CA2824423C - Producing heating using working fluids comprising z-1,1,1,4,4,4-hexafluoro-2-butene - Google Patents

Producing heating using working fluids comprising z-1,1,1,4,4,4-hexafluoro-2-butene Download PDF

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Publication number
CA2824423C
CA2824423C CA2824423A CA2824423A CA2824423C CA 2824423 C CA2824423 C CA 2824423C CA 2824423 A CA2824423 A CA 2824423A CA 2824423 A CA2824423 A CA 2824423A CA 2824423 C CA2824423 C CA 2824423C
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Canada
Prior art keywords
working fluid
condenser
heat pump
high temperature
hfc
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Application number
CA2824423A
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English (en)
French (fr)
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CA2824423A1 (en
Inventor
Konstantinos Kontomaris
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chemours Co FC LLC
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EI Du Pont de Nemours and Co
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Filing date
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Publication of CA2824423A1 publication Critical patent/CA2824423A1/en
Application granted granted Critical
Publication of CA2824423C publication Critical patent/CA2824423C/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
    • 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
    • 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
    • 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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B30/00—Heat pumps
    • F25B30/02—Heat pumps of the compression type
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25D—REFRIGERATORS; COLD ROOMS; ICE-BOXES; COOLING OR FREEZING APPARATUS NOT OTHERWISE PROVIDED FOR
    • F25D17/00—Arrangements for circulating cooling fluids; Arrangements for circulating gas, e.g. air, within refrigerated spaces
    • 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
    • C09K2205/122—Halogenated 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

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2824423A 2011-01-31 2012-01-31 Producing heating using working fluids comprising z-1,1,1,4,4,4-hexafluoro-2-butene Active CA2824423C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201161437964P 2011-01-31 2011-01-31
US61/437,964 2011-01-31
US201161525296P 2011-08-19 2011-08-19
US61/525,296 2011-08-19
PCT/US2012/023267 WO2012106305A1 (en) 2011-01-31 2012-01-31 Producing heating using working fluids comprising z 1,1,1,4,4,4-hexafluoro-2-butene

Publications (2)

Publication Number Publication Date
CA2824423A1 CA2824423A1 (en) 2012-08-09
CA2824423C true CA2824423C (en) 2017-03-21

Family

ID=45689002

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2824423A Active CA2824423C (en) 2011-01-31 2012-01-31 Producing heating using working fluids comprising z-1,1,1,4,4,4-hexafluoro-2-butene

Country Status (16)

Country Link
US (1) US9745496B2 (enExample)
EP (2) EP2670813B1 (enExample)
JP (1) JP6001561B2 (enExample)
KR (1) KR101914317B1 (enExample)
CN (1) CN103502380B (enExample)
AR (1) AR085045A1 (enExample)
AU (1) AU2012212450B2 (enExample)
BR (1) BR112013018849B1 (enExample)
CA (1) CA2824423C (enExample)
DK (1) DK3533853T3 (enExample)
ES (2) ES2873892T3 (enExample)
MX (1) MX355497B (enExample)
MY (1) MY168776A (enExample)
SG (1) SG192215A1 (enExample)
TW (1) TWI573971B (enExample)
WO (1) WO2012106305A1 (enExample)

