Fluorine-substituted ethers, and compositions, methods, and uses thereof.

Abstract

Fluoroether 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane ("HFE-347mcf") may be used as a refrigerant and / or heat transfer composition in single-phase and two-phase cooling systems, and a method for heating and / or cooling electronic components or devices comprises providing a heat transfer fluid containing at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, and transferring heat between the electronic components and the heat transfer fluid. Fluoroether 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane can be synthesized by reacting 2,2,3,3,3-pentafluoro-1-propanol with chlorodifluoromethane (R-22).

Description

Technical Field

[0001] (Cross - reference to related applications) This application claims the benefit of U.S. Provisional Patent Application No. 63 / 415,683, filed October 13, 2022, under 35 U.S.C. § 119(e), entitled "Fluorine substituted ethers derived from chlorodifluoromethane (R22), compositions, methods and uses including same", the entire disclosure of which is hereby incorporated by reference in its entirety.

[0002] The present disclosure is directed to fluorine - substituted ethers, compositions such as refrigerants and / or heat transfer compositions containing such ethers, and methods and uses including the thermal management of electronic devices such as immersion cooling.

Background Art

[0003] There continues to be a need for inert fluorinated compounds that provide high thermal stability, low toxicity, non - flammability, good solvency, and a wide operating temperature range while having a low global warming potential to meet the requirements of various applications.

[0004] The applicants have come to understand that developing new compounds and compositions for use in many important applications involves many challenging problems. Specifically, the applicants have come to understand the need for compositions, methods, and systems that are simultaneously environmentally acceptable (low GWP and low ODP), non-flammable, low-toxicity or non-toxic, and possess excellent properties required for specific applications (e.g., good dissolving power for vapor degreasing, or low dielectric constant when the application involves exposure or potential exposure to electronic equipment or components). There also continues to be a need for improved compounds for transferring heat and / or managing the temperature of devices and articles, including portable handheld devices, where the desire to miniaturize while adding functionality increases the thermal power density of the device during operation, and therefore makes cooling electronic components within such devices, including batteries, more difficult. As a general rule, the increasing computing power in desktop computers, data centers, and communication centers leads to increased thermal output when such devices are operating, and in this case too, the thermal management of such electronic devices becomes increasingly important, increasingly difficult, and more demanding. Another example of thermal management challenges arises as a result of the increasing use of electric vehicles, including cars, trucks, and motorcycles. In electric vehicles, thermal management is particularly important and challenging for several reasons, including the critical need to cool and / or heat the battery within a relatively narrow temperature range in a reliable, efficient, and safe manner, and the challenge of providing effective thermal battery management increases as the demand for battery-powered vehicles with wider ranges and faster charging speeds grows.

[0005] The efficiency and effectiveness of batteries, especially those supplying power to electric vehicles, are a function of the operating temperature in which they operate. Therefore, thermal management systems must be able to do more than simply remove heat from the battery during operation and / or charging; they must achieve cooling over a relatively narrow temperature range using the lowest possible cost and lightest possible equipment. This creates a need for heat transfer compositions in systems with a difficult combination of physical and performance characteristics. Furthermore, in some critical applications, thermal management systems must be able to heat the battery, particularly when the vehicle is started in cold weather, which makes discovering, developing, and obtaining effective compounds and / or compositions in such systems even more difficult, not only from the standpoint of thermal performance but also from a multitude of other viewpoints, including environmental, safety (flammability and toxicity), dielectric properties, and so on.

[0006] As a specific example of the importance of dielectric constant, one frequently used system for thermal management of electric vehicle batteries involves immersing the battery in a composition used for thermal management. Such a system imposes the further constraint that the composition used within such a system must be electronically compatible with close contact with the battery or other electronic devices or components during the operation of the battery or device. Generally, this means that the composition must not only be non-flammable, but also have low conductivity and a high level of stability at relatively high temperatures during operation while in contact with the battery or other electronic components while they are operating. The applicants have come to understand that such properties are also desirable in the indirect cooling of electronic devices and batteries in operation, since leakage of any such composition can result in contact with electronic components in operation.

[0007] Another example of the challenges in providing refrigerants for thermal management is the increasing use of electric vehicles, particularly cars, trucks, and motorcycles. In electric vehicles, thermal management is both critical and challenging for several reasons, including the critical need to cool and / or heat the battery within a relatively narrow temperature range in a reliable, efficient, and safe manner. As the demand for battery-powered vehicles with wider ranges and faster charging increases, the challenge of providing effective thermal battery management will only grow.

[0008] Perfluorinated compounds have been frequently used in many of these demanding applications. In addition, other thermal management compositions commonly used for battery cooling, including immersion cooling, are water / glycol combinations, but it has been noted that further other classes of materials, including some chlorofluorocarbons, fluorohydrocarbons, chlorohydrocarbons, and hydrofluoroethers, may be used. See, for example, U.S. Patent Application Publication 2018 / 0191038.

[0009] The following formula

[0010] [ka]

[0011] A fluorinated ether compound according to the formula (wherein n is 1 or 2, and when n is 1, m is any integer between 0 and 3, but when n is 2, m is 0 or 2) has been particularly proposed for use as a solvent for various fluorine-containing polyethers. See Japanese Patent Publication No. 202105950. This document shows that an embodiment of the above formula, said to have a 3-1 configuration (to be understood as meaning m=3 and n=1), has additional uses including drainage agents, foaming agents, heat transfer media, and fire extinguishing agents, although such uses are not specifically described or illustrated.

[0012] Accordingly, the applicants have come to understand the need for thermal management methods and systems that use heat transfer compositions that are environmentally acceptable (low GWP and low ODP), non-flammable, low-toxicity or non-toxic, have excellent insulating properties, and have thermal properties that provide effective cooling and / or heat (including use in electronic components operating at relatively high temperatures and / or in a relatively narrow temperature range, particularly preferably with low-cost, reliable, and lightweight devices).

[0013] Other applications of fluorinated ether compounds include aerosol propellants, foaming agents, gaseous dielectrics, fire suppressants, solvents, cleaning agents, power cycle working fluids, and starting materials for producing other organofluorine compounds. [Overview of the project]

[0014] This disclosure is based on the discovery that certain fluorinated ethers, particularly 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane, 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane (sometimes referred to herein as "HFE-347mcf"), 2-(difluoromethoxy)-1,1,1,3,3,3-hexafluoropropane, and 4-(difluoromethoxy)-1,1,1,2,2,3,3-heptafluorobutane, can be used as refrigerants and / or in heat transfer compositions, among other uses disclosed herein.

[0015] In one embodiment, the Disclosure provides a method for providing heat transfer to and from an electronic component, article, and / or device while the electronic component, article, and / or device is in operation, comprising: providing a heat transfer composition comprising at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane; and cooling the electronic component, article, and / or device by bringing the heat transfer composition into contact with the electronic component, article, and / or device while the electronic component, article, and / or device is in operation.

[0016] In another form, the Disclosure provides a method for heating and / or cooling an electronic component, article and / or device while the electronic component, article and / or device is in operation, comprising: (a) providing a heat transfer composition comprising at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane; (b) immersing the electronic component, article and / or device in the heat transfer composition while the electronic component, article and / or device is in operation; and (c) transferring heat between the immersed electronic component, article and / or device and the heat transfer composition.

[0017] In a further form, the present disclosure provides a method for synthesizing 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane by reacting 2,2,3,3,3-pentafluoro-1-propanol with chlorodifluoromethane in the presence of a base.

[0018] This disclosure further provides 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane (compound 1) and a composition containing the same (composition 1).

[0019] This disclosure also provides 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane (sometimes referred to herein as "HFE-347mcf") (Compound 2) and compositions comprising the same (Composition 2).

[0020] This disclosure also provides 2-(difluoromethoxy)-1,1,1,3,3,3-hexafluoropropane (compound 3) and compositions comprising the same (composition 3).

[0021] This disclosure also provides 4-(difluoromethoxy)-1,1,1,2,2,3,3-heptafluorobutane (compound 4) and compositions comprising the same (composition 4).

[0022] The present disclosure also provides a heat transfer composition comprising HFE-347mcf. The heat transfer composition according to this paragraph may be referred to herein as heat transfer composition 1 for convenience.

[0023] The present disclosure also provides a heat transfer composition comprising at least about 10 wt% of HFE-347mcf. The heat transfer composition according to this paragraph may be referred to herein as heat transfer composition 2 for convenience.

[0024] The present disclosure also provides a heat transfer composition comprising at least about 50 wt% of HFE-347mcf. The heat transfer composition according to this paragraph may be referred to herein as heat transfer composition 3 for convenience.

[0025] The present disclosure also provides a heat transfer composition comprising at least about 75 wt% of HFE-347mcf. The heat transfer composition according to this paragraph may be referred to herein as heat transfer composition 4 for convenience.

[0026] The present disclosure also provides a heat transfer composition comprising at least about 90 wt% of HFE-347mcf. The heat transfer composition according to this paragraph may be referred to herein as heat transfer composition 5 for convenience.

[0027] The present disclosure also provides a heat transfer composition consisting essentially of HFE-347mcf. The heat transfer composition according to this paragraph may be referred to herein as heat transfer composition 6 for convenience.

[0028] The present disclosure also provides a heat transfer composition consisting of HFE-347mcf. The heat transfer composition according to this paragraph may be referred to herein as heat transfer composition 7 for convenience.

[0029] The present disclosure also provides a heat transfer composition comprising Compound 1, which may be referred to herein as heat transfer composition 8 for convenience.

[0030] The present disclosure also provides a heat transfer composition comprising Compound 3, which may be referred to herein as heat transfer composition 9 for convenience.

[0031] This disclosure also provides a heat transfer composition comprising compound 4, which may be referred to herein for convenience as heat transfer composition 10. [Brief explanation of the drawing]

[0032] By considering the attached drawings and referring to the following description of embodiments of the present disclosure, the above and other characteristics of the present disclosure, as well as the ways in which they are achieved, will become clearer, and the present disclosure itself will be better understood.

[0033] [Figure 1] This is a schematic diagram of the thermal management system disclosed herein. [Figure 2A] This is a schematic diagram of the first exemplary immersion cooling system described herein. [Figure 2B] This is a schematic diagram of a second exemplary immersion cooling system as described herein. [Figure 3A] This is a schematic diagram of a battery thermal management system according to one embodiment of the present disclosure. [Figure 3B] This is a schematic diagram of a battery thermal management system according to one embodiment of the present disclosure. [Figure 4] This is a photograph showing a battery thermal management system according to one embodiment of the present disclosure. [Figure 5] This is an illustrative circuit diagram of an organic Rankine cycle. [Figure 6] This is an example circuit diagram of a heat pump. [Figure 7] This is a circuit diagram of an example of a secondary loop system. [Figure 8] This is a substantially schematic diagram of an example of a lithium-ion battery cooling system using the composition of the present disclosure. [Figure 9] This is a substantially schematic diagram of an example of a lithium-ion battery having the electrolyte formulation of the present disclosure. [Figure 10] This is a substantially schematic diagram of a heat pipe using the heat transfer composition of the present disclosure.

[0034] The examples provided herein are illustrative of embodiments of the disclosure and should not be construed as limiting the scope of the disclosure in any way. [Modes for carrying out the invention]

[0035] I. Definition

[0036] [Table 1]

[0037] The terms “electronic device” and related terms mean a device or component of a device, such as a battery, electric vehicle battery, data center, or integrated circuit, that is in the process of performing its intended function by receiving and / or transmitting and / or generating electrical energy and / or electronic signals. Therefore, as used herein, the term “operating electronic device” includes, for example, a battery in the process of supplying an electrical energy source to another component, and a battery being charged or recharged, for example.

[0038] The terms “operating electronic device” and related terms mean a device or component of a device that is in the process of performing its intended function by receiving and / or transmitting and / or generating electrical energy and / or electronic signals. Thus, as used herein, the term “operating electronic device” includes electric vehicle batteries, as well as batteries in the process of supplying an electrical energy source to another component, and batteries that are being charged or recharged, including, for example, batteries in data centers and integrated circuits.

[0039] The term “heat transfer composition” and related terms mean a composition in the form of a fluid (liquid or gas) used to transfer heat or energy from one fluid, article, or device to another fluid, article, or device, and thus include, for example, refrigerants for Rankine cycles, thermal management compositions, and working fluids.

[0040] When a heat transfer composition is used in thermal management (for example, in electronic cooling) to keep a device or article within a specific temperature range, it may be referred to herein as a thermal management composition.

[0041] In a heat transfer system (e.g., a vapor compression heat transfer system), components, components, or combinations of components present in a heat transfer composition for the purpose of transferring heat (as opposed to, for example, providing lubrication or stabilization) may be referred to herein as a refrigerant.

[0042] As used herein, the term “Rankine cycle” refers to a system comprising: 1) a boiler that converts liquid into steam under high pressure; 2) a turbine that expands the steam to extract mechanical energy; 3) a condenser that converts the low-pressure exhaust steam from the turbine into a low-pressure liquid; and 4) a pump that returns the condensate to the boiler under high pressure. Such systems are commonly used for power generation.

