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Definitions

• the present disclosure relates to a perfluorinated aminoolefm and methods of making and using the same.
• a perfluorinated aminoolefm compound is provided.
• X and Y are (i) independently selected from a perfluoroalkyl group having 1-4 carbon atoms, or (ii) bonded together to form a perfluorinated ring structure having 5-6 ring carbon atoms.
• catenated means an atom other than carbon (for example, oxygen or nitrogen) that is bonded to at least two carbon atoms in a carbon chain (linear or branched or within a ring) so as to form a carbon-heteroatom-carbon linkage; and
• perfluorinated means a group or a compound wherein all hydrogen atoms in the C-H bonds have been replaced by C-F bonds.
• Rf and Rf are (i) independently selected from a linear or branched perfluoroalkyl group having 1- 8 carbon atoms, optionally comprising at least one catenated O or N atom, or (ii) bonded together to form a perfluorinated ring structure having 4-8 ring carbon atoms, optionally comprising at least one ether linkage; and
• X and Y are (i) independently selected from a perfluoroalkyl group having 1-4 carbon atoms, or (ii) bonded together to form a perfluorinated ring structure having 5-6 ring carbon atoms.
• Rf and RF are independently selected from a linear or branched perfluoroalkyl group having 1-8 carbon atoms, 2-6 carbon atoms, or even 2-4 carbon atoms, optionally comprising at least one catenated oxygen atom (or ether linkage).
• exemplary Rf and RF groups include: -CF3; -(CF2) n CF3 where n is 1, 2, 3, 4, 5, or 6; C(CF3)2CF3 , and -CF(CF3)CF3.
• RF and RF are connected to form a ring structure moiety comprising a total of 4 to 8 carbon atoms in addition to optional catenary heteroatoms such as oxygen or nitrogen.
• the ring structure moiety may comprise a 4-, 5-, or 6- membered ring.
• the ring which is made up of the nitrogen atom from the carboximidate may also include an oxygen atom (ether linkage) in the ring.
• the ring may comprise pendent perfluorinated alkyl groups, which may optionally comprise at least one catenated atom selected from oxygen, nitrogen, or combinations thereof.
• Exemplary ringed structures include: 5- membered rings such as pyrroles, and 6-membered rings such pyridines, and 6-membered rings comprising a catenated oxygen (such as 1, 4-oxazines).
• X and Y are independently selected from a linear or branched perfluoroalkyl group having 1-4 carbon atoms.
• Exemplary X and Y groups include: -CF3; - (CF2) n CF3 where n is 1, 2, or 3; C(CF ) CF , and -CF(CF )CF .
• X and Y are connected to form a 5- or 6-membered perfluorinated ring structure.
• Exemplary compounds of the present disclosure include:
• the“F” within a ring structure means that each carbon within the ring structure is fluorinated and the wavy line in the isomeric structures above represents that the structure can be cis or trans in nature.
• a metal fluoride catalyst [M]F; where X, Y, Rf and RF are the same as defined above.
• the perfluorinated imine is selected from a perfluorinated imidoyl fluoride, a perfluorinated oxazine, or a perfluorinated pyrrole compound.
• a perfluorinated imidoyl fluoride a perfluorinated oxazine
• a perfluorinated pyrrole compound a perfluorinated pyrrole compound.
• Such compounds are commercially available or can be synthesized using methods such as those disclosed in H.V.
• Exemplary perfluorinated imines include:
• Such perfluoroolefins may be commercially available or synthesized using techniques known in the art.
• Exemplary perfluoroolefins include:
• Metal fluoride catalysts are known in the art and can include CsF, KF, AIF3, MgF , CaF , SrF , BaF , and combinations thereof. Because the metal fluoride catalyst is regenerated during the reaction, typically low amount (e.g., less than 50, 40, 30 or even 20 mole% versus the perfluorinated olefin) are used.
• perfluoroolefm of formula III and the perfluorinated imine of formula II are combined in the presence of the metal fluoride catalyst and heated, whether it is to ambient temperature or higher temperatures such as temperatures greater than 40, 50, or 70 °C.