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US8463441B2 (en) 2002-12-09 2013-06-11 Hudson Technologies, Inc. Method and apparatus for optimizing refrigeration systems
US9157018B2 (en) 2010-11-25 2015-10-13 Arkema France Compositions of chloro-trifluoropropene and hexafluorobutene
FR2968009B1 (fr) * 2010-11-25 2012-11-16 Arkema France Fluides frigorigenes contenant du (e)-1,1,1,4,4,4-hexafluorobut-2-ene
FR2968310B1 (fr) 2010-12-03 2012-12-07 Arkema France Compositions a base de 1,1,1,4,4,4-hexafluorobut-2-ene et de 3,3,4,4,4-pentafluorobut-1-ene
FR2977256B1 (fr) 2011-07-01 2013-06-21 Arkema France Compositions de 2,4,4,4-tetrafluorobut-1-ene et de cis-1,1,1,4,4,4-hexafluorobut-2-ene
FR2989084B1 (fr) 2012-04-04 2015-04-10 Arkema France Compositions a base de 2,3,3,4,4,4-hexafluorobut-1-ene
KR20150133769A (ko) * 2013-03-15 2015-11-30 허니웰 인터내셔널 인코포레이티드 냉동을 위한 조성물 및 방법
US9234123B2 (en) * 2013-03-21 2016-01-12 Hsi Fire & Safety Group, Llc Compositions for totally non-flammable aerosol dusters
DE102013211084A1 (de) * 2013-06-14 2014-12-18 Siemens Aktiengesellschaft Verfahren zum Betrieb einer Wärmepumpe und Wärmepumpe
MX394632B (es) 2014-02-07 2025-03-24 Chemours Co Fc Llc Proceso integrado para la produccion de z-1,1,1,4,4,4-hexafluoro-2-buteno.
CN106662369A (zh) * 2014-07-18 2017-05-10 科慕埃弗西有限公司 1,1,2,2‑四氟乙烷在高温热泵中的用途
EP3197976B1 (en) 2014-09-23 2020-12-09 The Chemours Company FC, LLC Use of (2e)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene in high temperature heat pumps
ES3022058T3 (en) * 2015-02-06 2025-05-28 Chemours Co Fc Llc Compositions comprising z-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof
US10513666B2 (en) * 2015-03-02 2019-12-24 Jxtg Nippon Oil & Energy Corporation Refrigerator oil and working fluid composition for refrigerators
CN115638554A (zh) * 2017-06-21 2023-01-24 霍尼韦尔国际公司 制冷系统和方法
CN107328128A (zh) * 2017-08-18 2017-11-07 广东高而美制冷设备有限公司 一种高温空调热泵系统及其工作方式
AU2019202101A1 (en) 2018-05-10 2019-11-28 Eavor Technologies Inc Fluid for use in power production environments
CN110964485B (zh) * 2019-11-18 2021-02-05 珠海格力电器股份有限公司 一种混合制冷剂
EP4511435A1 (en) * 2022-04-22 2025-02-26 The Chemours Company FC, LLC Compositions comprising tetrafluoropropene and hexafluorobutene
US20250066654A1 (en) * 2023-08-24 2025-02-27 Carbon Ventures, Llc Sterically hindered hydrofluoroolefins with dipole moment and their blends with sterically hindered-olefins as refrigerants for high temperature heat pumps and working fluid for organic rankine cycles
CN117588871A (zh) * 2023-12-20 2024-02-23 中天宽带技术有限公司 氟泵制冷压缩系统
KR102893236B1 (ko) * 2024-11-20 2025-12-03 주식회사 귀뚜라미 냉동기계 고온용 히트펌프용 R-245fa 및 R-1336mzz(Z)의 대체 혼합냉매 조성물
TWI918334B (zh) 2024-12-23 2026-03-11 承康研創股份有限公司 具有熱交換單元的電子設備