[0043] "Thermal contact" and its related forms include direct contact with a surface and indirect contact through another object or fluid that facilitates the flow of heat between the surface and the fluid.

[0044] "Thermal conductivity" refers to the dielectric breakdown voltage in kV, measured according to ASTM D7896-19.

[0045] The Global Warming Potential (GWP) was developed to allow comparisons of the global warming impacts of different gases. It measures how much energy is absorbed over a given period by one ton of a given gas release, relative to one ton of carbon dioxide release. A higher GWP indicates that a given gas will warm the Earth more than CO2 over that period. The period typically used for GWP is 100 years. GWP provides a common measure that allows analysts to sum up emission estimates for different gases.

[0046] The term "AMES negative" refers to a compound or composition that returns a negative result when tested under the Ames test as defined in the Toxic Substances Control Act of the United States.

[0047] The flash point is the lowest temperature at which a liquid vapor continues to burn after the ignition source has been removed, as determined according to ASTM D3828-16a.

[0048] In the context of heat management compositions or heat transfer compositions containing fluids, "non-flammable" means a compound or composition that does not have a flash point below 100°F (37.8°C) according to NFPA 30:Flammable and Combustible Liquid Code. The flash point of a heat management composition or fluid is determined according to ASTM D3828-16a, and refers to the lowest temperature at which the vapor of the composition continues to burn after the ignition source has been removed.

[0049] In the context of refrigerant compositions, compounds or compositions that are non-flammable and of low or no toxicity are classified as "A1" according to ASHRAE Standard 34-2016 Designation and Safety Classification of Refrigerants and Annex B1 of ASHRAE Standard 34-2016.

[0050] "Non-toxic or low-toxicity" means a fluid classified as Class "A" according to ASHRAE Standard 34-2016 Designation and Safety Classification of Refrigerants, and as described in Annex B1 of ASHRAE Standard 34-2016.

[0051] "Capacity" is the amount of cooling per BTU / hour provided by a refrigerant in a refrigeration system. This is experimentally determined by multiplying the change in the enthalpy (BTU / lb) of the refrigerant as it passes through the evaporator by the mass flow rate of the refrigerant. Enthalpy can be determined from measurements of the refrigerant's pressure and temperature. The capacity of a refrigeration system relates to its ability to maintain a specific temperature in the area being cooled. The capacity of a refrigerant represents the amount of cooling or heating it provides, and provides a certain degree of the compressor's ability to pump and deliver the amount of heat for a given volumetric flow rate of the refrigerant. In other words, given a particular compressor, a refrigerant with higher capacity will provide more cooling or heating power.

[0052] The coefficient of performance (COP) is a widely accepted measure of refrigerant performance, particularly useful for representing the relative thermodynamic efficiency of a refrigerant in a specific heating or cooling cycle involving evaporation or condensation of the refrigerant. In refrigeration engineering, the term represents the ratio of useful refrigeration or cooling capacity to the energy applied by the compressor during vapor compression, and therefore the ability of a given compressor to pump a given amount of heat for a given volumetric flow rate of a heat transfer fluid, such as a refrigerant. In other words, given a particular compressor, a refrigerant with a higher COP will provide more cooling or heating power. One means of estimating the COP of a refrigerant under specific operating conditions is from the thermodynamic properties of the refrigerant using standard refrigeration cycle analysis techniques (see, for example, RCDowning, FLUOROCARBON REFRIGERANTS HANDBOOK, Chapter 3, Prentice-Hall, 1988, which is incorporated herein in its entirety by reference).

[0053] "Steam degreasing" refers to a surface cleaning process that uses solvent vapor to wash away oil and other contaminants from an article or part of an article.

[0054] "Dielectric constant" refers to the dielectric constant measured at 20 gigahertz (GHz) at room temperature.

[0055] "Dielectric strength" refers to the dielectric breakdown voltage in kV, measured according to ASTM D87-13, Procedure A, with modifications such as a distance of 2.54 mm between electrodes and a rise rate of 500 V / sec.

[0056] The terms "R-1132(E)", "HFO-1132(E)", and "trans-HFO-1132(E)" each refer to the trans isomer of 1,2-difluoroethylene.

[0057] The terms "R-1132a" and "HFO-1132a" both refer to 1,1-difluoroethylene, respectively.

[0058] The terms "R-1234yf" and "HFO-1234yf" refer to 2,3,3,3-tetrafluoropropene.

[0059] The terms "R-1234ze(E)" and "HFO-1234ze(E)" refer to the trans isomers of 1,3,3,3-tetrafluoropropene.

[0060] The terms "R-1233zd(E)" and "HFCO-1233zd(E)" refer to the trans isomer of 1-chloro-3,3,3-trifluoropropene.

[0061] The terms "R-1233zd(Z)" and "HFCO-1233zd(Z)" refer to the cis isomers of 1-chloro-3,3,3-trifluoropropene.

[0062] The terms "R-1224yd(E)" and "HFCO-1224yd(E)" refer to the trans isomers of 1-chloro-2,3,3,3-tetrafluoropropane.

[0063] The terms "R-1224yd(Z)" and "HFCO-1224yd(Z)" refer to the cis isomers of 1-chloro-2,3,3,3-tetrafluoropropane.

[0064] The terms "R-1336mzz(E)" and "HFO-1336mzz(E)" refer to the trans isomer of 1,1,1,4,4,4-hexafluoro-2-butene.

[0065] The term "HFE-7000" refers to 1-methoxyheptafluoropropane (C3F7OCH3).

[0066] The term "HFE-7100" refers to 1-methoxy-nonafluorobutane (C4F9OCH3).

[0067] The term "HFE-7200" refers to ethoxy-nonafluorobutane (C4F9OC2H5).

[0068] The term "HFE-7300" refers to 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-trifluoromethylpentane.

[0069] The term "HFE-7500" refers to 2-trifluoromethyl-3-ethoxide decofluorohexane.

[0070] As used herein, the singular forms "a," "an," and "the" include multiple references unless otherwise explicitly indicated by the context.

[0071] When used herein, a numerical range indicated by an endpoint includes all numbers contained within that range (for example, 1 to 5 includes 1, 1.5, 2, 2.75, 3, 3.8, 4, and 5).

[0072] Unless otherwise indicated, all numbers used herein and in its embodiments to express quantities or components, measured values ​​of properties, etc., should be understood in all cases to be modified by the term “about.” Therefore, unless otherwise indicated, the numerical parameters described in the foregoing specification and the appended list of embodiments may vary depending on the desired properties that a person skilled in the art would seek to obtain using the teachings of this disclosure. At a minimum, and without attempting to limit the application of the doctrine of equivalents to the claimed embodiments, each numerical parameter should be interpreted by applying the usual rounding technique, at least in light of the reported significant figures.

[0073] Where used herein, the phrase "any range encompassing any two of these values ​​as endpoints" literally means that any range can be selected from any two of the values ​​listed before such phrase, regardless of whether the values ​​are in the lower or higher part of the enumeration. For example, a pair of values ​​could be selected from two lower values, two higher values, or a lower value and a higher value.

[0074] II. Synthesis and Properties of the Fluoroether

[0075] This disclosure is based on the following formula 1: CHF2O CH a (Cx1Fy1Hz1)(Cx2Fy2Hz2) (In the formula, a is 1 or 2, x1 is 1 to 4, y1 is between 3 and 9, z1 is between 0 and 6, x2 is between 0 and 3, y2 is between 0 and 7. This relates to the synthesis of fluoroether compounds (where z2 is between 0 and 4).

[0076] The fluoroether of formula I above can be synthesized in one step from any suitable fluoroalcohol and chlorodifluoromethane (R22), as shown in Scheme 1 below. Scheme 1

[0077] [ka]

[0078] The starting materials for this reaction may include R22 and any suitable fluoroalcohol. Suitable fluoroalcohols include 2,2,3,3-tetrafluoro-1-propanol, 2,2,3,3,3-pentafluoro-1-propanol, 2,2,2,3,3,3-hexafluoro-1-propanol, and 2,2,3,3,4,4,4-heptafluoro-1-butanol.

[0079] The fluoroether product may be any of the following: 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane, 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, 2-(difluoromethoxy)-1,1,1,3,3,3-hexafluoropropane, or 4-(difluoromethoxy)-1,1,1,2,2,3,3-heptafluorobutane.

[0080] Table 2 below provides a summary of the fluoroether products intended by this disclosure, their respective fluoroalcohol starting materials, and their physical properties.

[0081] [Table 2]

[0082] The starting fluoroalcohol and R22 may exist in stoichiometric ratios of 0.8:1.2 to 1.2:0.8.

[0083] The reaction can be carried out in organic solvents such as dimethylformamide (DMF), acetone, acetonitrile, dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), isopropanol, ethanol, and methanol.

[0084] The reaction can be catalyzed by a base such as NaOH or KOH.

[0085] The reaction can be carried out in a reactor using a level of stirring sufficient to produce a homogeneous reaction mixture. Suitable stirring can be achieved by using a mechanical stirrer or a magnetic stirring rod. The reaction vessel may be connected to a heating medium to maintain a suitable reaction temperature. The reaction vessel may be connected to a cooling bath containing any suitable cooling medium to maintain a suitable reaction temperature. The reaction vessel may also be connected to a condenser containing a cooling medium for condensing solvent vapors.

[0086] The entire reaction may be carried out in an autoclave at a high pressure, such as less than 300 psig.

[0087] The reaction can be carried out at low temperatures such as 0°C, 5°C, 10°C, 15°C, 20°C, and 25°C, or at high temperatures such as 30°C, 35°C, 40°C, 45°C, and 50°C, or at any temperature within a range that includes any two of the aforementioned values ​​as endpoints. For example, the reaction can be carried out at temperatures between 10 and 25°C.

[0088] Compounds 1-4 and / or heat transfer compositions 1-10 may have boiling points ranging from about 35°C to about 80°C, such as about 46°C.

[0089] Compounds 1-4 and / or heat transfer compositions 1-10 may have dielectric constants of less than 5 at 20 GHz, such as about 3.4 at 20 GHz.

[0090] Compounds 1-4 and / or heat transfer compositions 1-10 may be non-flammable.

[0091] III.Applications

[0092] The compounds and compositions of this disclosure, including but not limited to each of Compounds 1 to 4 and Compositions 1 to 4, and including heat transfer compositions, thermal management compositions, refrigerants, aerosol propellants, foaming agents, heat transfer media, gaseous dielectrics, fire suppressants, solvents, cleaning agents, aerosol propellants, power cycle working fluids, and starting materials for producing other organofluorine compounds, can be used in a variety of applications.

[0093] In heat transfer applications, compounds 1-4 and / or heat transfer compositions 1-10 of this disclosure may also be used with a variety of co-refrigerants (or co-heat transfer fluids). Preferred co-refrigerants include hexafluoroisopropyl ethyl ether, hexafluoroisopropyl methyl thioether, HFE-7000, HFE-7200, HFE-7100, HFE-7500, trans-1,2-dichloroethylene, n-pentane, cyclopentane, ethanol, perfluoro(2-methyl-3-pentanone) (Novec1230), cis-HFO-1336mzz, trans-HFO-1336mzz, HFO-1234yf, HFO-1234ze(E), HFO-1233zd(E), or HFO-1233zd(Z).

[0094] Table 3 below defines several preferred refrigerants, which are blends containing Compound 2 (HFE-347mcf) and at least one co-refrigerant. The first column of the table below identifies and defines the refrigerant blends by number, such as RB1, RB2, etc., and in that column, the abbreviations COMP, CEO, and CO are used to identify the properties of the blend components identified in columns 2 and 3. In particular, the notation COMP in column 1 indicates that the refrigerant contains Compound 2 and the indicated co-refrigerant. The notation CEO in column 1 means that the refrigerant is essentially made up of Compound 2 and the indicated co-refrigerant, and the notation CO in column 1 means that the refrigerant consists of Compound 2 and the indicated co-refrigerant. The second column shows the amount of Compound 2 that needs to be present in the blend in weight percentage, with "=>" meaning equal to or greater than. In the third column, the co-refrigerant is identified and similarly indicated if a certain amount of the co-refrigerant is required in the blend, with "=<" meaning equal to or less than.

[0095] [Table 3-1] [Table 3-2] [Table 3-3] [Table 3-4] [Table 3-5] [Table 3-6] [Table 3-7]

[0096] This disclosure includes a refrigerant blend of the present invention comprising each of RB1 to RB20, wherein the refrigerant in the blend is non-flammable.

[0097] This disclosure includes a refrigerant blend of the present invention comprising each of RB1 to RB20, wherein the refrigerant in the blend has a dielectric constant of less than 5 at 20 GHz.

[0098] This disclosure includes a refrigerant blend of the present invention comprising each of RB1 to RB20, wherein the refrigerant in the blend has a dielectric constant of less than 4 at 20 GHz.