• the ratio of the perfluoroolefm of formula III and the perfluorinated imine of formula II is typically less than 0.85 to 1, or even less than 0.70 to 1.
• a solvent may be used to solubilize the reactants for a reaction to occur.
• Useful solvents include organic solvents, such as polar aprotic solvents.
• Polar aprotic solvents include, ethers (such as bis(2-methoxyethyl) ether and tetraethylene glycol dimethyl ether), nitriles (such as acetonitrile, adiponitrile, and benzonitrile), dimethylsulfoxide, N-methylpyrrolidinone (NMP), N,N-dimethylformamide (DMF), and tetrahydrothiophene-l,l- dioxide (sulfolane), which can be used individually or as a mixture.
• NMP N-methylpyrrolidinone
• DMF N,N-dimethylformamide
• sulfolane tetrahydrothiophene-l,l- dioxide
• the resulting fluorinated compounds from the reaction can be purified to isolate the desired perfluorinated aminoolefm. Purification can be done by conventional means including distillation, absorption, extraction, chromatography and recry stallization. The purification can be done to isolate the compound of the present disclosure (in all of its stereoisomeric forms) from impurities, such as starting materials, byproducts, etc.
• the term “purified form” as used herein means the compound of the present disclosure is at least 75, 80, 85, 90, 95, 98, or even 99 wt% pure.
• the compounds of the present disclosure have good environmental properties as well as having good performance attributes, such as non-flammability, chemical inertness, high thermal stability, good solvency, etc.
• the compound of the present disclosure may have a low
• the compounds of the present disclosure may have a global warming potential (GWP) of less than 1000, 700, or even 500.
• GWP is a relative measure of the global warming potential of a compound based on the structure of the compound.
• IPCC Intergovernmental Panel on Climate Change
• the GWP of a compound, as defined by the Intergovernmental Panel on Climate Change (IPCC) in 1990 and updated in 2007, is calculated as the warming due to the release of 1 kilogram of a compound relative to the warming due to the release of 1 kilogram of CO2 over a specified integration time horizon (ITH).
• IPCC Intergovernmental Panel on climate Change
• ai is the radiative forcing per unit mass increase of a compound in the atmosphere (the change in the flux of radiation through the atmosphere due to the IR absorbance of that compound),
• C is the atmospheric concentration of a compound
• t is the atmospheric lifetime of a compound
• t is time
• / is the compound of interest.
• the commonly accepted ITH is 100 years representing a compromise between short-term effects (20 years) and longer-term effects (500 years or longer).
• the concentration of an organic compound, /, in the atmosphere is assumed to follow pseudo first order kinetics (i.e., exponential decay).
• the concentration of CO2 over that same time interval incorporates a more complex model for the exchange and removal of CO2 from the atmosphere (the Bern carbon cycle model).
• the compounds of the present disclosure have atmospheric lifetime of less than 10 years, or even less than 5 years when tested following the Atmospheric Lifetime Test Method disclosed in the Example Section.
• Non-flammability can be assessed by using standard methods such as ASTM D-3278-96 e-l“Standard Test Method for Flash Point of Liquids by Small Scale Closed-Cup Apparatus”.
• ASTM D-3278-96 e-l “Standard Test Method for Flash Point of Liquids by Small Scale Closed-Cup Apparatus”.
• the compound of the present disclosure is non-flammable based on closed-cup flashpoint testing following ASTM D-3278-96 e-l.
• the compound of the present disclosure is non-bioaccumulative in animal tissues.
• some compounds of the present disclosure may provide low log K ow values, indicating a reduced tendency to bioaccumulate in animal tissues, where K ow is the octanol/water partition coefficient, which is defined as the ratio of the given compound’s concentration in a two-phase system comprising an octanol phase and an aqueous phase.
• the log K ow value is less than 7, 6, 5, or even 4.
• the compound of the present disclosure is thermally stable, meaning that when the compound is heated, there is minimal loss of purity. For example, if the
• perfluorinated aminoolefin is heated at 60 °C for 24 hours, there is a loss of less than 5%, 3%, or even 1%. In one embodiment, if the perfluorinated aminoolefin is heated at 100, 120 or even 150 °C, for 24 hours, there is a loss of less than 5%, 3%, or even 1%.
