol compound to the hexafluoropropylene trimer is 5-10:1; when the alcohol compound is a fluorine-containing alcohol, the molar ratio of the alcohol compound to the hexafluoropropylene trimer is 1:5-10.

[0017] As a specific embodiment of the present 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, the quaternary ammonium salt is alkylammonium chloride or alkylammonium bromide, and the molar ratio of the inorganic alkaline compound to the quaternary ammonium salt is 1:0.01-0.1;

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

[0020] As a specific implementation of the present application, the molar ratio of the alcohol compound to the compound with a small molar feed 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 a small molar feed amount in the hexafluoropropylene trimer and the organic alkaline catalyst is 1:0.01 to 0.1.

[0021] As a specific implementation of the present application, the temperature of the elimination substitution reaction is 100 to 150° C., and the time is 8 to 24 hours.

[0022] The preparation method of the high-boiling-point hydrofluoroolefin ether compound provided in the embodiment of the present application has easy-to-obtain raw materials, simple process, high yield, and excellent cost advantage. Furthermore, the embodiment of 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, and the yield of the target product is as high as 87.14%, which effectively reduces the production cost.

[0023] This embodiment provides the use of the high boiling point hydrofluoroolefin ether compound described in the above technical solution or the high boiling point hydrofluoroolefin ether compound prepared by the preparation method described in the above technical solution as a temperature control working fluid in a temperature control system.

[0024] 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

[0025] Figure 1 This is a schematic structural 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 fluids, 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 fluid. DETAILED DESCRIPTION

[0026] The present application provides a high boiling point hydrofluoroolefin ether compound having a structure shown in Formula I:

[0027]

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

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

[0030] As a specific embodiment of the present application, the high boiling point hydrofluoroolefin ether compound is a compound of 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 compound provided in the embodiment of the present application has a boiling point of 152-211° C., which is a high-boiling-point hydrofluoroolefin ether compound; has excellent environmental performance, an ODP value of 0, a GWP value of <100; no flash point; excellent high temperature resistance and insulation performance, a breakdown voltage of >25 kV, and a volume resistivity of >10 10 Ω·cm, compared with silicone oil or mineral oil, it has better antioxidant performance.

[0039] The ODP value (Ozone Depletion Potential), also known as the 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 hydrofluoroolefin ether compounds provided in this application do not contain chlorine or bromine elements, and there is no risk of depletion of the ozone layer during the degradation process.

[0040] The GWP (Global Warming Potential) value, or global warming potential, 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 uses carbon dioxide as a benchmark to compare 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. The IPCC defines GWP 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. The calculation formula is as follows:

[0041]

[0042] x(t)=e -t / τ ;

[0043]

[0044] Wherein, TH is the time range (such as 20, 100 and 500 years), 100 years is taken in this application; t represents time; RF x and RF r are 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 and τ i is a constant published by the IPCC.

[0045] The present application provides a method for preparing the high-boiling-point hydrofluoroolefin ether compound described in the above technical solution, comprising the following steps:

[0046] The hexafluoropropylene trimer, an alcohol compound, an alkaline catalyst and a polar solvent are mixed to carry out an elimination substitution reaction to obtain the high-boiling-point hydrofluoroolefin ether compound;

[0047] The hexafluoropropylene trimer has a structure shown in Formula II; the alcohol compound has a structure shown in Formula III and is an alcohol or a fluorine-containing alcohol;

[0048] Rfh-OH formula III.

[0049] In the examples of the present application, unless otherwise specified, the raw materials involved are commercially available products well known in the art.