[0099] This disclosure includes a refrigerant blend of the present invention comprising each of RB1 to RB20, wherein the refrigerant in the blend has a dielectric constant of less than about 5 at 20 GHz, (ii) a boiling point of about 35°C to about 80°C, (iii) is nonflammable, and (iv) has Ames-negative toxicity.

[0100] This disclosure includes a refrigerant blend of the present invention comprising each of RB1 to RB20, wherein the refrigerants in the blend have a boiling point of about 35°C to about 80°C.

[0101] The refrigerant blends of this disclosure, each containing RB1 to RB20, will hereinafter be referred to as blends RB1 to RB20.

[0102] As discussed above, and particularly as shown in Table 4, compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 can be advantageously used in cooling and / or heating methods, devices, or systems in electronic devices.

[0103] As discussed herein, when the heat transfer compositions of this disclosure, each comprising compositions 1 to 4 and / or heat transfer compositions 1 to 10 and / or blends RB1 to RB20, are used in a method or device or system for cooling and / or heating in an electronic device, they may be referred to herein as thermal control compositions. Accordingly, thermal control compositions correspond to the heat transfer compositions discussed in this application.

[0104] Compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 are particularly useful as heat transfer compositions due to their low vapor pressure, low dielectric properties, high boiling point, and non-flammability. For example, compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 can be used in data centers when excess heat cannot be controlled by air cooling alone, such as during data tsunamis. Compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 can be used in immersion cooling systems to effectively remove heat while maintaining data transfer integrity, which is crucial for microprocessing devices.

[0105] These uses are explained below.

[0106] Heat transfer composition As described above, this disclosure provides various methods, processes, and uses of the compounds of this disclosure as heat transfer compositions. Compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 can be used to transfer heat from one place to another (or from one object, article, or fluid to another object, article, or fluid). For example, a heat transfer composition may be used to keep the temperature of a device below a specified upper temperature limit and / or above a specified lower temperature limit. In another example, a heat transfer composition can be used in energy conversion, such as in the capture of waste heat from industrial processes or other processes and its conversion to electrical or mechanical energy.

[0107] Accordingly, the Disclosure encompasses various methods, processes, and uses of the compounds of the Disclosure, including each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, as thermal control compositions (hereinafter sometimes referred to as TMCs) used to help maintain an article or device (preferably an electronic device or battery) or fluid within a specific temperature range while the article or device or fluid is operating in accordance with its intended purpose. For example, the TMCs of the Disclosure can be used to keep the temperature of a device below a specified upper temperature limit and / or above a specified lower temperature limit.

[0108] A preferred embodiment of the thermal management method is shown with Figure 1, where an operating electronic device is schematically shown as 10 and has an electrical energy source and / or signal 20 flowing into and / or out of the device 10, generating heat as a result of operation based on the electrical energy and / or signal 20. The thermal management composition of the present disclosure is provided in thermal contact with the operating device 10 so that the thermal management fluid removes the heat represented by the outflowing arrow 30. The heat is removed from the operating electronic device by sensible heat (i.e., raising the temperature of the liquid) added to the liquid thermal management composition of the present disclosure, or by causing a phase change (i.e., vaporizing the liquid) in the thermal management liquid, or by a combination thereof. In a preferred embodiment, the method provides a supply of the TMC of the present disclosure to the device 10, each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, so that the flow of heat from the device 10 through the heat transfer composition 30 keeps the operating electrical device within a preferred operating temperature range, or within a preferred operating temperature range. In a preferred embodiment, the preferred operating temperature range of the electrical device is about 70°C to about 150°C, more preferably about 70°C to about 120°C, and the flow of heat 30 from the device 10 through the heat transfer fluid energy of the present invention keeps the operating electrical device within such preferred temperature range or maintains it within such preferred range. Preferably, the TMC 30 of the present disclosure, having absorbed heat from the device, comes into thermal contact with a heat sink schematically represented as 40 at a temperature below the temperature of the heat transfer composition 30, thereby transferring the heat generated by the device 10 to the heat sink 40. In this way, the thermally depleted heat transfer fluid 50 of the present disclosure can be returned to the electronic device 10 to repeat the cooling cycle.

[0109] In a preferred embodiment of the method, the step of removing heat through the heat transfer composition of the Disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, includes evaporating the heat transfer composition of the Disclosure using heat generated by the operation of an electronic device, and the step of transferring the heat from the heat transfer composition to a heat sink includes condensing the heat transfer composition by returning the heat to the heat sink. In such a method, during the evaporation step, the temperature of the heat transfer composition of the Disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, is preferably above 50°C, preferably above about 55°C, preferably between about 55°C and about 85°C, or preferably between about 65°C and about 75°C. The applicants have found that the heat management composition provides excellent performance in such a method while enabling the provision of required cooling using relatively low-cost, lightweight, and reliable equipment, as further described in relation to the specific embodiments described in relation to Figure 2A below.

[0110] In a more preferred embodiment of the present method, the step of removing heat through the heat transfer composition comprising each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 includes the steps of: using the heat generated by the operation of the electronic device to add sensible heat to the liquid heat transfer composition of the present disclosure (for example, raising the liquid temperature to approximately atmospheric pressure to a maximum of about 70°C or less, i.e., the fluid does not need to be in a high-pressure vessel or vessel); and transferring the heat from the heat transfer composition to a heat sink, thereby lowering the liquid temperature by returning the heat to the heat sink. The cooled liquid is then returned to thermal contact with the electrical device, and the cycle is repeated. In a preferred embodiment, the temperature of the heat transfer fluid used to transfer heat to the heat sink is above about 40°C, preferably above about 55°C, preferably in the range of about 45°C to about 70°C, or preferably in the range of about 45°C to about 65°C, preferably at a pressure of approximately atmospheric pressure. The applicants have found that the heat transfer fluids, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, provide excellent performance in such a manner, while also enabling the provision of required cooling using relatively low-cost, lightweight, and reliable equipment, as will be further described in relation to the specific embodiments shown below in connection with Figure 2B.

[0111] Those skilled in the art will understand that this disclosure includes systems and methods that utilize both sensible heat transfer and phase-change heat transfer, as described above.

[0112] Here, a particular method according to the present disclosure is described in relation to Figures 2A and 2B, in which an electronic device 10 is housed in a suitable container 12, preferably a sealed container, and is in direct contact with, and preferably completely immersed in, a liquid heat transfer composition 11A of the present disclosure (circularly shown in gray shading) containing each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20. For convenience, such cooling methods, devices, and systems may be referred to herein as “immersion cooling” methods, devices, and systems.

[0113] In immersion cooling methods, devices, and systems used to cool electrical devices or electrical components, an operating electronic device 10 has an electrical energy source and / or signal 20 that flows into and / or out of a container 12 and into and / or out of the device 10, and generates heat as a result of operation based on the electrical energy and / or signal 20. As will be understood by those skilled in the art, a composition must not only provide all of the other properties described above, but must also be able to do so while in close contact with an operating electronic device, i.e., an electronic device with a flow of current / signal. Therefore, finding a heat transfer composition that can perform effectively in such applications is a critical task. It will be understood that many compositions that may otherwise be promising for use in such applications would be unsuitable for use because, when exposed to the conditions resulting from the operation of the electronic device, they would either short-circuit and degrade the device (degrading the cooling effect over time and / or degrading the operational stability of the device) or have some other properties that would be detrimental to operation when in contact with an operating electronic device.

[0114] In contrast, the present method yields superior unexpected results by providing the thermal management compositions of the present disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, in direct thermal and physical contact with the device 10 while it is operating. This operating heat is safely and effectively transferred to the thermal management composition 11A comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 by (a) evaporating the liquid phase of the fluid and causing the formation of vapor 11B, or (b) raising the temperature of the liquid thermal management composition 11A, or (c) a combination of (a) and (b).

[0115] If the thermal management composition is a single-phase liquid, it will remain liquid when heated by a heat-generating component. Therefore, the thermal management composition can come into contact with the heat-generating component, resulting in the removal of heat from the component and the generation of a higher-temperature thermal management composition. The thermal management composition is then transferred to a secondary refrigeration loop, such as a radiator or another cooling system. An example of such a system is shown in Figure 2, where the thermal management composition enters a battery pack enclosure containing several cells, absorbs heat from the battery pack, and exits the enclosure.

[0116] When the thermal control compositions of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, are present in two phases, a heat-generating component comes into thermal contact with the thermal control composition, transferring heat to the thermal control composition and causing it to boil. The thermal control composition is then condensed. An example of such a system is when a heat-generating component is immersed in the thermal control composition, and an external cooling circuit condenses the boiling fluid into a liquid state.

[0117] In the case of the phase-change heat transfer system of this disclosure, the foregoing refers to Figure 2A. In such operation, heat is carried away from the device 10 as the liquid evaporates and the vapor rises through the remaining heat management liquid containing each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 in the container 12. The heat management composition vapor 11B then returns the absorbed heat to a heat sink 40, which may be a closed heat sink 40A and / or an external heat sink 40B. An example of a heat sink inside the container 12 is condenser coils 30A and 30B having a circulating fluid, such as water, at a temperature below the condensation temperature of the heat management composition vapor. An example of a heat sink outside the container 12 is passing relatively cool ambient air over the container 12 (in this case preferably including cooling fins, etc.), which would serve to condense the heat transfer vapor 11B on the inner surface of the container. As a result of this condensation, the liquid heat management composition is returned to the pool of liquid fluid 11A into which the device 10 remains immersed during operation.

[0118] In the case of the sensible heat transfer system of the present disclosure, the foregoing refers to Figure 2B. In such operation, as the temperature of the liquid 11A containing each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 rises, heat is carried away from the device as it receives heat generated by a device immersed, preferably substantially completely immersed, in the heat management composition 11A of the present disclosure. The higher temperature heat management composition liquid 11A then returns the absorbed heat to a heat sink 40, which may be a closed heat sink 40A and / or an external heat sink 40B. An example of a heat sink inside the container 12 is cooling coils 30A and 30B having a circulating fluid, such as water, at a temperature below the temperature of the heated liquid. An example of a heat sink outside the container 12 is removing the heated liquid 11A from the container through a conduit 45, which comes into thermal contact with a cold fluid, which may be provided by relatively cold ambient air or cooled water or a coolant, and this functions to lower the temperature of the liquid. Next, the cooled liquid is returned through the conduit 46.

[0119] In certain embodiments, optionally but preferably, involving thermal management of a battery used in an electric vehicle, the thermal management system includes a heating element capable of heating a thermal management composition comprising each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, such as an electric heating element 60 which is also immersed in the thermal management composition. As those skilled in the art will understand, a battery in an electric vehicle (corresponding to the operating electronic device 10 in Figures 2A and 2B) can reach relatively low temperatures while parked outdoors in many geographical locations during the winter months, and such low-temperature conditions are often undesirable for battery operation. Therefore, the thermal management system of the present disclosure may include a sensor and control module (not shown) that turns on the heating element when the battery temperature falls below a predetermined level. In such a case, the heater 60 is activated and the thermal management fluid 11A is heated, thereby transferring this heat to the electronic device 10 until it reaches a minimum temperature. Subsequently, during operation, the thermal management compositions of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, perform the cooling function described above.

[0120] For the purposes of this disclosure, a thermal control composition comprising each of compounds 1 to 4 and / or heat transfer compositions 1 to 10 and / or blends RB1 to RB20 may come into direct or indirect contact with a heat-generating component.

[0121] When a thermal control composition comprising each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 is in indirect contact with a heat-generating component, the thermal control composition can be used in a closed system within an electronic device which may include at least two heat exchangers. When the thermal control composition is used to cool a heat-generating component, heat can typically be transferred from the heat-generating component to the thermal control composition through a heat exchanger in contact with at least a portion of the heat-generating component, or heat can be conducted to circulating air that can conduct heat to a heat exchanger in thermal contact with the thermal control composition.

[0122] In a particularly preferred feature of this disclosure, the thermal management composition, comprising each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, is in direct contact with the heat-generating component. In particular, the heat-generating component is completely or partially immersed in the thermal management composition. Preferably, the heat-generating component is completely immersed in the thermal management composition, comprising each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20. The thermal management composition may then be circulated to a heat exchanger as a heated fluid or as vapor, which takes heat from the fluid or vapor and transfers that heat to the external environment as a heat sink, such as ambient air or water cooled by ambient air or other means. After this heat transfer, the cooled thermal management composition (cooled or condensed) is returned to the system and recirculated to cool the heat-generating component.

[0123] The conductivity and / or dielectric strength of the thermal management composition are important when the fluid is in direct contact with the electronic components of an electronic device (such as direct immersion cooling), or when the thermal management composition leaks from the cooling loop or spills during maintenance and comes into contact with an electrical circuit. Therefore, each of the temperature management compositions of the present disclosure, as well as compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, is preferably an electrically insulating thermal management composition.

[0124] Each of the thermal management compositions of the present disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be passively or actively recirculated within a device by using mechanical devices such as pumps. In a preferred feature of the present disclosure, each of the thermal management compositions of the present disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, is passively recirculated within a device.