• the compound of the present disclosure has a wide operating range.
• the useful liquid range of a compound of the present disclosure is between its pour point and its boiling point.
• a pour point is the lowest temperature at which the compound is still able to be poured.
• the pour point can be determined, for example, by ASTM D 97-16“Standard Test Method for Pour Point of Petroleum Products”.
• the compound of the present disclosure has a pour point of less than 0°C, -20°C, -30°C, -40 °C or even -60°C.
• the compound of the present disclosure has a boiling point of at least l00°C, l50°C, or even 200°C at atmospheric pressure.
• the compound of the present disclosure has a boiling point from about 50°C to about 200°C, aboutl00°C to about l50°C, or even about 1 l0°C to about l30°C.
• the compounds of the present disclosure have a dielectric constant of less than 2.3, 2.2, 2.1, or even 2.0 as determined by ASTM D 150 measured at 1 kHz (kilohertz).
• the compounds of the present disclosure may be used in a heat transfer apparatus for transferring heat to or from the device.
• the provided apparatus for heat transfer may include a device.
• the device may be a component, work-piece, assembly, etc. to be cooled, heated or maintained at a predetermined temperature or temperature range.
• Such devices include electrical components, mechanical components and optical components.
• Examples of devices of the present disclosure include, but are not limited to microprocessors, wafers used to manufacture semiconductor devices, power control semiconductors, electrical distribution switch gear, power transformers, circuit boards, multi-chip modules, packaged and unpackaged semiconductor devices, lasers, chemical reactors, fuel cells, and electrochemical cells.
• the device can include a chiller, a heater, or a combination thereof.
• the provided apparatus may include a mechanism for transferring heat.
• the mechanism may include a heat transfer fluid.
• the heat transfer fluid may include one or more perfluorinated aminoolefm compounds of formula (I).
• Heat may be transferred by placing the heat transfer mechanism in thermal contact with the device.
• the heat transfer mechanism when placed in thermal contact with the device, removes heat from the device or provides heat to the device, or maintains the device at a selected temperature or temperature range.
• the direction of heat flow (from device or to device) is determined by the relative temperature difference between the device and the heat transfer mechanism.
• the heat transfer mechanism may include facilities for managing the heat-transfer fluid, including, but not limited to pumps, valves, fluid containment systems, pressure control systems, condensers, heat exchangers, heat sources, heat sinks, refrigeration systems, active temperature control systems, and passive temperature control systems.
• suitable heat transfer mechanisms include, but are not limited to, temperature controlled wafer chucks in plasma enhanced chemical vapor deposition (PECVD) tools, temperature-controlled test heads for die performance testing, temperature-controlled work zones within semiconductor process equipment, thermal shock test bath liquid reservoirs, and constant temperature baths.
• PECVD plasma enhanced chemical vapor deposition
• the upper desired operating temperature may be as high as l70°C, as high as 200°C, or even as high as 230°C.
• a method of transferring heat includes providing a device and transferring heat to or from the device using a mechanism.
• the mechanism can include a heat transfer fluid such as the perfluorinated aminoolefm compounds of formula (I).
• a heat transfer fluid such as the perfluorinated aminoolefm compounds of formula (I).
• the compound of the present disclosure may be used as a working fluid to convert thermal energy into mechanical energy in a Rankine cycle.
• the apparatus may further include a heat source to vaporize the working fluid and form a vaporized working fluid, a turbine through which the vaporized working fluid is passed thereby converting thermal energy into mechanical energy, a condenser to cool the vaporized working fluid after it is passed through the turbine, and a pump to recirculate the working fluid.
• a process for converting thermal energy into mechanical energy in a Rankine cycle includes a working fluid that includes one or more perfluorinated aminoolefm compounds of formula (I).
• a typical Rankine cycle system 100 is shown that includes an evaporator/boiler 120 which receives heat from an external source. The evaporator/boiler 120 vaporizes an organic Rankine working fluid contained within the closed system 100.