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GB1578933A (en) 1977-05-24 1980-11-12 Ici Ltd Manufacture of halogenated hydrocarbons
EP0127365A3 (en) * 1983-05-20 1988-03-16 Imperial Chemical Industries Plc Heat pumps
US6274781B1 (en) 1993-11-01 2001-08-14 E. I. Du Pont De Nemours And Company Production of dihalomethanes containing fluorine and azeotropes of dihalomethanes containing chlorine with HF
DE10056606A1 (de) * 2000-11-15 2002-05-23 Solvay Fluor & Derivate Verwendung von Gemischen,die 1,1,1,3,3-Pentafluorbutan enthalten, als Kältemittel oder Wärmerträger
US7897823B2 (en) 2004-10-29 2011-03-01 E. I. Du Pont De Nemours And Company Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes
JP2008531975A (ja) * 2005-03-04 2008-08-14 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー エンジン排ガス駆動タービンを動力源とする冷凍／空気調節装置
US7708903B2 (en) * 2005-11-01 2010-05-04 E.I. Du Pont De Nemours And Company Compositions comprising fluoroolefins and uses thereof
FR2894014B1 (fr) * 2005-11-30 2008-02-22 Gerard Llurens Unite solaire de production frigorifique pour installation de climatisation et procede de controle correspondant
US8618339B2 (en) 2007-04-26 2013-12-31 E I Du Pont De Nemours And Company High selectivity process to make dihydrofluoroalkenes
KR102171637B1 (ko) 2007-04-27 2020-10-29 더 케무어스 컴퍼니 에프씨, 엘엘씨 Ｚ-1,1,1,4,4,4-헥사플루오로-2-부텐의 공비 및 공비-유사 조성물
US8024937B2 (en) * 2007-06-21 2011-09-27 E. I. Du Pont De Nemours And Company Method for leak detection in heat transfer systems
US20110094259A1 (en) * 2007-10-10 2011-04-28 Alexander Lifson Multi-stage refrigerant system with different compressor types
TW200930801A (en) * 2007-10-31 2009-07-16 Du Pont Compositions comprising iodotrifluoromethane and uses thereof
KR20160040314A (ko) 2008-06-20 2016-04-12 이 아이 듀폰 디 네모아 앤드 캄파니 Ｚ-1,1,1,4,4,4-헥사플루오로-2-부텐의 공비 및 공비-유사 조성물
BRPI0910129A2 (pt) 2008-07-08 2015-12-29 Du Pont composição, processo, processo para a produção de resfriamento, processo para transferir calor, aparelho de sistema de ciclo de absorção e sistema
FR2948678B1 (fr) * 2009-07-28 2011-10-14 Arkema France Procede de transfert de chaleur
CN102695772B (zh) * 2009-09-16 2015-09-16 纳幕尔杜邦公司 装有反式-1,1,1,4,4,4-六氟-2-丁烯的冷却器设备以及在其中制冷的方法
MY160233A (en) 2009-09-16 2017-02-28 Du Pont Composition comprising cis-1,1,1,4,4,4-hexafluoro-2-butene and trans-1,2-dichloroethylene, apparatus containing same and methods of producing cooling therein
US20110144216A1 (en) * 2009-12-16 2011-06-16 Honeywell International Inc. Compositions and uses of cis-1,1,1,4,4,4-hexafluoro-2-butene

Also Published As

Publication number Publication date
US9745496B2 (en) 2017-08-29
AR085045A1 (es) 2013-08-07
JP6001561B2 (ja) 2016-10-05
BR112013018849A2 (pt) 2016-09-27
JP2014505228A (ja) 2014-02-27
KR101914317B1 (ko) 2018-11-01
CA2824423A1 (en) 2012-08-09
EP2670813A1 (en) 2013-12-11
ES2873892T3 (es) 2021-11-04
EP2670813B1 (en) 2019-04-24
CN103502380A (zh) 2014-01-08
US20130298581A1 (en) 2013-11-14
MX355497B (es) 2018-04-20
KR20140015352A (ko) 2014-02-06
MX2013008695A (es) 2013-08-21
AU2012212450A1 (en) 2013-07-18
EP3533853A1 (en) 2019-09-04
CN103502380B (zh) 2016-02-17
EP3533853B1 (en) 2021-03-10
AU2012212450A2 (en) 2013-08-01
BR112013018849B1 (pt) 2021-01-12
TW201233965A (en) 2012-08-16
ES2734475T3 (es) 2019-12-10
MY168776A (en) 2018-12-04
SG192215A1 (en) 2013-09-30
WO2012106305A1 (en) 2012-08-09
TWI573971B (zh) 2017-03-11
DK3533853T3 (da) 2021-06-07
AU2012212450B2 (en) 2015-12-17

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