[0125] A passive recirculation system typically functions by transferring heat from a heat-generating component to a heat-managed composition until the heat-managed composition vaporizes, the heated vapor proceeding to a heat exchange surface, transferring heat to the heat exchanger surface, and condensing back into a liquid. It will be understood that the heat exchange surface may be part of a separate heat exchange unit and / or integrated with a container, for example, as described above in relation to Figure 2. The condensed liquid then returns to the heat-managed composition in contact with the heat-generating component, preferably entirely passively by gravity and / or a wicking structure. Thus, in a preferred feature of the present disclosure, the step of transferring heat from the heat-generating component to the heat-managed fluid of the present disclosure, each containing each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, causes the heat-managed fluid to vaporize.

[0126] Examples of passive recirculation systems include heat pipes or thermal siphons. Such systems passively recirculate the thermal management compositions of the Disclosure, each comprising each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, using gravity. In such systems, the thermal management composition is heated by a heat-generating component, resulting in a heated thermal management composition that is less dense and more buoyant. This thermal management composition moves to a storage container, such as a tank, where the thermal management fluid cools and condenses. The cooled thermal management composition then returns to the heat source. Cooling of electrical devices

[0127] This disclosure includes using the Compounds, each comprising Compounds 1-4 and / or Heat Transfer Compositions 1-10 and / or Blends RB1-RB20, to manufacture a component that is a heat-generating component or to cool and optionally heat an electronic device containing such a component. A heat-generating component may be any component that includes an electronic element that generates heat as part of its operation. For the purposes of this disclosure, examples of heat-generating components include, but are not limited to, microprocessors, wafers used to manufacture semiconductor devices, power control semiconductors, power distribution switchgears, power transformers, circuit boards, multi-chip modules, packaged or unpackaged semiconductor devices, semiconductor integrated circuits, fuel cells, lasers (conventional or laser diodes), light-emitting diodes (LEDs), and semiconductor integrated circuits (ICs), electrochemical cells, power transistors, resistors, and electroluminescent elements, such as electrochemical cells used in high-power applications, such as hybrid or electric vehicles.

[0128] For the purposes of this disclosure, electronic devices include, but are not limited to, personal computers, microprocessors, servers, mobile phones, tablets, digital consumer electronics (e.g., televisions, media players, game consoles, etc.), personal digital assistants, data centers, both stationary and automotive batteries including lithium-ion batteries, hybrid or electric vehicles, wind turbines, train engines, or other batteries used in generators. Preferably, the electronic device is a hybrid or electric vehicle.

[0129] This disclosure further relates to an electronic device comprising a thermal control composition of this disclosure, each comprising each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20. For the purposes of this disclosure, the thermal control composition is provided for cooling and / or heating an electronic device.

[0130] The present disclosure further relates to an electronic device comprising a heat-generating component and a thermal management composition of the present disclosure, each comprising each of compounds 1 to 4 and / or heat transfer compositions 1 to 10 and / or blends RB1 to RB20 for cooling and, optionally, heating the electronic device.

[0131] This disclosure further relates to an electronic device comprising a heat-generating component, a heat exchanger, a pump, and a thermal management composition of this disclosure, each comprising each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20. For the purposes of this disclosure, the electronic device may be any such device, including but not limited to personal computers, microprocessors, servers, mobile phones, tablets, digital home appliances (e.g., televisions, media players, game consoles, etc.), personal digital assistants, data centers, hybrid or electric vehicles, both stationary and on-board batteries, electric drive motors, fuel cells (e.g., hydrogen fuel cells), and generators, preferably the electronic device is located in a hybrid or electric vehicle, or a wind turbine, or a train.

[0132] For the purposes of this disclosure, a heat-generating component is any electrical component that generates heat during operation, but is preferably an electronic component that generates heat at a high level of thermal flux. Examples of heat-generating components that can be cooled in accordance with this disclosure include microprocessors, wafers used to manufacture semiconductor devices, power control semiconductors, power distribution switchgears, power transformers, printed circuit boards (PCBs), multi-chip modules, packaged or unpackaged semiconductor devices, semiconductor integrated circuits, fuel cells, lasers (conventional or laser diodes), light-emitting diodes (LEDs), and semiconductor integrated circuits (ICs), electrochemical cells, power transistors, resistors, and electroluminescent elements, such as electrochemical cells used in high-power applications, such as hybrid or electric vehicles.

[0133] Lithium-ion battery cooling system Herein, embodiments of the thermal management methods of the present invention useful for cooling lithium-ion batteries, including heat transfer methods 1 and 2, and thermal management methods 1 and 2, will be described in reference to Figure 8. A vehicle battery pack having an integrated liquid cooling system 10 including a module 12 formed of a container 14 having an internal space 16 for supporting a battery assembly 18. The container 14 is a closed and sealed container 14 for forming the integrated liquid cooling system 10. The battery assembly 18 includes a plurality of battery cells 20, such as a plurality of lithium-ion (Li-ion) batteries for use in a hybrid vehicle. In another embodiment, the plurality of battery cells 20 are Li-ion batteries for use in a battery electric vehicle (BEV). Additional batteries for use in conjunction with other motorized vehicles may be provided in the liquid cooling system 10 of the present disclosure, and each battery cell contains an active material for generating electricity from an electrochemical reaction in the internal space 16 of the container 14. Preferably, the battery cells 20 are stacked to form a battery cell stack 22. In the embodiment shown, the gap 24 between each battery cell 20 is 0.25 to 0.50 mm, forming a fluid channel 26 between each battery cell 20. In another embodiment, the gap 24 may be less than 0.25 mm. It is understood that other gap sizes may be used as needed.

[0134] Each of the compositions of the present disclosure, comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, is disposed within the internal space 16 of a container 14, and the indicated fluid level is such that the battery assembly 18 is completely immersed in the composition of the present disclosure. Each of the compositions of the present disclosure, comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, is in contact with the battery cell 20 through a fluid channel 26 formed by a gap 24.

[0135] The heating element 34 is located in the base region 36 of the container 14. The heating element 34 shown is an electronic heating element. It is understood that other types of heating elements may be used. The heating element 34 is shown as a single element. However, multiple heating elements 34, such as heating plates, may be provided.

[0136] The cooling element 38 is located in the upper region 40 of the container 14. The cooling element 38 may be a chilled water condenser having an inlet 42 and an outlet 44 that extend beyond the wall of the sealed container 14 for supplying and discharging water for the cooling element 38. In another embodiment, the cooling element 38 may be a chilled water plate. In yet another embodiment, the cooling element 38 may be a thin aluminum heat sink having external chilled water flowing through the cooling element 38. The cooling element 38 may be graphite foil impregnated with an electrically nonconductive polymer. The cooling element may also be formed from copper.

[0137] In the embodiments shown, arrows "A" and "B" indicate the flow 28 of the composition of the present disclosure, each containing each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, as well as each of the heat transfer compositions. When each battery cell 20 is heated by the heating element 34, the coolant 28 of the present disclosure, each containing compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, will be exposed to the front surface region 30 and rear surface region 32 of the battery cell 20 and will boil. The heated coolant 28 will rise and flow to the top of the battery cell stack 22 and will be cooled by the cooling element 38. The cooled coolant 28 will generally return to the base region 36 according to either coolant path "A" or "B". If the general position of the coolant 28 at the moment of boiling is within the fluid channel 26 of the battery cell 20 in the central region and facing the side surface 50 of the container 14, the coolant 28 will tend to follow flow path "A". Similarly, if the general position of the coolant 28 at the moment of boiling is within the fluid channel 26 of the battery cell 20 in the central region and facing the opposing side surface 52 of the container 14, the dielectric coolant 28 will tend to follow flow path "B".

[0138] The coolant temperature sensor 46 is located on or near the cooling element 38. In the shown embodiment, the temperature sensor 46 is located within the region of the outlet 44 of the cooling element 38 and measures the temperature of the dielectric coolant 28 of the present disclosure at the point of exposure to the cooling element. The temperature sensor 46 can be located anywhere in the battery cell stack 22 as needed.

[0139] A coolant level sensor 48 is also provided, located near the upper region 40 of the container 14, to measure the fluid level of the dielectric coolant 28 inside the container 14 and to ensure complete immersion of the battery assembly 18 in the dielectric coolant 28.

[0140] Cooling and heating of heat pipes Herein, an example of the heat transfer method using heat pipes is described with respect to Figure 10, which is a specific example of heat pipes in an energy storage assembly 1 according to one exemplary embodiment of the present disclosure. The energy storage assembly 1 may be part of an automobile 12, in particular a hybrid or electric vehicle, and is provided on the side of the automobile to supply power to an electrical consuming device, such as an electric drive unit (not shown). The energy storage assembly 1 includes a plurality of electrical energy storage units 2. The electrical energy storage units 2 are electrically connected, i.e., in series or parallel, via electrical connection elements (not shown), in particular in the form of conductive rails or conductor rails ("busbars"). The electrical connection elements are in contact with corresponding electrical connectors (not shown) provided herein, which are located on the exposed outer wall areas of the corresponding energy storage housings (not shown) of the energy storage units 2 arranged adjacent to each other in a parallel arrangement, thereby forming an energy storage stack ("stack"). Plate-shaped spacer elements 3 are respectively placed between the energy storage units 2 to separate them and at the same time have thermal conductivity properties. Therefore, the spacer element 3 provides, on the one hand, a gap between directly adjacent energy storage units 2 so that the directly adjacent energy storage units 2 do not come into electrical or mechanical contact with each other. On the other hand, the spacer element 3 acts as a thermal conductor, as a result of their thermal conductivity, for the purpose of cooling the energy storage units 2 or energy storage assembly 1 by dissipating heat, particularly from the energy storage units 2 that are in contact with it, or for the purpose of heating the energy storage units 2 or energy storage assembly 1 by supplying heat, particularly to the energy storage units 2 that are in contact with it. The heat pipe 4 of the first heat pipe assembly 5 and the heat pipe 6 of the second heat pipe assembly 7 are provided. Therefore, the heat pipes 4 and 6 extend along this side surface of the energy storage stack and are thermally connected to the spacer element 3, respectively. Thus, the spacer element 3 forms thermal bridges, on the one hand, between the heat pipe 4 of the first heat pipe assembly 5 and the heat pipe 6 of the second heat pipe assembly 7, and on the other hand, between the energy storage units 2.Each heat pipe 4 of the first heat pipe assembly 5 is positioned and aligned such as by being thermally connected to its respective evaporation zone, in which the contained thermal management composition of the present disclosure, particularly including each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be evaporated to the spacer element 3. Thus, the heat required for the evaporation of the present TMC (heat of evaporation) is removed from the spacer element 3 or from the energy storage unit 2 via the spacer element 3. Thus, the energy storage unit 2, including the energy storage assembly 1, can be cooled via the heat pipes 4 of the first heat pipe assembly 5. Furthermore, each condensation zone of the heat pipe 4 of the first heat pipe assembly 5 (in which the contained gaseous thermal management composition of the present disclosure, particularly including each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be condensed) is thermally connected to a heat sink 8 in the form of an automotive-side heat exchanger. Thus, the heat generated during the condensation of the TMC of the present invention (heat of condensation) can be transferred to the heat sink 8. The heat exchanger may be part of the energy storage assembly 1, that is, it may belong to or be associated with the energy storage assembly 1. Each heat pipe 6 of the second heat pipe assembly 7 is positioned and aligned such that it is thermally connected to a spacer element 3 in each condensation zone in which the contained gaseous TMC of the Disclosure can be condensed. Thus, heat (heat of condensation) can be transferred to or via the spacer element 3 to the energy storage unit 2 during the condensation of the present TMC. Thus, the energy storage unit 2 and the energy storage assembly 1 can be heated via the heat pipes 6 of the second heat pipe assembly 7. Furthermore, each evaporation zone of the heat pipe 6 of the second heat pipe assembly 7, which can evaporate the contained TMC of the Disclosure, is thermally connected to a heat source 9 in the form of a functional component associated with the energy storage assembly 1, i.e., a charger or control device or control electronic equipment. Thus, the heat (heat of evaporation) required for the evaporation of the TMC can be removed from the heat source 9.Therefore, the functional components can be cooled via the heat pipe 6 of the second heat pipe assembly 7. The two heat pipe assemblies 5, 7 and their associated heat pipes 4, 6 enable the implementation of a temperature control device for controlling the temperature of the energy storage section 2 of the energy storage assembly 1, i.e., for heating or cooling. Useful heat pipes according to this disclosure include both gravity return heat pipes, capillary return heat pipes, and gravity / capillary return heat pipes.

[0141] The following table defines several preferred uses of the Compound and methods of using the Compound, including those related to the examples herein. The first column of the following table identifies and defines uses as Use 1, Use 2, etc., and the second column identifies and defines one or more of the refrigerants (Ref.) identified above as Compounds 1-4 and / or Heat Transfer Compositions 1-7 and / or Blends RB1-RB20, using abbreviations such as TMC1, TMC2, etc. Devices or articles are as specified, “EV Battery” means electric vehicle battery, and “IC” means integrated circuit. The notation “NR” is understood to mean that no parts or characteristics are required (but may be present) for the use defined in each particular column of the table.