[0050] In the embodiment of the present application, the alcohol compound is an alcohol or a fluorine-containing alcohol. As a specific embodiment of the present application, the alcohol may be methanol or ethanol, and the fluorine-containing alcohol may 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 the present application, when the alcohol compound is 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 by T2 in the embodiment) can be approximately 5 to 10:1, specifically 5:1, 8:1 or 10:1, wherein the molar feed amount of the hexafluoropropylene trimer is small, the purpose is to make the cheap methanol or ethanol excessive, to promote the conversion rate of the raw material hexafluoropropylene trimer which is relatively expensive relative to methanol and ethanol, and to effectively reduce the production cost, and the excess cheap 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 the present application, when the alcohol compound is a fluorine-containing alcohol, such as when preparing compounds of structures 3 to 7 (in preparing structures 3 to 7, the fluorine-containing alcohols used are 2,2-difluoroethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoropropanol, hexafluoroisopropanol, and hexafluorobutanol, respectively), 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, wherein the molar feed amount of the fluorine-containing alcohol is small, the purpose of which is to make the hexafluoropropylene trimer raw material, which is cheaper than the fluorine-containing alcohol, excessive, promote the conversion rate of the high-priced fluorine-containing alcohol, and effectively reduce the production cost. The excess cheap raw material hexafluoropropylene trimer can be recovered and reused by distillation during the purification process after the reaction.

[0053] As a specific implementation of the present application, the alkaline catalyst may be an inorganic alkaline composite catalyst or an organic alkaline catalyst.

[0054] As a specific embodiment of the present application, the inorganic alkaline composite catalyst may include an inorganic alkaline compound and a quaternary ammonium salt. As a specific embodiment of the present application, the inorganic alkaline compound may be KF or KOH; when preparing compounds of structure 1, structure 3, structure 4 and structure 6, the inorganic alkaline compound may be KOH; when preparing compounds of structure 2, structure 5 and structure 7, the inorganic alkaline compound may be KF. As a specific embodiment of the present application, the quaternary ammonium salt may be an alkylammonium chloride or an alkylammonium bromide (i.e., the inorganic alkaline composite catalyst is KF+alkylammonium chloride, KF+alkylammonium bromide, KOH+alkylammonium chloride, KOH+alkylammonium bromide), and the alkylammonium chloride and alkylammonium bromide act as phase transfer catalysts to increase the solubility of organic matter in the solvent, which is more conducive to the reaction. As a specific embodiment of the present application, the alkylammonium chloride can be one or more of benzyltrimethylammonium chloride, trimethyloctadecylammonium chloride, trimethylhexadecylammonium chloride, trimethyltetradecylammonium chloride and benzyldimethylhexadecylammonium chloride; the alkylammonium bromide can be one or more of benzyltrimethylammonium bromide, trimethyloctadecylammonium bromide, trimethylhexadecylammonium bromide, trimethyltetradecylammonium bromide and benzyldimethylhexadecylammonium bromide. As a specific embodiment of the present application, the molar ratio of the inorganic alkaline compound to the quaternary ammonium salt can 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 a specific implementation of the present application, the organic alkaline catalyst may be one or more of pyridine, 4-dimethylaminopyridine and triethylamine.

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

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

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

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

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

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

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

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

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

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

[0066] When preparing the compound of structure 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 the compound of structure 2, hexafluoropropylene trimer:triethylamine=1:0.01; or, hexafluoropropylene trimer:triethylamine=1:0.05; or, hexafluoropropylene trimer:triethylamine=1:0.1;

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

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

[0070] As a specific embodiment of the present 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 ratio of the volume of the polar solvent to the total volume of the hexafluoropropylene trimer and the alcohol compound can be approximately 1 to 1.5:1, specifically 1:1, 1.2:1 or 1.5:1.

[0071] As a specific embodiment of the present application, the method for mixing the hexafluoropropylene trimer, the alcohol compound, the alkaline catalyst and the polar solvent can be: mixing the alkaline catalyst and the polar solvent, adding the hexafluoropropylene trimer thereto to obtain a mixed solution; and adding the alcohol compound dropwise to the mixed solution using a dropping funnel. As a specific embodiment of the present application, the alcohol compound can be added dropwise for 60 minutes.

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

[0073] In the examples of the present application, the reaction formula involved in the elimination substitution reaction is as follows (in the reaction formula, Rfh is: -CH3, -CH2CH3, -CH2CHF2, -CH2CF3, -CH2CH2CF3, -CH(CF3)2 or -CH2CF2CHFCF3):

[0074]

[0075] As a specific implementation of the present application, after the elimination substitution reaction, the obtained reaction solution may be post-treated.

