Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
  • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
  • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
  • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
  • C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
  • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
  • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
  • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
  • C08J9/143—Halogen containing compounds
  • C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
  • C08J9/146—Halogen containing compounds containing carbon, halogen and hydrogen only only fluorine as halogen atoms
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K3/00—Materials not provided for elsewhere
  • C09K3/30—Materials not provided for elsewhere for aerosols
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
  • C09K5/02—Materials undergoing a change of physical state when used
  • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
  • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
  • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
  • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5036—Azeotropic mixtures containing halogenated solvents
  • C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
  • C11D7/505—Mixtures of (hydro)fluorocarbons
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5036—Azeotropic mixtures containing halogenated solvents
  • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
  • C11D7/5072—Mixtures of only hydrocarbons
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
  • C09K2205/10—Components
  • C09K2205/12—Hydrocarbons
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
  • C09K2205/10—Components
  • C09K2205/12—Hydrocarbons
  • C09K2205/126—Unsaturated fluorinated hydrocarbons
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
  • C09K2205/22—All components of a mixture being fluoro compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
  • C09K2205/32—The mixture being azeotropic

Definitions

• the present disclosure relates to azeotropic and azeotrope-like compositions of E-1 ,3,4,4,4-pentafluoro-3-trifluoromethyl-1 -butene and Z- 1 ,1 ,1 ,4,4,4-hexafluoro-2-butene.
• CFCs chlorofluorocarbons
• HCFCs hydrochlorofluorocarbons
• HFCs hydrofluorocarbons
• the HFCs do not contribute to the destruction of stratospheric ozone, but are of concern due to their contribution to the "greenhouse effect", i.e., they contribute to global warming. As a result of their contribution to global warming, the HFCs have come under scrutiny, and their widespread use may also be limited in the future. Thus, there is a need for compositions that do not contribute to the destruction of stratospheric ozone and also have low global warming potentials (GWPs).
• GWPs global warming potentials
• composition consisting essentially of (a) E-HFO-1438ezy and a second component present in an effective amount to form an azeotrope or azeotrope like mixture.
• the second component includes Z-HFO-1336mzz or cyclopentane.
• FIG. 1 - FIG. 1 is a graphical representation of an azeotropic composition of E-HFO-1438ezy and Z-HFO-1336mzz at a temperature of about 25 °C.
• FIG. 2 - FIG. 2 is a graphical representation of an azeotropic composition of E-HFO-1438ezy and cyclopentane at a temperature of about 25.0 °C.
• a pure single component or an azeotropic or azeotrope-like mixture is desirable.
• a blowing agent composition also known as foam expansion agents or foam expansion compositions
• the composition may change during its application in the foam forming process. Such change in composition could detrimentally affect processing or cause poor performance in the application.
• a refrigerant is often lost during operation through leaks in shaft seals, hose connections, soldered joints and broken lines. In addition, the refrigerant may be released to the atmosphere during maintenance procedures on refrigeration equipment.
• the refrigerant composition may change when leaked or discharged to the atmosphere from the refrigeration equipment.
• the change in refrigerant composition may cause the refrigerant to become flammable or to have poor refrigeration performance.
• HFO-1438ezy may exist as one of two configurational isomers, E or
• HFO-1438ezy refers to the isomers, Z-HFO-1438ezy or E-HFO-1438ezy, as well as any combinations or mixtures of such isomers.
• HFO-1336mzz may exist as one of two configurational isomers, E or Z.
• HFO-1336mzz as used herein refers to the isomers, Z-HFO- 1336mzz or E-HFO-1336mzz, as well as any combinations or mixtures of such isomers.
• the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
• a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
• “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
• Z-HFO-1336mzz is a known compound, and can be made by the selective hydrogenation of hexafluoro-2-butyne with a Lindlar catalyst and hydrogen, such as disclosed in U.S. Patent Publication No. 2008- 0269532.
• compositions consisting essentially of (a) E-HFO-1438ezy and (b) Z-HFO-1336mzz; wherein the Z-HFO-1336mzz is present in an effective amount to form an azeotropic or azeotrope-like mixture with E-HFO-1438ezy.
• effective amount is meant an amount of Z-HFO-1336mzz, which, when combined with E-HFO-1438ezy, results in the formation of an azeotropic or azeotrope-like mixture.
• effective amount an amount of cyclopentane, which, when combined with E-HFO-1438ezy, results in the formation of an azeotropic or azeotrope-like mixture.
• This definition includes the amounts of each component, which amounts may vary depending on the pressure applied to the composition so long as the azeotropic or azeotrope-like compositions continue to exist at the different pressures, but with possible different boiling points.
• effective amount includes the amounts, such as may be expressed in weight or mole percentages, of each component of the compositions of the instant invention which form azeotropic or azeotrope- like compositions at temperatures or pressures other than as described herein.
