WO2014022638A1 - 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 and uses thereof - Google Patents

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 and uses thereof Download PDF

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Publication number
WO2014022638A1
WO2014022638A1 PCT/US2013/053175 US2013053175W WO2014022638A1 WO 2014022638 A1 WO2014022638 A1 WO 2014022638A1 US 2013053175 W US2013053175 W US 2013053175W WO 2014022638 A1 WO2014022638 A1 WO 2014022638A1
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WO
WIPO (PCT)
Prior art keywords
azeotrope
azeotropic
composition
hfo
compositions
Prior art date
Application number
PCT/US2013/053175
Other languages
English (en)
French (fr)
Inventor
Mark L. Robin
Original Assignee
E. I. Du Pont De Nemours And Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E. I. Du Pont De Nemours And Company filed Critical E. I. Du Pont De Nemours And Company
Priority to BR112015002214A priority Critical patent/BR112015002214A2/pt
Priority to KR20157002169A priority patent/KR20150036220A/ko
Priority to EP13748428.3A priority patent/EP2880086A1/en
Priority to US14/410,578 priority patent/US20150191576A1/en
Priority to CN201380040342.XA priority patent/CN104508026A/zh
Priority to CA2879541A priority patent/CA2879541A1/en
Publication of WO2014022638A1 publication Critical patent/WO2014022638A1/en

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Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/16—Unsaturated hydrocarbons
    • C08J2203/162—Halogenated unsaturated hydrocarbons, e.g. H2C=CF2
    • C08J2203/164—Perhalogenated unsaturated hydrocarbons, e.g. F2C=CF2
    • 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.
  • 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
  • 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.
  • 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.
  • 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.
  • 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
  • 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 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)).
  • 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.
  • 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 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 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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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fireproofing Substances (AREA)
  • Detergent Compositions (AREA)
PCT/US2013/053175 2012-08-01 2013-08-01 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 and uses thereof WO2014022638A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BR112015002214A BR112015002214A2 (pt) 2012-08-01 2013-08-01 composição e processos de preparação de uma espuma termoplástica ou termofixa, de produção de refrigeração, de produção de um produto em aerosol e para extinção ou supressão de incêndio
KR20157002169A KR20150036220A (ko) 2012-08-01 2013-08-01 E-1,3,4,4,4-펜타플루오로-3-트라이플루오로메틸-1-부텐 및 z-1,1,1,4,4,4-헥사플루오로-2-부텐의 공비 및 공비-유사 조성물 및 그의 용도
EP13748428.3A EP2880086A1 (en) 2012-08-01 2013-08-01 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 and uses thereof
US14/410,578 US20150191576A1 (en) 2012-08-01 2013-08-01 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 and uses thereof
CN201380040342.XA CN104508026A (zh) 2012-08-01 2013-08-01 E-1,3,4,4,4-五氟-3-三氟甲基-1-丁烯和z-1,1,1,4,4,4-六氟-2-丁烯的共沸和类共沸组合物及它们的用途
CA2879541A CA2879541A1 (en) 2012-08-01 2013-08-01 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 and uses thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201261678260P 2012-08-01 2012-08-01
US61/678,260 2012-08-01

Publications (1)

Publication Number Publication Date
WO2014022638A1 true WO2014022638A1 (en) 2014-02-06

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PCT/US2013/053175 WO2014022638A1 (en) 2012-08-01 2013-08-01 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 and uses thereof

Country Status (6)

Country Link
EP (1) EP2880086A1 (pt)
KR (1) KR20150036220A (pt)
CN (1) CN104508026A (pt)
BR (1) BR112015002214A2 (pt)
CA (1) CA2879541A1 (pt)
WO (1) WO2014022638A1 (pt)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016025138A1 (en) * 2014-08-12 2016-02-18 The Chemours Company Fc, Llc Azeotropic and azeotrope-like compositions of hfo-e-1,3,4,4,4-pentafluoro-3-trifluoromethyl-1-butene and uses thereof
WO2016039944A1 (en) * 2014-09-12 2016-03-17 The Chemours Company Fc, Llc Use of e-1,3,4,4,4-pentafluoro-3-trifluoromethyl-1-butene in chillers

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080051612A1 (en) * 2006-08-24 2008-02-28 E. I. Dupont De Nemours And Company Processes for separation of fluoroolefins from hydrogen fluoride by azeotropic distillation
WO2008134061A2 (en) * 2007-04-27 2008-11-06 E. I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene
WO2009085857A2 (en) * 2007-12-19 2009-07-09 E. I. Du Pont De Nemours And Company Foam-forming compositions containing azeotropic or azeotrope-like mixtures containing z-1,1,1,4,4,4-hexafluoro-2-butene and their uses in the preparation of polyisocyanate-based foams

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080051612A1 (en) * 2006-08-24 2008-02-28 E. I. Dupont De Nemours And Company Processes for separation of fluoroolefins from hydrogen fluoride by azeotropic distillation
WO2008134061A2 (en) * 2007-04-27 2008-11-06 E. I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene
WO2009085857A2 (en) * 2007-12-19 2009-07-09 E. I. Du Pont De Nemours And Company Foam-forming compositions containing azeotropic or azeotrope-like mixtures containing z-1,1,1,4,4,4-hexafluoro-2-butene and their uses in the preparation of polyisocyanate-based foams

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016025138A1 (en) * 2014-08-12 2016-02-18 The Chemours Company Fc, Llc Azeotropic and azeotrope-like compositions of hfo-e-1,3,4,4,4-pentafluoro-3-trifluoromethyl-1-butene and uses thereof
CN107001919A (zh) * 2014-08-12 2017-08-01 科慕埃弗西有限公司 Hfo‑e‑1,3,4,4,4‑五氟‑3‑三氟甲基‑1‑丁烯的共沸组合物和类共沸组合物及它们的用途
US10188887B2 (en) 2014-08-12 2019-01-29 The Chemours Company Fc, Llc Azeotropic and azeotrope-like compositions of HFO-E-1,3,4,4,4-PENTAFLUORO-3-trifluoromethyl-1-butene and uses thereof
US10286242B2 (en) 2014-08-12 2019-05-14 The Chemours Company Fc, Llc Azeotropic and azeotrope-like compositions of HFO-E-1,3,4,4,4-pentafluoro-3-Trifluoromethyl-1-butene and uses thereof
US10434349B2 (en) 2014-08-12 2019-10-08 The Chemours Company Fc, Llc Azeotropic and azeotrope-like compositions of HFO-E-1,3,4,4,4-pentafluoro-3-trifluoromethyl-1-butene and uses thereof
EP3613824A1 (en) * 2014-08-12 2020-02-26 The Chemours Company FC, LLC Azeotropic and azeotrope-like compositions of hfo-e-1,3,4,4,4-pentafluoro-3-trifluoromethyl-1-butene and uses thereof
WO2016039944A1 (en) * 2014-09-12 2016-03-17 The Chemours Company Fc, Llc Use of e-1,3,4,4,4-pentafluoro-3-trifluoromethyl-1-butene in chillers

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CN104508026A (zh) 2015-04-08
CA2879541A1 (en) 2014-02-06
EP2880086A1 (en) 2015-06-10
KR20150036220A (ko) 2015-04-07
BR112015002214A2 (pt) 2017-07-04

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