[0076] As a specific embodiment of the present application, when the alkaline catalyst is an inorganic alkaline composite catalyst and the polar solvent is water, the post-treatment method can be: distilling the reaction liquid to distill out 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 filtering the liquids to obtain a crude product of a hydrofluoroolefin ether compound; and distilling and purifying the crude product of a hydrofluoroolefin ether compound to obtain a high-purity hydrofluoroolefin ether compound.

[0077] As a specific embodiment of the present 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: distilling the reaction liquid to distill out all liquid substances to obtain a liquid fraction; distilling and purifying the liquid fraction again to purify excess raw materials (hexafluoropropylene trimer or alcohol compound) and solvent to obtain a bottom liquid; washing the bottom liquid with water and filtering the liquids to obtain a crude product of hydrofluoroolefin ether compounds; distilling and purifying the crude product to obtain a high-purity hydrofluoroolefin ether compound. As a specific embodiment of the present application, the excess raw materials (hexafluoropropylene trimer or alcohol compound) and solvent distilled out can be recycled and reused; the water washing can be performed three times.

[0078] As a specific embodiment of the present application, when the alkaline catalyst is an organic alkaline catalyst, the post-treatment method can be: distilling the reaction liquid to distill off excess raw materials and solvents to obtain a bottom liquid; washing the bottom liquid with water and filtering the liquids to obtain a crude product of a hydrofluoroolefin ether compound; and distilling and purifying the crude product to obtain a high-purity hydrofluoroolefin ether compound.

[0079] The preparation method provided in the embodiment of the present application has readily available raw materials, a simple process, and an excellent cost advantage, thereby providing an additional option for market application.

[0080] The embodiments of the present application provide the use of the high boiling point hydrofluoroolefin ether compound described in the above technical solution or the high boiling point hydrofluoroolefin ether compound prepared by the preparation method described in the above technical solution as a temperature control working fluid in a temperature control system.

[0081] As a specific implementation of the present application, the temperature control system may include a battery direct contact immersion thermal management system, new energy charging equipment, a temperature control device during semiconductor manufacturing and testing, or an immersion liquid cooling system for a server data center.

[0082] The hydrofluoroolefin ether compound provided in the embodiment of the present application has excellent properties and a wide temperature range. It can be selected between -60℃ and 200℃ for suitable application scenarios and used as high-temperature or low-temperature temperature control liquids; it has no flash point and is not easy to burn, and even has a fire extinguishing effect, without fire hazards; it has excellent insulation performance and has obvious advantages in some scenes requiring insulation; it has good material compatibility and is non-corrosive to various metals, polymer materials, and glass ceramic materials. As a specific embodiment of the present application, the hydrofluoroolefin ether compound can be used as a fluid medium for a low-temperature thermostat, a low-temperature circulation pump, an industrial refrigerator, a high-low temperature integrated machine, or a high-temperature circulation pump, or as a semiconductor test temperature control liquid, a liquid-cooled charging pile coolant, a lithium battery energy storage temperature control liquid, and a high-temperature heat-conducting medium. The hydrofluoroolefin ether compound is used as a heat-carrying fluid or a cold-carrying fluid, and a heat medium or a cold medium is transported by a liquid delivery pump, or a heat exchange of a heat medium or a cold medium is performed by a liquid circulation pump to achieve the purpose of precise temperature control.

[0083] 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.

[0084] 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.

[0085] In order to further illustrate the present application, the high-boiling-point hydrofluoroolefin ether compounds provided in the present application and their preparation methods and applications are described in detail below in combination with examples, but they should not be construed as limiting the scope of protection of the present application.

[0086] Example 1

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

[0088] In a 5L 316 stainless steel reactor equipped with a dripping device, add solvent water and inorganic alkaline composite catalyst (KOH + alkyl ammonium) as substrates, stir and mix at room temperature for 1h, then add 900g of hexafluoropropylene trimer (represented by T2, structure as shown in formula II, the same below), and then use a dropping funnel to drip methanol into the substrate, and control the dripping rate to complete the dripping for 60min. After the dripping is completed, control the reaction conditions: continue to stir and react at 100-150℃ for 8-24h. After the 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 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 filtered to collect the crude product of structure 1 compound; the upper aqueous phase is the excess raw material methanol-water solution phase, which can be distilled to recover the raw material methanol. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound of structure 1) and calculate the yield of the target product (compound of structure 1); the crude product was distilled and purified to obtain a high-purity target product (compound of structure 1), and its gas chromatography purity was measured. The reaction conditions and reaction results of Example 1 (1) are shown in Table 1.