• an azeotropic composition is an admixture of two or more different components which, when in liquid form under a given pressure, will boil at a substantially constant temperature, which temperature may be higher or lower than the boiling temperatures of the individual components, and which will provide a vapor composition essentially identical to the overall liquid composition undergoing boiling, (see, e.g., M. F. Doherty and M.F. Malone, Conceptual Design of
• an azeotropic composition is that at a given pressure, the boiling point of the liquid composition is fixed and that the composition of the vapor above the boiling composition is essentially that of the overall boiling liquid composition (i.e., no
• an azeotropic composition may be defined in terms of the unique relationship that exists among the components or in terms of the compositional ranges of the components or in terms of exact weight percentages of each component of the composition characterized by a fixed boiling point at a specified pressure.
• an azeotrope-like composition means a composition that behaves like an azeotropic composition (i.e., has constant boiling characteristics or a tendency not to fractionate upon boiling or evaporation). Hence, during boiling or evaporation, the vapor and liquid compositions, if they change at all, change only to a minimal or negligible extent. This is to be contrasted with non-azeotrope-like compositions in which during boiling or evaporation, the vapor and liquid compositions change to a substantial degree.
• compositions with a difference in dew point pressure and bubble point pressure of less than or equal to 5 percent (based upon the bubble point pressure) is considered to be azeotrope-like.
• Relative volatility is the ratio of the volatility of component 1 to the volatility of component 2.
• the ratio of the mole fraction of a component in vapor to that in liquid is the volatility of the component.
• FIG. 1 The pressures measured versus the compositions in the PTx cell for E-HFO-1438ezy/Z-HFO-1336mzz mixtures are shown in FIG. 1 , which graphically illustrates the formation of an azeotropic composition consisting essentially of E-HFO-1438ezy and Z-HFO-1336mzz as indicated by a mixture of about 63.7 mole % E-HFO-1438ezy and about 36.3 mole % Z-HFO-1336mzz having the highest pressure over the range of compositions at about 25 °C.
• E-HFO-1438ezy and Z-HFO-1336mzz form azeotropic compositions ranging from about 64.0 mole percent to about 61 .3 mole percent E-HFO-1438ezy and from about 36.0 mole percent to about 38.7 mole percent Z-HFO-1336mzz (which form azeotropic compositions boiling at a temperature of from about -50 °C to about 140 °C and at a pressure of from about 0.2 psia (1 .4 kPa) to about 261 psia (1799 kPa)).
• the azeotropic composition consists essentially of about 63.7 mole % E-HFO-1438ezy and about 36.3 mole % Z-HFO-1336mzz.
• the azeotropic composition consists essentially of about 63.8 mole % E-HFO- 1438ezy and about 36.2 mole % Z-HFO-1336mzz.
• azeotrope-like compositions containing E-HFO- 1438ezy and Z-HFO-1336mzz may also be formed.
• an azeotrope-like composition consists essentially of 1 -99 mole % E-HFO-1438ezy and 99-1 mole % Z-HFO-1336mzz at a
• an azeotrope-like composition consists essentially of 5-95 mole % E-HFO-1438ezy and 95-5 mole % Z-HFO- 1336mzz at a temperature ranging from about -40 °C to about 140 °C (i.e., over this temperature range, the difference in dew point pressure and bubble point pressure of the composition at a particular temperature is less than or equal to 5 percent (based upon the bubble point pressure)).
• Such azeotrope-like compositions exist around azeotropic compositions. Some embodiments of azeotrope-like compositions are listed in Table 2. Additional embodiments of azeotrope-like compositions are listed in Table 3.
• the azeotropic or azeotrope-like compositions of the present invention can be prepared by any convenient method including mixing or combining the desired amounts.
• an azeotropic or azeotrope-like composition can be prepared by weighing the desired component amounts and thereafter combining them in an appropriate container.
• azeotropic or azeotrope-like compositions of the present invention can be used in a wide range of applications, including their use as aerosol propellants, refrigerants, solvents, cleaning agents, blowing agents (foam expansion agents) for thermoplastic and thermoset foams, heat transfer media, gaseous dielectrics, fire extinguishing and
• thermoplastic or thermoset foam provides a process for preparing a thermoplastic or thermoset foam.
• the process comprises using an azeotropic or azeotrope-like composition as a blowing agent, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO- 1438ezy and Z-HFO-1336mzz.
• thermoplastic foams this process includes mixing the blowing agent with a liquid resin under elevatged temperatures and pressures, and extruding the resin to form the foam.
• thermoset foams this process includes mixing the blowing agent with a polyol, and mixing the polyol with an isocyanate to form the foam
• Another embodiment of this invention provides a process for producing refrigeration.
• the process comprises condensing an azeotropic or azeotrope-like composition and thereafter evaporating said azeotropic or azeotrope-like composition in the vicinity of the body to be cooled, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO-1438ezy and Z-HFO-1336mzz.
• Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as a solvent, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO- 1438ezy and Z-HFO-1336mzz.
• This process includes the step of contacting the composition to a surface to be cleaned and then removing the composition or removing the surface.
• Another embodiment of this invention provides a process for producing an aerosol product.
• the process comprises using an azeotropic or azeotrope-like composition as a propellant, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO-1438ezy and Z- HFO-1336mzz.
• Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as a heat transfer media, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO-1438ezy and Z-HFO-1336mzz.