[0142] [Table 4-1] [Table 4-2] [Table 4-3] [Table 4-4] [Table 4-5] [Table 4-6] [Table 4-7] [Table 4-8] [Table 4-9] [Table 4-10] [Table 4-11] [Table 4-12] [Table 4-13] [Table 4-14]

[0143] Organic Rankine Cycle System When the heat transfer fluids of this disclosure, comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, are used in an organic Rankine cycle, they may be referred to as working fluids.

[0144] Therefore, the working fluid corresponds to the heat transfer fluid considered in this application. All preferred characteristics of the heat transfer fluid are applicable to the working fluid described herein.

[0145] The Rankine cycle system is known to be a simple and reliable means of converting thermal energy into mechanical energy in the form of shaft power. In industrial environments, it may be possible to use flammable working fluids such as toluene and pentane, especially when the industrial environment already has large quantities of flammable materials in operation or storage on site. However, in cases where the risks associated with the use of flammable and / or toxic working fluids are unacceptable, such as in power generation in densely populated areas or near buildings, it is necessary, or at least highly desirable, to use non-flammable and / or non-toxic refrigerants as working fluids. There is also a movement within the industry to make these materials environmentally acceptable from a GWP perspective.

[0146] The process for recovering waste heat in an organic Rankine cycle according to the present disclosure preferably involves pumping a liquid-phase working fluid of the present disclosure, each containing compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, through a boiler, where an external (waste) heat source, such as a process flow, heats the working fluid, causing it to evaporate into saturated or superheated steam. This steam expands through a turbine, and the waste heat energy is converted into mechanical energy. Subsequently, the gas-phase working fluid is condensed into a liquid and pumped back into the boiler to repeat the heat extraction cycle.

[0147] Referring to Figure 4, in the exemplary organic Rankine cycle system 70, the working fluid of the present disclosure, each containing compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, is circulated between the evaporator 71 and the condenser 75, with a pump 72 and an expansion device 74 functionally arranged between them. In the exemplary embodiment, the external flow of the fluid is directed to the evaporator 71 via an external warm conduit 76. The external warm conduit 76 can carry the fluid from a warm heat source such as industrial processes (e.g., power generation), flue gas, exhaust gas, or waste heat from a geothermal source.

[0148] The evaporator 71 is preferably configured as a heat exchanger, which may include, for example, a series of thermally connected but fluidly isolated tubes that carry fluid from a warm conduit 76 and fluid from a working fluid conduit 77B, respectively. Thus, the evaporator 71 facilitates the transfer of heat QIN from the warm fluid arriving from the external warm conduit 76 to the relatively cooler (e.g., "low-temperature") working fluid arriving from the expansion device 74 via the working fluid conduit 77B.

[0149] Accordingly, the working fluid of the present disclosure, each containing compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, exits the evaporator 71, which has been heated by the absorption of heat QIN, and then moves through the working fluid conduit 78A to the pump 72. The pump 72 pressurizes the working fluid, thereby further heating the fluid through an external energy input (e.g., electricity). The resulting "hot" fluid moves through conduit 78B and, optionally, through a regenerator 73 as described below, to the input of the condenser 75.

[0150] The condenser 75 is configured as a heat exchanger similar to the evaporator 71 and may include, for example, a series of thermally connected but fluidly isolated tubes that carry fluid from a cold conduit 79 and fluid from a working fluid conduit 78B, respectively. The condenser 75 facilitates the transfer of heat QOUT from the cold conduit 79 to the cold fluid arriving from the external cold conduit 79 to the relatively warmer (e.g., "high temperature") working fluid of the Disclosure, which includes each of compositions 1 to 4, arriving from the pump 72 via the working fluid conduit 78B.

[0151] The working fluid compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 of the Disclosure, having exited the condenser 75 and thus cooled by the loss of heat QOUT, then move through the working fluid conduit 77A to the expansion device 74. The expansion device 74 allows the working fluid to expand, thereby further cooling the fluid. At this stage, the fluids of the Disclosure, each containing compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can perform operation, for example, by driving a turbine. The resulting “cold” fluid moves through the conduit 77B and, optionally, through the regenerator 73 as described below, to the input of the evaporator 71, where a new cycle begins.

[0152] Therefore, the working fluid conduits 77A, 77B, 78A, and 78B define a closed loop, and as a result, the working fluid contained within them can be reused indefinitely or until maintenance of the conduit is required.

[0153] In the exemplary embodiment, the regenerator 73 may be functionally positioned between the evaporator 71 and the condenser 75. The regenerator 73 allows the “high-temperature” working fluid of the disclosure, which includes each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, exiting from the pump 72, and the “low-temperature” working fluid exiting from the expansion device 74 to exchange some heat, with a potentially time lag between the deposition of heat from the high-temperature working fluid and the release of that heat to the low-temperature working fluid. In some applications, this may increase the overall thermal efficiency of the Rankine cycle system 70.

[0154] Accordingly, this disclosure relates to an organic Rankine cycle including the working fluid of this disclosure, each of which comprises compounds 1 to 4 and / or heat transfer compositions 1 to 10 and / or blends RB1 to RB20.

[0155] The Disclosure also provides a process for converting thermal energy into mechanical energy in a Rankine cycle, the method comprising: i) vaporizing a working fluid of the Disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, with a heat source to expand the resulting vapor; and ii) cooling the working fluid with a heat sink to condense the vapor, wherein the working fluid is a refrigerant or heat transfer composition of the Disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20.

[0156] Mechanical work can be transmitted to electrical devices such as generators to produce electricity.

[0157] The heat source may be selected from, for example, industrial waste heat, solar energy, geothermal hot water, low-pressure steam, distributed power generation equipment utilizing fuel cells, prime movers, or internal combustion engines. Low-pressure steam is preferably low-pressure geothermal steam or provided by a power plant powered by fossil fuels.

[0158] The heat source is preferably provided by a thermal energy source selected from industrial waste heat or an internal combustion engine.

[0159] While the heat source temperature can vary widely, for example, from approximately 90°C to over 800°C, it should be understood that for certain combustion gases and some fuel cells, it can depend on countless factors such as geography and season.

[0160] For example, systems based on sources such as wastewater or low-pressure steam from plastic manufacturing plants and / or chemical plants or other industrial plants, petroleum refineries and related forms, as well as geothermal sources, may have source temperatures as low as approximately 175°C or below, or approximately 100°C or below, and in some cases as low as approximately 90°C, or even as low as approximately 80°C. Gaseous heat sources such as exhaust gas from combustion processes where subsequent processing to remove particulate matter and / or corrosive species results in low temperatures, or from any heat source, may also have source temperatures as low as approximately 200°C or below, approximately 175°C or below, approximately 130°C or below, approximately 120°C or below, approximately 100°C or below, and in some cases as low as approximately 90°C, or even as low as approximately 80°C.

[0161] However, in some applications, it is preferable that the heat source has a temperature of at least about 200°C, for example, about 200°C to about 400°C.

[0162] In an alternative preferred embodiment, the heat source has a temperature of 400 to 800°C, more preferably 400 to 600°C.

[0163] heat pump As discussed above, when the heat transfer fluids of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, are used in a heat pump, they are referred to as refrigerants. Thus, refrigerants correspond to the heat transfer fluids discussed in this application. All preferred characteristics of the heat transfer fluids described apply to the refrigerants described herein.

[0164] The refrigerants or heat transfer compositions of this disclosure, each comprising compounds 1 to 4 and / or heat transfer compositions 1 to 10 and / or blends RB1 to RB20, can be used in high-temperature heat pump systems.

[0165] Referring to Figure 5, in one exemplary heat pump system, a compressor 80, such as a rotary, piston, screw, or scroll compressor, compresses a refrigerant of the Disclosure, each containing compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, the refrigerant is carried to a condenser 82 to release heat QOUT to a first position, then passes the refrigerant through an expansion device 84 to reduce the refrigerant pressure, then passes the refrigerant through an evaporator 86 to absorb heat QIN from a second position. The refrigerant is then returned to the compressor 80 for compression.

[0166] The present disclosure provides a method for heating a fluid or object using a high-temperature heat pump, the method comprising: (a) condensing or heating the refrigerant compositions, compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 of the present disclosure around the fluid of the object; and (b) evaporating the refrigerant.

[0167] Examples of high-temperature heat pumps include heat pump tumble dryers or industrial heat pumps. It will be understood that the heat pump may be equipped with a suction line / liquid line heat exchanger (SL-LL HX). "High-temperature heat pump" means a heat pump capable of generating a temperature of at least about 80°C, preferably at least about 90°C, preferably at least about 100°C, and more preferably at least about 110°C.

[0168] Secondary loop system When the heat transfer fluids of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, are used in a secondary loop system, they are referred to as refrigerants.

[0169] The refrigerants of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used as secondary refrigerant fluids in a secondary loop system.

[0170] A secondary loop system includes a primary vapor compression system loop that uses a primary refrigerant, the vapor of which cools the fluid in the secondary loop. A secondary refrigerant fluid, each containing compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, then provides the cooling required for the application. Since the fluid in such a loop is potentially exposed to humans near the cooled space, the secondary refrigerant fluid must preferably be non-flammable and low-toxicity. In other words, the refrigerants or heat transfer compositions of the present disclosure, each containing compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used as a “secondary refrigerant fluid” in a secondary loop system.

[0171] Referring to Figure 6, one exemplary secondary loop system includes a primary loop 90 and a secondary loop 92. In the primary loop 90, a compressor 94, such as a rotary, piston, screw, or scroll compressor, compresses the primary refrigerant, which is then carried to a condenser 96 to release heat QOUT to a first position, and subsequently the primary refrigerant is passed through an expansion device 98 to reduce the refrigerant pressure, and subsequently the primary refrigerant is passed through a refrigerant / secondary fluid heat exchanger 100 to exchange heat QIN with a secondary fluid containing each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, and the secondary fluid is pumped through the secondary loop 92 to a secondary loop heat exchanger 104 via a pump 102 to absorb heat QIN-S to provide cooling to, for example, a further position.

[0172] The primary fluid used in the primary loop (the vapor compression cycle of the loop, the external / outdoor portion) may be selected from, but is not limited to, HFO-1234ze(E), HFO-1234yf, propane, R455A, R32, R466A, R44B, R290, R717, R452B, R448A, and R449A, preferably HFO-1234ze(E), HFO-1234yf, or propane.

[0173] The secondary loop system may be used for refrigeration or air conditioning purposes; that is, the secondary loop system may be a secondary loop refrigeration system or a secondary loop air conditioning system.

[0174] Examples of refrigeration systems that may include a secondary loop refrigeration system containing the secondary refrigerant of the Disclosure, each containing one of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 include low-temperature refrigeration systems, medium-temperature refrigeration systems, commercial refrigerators, commercial freezers, industrial freezers, industrial refrigerators, and chillers.

[0175] Examples of air conditioning systems that may include a secondary loop air conditioning system utilizing the refrigerant of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, include mobile air conditioning systems and stationary air conditioning systems. Mobile air conditioning systems include air conditioning for road vehicles such as automobiles, trucks and buses, as well as air conditioning for boats and trains. For example, when the vehicle includes a battery or power source.

[0176] Examples of fixed air conditioning systems that may include secondary loop air conditioning systems utilizing the refrigerants of the Disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, include chillers, particularly positive displacement chillers, especially air-cooled or water-cooled direct expansion chillers, whether modular or conventionally packaged as standalone units; residential air conditioning systems, particularly duct-split or ductless-split air conditioning systems; residential heat pumps; residential air-water heat pump / hot water systems; industrial air conditioning systems; commercial air conditioning systems, particularly packaged rooftop units and variable refrigerant flow (VRF) systems; and commercial air-source, water-source, or soil-source heat pump systems.

[0177] A particularly preferred heat transfer system according to the present disclosure is an automotive air conditioning system comprising a vapor compression system (primary loop) and a secondary loop air conditioning system, wherein the primary loop contains HFO-1234yf as a refrigerant, and the secondary loop contains the refrigerant or heat transfer composition of the present disclosure, each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20. In particular, the secondary loop may be used to cool components within an automotive engine, such as a battery.

[0178] It will be understood that secondary loop air conditioning or refrigeration systems may be equipped with suction line / liquid line heat exchangers (SL-LL HX).

[0179] The heat transfer fluid or heat transfer composition, which may include a secondary loop air conditioning system utilizing the refrigerant of the Disclosure comprising each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used as a substitute for existing fluids.

[0180] The present disclosure includes a method for replacing an existing heat transfer fluid in a heat transfer system, the method comprising (a) removing at least a portion of the existing heat transfer fluid from the system, and (b) introducing the heat transfer fluid of the present disclosure into the system. Step (a) may include removing at least about 5% by weight, at least about 10% by weight, at least about 15% by weight, at least about 50% by weight, at least about 70% by weight, at least about 90% by weight, at least about 95% by weight, at least about 99% by weight, or at least about 99.5% by weight, or substantially all of the existing heat transfer fluid from the system prior to step (b).