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

[0090]

[0091]

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

[0093] In a 5L 316 stainless steel reactor equipped with a dripping device, add acetonitrile solvent and inorganic alkaline composite catalyst (KF+alkylammonium) as substrate, stir and mix at room temperature for 1h, then add 900g of hexafluoropropylene trimer (T2), and then use a dropping funnel to drip methanol into the substrate, and control the dripping rate to complete the dripping for 60min. After the dripping is completed, control the reaction conditions: 100-150℃ and continue to stir and react for 8-24h. After the reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is the inorganic alkaline composite catalyst, which can be recycled and reused. All distilled liquid fractions are distilled and purified again, and the first fraction is the excess 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 then separated and filtered again, and the lower organic phase is collected, that is, the crude product of structure 1 compound. The crude product received is analyzed by gas chromatography (GC), the content of the target product (structure 1 compound) is determined, and the yield of the target product (structure 1 compound) is calculated. The crude product was distilled and purified to obtain a high-purity target product (compound of structure 1), and its gas chromatography purity was measured. The reaction conditions and reaction results of Example 1 (2) are shown in Table 2.

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

[0095]

[0096] Example 2

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

[0098] In a 5L 316 stainless steel reactor equipped with a dripping device, add solvent water and inorganic alkaline composite catalyst (KOH + alkyl ammonium) as substrates, stir and mix at room temperature for 1h, then add 900g of hexafluoropropylene trimer (T2), and then use a dropping funnel to drip ethanol into the substrate, and control the dripping rate to complete the dripping for 60min. After the dripping is completed, control the reaction conditions: continue to stir and react at 100-150℃ for 8-24h. After the reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is the 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 then separated and filtered again to collect the crude product of structure 2 compound; the upper aqueous phase is the excess raw material ethanol-water solution phase, which can be distilled to recover the raw material ethanol. The crude product received is analyzed by gas chromatography (GC), the content of the target product (structure 2 compound) is determined, and the yield of the target product (structure 2 compound) is calculated. The crude product was distilled and purified to obtain a high-purity target product (compound of structure 2), and its gas chromatography purity was measured. The reaction conditions and reaction results of Example 2 (1) are shown in Table 3.

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

[0100]

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

[0102] In a 5L 316 stainless steel reactor equipped with a dripping device, add acetonitrile solvent and inorganic alkaline composite catalyst (KF+alkylammonium) as substrate, stir and mix at room temperature for 1h, then add 900g of hexafluoropropylene trimer (T2), and then use a dropping funnel to drip ethanol into the substrate, and control the dripping rate to complete the dripping for 60min. After the dripping is completed, control the reaction conditions to 100-150℃ and continue to stir and react for 8-24h. After the reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances, and the bottom solid is the inorganic alkaline composite catalyst, which can be recycled and reused. All distilled liquid fractions are distilled and purified again, and the first fraction is the excess raw material ethanol-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 then separated and filtered again, and the lower organic phase is collected, that is, the crude product of structure 2 compound. The crude product received is analyzed by gas chromatography (GC), the content of the target product (structure 2 compound) is determined, and the yield of the target product (structure 2 compound) is calculated. The crude product was distilled and purified to obtain a high-purity target product (compound of structure 2), and its gas chromatography purity was measured. The reaction conditions and reaction results of Example 2 (2) are shown in Table 4.