• Another embodiment of this invention provides a process for extinguishing or suppressing a fire.
• the process comprises using an azeotropic or azeotrope-like composition as a fire extinguishing or suppression agent, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO-1438ezy and Z-HFO-1336mzz.
• the process includes detecting a fire or incipient ignition, and delivering a sufficient amount of the composition to the fire or incipient ignition to reach an extinguishing concentration that suppresses or extinguishes the fire.
• Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as dielectrics, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO- 1438ezy and Z-HFO-1336mzz.
• FIG. 1 The pressures measured versus the compositions in the PTx cell for E-HFO-1438ezy/cyclopentane mixtures are shown in FIG. 1 , which graphically illustrates the formation of an azeotropic composition consisting essentially of E-HFO-1438ezy and cyclopentane as indicated by a mixture of about 67.7 mole % E-HFO-1438ezy and about 32.3 mole % cyclopentane having the highest pressure over the range of
• E-HFO-1438ezy and cyclopentane form azeotropic compositions ranging from about 66.8 mole percent to about 95.2 mole percent E-HFO-1438ezy and from about 33.2 mole percent to about 4.8 mole percent cyclopentane (which form azeotropic compositions boiling at a temperature of from about -50 °C to about 140 °C and at a pressure of from about 0.2 psia (1 .4 kPa) to about 250 psia (1724 kPa)).
• the azeotropic composition consists essentially of about 67.7 mole % E-HFO-1438ezy and about 32.3 mole % cyclopentane.
• the azeotropic composition consists essentially of about 67.9 mole % E-HFO-1438ezy and about 32.1 mole % cyclopentane.
• an azeotrope-like composition consists essentially of 99-48 mole % E-HFO-1438ezy and 1 -52 mole % cyclopentane at a temperature ranging from about -40 °C to about 140 °C (i.e., over this temperature range, the difference in dew point pressure and bubble point pressure of the composition at a particular temperature is less than or equal to 5 percent (based upon the bubble point pressure)).
• an azeotrope-like composition consists essentially of 1 -4 mole % E-HFO-1438ezy and 99-96 mole % cyclopentane at a temperature ranging from about 120 °C to about 140 °C (i.e., over this temperature range, the difference in dew point pressure and bubble point pressure of the composition at a particular temperature is less than or equal to 5 percent (based upon the bubble point pressure)).
• an azeotrope-like composition consists essentially of 48-95 mole % E-HFO-1438ezy and 52-5 mole % cyclopentane at a temperature ranging from about -40 °C to about 140 °C (i.e., over this temperature range, the difference in dew point pressure and bubble point pressure of the composition at a particular temperature is less than or equal to 5 percent (based upon the bubble point pressure)).
• Such azeotrope-like compositions exist around azeotropic compositions. Some embodiments of azeotrope-like compositions are listed in Table 2. Additional embodiments of azeotrope-like compositions are listed in Table 3.
• the azeotropic or azeotrope-like compositions of the present invention can be prepared by any convenient method including mixing or combining the desired amounts.
• an azeotropic or azeotrope-like composition can be prepared by weighing the desired component amounts and thereafter combining them in an appropriate container.
• azeotropic or azeotrope-like compositions of the present invention can be used in a wide range of applications, including their use as aerosol propellants, refrigerants, solvents, cleaning agents, blowing agents (foam expansion agents) for thermoplastic and thermoset foams, heat transfer media, gaseous dielectrics, fire extinguishing and
• thermoplastic or thermoset foam provides a process for preparing a thermoplastic or thermoset foam.
• the process comprises using an azeotropic or azeotrope-like composition as a blowing agent, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO- 1438ezy and cyclopentane.
• this process includes mixing the blowing agent with a liquid resin under elevatged temperatures and pressures, and extruding the resin to form the foam.
• thermoset foams this process includes mixing the blowing agent with a polyol, and mixing the polyol with an isocyanate to form the foam
• Another embodiment of this invention provides a process for producing refrigeration.
• the process comprises condensing an azeotropic or azeotrope-like composition and thereafter evaporating said azeotropic or azeotrope-like composition in the vicinity of the body to be cooled, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO-1438ezy and cyclopentane.
• Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as a solvent, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO- 1438ezy and cyclopentane.
• This process includes the step of contacting the composition to a surface to be cleaned and then removing the composition or removing the surface.
• Another embodiment of this invention provides a process for producing an aerosol product.
• the process comprises using an azeotropic or azeotrope-like composition as a propellant, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO-1438ezy and cyclopentane.
• Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as a heat transfer media, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO-1438ezy and cyclopentane.
• Another embodiment of this invention provides a process for extinguishing or suppressing a fire.
• the process comprises using an azeotropic or azeotrope-like composition as a fire extinguishing or suppression agent, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO-1438ezy and cyclopentane.
• Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as dielectrics, wherein said azeotropic or azeotrope-like composition consists essentially of E-HFO- 1438ezy and cyclopentane.

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  • 2013-08-01 EP EP13748428.3A patent/EP2880086A1/de not_active Withdrawn
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  • 2013-08-01 CN CN201380040342.XA patent/CN104508026A/zh active Pending
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