• the Rankine cycle system 100 also includes a turbine 160 which is driven by the vaporized working fluid in the system and is used to turn a generator 180 thus producing electrical power.
• the vaporized working fluid is then channeled through a condenser 140 removing excess heat and reliquifying the liquid working fluid.
• a power pump 130 increases the pressure of the liquid leaving the condenser 140 and also pumps it back into the evaporator/boiler 120 for further use in the cycle. Heat released from the condenser 140 can then be used for other purposes including driving a secondary Rankine system (not shown).
• Rankine cycle efficiency can be improved through the use of an extra heat exchanger (or recuperator) to recover heat from vapor exiting the expander and using the recovered heat to pre-heat liquid coming out of the pump.
• Fig. 2 is an illustration of Rankine cycle system that includes a recuperator.
• a Rankine cycle system 200 that includes an evaporator/boiler 220 which receives heat from an external source.
• the evaporator/boiler 220 vaporizes an organic Rankine working fluid contained within the closed system 200.
• the Rankine cycle system 200 also includes a turbine 260 which is driven by the vaporized working fluid in the system and is used to turn a generator 270 thus producing electrical power.
• the vaporized working fluid is then channeled through a recuperator 280 removing some excess heat and from there to the condenser 250, where the working fluid condenses back to liquid.
• a power pump 240 increases the pressure of liquid leaving the condenser 250 and also pumps it back into the recuperator 280, where it is preheated before going back into the evaporator/boiler 220 for further use in the cycle. Heat released from the condenser 250 can then be used for other purposes including driving a secondary Rankine system (not shown).
• the present disclosure relates to a process for converting thermal energy into mechanical energy in a Rankine cycle.
• the process may include using a heat source to vaporize a working fluid that includes one or more perfluorinated aminoolefm compounds of formula (I) to form a vaporized working fluid.
• the heat is transferred from the heat source to the working fluid in an evaporator or boiler.
• the vaporized working fluid may be pressurized and can be used to do work by expansion.
• the heat source can be of any form such as from fossil fuels, e.g., oil, coal, or natural gas. Additionally, in some embodiments, the heat source can come from nuclear power, solar power, or fuel cells.
• the heat can be “waste heat” from other heat transfer systems that would otherwise be lost to the atmosphere.
• The“waste heat,” in some embodiments, can be heat that is recovered from a second Rankine cycle system from the condenser or other cooling device in the second Rankine cycle.
• An additional source of“waste heat” can be found at landfills where methane gas is flared off.
• Other sources of“waste heat” that can be useful in the provided processes are geothermal sources and heat from other types of engines such as gas turbine engines that give off significant heat in their exhaust gases and to cooling liquids such as water and lubricants.
• the vaporized working fluid may be expanded though a device that can convert the pressurized working fluid into mechanical energy.
• the vaporized working fluid is expanded through a turbine which can cause a shaft to rotate from the pressure of the vaporized working fluid expanding.
• the turbine can then be used to do mechanical work such as, in some embodiments, operate a generator, thus generating electricity.
• the turbine can be used to drive belts, wheels, gears, or other devices that can transfer mechanical work or energy for use in attached or linked devices.
• the vaporized (and now expanded) working fluid can be condensed using a cooling source to liquefy for reuse.
• the heat released by the condenser can be used for other purposes including being recycled into the same or another Rankine cycle system, thus saving energy.
• the condensed working fluid can be pumped by way of a pump back into the boiler or evaporator for reuse in a closed system.
• the perfluorinated aminoolefms disclosed herein can be used as nucleating agents in the production of polymeric foams and in particular in the production of polyurethane foams and phenolic foams.
• the present disclosure is directed to a foamable composition that includes one or more blowing agents, one or more foamable polymers or precursor compositions thereof, and one or more nucleating agents that include a perfluorinated aminoolefm compound of formula (I).
• blowing agents may be used in the provided foamable compositions including liquid or gaseous blowing agents that are vaporized in order to foam the polymer or gaseous blowing agents that are generated in situ in order to foam the polymer.