[0181] This method may optionally include a step of flushing the system with a solvent after performing step (a) and before performing step (b).

[0182] For the purposes of this disclosure, the heat transfer fluids of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used to replace existing fluids in electronic devices, organic Rankine cycles, high-temperature heat pumps, or secondary loops.

[0183] For example, the thermal management compositions of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used as substitutes for existing fluids such as HFC-4310mee, HFE-7100, and HFE-7200. Alternatively, the thermal management compositions, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used to replace water and glycol. The substitutes may be in existing systems or in new systems designed to function with existing fluids. Alternatively, the thermal management compositions, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used in applications where existing refrigerants were previously used. Alternatively, the refrigerants of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used to improve existing refrigerants in existing systems. Alternatively, the refrigerants of this disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, can be used in novel systems designed to work with existing refrigerants.

[0184] This disclosure provides a method for replacing an existing refrigerant in a heat transfer system, the method comprising: (a) removing at least a portion of the existing refrigerant from the system; and (b) introducing a refrigerant of the disclosure, comprising each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, into the system. The existing refrigerant may be selected from, for example, HFC-4310mee, HFE-7100, and HFE-7200.

[0185] Step (a) may include removing from the system at least about 5% by weight, at least about 10% by weight, at least about 15% by weight, at least about 50% by weight, at least about 70% by weight, at least about 90% by weight, at least about 95% by weight, at least about 99% by weight, or at least about 99.5% by weight of the existing refrigerant before step (b).

[0186] This method may optionally include a step of flushing the system with a solvent after performing step (a) and before performing step (b).

[0187] Use, methods, and systems of solvents and washing. This disclosure provides methods for solvation. Such methods generally include cleaning methods, etching methods, and carrier solvent applications (including, for example, those related to the coating of medical devices heparin and PTFE, coating applications, lubricant deposition, silicone deposition, and other coatings).

[0188] With regard to cleaning methods, all such methods are included within the scope of this disclosure. A preferred cleaning method involves vapor degreasing by bringing an article, device, or part thereof into contact with a composition of this disclosure comprising each of compounds 1-4 and compositions 1-4. A wide variety of contaminants can be removed from a wide variety of articles, devices, and parts. Examples of contaminants that can be removed using compositions 1-4 and compositions of this disclosure comprising each of compositions 1-4 include, for example, diesel fuel, medium oil, fluorolube, grease, and silicones and waxes. Examples of articles, devices, and parts that can be cleaned using compositions of this disclosure comprising each of compounds 1-4 and compositions 1-4 include, for example, electronic components (including silicon wafers, PCBs, and semiconductor surfaces), precision parts (including aircraft parts and components), diesel fuel, medium oil, fluorolube, grease, and silicones and waxes.

[0189] A preferred solvent vapor phase degreasing and flux removal method of the present disclosure comprises immersing a soiled substrate or component (e.g., a printed circuit board or processed metal, glass, ceramic, plastic, or elastomer component, or composite material) or a portion of the substrate or component in a boiling non-flammable liquid of the present disclosure containing each of compounds 1 to 4 and compositions 1 to 4; and then rinsing the component in a second tank or washing zone by immersion or distillate spray with a clean solvent which may be any one of the compositions of the present disclosure. The component is then dried by maintaining the cooled component in condensed vapor until the temperature reaches equilibrium.

[0190] Solvent cleaning of various types of parts generally occurs in batches, hoist-assisted batches, conveyor batches, or in-line type conveyor degreasing and flux removal equipment. Parts can also be cleaned in open-top flux removal or degreasing equipment. In both types of apparatus, the inlet and / or outlet ends of the apparatus can be in open communication with both the ambient environment and the solvent within the apparatus. To minimize solvent loss from the apparatus by either convection or diffusion, common practices in the art should be employed.

[0191] This disclosure includes solvent compositions comprising any of compounds 1 to 4 in combination with a cosolvent. The cosolvent may be selected from the group consisting of hexafluoroisopropyl ethyl ether, hexafluoroisopropyl methyl thioether, HFE-7000, HFE-7200, HFE-7100, HFE-7300, HFE-7500, HFE-7600, trans-1,2-dichloroethylene, n-pentane, cyclopentane, ethanol, perfluoro(2-methyl-3-pentanone) (Novec1230), cis-HFO-1336mzz, trans-HFO-1336mzz, HF-1234yf, HFO-1234ze(E), HFO-1233zd(E), and HFO-1233zd(Z).

[0192] Electrolyte formulations and batteries The Disclosure also provides electrolyte formulations and batteries containing the electrolyte formulations, each comprising Compounds 1-4 and Compositions 1-4. Generally, an electrolyte formulation comprises (a) an electrolyte, (b) an organic solvent for the electrolyte, and (c) an additive included in the formulation to provide a desired property of the electrolyte formulation and / or a battery containing the electrolyte, or an improvement to a desired property. The compounds of the Disclosure, each comprising Compounds 1-4 and Compositions 1-4, may be included in the formulation as a solvent (or co-solvent) for the electrolyte and / or as an additive.

[0193] Accordingly, the present disclosure provides an electrolyte formulation comprising (b) a salt, preferably a lithium ion salt, a solvent for the salt, the solvent comprising the compound of the present disclosure comprising each of the compounds 1 to 4 and compositions 1 to 4, which may or may not contain a cosolvent, and one or more additives different from the compound of the present disclosure. The present disclosure also provides an electrolyte formulation comprising (b) an electrolyte, preferably a lithium ion electrolyte, a solvent for the lithium ion electrolyte, and (c) an additive comprising the compound of the present disclosure comprising each of the compounds 1 to 4 and compositions 1 to 4, which may or may not contain an additional additive.

[0194] The Disclosure also provides batteries in general, and in particular rechargeable lithium-ion batteries, which include each of the compounds 1-4 and compositions 1-4, and an electrolyte formulation containing the compounds of the Disclosure. An exemplary rechargeable lithium-ion battery is shown in Figure 9 of this Specification, which shows the cathode and anode, and the electrolyte formulation of the Disclosure that facilitates the flow of lithium ions between the cathode and anode.

[0195] The electrolyte formulations of the present invention are intended to be useful in batteries in general, but in preferred embodiments, the electrolyte formulations include lithium-ion electrolytes useful in rechargeable batteries. Non-limiting examples of lithium salts that can constitute the electrolyte portion of the formulations include LiPF6, LiAsF6, LiCIO4*LiBF4, LiBC4Og(LiBOB), LiBCO4F,(LiODFB), LiPF3(C2F5)3(LiFAP), LiBF3(C2F5)LiPF3(C,F5)3(LiFAB), LiN, (CF3SO,)LiN(C,F5SO,), LiCF3SO3,LiC(CF3SO)3, LiPF4(CF3)2,LiPF3(CF3)3, LiPF3(iSO-C3C7)3, and LiPF5(iso-C3F7). The overall salt concentration may vary depending on the specific needs of the application, and in some embodiments, the electrolyte may be present in the formulation in amounts of about 0.3 M to about 2.5 M, or about 0.7 M to about 1.5 M. [Examples]

[0196] Example 1-3 Synthesis of (difluoromethoxy)-1,1,2,2-tetrafluoropropane Before air could enter, a 2 L three-necked flask equipped with a mechanical stirrer and a water-cooled condenser connected to a dry eye trap was filled with 400 ml of diglym, 153.0 g of 2,2,3,3,3-pentafluoro-1-propanol, and 800 g of 25 wt% NaOH. The mixture was heated to 30°C while stirring, and 103.8 g of R22 was blown into the mixture at a rate of 150 ml / min through a spurge (for a duration of approximately 3.5 hours). Heating was stopped when the addition of R22 began. When the internal temperature rose to 40°C, the R22 rate was controlled and the internal temperature was maintained at approximately 30°C by intermittent ice water cooling. After completion, the mixture was cooled to room temperature and quenched in 3 L of ice water. The bottom organic layer was collected, and 185.6 g of the crude mixture was separated, with a GC yield of 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane of 32%.

[0197] Example 2-3 Synthesis of (difluoromethoxy)-1,1,2,2-tetrafluoropropane In a 600 ml SS autoclave, 147.6 g of 2,2,3,3-tetrafluoro-1-propanol, 50 ml of diglym, 2.3 g of aliquot 336, and 116.8 g of difluorochloromethane were reacted with 361.2 g of 50 wt% sodium hydroxide at 15-30°C for 4 hours, followed by overnight at 23°C. After completion, the pressure inside the autoclave was released by passing it through a 10% potassium hydroxide solution, and the reaction contents were quenched in 1.5 L of DI water. A clear liquid of 195.0 g from the bottom organic layer was collected. GC showed 65.9% of the product 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane in the mixture, and the GC yield was 63.2%.

[0198] Example 3 - Synthesis of 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane In a 600 ml SS autoclave, 143.2 g of 2,2,3,3-tetrafluoro-1-propanol, 50 ml of diglym, 2.1 g of aliquot 336, and 114.8 g of difluorochloromethane were reacted with 353 g of 50 wt% sodium hydroxide at 15-45°C for 4 hours, followed by overnight at 23°C. After completion, the pressure inside the autoclave was released by passing it through a 10% potassium hydroxide solution, and the reaction contents were quenched in 1.5 L of DI water. A clear liquid of 184.0 g from the bottom organic layer was collected. GC showed 55.3% of the product 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane in the mixture, and the GC yield was 51.5%.

[0199] The crude 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane products collected from Examples 5 and 6 typically contained 3.8% by-products 1,1,2,2-tetrafluoro-3-fluoro(2,2,3,3-tetrafluoropropoxy)methoxy)propane ((CF2HCF2CH2O)2CHF) and 2.8% tris(2,2,3,3-tetrafluoropropoxy)methane ((CF2HCF2CH2O)3CH) plus some solvent. The dimer (CF2HCF2CH2O)2CHF tended to lose HF during storage and distillation and was corrosive to glassware. Therefore, the crude product mixtures were combined and rotated under a vacuum of 100 Torre. The liquid product collected in a dry eye trap did not contain the dimer or trimer. The crude mixture 531.5 (GC 53.2%), after rotary evaporation, provided 304 g of a clear liquid with a GC purity of 88.2%, in addition to some of the starting material and solvent, and there were no further dimers or trimers in the mixture.

[0200] Example 4-3 Synthesis of (difluoromethoxy)-1,1,1,2,2-pentafluoropropane In a 600 ml SS autoclave, 153.0 g of 2,2,3,3,3-pentafluoro-1-propanol, 50 ml of diglym, 2.2 g of aliquot 336, and 124.2 g of difluorochloromethane (R22) were reacted with 411.8 g of 50 wt% sodium hydroxide at 15-23°C for 16 hours. After completion, the pressure inside the autoclave was released by passing it through a 10% potassium hydroxide caustic solution, and the reaction contents were quenched in 1.5 L of DI water. A clear liquid of 186.9 g from the bottom organic layer was collected. GC showed 46.94% of the product 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane in the mixture, and the GC yield was 42.9%.

[0201] Example 5-3 Synthesis of (difluoromethoxy)-1,1,1,2,2-pentafluoropropane A 2 L three-necked flask equipped with a mechanical stirrer was packed with 100 ml of dioxane, 148.8 g of 2,2,3,3,3-pentafluoro-1-propanol, and 408 g of 50 wt% NaOH. The mixture was heated to 50°C while bubbling R22 into the solution at 100 ml / min for 4.5 hours, then stopped. GC-MS showed that 13% of the starting material remained, and R22 was continued for a further 1.5 hours until no more starting material remained in the mixture. The mixture was cooled to 20°C and quenched in 1.5 L of ice water. 81.9 g of clear liquid was collected from the bottom layer, and GC showed 59.4% of the product plus other by-products, with a GC yield of 24.3%.

[0202] Example 6-3 Synthesis of (difluoromethoxy)-1,1,1,2,2-pentafluoropropane In a 600 ml SS autoclave, 150.5 g of 2,2,3,3,3-pentafluoro-1-propanol and 70 ml of diglym were cooled to -60°C with a dry ice acetone mixture and then vacuumed. 110 g of difluorochloromethane (R22) was condensed into a container and sealed. 409 g of 50 wt% sodium hydroxide was added at a rate of 1.5 ml / min via an Eldex liquid pump while stirring at 23-39°C for 4 hours, and after addition, the mixture was stirred overnight at 23°C. After completion, the pressure inside the autoclave was released by passing it through a 10% potassium hydroxide caustic solution, and the reaction contents were quenched in 1.5 L of DI water. A clear liquid of 143.5 g from the bottom organic layer was collected. GC showed 53.6% of the product 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane in the mixture, and the GC yield was 38.4%.