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

[0104]

[0105]

[0106] Example 3

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

[0108] In a 20L 316 stainless steel reactor equipped with a dripping device, solvent water and an inorganic alkaline composite catalyst (KOH+alkylammonium) are added as substrates, stirred and mixed at room temperature for 1h, and then hexafluoropropylene trimer (T2) is added in an amount of 5 to 10 times the molar amount of the fluorinated alcohol, and then 2,2-difluoroethanol (164g) 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 to be 100 to 150°C and the stirring reaction is continued for 8 to 24h. After the 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 distilled liquid fractions are distilled and purified again. The first fraction is the excess raw material hexafluoropropylene trimer (T2)-water solvent layer. After separation, the raw material T2 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 and filtered again, and the lower organic phase, i.e., the crude product of the structure 3 compound, is collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound of structure 3) and calculate the yield of the target product (compound of structure 3). The crude product was subjected to rectification and purification to obtain a high-purity target product (compound of structure 3), and its gas chromatography purity was measured. The reaction conditions and reaction results of Example 3 are shown in Table 5.

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

[0110]

[0111] Example 4

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

[0113] In a 20L 316 stainless steel reactor equipped with a dripping device, add solvent water and an inorganic alkaline composite catalyst (KOH+alkylammonium) as a substrate, stir and mix at room temperature for 1h, then add hexafluoropropylene trimer (T2), the amount of which is 5 to 10 times the molar amount of the fluorinated alcohol, and then use a dropping funnel to drop 2,2,2-trifluoroethanol (200g) into the substrate, and control the drop rate to complete the dropwise addition for 60min. After the dropwise addition is completed, control the reaction conditions to 100 to 150°C and continue to stir and react for 8 to 24h. After the 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 distilled liquid fractions are distilled and purified again, and the first fraction is the excess raw material hexafluoropropylene trimer (T2)-water solvent layer. After separation, the raw material T2 can be recycled and reused; the bottom liquid is the product layer, the product layer is washed with water three times, and then separated and filtered again, and the lower organic phase, i.e., the crude product of the structure 4 compound, is collected. The crude product was analyzed by gas chromatography (GC) to determine the content of the target product (compound of structure 4) and calculate the yield of the target product (compound of structure 4). The crude product was subjected to rectification and purification to obtain a high-purity target product (compound of structure 4), and its gas chromatography purity was measured. The reaction conditions and reaction results of Example 4 are shown in Table 6.

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

[0115]

[0116] Example 5

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

[0118] In a 20L 316 stainless steel reactor equipped with a dripping device, add acetonitrile solvent and inorganic alkaline composite catalyst (KF+alkylammonium) as substrate, stir and mix at room temperature for 1h, then add hexafluoropropylene trimer (T2), the amount of which is 5 to 10 times the molar amount of the fluorinated alcohol, and then use a dropping funnel to drop 3,3,3-trifluoropropanol (228g) into the substrate, and control the drop rate to complete the dropwise addition for 60min. After the dropwise addition is completed, control the reaction conditions to 100 to 150°C and continue to stir the reaction for 8 to 24h. After the 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 the hexafluoropropylene trimer (T2)-acetonitrile solvent layer, which can be recycled and extracted for excess hexafluoropropylene trimer (T2) and solvent acetonitrile. The bottom liquid is the product layer. The product layer is washed three times with water, and then filtered again to collect the lower organic phase, i.e., the crude product of structure 5. The crude product is analyzed by gas chromatography (GC), the content of the target product (structure 5 compound) is determined, and the yield of the target product (structure 5 compound) is calculated. The crude product is distilled and purified to obtain a high-purity target product (structure 5 compound), and its gas chromatography purity is measured. The reaction conditions and reaction results of Example 5 are shown in Table 7.

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

[0120]

[0121] Example 6

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

[0123] In a 20L 316 stainless steel reactor equipped with a dripping device, add solvent water and inorganic alkaline composite catalyst (KOH + alkyl ammonium) as substrates, stir and mix at room temperature for 1h, then add hexafluoropropylene trimer (T2), the amount of which is 5 to 10 times the molar amount of the fluorine-containing alcohol, and then use a dropping funnel to drop 1,1,1,3,3,3-hexafluoro-2-propanol (i.e., hexafluoroisopropanol, 336g) into the substrate, and control the drop rate to complete the dropwise addition for 60min. After the dropwise addition is completed, control the reaction conditions: continue to stir and react at 100 to 150°C for 8 to 24h. After the 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 the hexafluoropropylene trimer (T2)-water solvent layer, and the excess hexafluoropropylene trimer (T2) can be recycled and extracted for reuse. The bottom liquid is the product layer. The product layer is washed three times with water, filtered again, and the lower organic phase is collected, which is the crude product of the compound of structure 6. The crude product is analyzed by gas chromatography (GC), the content of the target product (compound of structure 6) is determined, and the yield of the target product (compound of structure 6) is calculated. The crude product is distilled and purified to obtain a high-purity target product (compound of structure 6), and its gas chromatography purity is measured.