• blowing agents include hydrochlorofluorocarbons (HCFCs), hydrofluorocarbons (HFCs), hydrochlorocarbons (HCCs), iodofluorocarbons (IFCs), hydrofluoroolefms (HFO), hydrocarbons, and hydrofluoroethers (HFEs).
• the blowing agent for use in the provided foamable compositions can have a boiling point of from about -45°C to about l00°C at atmospheric pressure. Typically, at atmospheric pressure the blowing agent has a boiling point of at least about l5°C, more typically between about 20°C and about 80°C.
• the provided foamable composition may also include one or more foamable polymers or a precursors composition thereof.
• Foamable polymers suitable for use in the provided foamable compositions include, for example, polyolefins, e.g., polystyrene, poly(vinyl chloride), and polyethylene. Foams can be prepared from styrene polymers using conventional extrusion methods. The blowing agent composition can be injected into a heat-plastified styrene polymer stream within an extruder and admixed therewith prior to extrusion to form foam.
• Suitable styrene polymers include, for example, the solid homopolymers of styrene, a-methylstyrene, ring-alkylated styrenes, and ring-halogenated styrenes, as well as copolymers of these monomers with minor amounts of other readily copolymerizable olefinic monomers, e.g., methyl methacrylate, acrylonitrile, maleic anhydride, citraconic anhydride, itaconic anhydride, acrylic acid, N-vinylcarbazole, butadiene, and divinylbenzene.
• methyl methacrylate acrylonitrile
• maleic anhydride citraconic anhydride
• itaconic anhydride acrylic acid
• N-vinylcarbazole butadiene
• divinylbenzene divinylbenzene
• Suitable vinyl chloride polymers include, for example, vinyl chloride homopolymer and copolymers of vinyl chloride with other vinyl monomers. Ethylene homopolymers and copolymers of ethylene with, e.g., 2-butene, acrylic acid, propylene, or butadiene may also be useful. Mixtures of different types of polymers can be employed.
• Precursors of foamable polymers suitable for use in the provided foamable compositions may include, for example, precursors of phenolic polymers, silicone polymers, and isocyanate- based polymers, e.g., polyurethane, polyisocyanurate, polyurea, polycarbodiimide, and polyimide. Typically, precursors of isocyanate-based polymers are utilized as the blowing agent for preparing polyurethane or polyisocyanurate foams.
• Polyisocyanates suitable for use in the provided foamable compositions include aliphatic, alicyclic, arylaliphatic, aromatic, or heterocyclic polyisocyanates, or combinations thereof. Any polyisocyanate which is suitable for use in the production of polymeric foams can be utilized. For example, aromatic diisocyanates such as toluene and diphenylmethane diisocyanates in pure, modified, or crude form may be employed.
• MDI variants diphenylmethane diisocyanate modified by the introduction of urethane, allophanate, urea, biuret, carbodiimide, uretonimine, or isocyanurate residues
• crude or polymeric MDI polymethylene polyphenylene polyisocyanates
• suitable polyisocyanates include, for example, ethylene diisocyanate, l,4-tetramethylene diisocyanate, l,6-hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, l,l2-dodecane diisocyanate, cyclobutane- 1, 3-diisocyanate, cyclohexane-l,3- and -1, 4-diisocyanate (and mixtures of these isomers), diisocyanato-3,3,5- trimethyl-5-isocyanatomethyl cyclohexane, 2,4- and 2,6-toluene diisocyanate (and mixtures of these isomers), diphenylmethane-2,4'- and/or -4,4'-diisocyanate, naphthalene- 1,5 -diisocyanate, the reaction products of four equivalents of the aforementioned isocyanate-containing compounds with compounds containing
• Reactive hydrogen-containing compounds suitable for use in the foamable compositions of the present disclosure are those having at least two isocyanate-reactive hydrogen atoms, for example, in the form of hydroxyl, primary or secondary amine, carboxylic acid, or thiol groups, or a combination thereof.
• Polyols i.e., compounds having at least two hydroxyl groups per molecule, due to their desirable reactivity with polyisocyanates, may be employed.
• Such polyols can be, e.g., polyesters, polyethers, polythioethers, polyacetals, polycarbonates, polymethacrylates, polyester amides, or hydroxyl-containing prepolymers of these compounds and a less than stoichiometric amount of polyisocyanate.