[0203] The crude 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane products collected from Examples 5 and 6 typically contained 10.6% by-products 1,1,1,2,2-pentafluoro-3-fluoro(2,2,3,3,3-pentafluoropropoxy)methoxy)propane ((CF3CF2CH2O)2CHF) and 2.5% tris(2,2,3,3,3-tetrafluoropropoxy)methane ((CF3CF2CH2O)3CH) plus some solvent. The combined crude product of 298.7 g (GC 31%) was distilled through a 1-foot packed column to obtain several fractions containing 101.8 g of 98.5% 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane plus impurities.

[0204] Example 7-4 Synthesis of (difluoromethoxy)-1,1,1,2,2,3,3-heptafluorobutane 100g of 2,2,3,3,4,4,4-heptafluoro-1-butanol, 400ml of 21% NaOH aqueous solution, and 350ml of diglym were added to a 1L autoclave (leak-tested) and sealed. The temperature and pressure inside the autoclave were recorded. The autoclave was heated to 50°C, and the heat jacket was removed when the temperature reached the specified temperature. 60g of R22 (CHF2Cl) was blown into the autoclave at a rate of 0.25g to 0.4g / min while stirring.

[0205] After the addition of R22 was complete, stirring was continued for a further 2-3 hours. The reaction mixture was then transferred to a 5 L flask and subjected to vacuum transfer for 1.5 hours, after which the product was collected by dry ice and then liquid nitrogen trap. The product in the trap was warmed to room temperature and then washed twice with 50 ml of water in a separate funnel. 76 g of the bottom organic layer was collected, and GC showed 85% 4-(difluoromethoxy)-1,1,1,2,2,3,3-heptafluorobutane in the mixture, with a GC yield of 52%.

[0206] Example 8 - Dielectric Constant Measurement The static dielectric constants of the new molecules were calculated using Kirkwood theory, as described in the papers by Wang and Anderko [P. Wang and A. Anderko, Computation of dielectric constants of solvent mixtures and electrolyte solutions, Fluid Phase Equilibria 186(2001)103-122] and Harvey and Lemmon [AH Harvey and EW Lemmon, Method for estimating dielectric constant of natural gas mixtures, International Journal of Thermophysics 26(2005)31-46].

[0207] Experimental dielectric properties were measured for all liquids using an Agilent 85070 Dielectric Probe. All measurements were performed at ambient pressure and room temperature (approximately 23°C). Before measurement, the system was calibrated from 1 GHz to 20 GHz using open-circuit, short-circuit, and DI water (@22.4°C) standards. The calibration results for DI H2O are shown in Table 5 below and are in agreement with DI water at 22.4°C. Probe accuracy is obtained as dielectric constant, er' = er' + / - 0.05|er*|, and er” = er” + / - 0.05|er*|, as well as (loss = er” / er').

[0208] [Table 5]

[0209] Example 9 - Organic Rankine Cycle This embodiment demonstrates that the compositions of the present disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, are useful as working fluids in an organic Rankine cycle, based on a comparison of the estimated thermal efficiencies of various working fluids in an organic Rankine cycle. In this embodiment, the ORC system is assumed to house a condenser, pump, boiler, and turbine, and the following qualitative results will be obtained, as shown in Table 6 below.

[0210] [Table 6]

[0211] Example 10 Electric vehicle batteries generate heat during charging and discharging. Typical vehicle battery designs differ between three types: cylindrical cells, pouch cells, and prism cells. All three types have different considerations regarding heat transfer due to their shape. Prism cells and pouch cells are often used with cooling plates due to their straight outer surface. Cylindrical cells use cooling ribbons that make thermal contact with the cell's outer shell. Significant heat generation during cell charging and discharging can lead to temperature increases that can degrade performance and reduce battery life.

[0212] A battery cooling plate setup can be used to provide active cooling to a battery and remove heat (for example, to remove heat from an electric vehicle battery). In this embodiment, the performance of each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, as well as the fluids of the present disclosure including 3M Novec7200, is analyzed for their ability to provide cooling in single-phase heat transfer.

[0213] It will be understood that convective heat transfer can occur either by direct contact, i.e., when the battery is immersed in a fluid that can be pumped through the battery enclosure, or indirectly, i.e., by using a cooling plate with a combination of convective and conductive heat transfer.

[0214] This embodiment used a circular tube with an inner diameter of 0.55 inches to provide a cooling load of 10246 BTU / h (3kW). The length of the tube was 30 ft (9.14 m) with an estimated pressure loss of 2.9 PSI (20 kPa). The fluid temperature was 7.2°C (45°F). The internal heat transfer coefficient was determined for turbulence. The mass flow rate required to remove the cooling load was determined for both fluids. The comparison results are shown in Table 7 below. The results show that the mass flow rate required to remove the generated heat is approximately the same as or less than that for the 3M Novec 7200, and the useful output (i.e., heat transfer coefficient) is approximately the same as or higher than that of the 3M Novec 7200.

[0215] [Table 7]

[0216] Example 11 - Secondary AC System The efficiency of a secondary loop air conditioning system is evaluated using R1234ze(E) and R1234yf as primary refrigerant options, and propane, compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, each with their respective heats, as secondary refrigerants, determined by the estimated coefficient of performance (COP). This system consists of a vapor compression primary loop and a pump-type two-phase secondary loop thermally connected by an internal heat exchanger. This internal heat exchanger acts as an evaporator for the primary loop and as a condenser for the secondary loop. The COP is evaluated for the performance of R410A in the air conditioning system using the thermodynamic properties of the primary and secondary refrigerants under specified conditions for each unit operation, as defined in Table 8 (see Table 9).

[0217] [Table 8]

[0218] [Table 9]

[0219] Table 9 shows the thermodynamic performance of secondary AC systems containing different primary refrigerants and using each of compounds 1-4 as a secondary refrigerant, and the performance of the secondary AC systems is comparable to that of the R410A system in all cases.

[0220] Example 12 - High-temperature heat pump application High-temperature heat pumps can utilize waste heat to provide high heat sink temperatures. Compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 in Table 4 of this disclosure each provide efficiency approximately equal to or better than R245fa over a wide range of condensation temperatures. The following operating conditions were used. ● Condensation temperature varied between 90°C, 100°C, and 110°C. ●Supercooling: 10℃ ●Evaporation temperature: 25℃ ● Evaporator overheating: 15℃ ●Isentropic efficiency: 65%

[0221] [Table 10]

[0222] Example 13 - Thermodynamic performance of a secondary loop medium-temperature refrigeration system The efficiency of a secondary loop medium-temperature refrigeration system is evaluated by determining the estimated coefficient of performance (COP) for each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, using R1234ze(E), R1234yf, and propane as primary refrigerant options. This system consists of a vapor-compressed primary loop and a pump-driven two-phase secondary loop thermally connected by an internal heat exchanger. This internal heat exchanger acts as an evaporator for the primary loop and as a condenser for the secondary loop. The COP is evaluated relative to the performance of R134a in the air conditioning system, and each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 is found to be approximately equivalent to or superior to the efficiency of R134a.

[0223] Example 14A - Single-phase sensible heat immersion cooling in battery applications Electric vehicle batteries generate heat during charging and discharging. Typical vehicle battery designs differ among three types: cylindrical cells, pouch cells, and prism cells. All three types have different considerations regarding heat transfer due to their shape. Significant heat generation during cell charging and discharging can lead to temperature increases that can degrade performance and reduce battery life.

[0224] Compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 preferably have a low dielectric constant, high dielectric strength, and are non-flammable fluids, enabling direct cooling of battery cells immersed in each of compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20.

[0225] This example considers a battery module consisting of 1792 cylindrical battery cells of the 18650 type. In some cases, the battery module is cooled by a 50 / 50 mixture of water / glycol in a flat tube heat exchanger in contact with the battery cells. In other cases, the cells are immersed in each of Compounds 1 - 4 and / or Heat Transfer Compositions 1 - 10 and / or Blends RB1 - RB20, i.e., in direct contact with the fluid. The waste heat of the battery module is 8750 W and is uniformly distributed over the total number of cells. The assumptions and operating conditions are listed in Tables 11 and 12.

[0226] [Table 11]

[0227] [Table 12]

[0228] Example 14B - Single - Phase Sensible Heat Data Center Cooling The data center, also described herein as a server bank or server hub, is designed to maximize computing and storage capacity while minimizing space requirements. This results in a densely packed array of servers and network gear, which can lead to concentrated heat generation. In addition, the data center operates continuously and further contributes to heat accumulation. Effective cooling can improve the efficiency and lifespan of server hardware.

[0229] Compounds 1 - 4 and / or Heat Transfer Compositions 1 - 10 and / or Blends RB1 - RB20 preferably have a low dielectric constant, high dielectric strength, and are non - flammable fluids that enable direct cooling of the data center immersed in each of Compounds 1 - 4 and / or Heat Transfer Compositions 1 - 10 and / or Blends RB1 - RB20.

[0230] The data center is cooled by compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, and the system operates effectively, efficiently, safely, and reliably. Electronic components are kept within the most desirable operating temperature range while the data center is performing its functions.

[0231] Example 15A - Two-phase immersion cooling in data center applications An example of data center cooling is provided with reference to Figure 7. A data center generally represented as 200 includes a plurality of electronic subsystems 220 housed in one or more electronic equipment racks 210. At least one, preferably a plurality, preferably all of the electronic subsystems 220 are associated with a cooling station 240 which (in one embodiment) includes a vertically extending liquid-air heat exchanger 243 and supply and return ducts 241, 242 for directing a cooling airflow 244 across the liquid-air heat exchanger 243. A cooling subsystem 219 is associated with at least one, preferably a plurality, preferably all of the plurality of electronic subsystems 220. In a preferred embodiment, as shown in Figure 7, all subsystems 220 are associated with the cooling station 240 and the cooling subsystem 219. Each cooling subsystem 219 comprises a housing 221 (preferably a low-pressure housing) surrounding each electronic subsystem 220 which includes a plurality of electronic components 223. Electronic components operate as part of a data center and generate heat as a result of performing their functions within the data center. Examples of electronic components include printed circuit boards, microprocessor modules, and memory devices. Each electronic subsystem, when operating, has its heat-generating components immersed in a thermal management composition 224 of the present disclosure, each comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20. The fluid 224 boils during typical operation, generating dielectric vapor 225 according to the present disclosure. In an exemplary embodiment, an electronic subsystem 220 is angled by providing upwardly inclined support rails 222 within an electronic equipment rack 210 to accommodate the electronic subsystem 220 at an angle. The angled electronic subsystem facilitates buoyancy-driven circulation of vapor 225 between a cooling subsystem 219 and a liquid-air heat exchanger 243 of an associated local cooling station 240. However, the excellent results according to the present disclosure and its embodiments are equally well achieved when such angled configuration is not used.Multiple coolant loops 226 are connected in fluid and thermal contact to the respective portions of the liquid-cooled electronic subsystem and the liquid-air heat exchanger 243. Specifically, multiple tubular sections 300 penetrate the liquid-air heat exchanger 243, which in this embodiment includes multiple air-cooling fins 310. Steam 225 is buoyantly driven from the housing 221 to the corresponding tubular sections 300 of the liquid-air heat exchanger 243, where the steam condenses and is then returned as a liquid to the associated liquid-cooled electronic subsystem. Cooling airflow 244 is provided in parallel to supply ducts 241 for multiple local cooling stations 240 of the data center 200, and the heated airflow is exhausted through return ducts 242. Although not a fluid of this disclosure, the apparatus described herein is disclosed in U.S. Patent Application Publication No. 2013 / 0019614, which is incorporated herein by reference.

[0232] The system described above operates using a thermal management composition comprising each of the compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, and ambient air as a heat sink for a condenser, the system operates to effectively, efficiently, safely and reliably maintain electronic components within the most desirable operating temperature range while the system is performing its function in a data center in operation.

[0233] Example 15B - Two-phase immersion cooling of a battery As described in Example 15A above, compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 are suitable as thermal management compositions for two-phase immersion cooling systems.

[0234] In this embodiment, the battery array is cooled using the two-phase immersion cooling system of Example 15A. The immersion cooling system effectively, efficiently, safely, and reliably maintains the batteries within the most desirable operating temperature range.

[0235] Example 16 - Compounds 1-4 as solvents or additives in lithium-ion batteries Electrolyte solvents and additives play a crucial role in the performance of lithium-ion batteries (LIBs). Compounds 1-4 of this disclosure are used as solvents or additives for various electrolyte compositions of lithium-ion batteries. Typically, electrolyte compositions include solvents or combinations of solvents containing components such as dissolved Li salts like lithium hexafluorophosphate (LiPF6), lithium bis(fluorosulfonyl)imide (LiFSI), lithium trifluoromethanesulfonate (LiTf), ethylene carbonate (EC), propylene carbonate (PC), diethylene carbonate (DEC), dimethylene carbonate (DMC), and many other organic carbonates and esters, as well as additives such as vinylene carbonate, crown ethers, borates, boronates, and many other compounds. The role of the solvent in a lithium-ion battery (LIB) is to act as a medium for the transfer of charge, in the form of ions, between a pair of electrodes. Various modifications of the electrolyte, including different components of the solvent or additives, are also known; for a detailed explanation, see Kang Xu, “Non-Aqueous Electrolytes for Lithium Based Rechargeable Batteries” Chem. Rev., 2012, 104, 4303-4417. Since the material possesses desirable properties such as chemical and thermal stability, desirable dielectric constant, and electrochemical window, the compounds of this disclosure, including compounds 1-4, can be added as solvents and / or additives to improve the performance of lithium-ion batteries. The compounds and compositions can be used in a variety of electrolyte compositions, for example, as a solvent in the range of 5-50% by weight of the solvent, and as an additive in the range of 0.1-5% by weight.