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

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

[0126]

[0127] Example 7

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

[0129] In a 20L 316 stainless steel reactor equipped with a dripping device, add acetonitrile as solvent and inorganic alkaline composite catalyst (KF+alkylammonium) as substrate, stir and mix at room temperature for 1h, then add hexafluoropropylene trimer (T2), the amount added is 5 to 10 times the molar amount of fluorine-containing alcohol, and then use a dropping funnel to drop 2,2,3,4,4,4-hexafluoro-1-butanol (364g) into the substrate, and control the drop rate to drop for 60min. After the drop addition is completed, control the reaction conditions: continue to stir and react at 100 to 150℃ for 8 to 24h. After the reaction is completed, the reaction liquid is directly distilled to distill out all liquid substances. The bottom solid is an inorganic alkaline composite catalyst, which can be recycled and reused. All the liquid substances distilled out are rectified and purified again. The first fraction is the hexafluoropropylene trimer (T2)-acetonitrile solvent layer, which can be used to recover and extract the excess hexafluoropropylene trimer (T2) and solvent acetonitrile for reuse; the bottom liquid is the product layer, the product layer is washed with water three times, and filtered again to collect the lower organic phase, i.e., the crude product of structure 7 compound. The crude product is analyzed by gas chromatography (GC), the content of the target product (structure 7 compound) is determined, and the yield of the target product (structure 7 compound) is calculated. The crude product is rectified and purified to obtain a high-purity target product (structure 7 compound), and its gas chromatographic purity is measured. The reaction conditions and reaction results of Example 7 are shown in Table 9.

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

[0131]

[0132] Example 8

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

[0134] In a 5L volume 316 stainless steel reactor equipped with a dripping device, add solvent, organic base catalyst (4-dimethylaminopyridine) as substrate, stir and mix at room temperature for 1h, then add 900g of hexafluoropropylene trimer (T2), and then use a dropping funnel to drip methanol into the substrate, control the dripping rate to complete the dripping for 60min. After the dripping is completed, control the reaction conditions to 100-150°C and continue to stir the reaction for 8-24h. After the reaction is completed, the reaction liquid is directly distilled to distill out excess methanol and solvent for recycling. The bottom liquid organic phase is the product phase, the product phase is washed with water three times, and then separated and filtered again to collect the target product, i.e., the crude product of structure 1 compound. The crude product received is analyzed by gas chromatography (GC), the content of the target product (structure 1 compound) is determined, and the yield of the target product (structure 1 compound) is calculated. The crude product phase is distilled and purified to obtain a high-purity target product (structure 1 compound), and its gas chromatographic purity is measured. The reaction conditions and reaction results of Example 8 are shown in Table 10.

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

[0136]

[0137] Example 9

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

[0139] In a 5L volume 316 stainless steel reactor equipped with a dripping device, add solvent acetonitrile and organic base catalyst (triethylamine) as substrates, stir and mix at room temperature for 1h, then add 900g of hexafluoropropylene trimer (T2), and then use a dropping funnel to drip ethanol into the substrate, control the dripping rate to complete the dripping for 60min. After the dripping is completed, control the reaction conditions to 100-150°C and continue to stir the reaction for 8-24h. After the reaction is completed, the reaction liquid is directly distilled to distill out excess ethanol and solvent acetonitrile for recycling. The bottom liquid organic phase is the product phase, the product phase is washed with water three times, and then separated and filtered again to collect the target product, i.e., the crude product of structure 2 compound. The crude product received is analyzed by gas chromatography (GC), the content of the target product (structure 2 compound) is determined, and the yield of the target product (structure 2 compound) is calculated. The crude product is distilled and purified to obtain a high-purity target product (structure 2 compound), and its gas chromatographic purity is measured. The reaction conditions and reaction results of Example 9 are shown in Table 11.