• Useful polyols include ethylene glycol, 1,2- and 1, 3-propylene glycol, 1,4- and 2,3- butylene glycol, 1, 5-pentane diol, 1, 6-hexane diol, 1, 8-octane diol, neopentyl glycol, 1,4- bis(hydroxymethyl)cyclohexane, 2-methyl- 1,3 -propane diol, dibromobutene diol, glycerol, trimethylolpropane, l,2,6-hexanetriol, trimethylolethane, pentaerythritol, quinitol, mannitol, sorbitol, diethylene glycol, triethylene glycol, tetraethylene glycol, higher polyethylene glycols, dipropylene glycol, higher polypropylene glycols, dibutylene glycol, higher polybutylene glycols, 4,4'-dihydroxydiphenyl propane, and di
• suitable polyols include the condensation products of polybasic acids and polyols such as polyethylene adipate and poly caprolactone -based polyols, as well as the mixtures of hydroxy aldehydes and hydroxy ketones (“formose”) and the polyhydric alcohols obtained therefrom by reduction (“formitol”) that are formed in the autocondensation of formaldehyde hydrate in the presence of metal compounds as catalysts and compounds capable of enediol formation as co-catalysts as known in the art.
• polyols condensation products of polybasic acids and polyols such as polyethylene adipate and poly caprolactone -based polyols, as well as the mixtures of hydroxy aldehydes and hydroxy ketones (“formose”) and the polyhydric alcohols obtained therefrom by reduction (“formitol”) that are formed in the autocondensation of formaldehyde hydrate in the presence of metal compounds as catalysts and compounds capable of enedio
• Solutions of polyisocyanate polyaddition products particularly solutions of polyurethane ureas containing ionic groups and/or solutions of polyhydrazodicarbonamides, in low molecular weight polyhydric alcohols can also be used (see DE 2,638,759).
• Phenolic polymer precursors suitable for use in the provided foamable compositions include, for example, the reaction product of a phenol and an aldehyde in the presence of a catalyst.
• Illustrative uses of phenolic foams of this disclsoure include use for roofing insulation, as sheathing products for external wall insulation for building applications, and for shaped parts such as pipe and block insulation for industrial applications.
• the provided foamable compositions may include a nucleating agent that includes a perfluorinated aminoolefin compound as described above with respect to formula (I).
• a nucleating agent that includes a perfluorinated aminoolefin compound as described above with respect to formula (I).
• the foamable compositions of the present disclosure may have a molar ratio of nucleating agent to blowing agent of no more than 1:50, 1:25, 1:9, or 1:7, 1:3, or 1 :2.
• Other conventional components of foam formulations can, optionally, be present in the foamable compositions of the present disclosure.
• cross-linking or chain-extending agents, foam-stabilizing agents or surfactants, catalysts and fire-retardants can be utilized.
• Other possible components include fillers (e.g., carbon black), colorants, fungicides, bactericides, antioxidants, reinforcing agents, antistatic agents, and other additives or processing aids.
• polymeric foams can be prepared by vaporizing at least one liquid or gaseous blowing agent or generating at least one gaseous blowing agent in the presence of at least one foamable polymer or a precursor composition thereof and a nucleating agent as described above.
• polymeric foams can be prepared using the provided foamable compositions by vaporizing (e.g., by utilizing the heat of precursor reaction) at least one blowing agent in the presence of a nucleating agent as described above, at least one organic polyisocyanate and at least one compound containing at least two reactive hydrogen atoms.
• the polyisocyanate, reactive hydrogen-containing compound, and blowing agent composition can generally be combined, thoroughly mixed (using, e.g., any of the various known types of mixing head and spray apparatus), and permitted to expand and cure into a cellular polymer. It is often convenient, but not necessary, to preblend certain components of the foamable composition prior to reaction of the polyisocyanate and the reactive hydrogen-containing compound. For example, it is often useful to first blend the reactive hydrogen-containing compound, blowing agent composition, and any other components (e.g., surfactant) except the polyisocyanate, and to then combine the resulting mixture with the polyisocyanate. Alternatively, all components of the foamable composition can be introduced separately. It is also possible to pre-react all or a portion of the reactive hydrogen-containing compound with the polyisocyanate to form a prepolymer.