[0236] Example 17 - Cooling of an integrated circuit The working fluids of this disclosure, comprising compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20, are used to cool integrated circuits such as computer chips and circuit boards, and / or any heat sinks or heat spreaders associated with or connected to computer chips or circuit boards, by circulating compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20 around the integrated circuit components, or by immersing the integrated circuit components in compounds 1-4 and / or heat transfer compositions 1-10 and / or blends RB1-RB20. The cooling system effectively, efficiently, safely, and reliably maintains the integrated circuit components within the most desirable operating temperature range.

[0237] Example 18 - Solvent degreasing The working fluid of this disclosure, containing compounds 1 to 4, is used as a solvent in a degreasing apparatus to successfully remove various contaminants, including all of the aforementioned contaminants, from a variety of substrates, including all of the aforementioned substrates.

[0238] manner Embodiment 1 is a method for providing heat transfer to and from an electronic component, article, and / or device while the device is in operation, comprising: providing a heat transfer composition comprising at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane; and cooling the heat transfer composition by bringing it into contact with the electronic component, article, and / or device while the electronic component, article, and / or device is in operation.

[0239] Embodiment 2 is the method of Embodiment 1, wherein the heat transfer composition has a dielectric constant of less than about 5 at 20 GHz.

[0240] Embodiment 3 is the method of Embodiment 2, wherein the heat transfer composition has a dielectric constant of about 3.4 at 20 GHz.

[0241] Embodiment 4 is one of the methods described in Embodiments 1 to 3, wherein the heat transfer composition has a boiling point of about 35°C to about 80°C.

[0242] Aspect 5 is the method of Aspect 4, wherein the heat transfer composition has a boiling point of about 46 °C.

[0243] Aspect 6 is the method of any one of Aspects 1 - 5, wherein the heat transfer composition has a global warming potential (GWP) of about 500 or less.

[0244] Aspect 7 is the method of any one of Aspects 1 - 6, wherein the heat transfer composition is non - flammable.

[0245] Aspect 8 is the method of any one of Aspects 1 - 7, wherein the heat transfer composition comprises at least about 50 wt% of 3 - (difluoromethoxy) - 1,1,1,2,2 - pentafluoropropane.

[0246] Aspect 9 is the method of any one of Aspects 1 - 8, wherein the electronic device is selected from a data center and a battery.

[0247] Aspect 10 is a method of heating and / or cooling an electronic component, an article, and / or a device, comprising: (a) providing a refrigerant comprising at least about 10 wt% of 3 - (difluoromethoxy) - 1,1,1,2,2 - pentafluoropropane; (b) immersing the electronic component, the article, and / or the device in the refrigerant while the electronic component, the article, and / or the device is operating; and (c) transferring heat between the immersed electronic component, article, and / or device and the refrigerant.

[0248] Aspect 11 is the method of Aspect 10, wherein the refrigerant has a dielectric constant of less than about 5 at 20 GHz.

[0249] Aspect 12 is the method of Aspect 11, wherein the refrigerant has a dielectric constant of about 3.4 at 20 GHz.

[0250] Aspect 13 is the method of any one of Aspects 10 - 12, wherein the refrigerant has a boiling point of about 35 °C to about 80 °C.

[0251] Embodiment 14 is the method of Embodiment 13, wherein the refrigerant has a boiling point of approximately 46°C.

[0252] Embodiment 15 is one of the methods described in Embodiments 10 to 14, wherein the refrigerant has a global warming potential (GWP) of approximately 500 or less.

[0253] Embodiment 16 is one of the methods of Embodiments 10 to 15, wherein the refrigerant is non-flammable.

[0254] Embodiment 17 is any one of embodiments 10 to 16, wherein the refrigerant comprises at least about 50% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane.

[0255] Embodiment 18 is one of embodiments 10 to 17, wherein the electronic device is selected from a data center and a battery.

[0256] Embodiment 19 is a method for synthesizing 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, comprising reacting 2,2,3,3,3-pentafluoro-1-propanol with chlorodifluoromethane in the presence of a base.

[0257] Embodiment 20 is the method of Embodiment 19, further comprising at least one of the following: the reaction step is carried out in the presence of an organic solvent selected from diglyme, dioxane, and combinations thereof; the base is NaOH; and the reaction step is carried out at a temperature of about 10°C to about 45°C.

[0258] Embodiment 21 is Equation 1: CHF2O CH a (Cx1Fy1Hz1)(Cx2Fy2Hz2) (In the formula, a is 1 or 2, x1 is 1 to 4, y1 is between 3 and 9, z1 is between 0 and 6, x2 is between 0 and 3, y2 is between 0 and 7. The composition contains a fluoroether (where z2 is between 0 and 4).

[0259] Embodiment 22 describes a fluoroether, 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane (CHF2CF2CH2OCHF2), 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane (CF3CF2CH2OCHF2), 2-(difluoromethoxy)-1,1,1,3,3,3-hexafluoropropane((CF 32 CHOCHF2), The composition according to embodiment 21 comprises at least one of 4-(difluoromethoxy)-1,1,1,2,2,3,3-heptafluorobutane (CF3CF2CF2CH2OCHF2) and combinations thereof.

[0260] Embodiment 23 is a heat transfer composition comprising the fluoroether composition of Embodiment 21 or Embodiment 22.

[0261] Embodiment 24 is a thermal management composition comprising the fluoroether composition of Embodiment 21 or Embodiment 22.

[0262] Embodiment 25 is an electrolyte composition comprising the fluoroether composition of Embodiment 21 or Embodiment 22.

[0263] Embodiment 26 is a solvent composition comprising the fluoroether composition of Embodiment 21 or Embodiment 22.

[0264] Embodiment 27 is Equation 1: CHF2O CH a (Cx1Fy1Hz1)(Cx2Fy2Hz2) (In the formula, a is 1 or 2, x1 is 1 to 4, y1 is between 3 and 9, z1 is between 0 and 6, x2 is between 0 and 3, y2 is between 0 and 7. A method for synthesizing fluoroethers (where z2 is 0-4), The method includes reacting a fluoroalcohol with chlorodifluoromethane in the presence of a catalyst to provide a fluoroether of formula 1.

[0265] Embodiment 28 is the method of Embodiment 27, wherein the fluoroalcohol is 2,2,3,3-tetrafluoro-1-propanol and the fluoroether is 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane.

[0266] Embodiment 29 is the method of Embodiment 27, wherein the fluoroalcohol is 2,2,3,3,3-pentafluoro-1-propanol and the fluoroether is 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane.

[0267] Embodiment 30 is the method of Embodiment 27, wherein the fluoroalcohol is 2,2,2,3,3,3-hexafluoro-1-propanol and the fluoroether is 2-(difluoromethoxy)-1,1,1,3,3,3-hexafluoropropane.

[0268] Embodiment 31 is the method of Embodiment 27, wherein the fluoroalcohol is 2,2,3,3,4,4,4-heptafluoro-1-butanol and the fluoroether is 4-(difluoromethoxy)-1,1,1,2,2,3,3-heptafluorobutane.

[0269] Embodiment 32 is any of the methods of Embodiments 27 to 31, wherein the reaction step further includes carrying out the reaction in the presence of an organic solvent.

[0270] Embodiment 33 is the method of Embodiment 32, wherein the organic solvent is selected from diglyme, dioxane, and combinations thereof.

[0271] Embodiment 34 is any of the methods of Embodiments 27 to 31, wherein the catalyst is NaOH.

[0272] Embodiment 35 is any of the methods of Embodiments 27 to 31, wherein the reaction step further comprises carrying out the reaction at a temperature of 10 to 45°C.

[0273] Embodiment 36 is a method for cooling an electronic device in operation, wherein formula 1: CHF2O CH a (Cx1Fy1Hz1)(Cx2Fy2Hz2) (In the formula, a is 1 or 2, x1 is 1 to 4, y1 is between 3 and 9, z1 is between 0 and 6, x2 is between 0 and 3, y2 is between 0 and 7. To provide a refrigerant containing a fluoroether (where z2 is 0-4), A method comprising immersing an electronic device or component in a refrigerant.

[0274] Embodiment 37 is the method of Embodiment 36, wherein the refrigerant has a global warming potential (GWP) of approximately 200 or less.

[0275] Embodiment 38 is the method of Embodiment 36 or Embodiment 37, wherein the refrigerant is non-flammable.

[0276] Embodiment 39 is a method according to any of Embodiments 36 to 38, wherein the refrigerant has a dielectric constant of less than 5 at 20 GHz.

[0277] Embodiment 40 is any of the methods according to Embodiments 36 to 39, wherein the refrigerant has a boiling point of about 35°C to about 80°C.

[0278] Embodiment 41 is a method according to any of Embodiments 36 to 40, wherein the refrigerant (i) has a dielectric constant of less than 5 at 20 GHz, (ii) has a boiling point of about 35°C to about 80°C, (iii) is non-flammable, and (iv) has Ames-negative toxicity.

[0279] Embodiment 42 is a refrigerant comprising at least about 50% by weight of Formula 1: CHF2O CH a(Cx1Fy1Hz1)(Cx2Fy2Hz2) (In the formula, a is 1 or 2, x1 is 1 to 4, y1 is between 3 and 9, z1 is between 0 and 6, x2 is between 0 and 3, y2 is between 0 and 7. The method is one of embodiments 36 to 41, comprising a fluoroether (where z2 is 0 to 4).

[0280] Embodiment 43 is any method of Embodiments 36 to 42, wherein the electronic device or component includes one or more of the following: a battery, a semiconductor integrated circuit (IC), an electrochemical cell, a power transistor, a resistor, an electroluminescent element, a microprocessor, a power control semiconductor, a power distribution switchgear, a power transformer, a printed circuit board, a multichip module, a packaged or unpackaged semiconductor device, a semiconductor integrated circuit, a fuel cell, a laser light-emitting diode (LED), an electrochemical cell, an electric drive motor, and combinations thereof.

[0281] Embodiment 44 is any of the methods of Embodiments 36 to 43, performed in an electric vehicle and / or a hybrid gas / electric vehicle and / or a data center and / or a server and / or a crypto mining center.

[0282] It should be understood that the foregoing description is merely illustrative of the present disclosure. Various alternative and modified forms can be devised by those skilled in the art without departing from the present disclosure. Accordingly, the present disclosure is intended to encompass all such alternative forms, modifications, and variations that fall within the scope of the appended claims.

Claims

1. A method for providing heat transfer to and from electronic components, articles, and / or the device while the device is in operation, To provide a heat transfer composition containing at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, A method comprising cooling the electronic component, article, and / or device by bringing the heat transfer composition into contact with the electronic component, article, and / or device during its operation.

2. The method according to claim 1, wherein the heat transfer composition has a dielectric constant of less than 5 at 20 GHz.

3. The method according to claim 2, wherein the heat transfer composition has a dielectric constant of about 3.4 at 20 GHz.

4. The method according to any one of claims 1 to 3, wherein the heat transfer composition has a boiling point of about 35°C to about 80°C.

5. The heat transfer composition is Boiling point of approximately 46°C It also includes a global warming potential (GWP) of approximately 500 or less. The method according to claim 1, wherein the method is non-flammable.

6. The method according to any one of claims 1 to 5, wherein the heat transfer composition comprises at least about 50% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane.

7. The method according to any one of claims 1 to 6, wherein the electronic device is selected from a data center and a battery.

8. A method for heating and / or cooling electronic components, articles, and / or devices, (a) To provide a refrigerant containing at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, (b) Immersing the electronic components, articles, and / or devices in the refrigerant while the electronic components, articles, and / or devices are operating, (c) A method comprising transferring heat between the immersed electronic components, articles, and / or devices and the coolant.

9. The method according to claim 8, wherein the refrigerant has a dielectric constant of less than 5 at 20 GHz.

10. The method according to claim 9, wherein the refrigerant has a dielectric constant of about 3.4 at 20 GHz.

11. The method according to any one of claims 8 to 10, wherein the refrigerant has a boiling point of about 35°C to about 80°C.

12. The aforementioned refrigerant, Boiling point of approximately 46°C It also includes a global warming potential (GWP) of approximately 500 or less. The method according to claim 8, which is non-flammable.

13. The method according to any one of claims 8 to 12, wherein the refrigerant comprises at least about 50% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane.

14. The method according to any one of claims 8 to 13, wherein the electronic device is selected from a data center and a battery.

15. A method for synthesizing 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, comprising reacting 2,2,3,3,3-pentafluoro-1-propanol with chlorodifluoromethane in the presence of a base.

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