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

[0141]

[0142] Example 10

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

[0144] In a 20L 316 stainless steel reactor equipped with a dripping device, add solvent and organic base catalyst (triethylamine) as substrate, stir and mix at room temperature for 1h, then add hexafluoropropylene trimer (T2), the amount of which is 5 to 10 times the molar amount of the fluorinated alcohol, and then use a dropping funnel to drop 2,2-difluoroethanol 164g into the substrate, and control the dropping rate to complete the dropwise addition for 60min. After the dropwise addition is completed, control the reaction conditions to 100 to 150°C and continue to stir the reaction for 8 to 24h. After the reaction is completed, the reaction liquid is directly distilled to distill out the excess hexafluoropropylene trimer (T2) and solvent for recycling. The bottom liquid organic phase is the product phase, and the product phase is washed with water three times, and then separated and filtered again to collect the target product, i.e., the crude product of structure 3 compound. The crude product received is analyzed by gas chromatography (GC), the content of the target product (structure 3 compound) is determined, and the yield of the target product (structure 3 compound) is calculated. The crude product was distilled and purified to obtain a high-purity target product (compound of structure 3), and its gas chromatography purity was measured. The reaction conditions and reaction results of Example 10 are shown in Table 12.

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

[0146]

[0147] Embodiment 11

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

[0149] In a 20L 316 stainless steel reactor equipped with a dripping device, add 3L of solvent acetonitrile and an organic base catalyst (4-dimethylaminopyridine) as a substrate, stir and mix at room temperature for 1h, then add hexafluoropropylene trimer (T2), the amount of which is 5 to 10 times the molar amount of the fluorinated alcohol, and then use a dropping funnel to drop 2,2,3,4,4,4-hexafluoro-1-butanol (364g) into the substrate, and control the drop rate to complete the dropwise addition for 60min. After the dropwise addition is completed, control the reaction conditions at 100 to 150°C and continue to stir the reaction for 8 to 24h. After the reaction is completed, the reaction liquid is directly distilled to distill out the excess hexafluoropropylene trimer (T2) and solvent acetonitrile for recycling. The bottom liquid organic phase is the product phase, the product phase is washed with water three times, and then separated and filtered again to collect the target product, i.e., the crude product of the structure 7 compound. 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 subjected to rectification and purification to obtain a high-purity target product (compound of structure 7), and its gas chromatography purity was measured. The reaction conditions and reaction results of Example 11 are shown in Table 13.

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

[0151]

[0152]

[0153] In the above embodiments, the compounds of structures 1 to 7 were selected as the products with the highest purity after distillation and purification, and physical property tests and compatibility tests were performed respectively:

[0154] (I) Physical property test

[0155] Boiling point test: in accordance with the national standard GB / T616-2006 "General method for determination of boiling point of chemical reagents"; flash point test in accordance with the national standard GB / T261-2021 "Flash point-Pinsky-Martin closed cup method"; breakdown voltage test in accordance with the national standard GB / T1408.1-2006 "Electrical strength test method for insulating materials"; volume resistivity test 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 in accordance with the "Transient hot wire method", reference standard ASTM D7896; specific heat capacity in accordance with the specific heat capacity definition formula: Q = Cp m δt test calculation (where Cp represents specific heat capacity, Q represents the amount of heat absorbed or released, m represents the mass of the substance, δt represents the temperature change), kinematic viscosity in accordance with the national standard: GB / T 265-88 "Determination of kinematic viscosity of petroleum products". The test results are shown in Table 14.

[0156] Table 14 Physical properties of compounds of structures 1 to 7

[0157] physical properties Boiling Point density Specific heat 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] It can be seen from the data in Table 14 that compounds of structures 1 to 7 have the advantages of excellent environmental protection, high boiling point, low viscosity at low temperatures, good insulation, etc., and fully meet the requirements of temperature control liquid working fluids.