• the present disclosure is directed to dielectric fluids that include one or more a perfluorinated aminoolefm compounds of formula (I), as well as electrical devices (e.g., capacitors, switchgear, transformers, or electric cables or buses) that include such dielectric fluids.
• dielectric fluid is inclusive of both liquid dielectrics and gaseous dielectrics. The physical state of the fluid, gaseous or liquid, is determined at the operating conditions of temperature and pressure of the electrical device in which it is used.
• the dielectric fluids include one or more perfluorinated aminoolefm compounds of formula (I) and, optionally, one or more second dielectric fluids.
• Suitable second dielectric fluids include, for example, air, nitrogen, nitrous oxide, oxygen, helium, argon, carbon dioxide, heptafluoroisobutyronitrile, 2,3,3,3-tetrafluoro-2-(trifluoromethoxy)propanenitrile, l,l,l,3,4,4,4-heptafluoro-3-(trifluoromethyl)butan-2-one, SF 6 , or combinations thereof.
• the second dielectric fluid may be a non-condensable gas or an inert gas.
• the second dielectric fluid may be used in amounts such that vapor pressure is at least 70 kPa at 25°C, or at the operating temperature of the electrical device.
• the dielectric fluids of the present application are useful for electrical insulation and for arc quenching and current interruption equipment used in the transmission and distribution of electrical energy.
• the dielectric fluid of the present disclosure can be used: (1) gas-insulated circuit breakers and current- interruption equipment, (2) gas-insulated transmission lines, and (3) gas-insulated transformers or (4) gas-insulated substations.
• gas-insulated equipment is a major component of power transmission and distribution systems.
• the present disclosure provides electrical devices, such as capacitors, comprising metal electrodes spaced from each other such that the gaseous dielectric fills the space between the electrodes.
• the interior space of the electrical device may also comprise a reservoir of the liquid dielectric fluid which is in equilibrium with the gaseous dielectric fluid. Thus, the reservoir may replenish any losses of the dielectric fluid.
• the present disclosure relates to coating compositions that include a solvent composition that includes one or more perfluorinated aminoolefm compounds of formula (I), and one or more coating materials which are soluble or dispersible in the solvent composition.
• suitable coating materials include titanium dioxide, iron oxides, magnesium oxide, perfluoropolyethers, polysiloxanes, stearic acid, acrylic adhesives, polytetrafluoroethylene, amorphous copolymers of tetrafluoroethylene, or combinations thereof.
• the present disclosure describes the use of the perfluorinated aminoolefm compound as two-phase immersion cooling fluids for electronic devices, including computer servers.
• a heat generating component 325 may be disposed within the interior space 315 such that it is at least partially immersed (and up to fully immersed) in the liquid phase 320 of the working fluid. That is, while heat generating component 325 is illustrated as being only partially submerged below the upper liquid surface 320A, in some embodiments, the heat generating component 325 may be fully submerged below the upper liquid surface 320A. In some embodiments, the heat generating components may include one or more electronic devices, such as computer servers.
• a rising vapor phase 320B of the working fluid may be condensed back to liquid phase or condensate 320C by releasing latent heat to the heat exchanger 330 as the rising vapor phase 320B comes into contact with the heat exchanger 330.
• the resulting condensate 320C may then be returned to the liquid phase 320 disposed in the lower volume of 315 A.
• the method may further include transferring heat from the heat generating electronic component using the compound of the present disclosure or a working fluid comprising the compound of the present disclsoure.
• the compounds of the present disclosure can be used as a thermal management system in electrochemical cells (e.g., lithium-ion batteries) to prevent catastrophic failure known as thermal runaway under certain conditions.
• Thermal runaway is a series of internal exothermic reactions that are triggered by heat.
• the creation of excessive heat can be from electrical over-charge, thermal over-heat, or from an internal electrical short.