[0159] (II) Compatibility test

[0160] The compatibility test is divided into room temperature compatibility test and high temperature compatibility test. The test method is: 50mL of the distilled and purified compounds of structure 1 to structure 7 are placed in a stainless steel hydrothermal reactor with a volume of 100mL, and then various types of materials are added to conduct room temperature immersion test for 25℃-168h and high temperature immersion test for 100℃-168h. The compatibility test results are shown in Tables 15 and 16.

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

[0162]

[0163]

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

[0165]

[0166] From the data in Tables 15 to 16, it can be seen that compounds of structures 1 to 7 have excellent material compatibility, have a slight swelling effect on silicone rubber sealing rings, and have a slight swelling effect on fluororubber sealing rings, and their compatibility is slightly poor.

[0167] The application scenarios of the high boiling point hydrofluoroolefin ether compound temperature control fluid provided in this application are as follows:

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

[0169] The high boiling point hydrofluoroolefin ether 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 the 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 achieve the purpose of controlling the operating temperature of the energy storage battery system and achieving 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.

[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 cooling liquid 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.

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

[0173] 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 substance with a specific boiling point in the structural compounds 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: Server data center immersion liquid cooling system

[0175] 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 working fluid exchanges heat with the hardware heat source of the computer through the transportation flow of the pump, thereby transferring heat from the server. The liquid working fluid used for single-phase immersion cooling of the server 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.

[0176] The above is only a preferred implementation of the present application and does not limit the present application in any form. It should be noted that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principles of the present application, and these improvements and modifications should also be regarded as the protection scope of the present application.

Claims

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

2. The high boiling point hydrofluoroolefin ether compound according to claim 1, characterized in that: The alkyl group is -CH3 or CH3CH2-, and the fluoroalkyl group is CHF2CH2-, CF3CH2-, CF3CH2CH2-, -CH(CF3)2 or CF3CHFCF2CH2-.

3. The method for preparing the high boiling point hydrofluoroolefin ether compound according to claim 1 or 2, characterized in that: The following steps are involved: The hexafluoropropylene trimer, an alcohol compound, an alkaline catalyst and a polar solvent are mixed to carry out an elimination substitution reaction to obtain the high-boiling-point hydrofluoroolefin ether compound; The hexafluoropropylene trimer has a structure shown in Formula II; the alcohol compound has a structure shown in Formula III and is an alcohol or a fluorine-containing alcohol; Rfh-OH formula III.

4. The preparation method according to claim 3, characterized in that: The alcohol is methanol or ethanol; the fluorine-containing alcohol is 2,2-difluoroethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoropropanol, hexafluoroisopropanol or hexafluorobutanol.

5. The preparation method according to claim 3, characterized in that: When the alcohol compound is alcohol, the molar ratio of the alcohol compound to the hexafluoropropylene trimer is 5-10:1; when the alcohol compound is fluorine-containing alcohol, the molar ratio of the alcohol compound to the hexafluoropropylene trimer is 1:5-10.

6. The preparation method according to claim 3, 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, the quaternary ammonium salt is alkylammonium chloride or alkylammonium bromide, and the molar ratio of the inorganic alkaline compound to the quaternary ammonium salt is 1:0.01-0.1; The organic alkaline catalyst is one or more of pyridine, 4-dimethylaminopyridine and triethylamine.

7. The preparation method according to claim 6, characterized in that: The molar ratio of the alcohol compound to the compound with a small molar feed amount in the hexafluoropropylene trimer and the inorganic alkaline compound in the inorganic alkaline composite catalyst is 1:1-1.5; the molar ratio of the alcohol compound to the compound with a small molar feed amount in the hexafluoropropylene trimer and the organic alkaline catalyst is 1:0.01-0.

1.

8. The preparation method according to claim 3, characterized in that: The temperature of the elimination substitution reaction is 100-150° C., and the time is 8-24 hours.

9. Use of the high boiling point hydrofluoroolefin ether compound according to claim 1 or 2 or the high boiling point hydrofluoroolefin ether compound prepared by the preparation method according to any one of claims 3 to 8 as a temperature control working fluid in a temperature control system.

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 high boiling point hydrofluoroolefin ether compound according to claim 1 or 2 or the high boiling point hydrofluoroolefin ether compound prepared by the preparation method according to any one of claims 3 to 8.

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