• Internal shorts are typically caused by manufacturing defects or impurities, dendritic lithium formation and mechanical damage. While there is typically protective circuitry in the charging devices and in the battery packs that will disable the battery in the event of overcharging or overheating, it cannot protect the battery from internal shorts caused by internal defects or mechanical damage.
• the fluorous phase was separated, collected, and analyzed by GC-FID which indicated complete conversion of the 2, 2, 3, 3, 4,4,5- heptafluoropyrrole starting material.
• the fluorous phase was purified via concentric tube distillation affording 2,2,3,3,5,5,6,6-octafluoro-4-(perfluorocyclopent-l-en-l-yl)morpholine (129 °C/740 mmHg, 141.3 g, 79% isolated yield) as a colorless liquid.
• 19F NMR analysis confirmed the isolated compound to be that of the desired 2,2,3,3,5,5,6,6-octafluoro-4-(perfluorocyclopent-l-en- l-yl)morpholine.
• the fluorous layer was analyzed by GC-FID and showed complete conversion of the 2,2,3,3,4,4,5-heptafluoropyrrole starting material.
• the fluorous phase was purified via single-plate distillation affording 2, 2, 3, 3, 4, 4,5,5- octafluoro-l-(perfluoropent-2-en-2-yl)pyrrolidine (125 °C/740 mmHg, 9.9 g, 18% isolated yield) as a colorless liquid.
• GC-MS analysis confirmed the isolated compound to be that of the desired 2,2,3 ,3 ,4,4,5 ,5 -octafluoro- 1 -(perfluoropent-2-en-2-yl)pyrrolidine .
• the lower phase was water washed, dried with magnesium sulphate and filtered to provide 300 grams of material which was purified by fractionation using at l5-tray vacuum jacketed Oldershaw column to provide 132.6 grams of 2,2,3,3,6,6-hexafluoro-5-[l,2,2,2-tetrafhioro-l-(trifhioromethyl)ethyl]-l,4-oxazine with a purity of >98.5% with a boiling point of about 80 °C
• the structure was confirmed by GC-MS and 19 F NMR analyses. The results indicate that addition of certain olefmic C-F bonds, such as
• Thermal stability was measured by charging 1.0 g of PE-l into glass vials and then adding a weighed amount of absorbent. The samples were stirred for 24 hours at 60 °C, allowed to cool, and then analyzed by GC-FID for decomposition and purity changes. The thermal stability testing results with various absorbents are shown in the Table 2.
• the atmospheric lifetime of PE-l was determined from its rate of reaction with hydroxyl radicals.
• the pseudo-first order rates for the reaction of gaseous PE-l with hydroxyl radical was measured in a series of experiments relative to reference compounds such as chloromethane and ethane. The measurements were performed in a 5.7 L, heated Fourier-transform infrared (FTIR) gas cell equipped with a polished semiconductor-grade quartz window.
• FTIR heated Fourier-transform infrared
• An ORIELInstruments UV Lamp, Model 66921 (Newport Corporation, Irvine, CA, USA) equipped with a 480W mercury-xenon bulb was used to generate hydroxyl radicals by photolyzing ozone in the presence of water vapor.
• the concentrations of PE-l and the reference compound were measured as a function of reaction time using an I-Series FTIR from Midac Corporation
• x x is the atmospheric lifetime of PE-l
• x r is the atmospheric lifetime of the reference compound
• k x and k r are the rate constants for the reaction of hydroxyl radical with the PE-l and the reference compound, respectively. It was found that the atmospheric lifetime of PE-l is 5.0 years.
• GWP Global warming potential
• IPCC Intergovernmental Panel on climate Change
• ITH 100 year integration time horizon
• the radiative efficiencies used in this calculation were based upon the infrared cross-sections measured on PE-l. It was found that PE-l has a GWP of 416. In comparison, for saturated perfluorocarbons, saturated perfluorocarbons typically have a GWP of greater than 5000.
• the dielectric constant (tested per ASTM D150-11) of PE-l was measured.
• the dielectric constant measured at 1 kHz was 1.98.
• the dielectric constant is comparable to FC-43 (1.9), FC-70 (1.98), and FC-71 (1.97).

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