CA2745762C - Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids - Google Patents

Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids Download PDF

Info

Publication number
CA2745762C
CA2745762C CA2745762A CA2745762A CA2745762C CA 2745762 C CA2745762 C CA 2745762C CA 2745762 A CA2745762 A CA 2745762A CA 2745762 A CA2745762 A CA 2745762A CA 2745762 C CA2745762 C CA 2745762C
Authority
CA
Canada
Prior art keywords
working fluid
rankine cycle
chloro
trifluoropropene
heat source
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CA2745762A
Other languages
English (en)
French (fr)
Other versions
CA2745762A1 (en
Inventor
Gary Zyhowski
Ryan Hulse
Haridasan K. Nair
David Nalewajek
Rajiv R. Singh
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.)
Honeywell International Inc
Original Assignee
Honeywell International Inc
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
Priority claimed from US12/351,807 external-priority patent/US9499729B2/en
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Publication of CA2745762A1 publication Critical patent/CA2745762A1/en
Application granted granted Critical
Publication of CA2745762C publication Critical patent/CA2745762C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • C09K5/048—Boiling liquids as heat transfer materials
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/14—Acyclic saturated compounds containing halogen atoms containing fluorine and bromine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • 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
    • F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
    • F01K—STEAM ENGINE PLANTS; STEAM ACCUMULATORS; ENGINE PLANTS NOT OTHERWISE PROVIDED FOR; ENGINES USING SPECIAL WORKING FLUIDS OR CYCLES
    • F01K23/00—Plants characterised by more than one engine delivering power external to the plant, the engines being driven by different fluids
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
    • F01K—STEAM ENGINE PLANTS; STEAM ACCUMULATORS; ENGINE PLANTS NOT OTHERWISE PROVIDED FOR; ENGINES USING SPECIAL WORKING FLUIDS OR CYCLES
    • F01K25/00—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
    • F01K—STEAM ENGINE PLANTS; STEAM ACCUMULATORS; ENGINE PLANTS NOT OTHERWISE PROVIDED FOR; ENGINES USING SPECIAL WORKING FLUIDS OR CYCLES
    • F01K25/00—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for
    • F01K25/06—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for using mixtures of different fluids
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F01—MACHINES OR ENGINES IN GENERAL; ENGINE PLANTS IN GENERAL; STEAM ENGINES
    • F01K—STEAM ENGINE PLANTS; STEAM ACCUMULATORS; ENGINE PLANTS NOT OTHERWISE PROVIDED FOR; ENGINES USING SPECIAL WORKING FLUIDS OR CYCLES
    • F01K25/00—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for
    • F01K25/08—Plants or engines characterised by use of special working fluids, not otherwise provided for; Plants operating in closed cycles and not otherwise provided for using special vapours
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • 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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/40—Solar thermal energy, e.g. solar towers
    • Y02E10/46—Conversion of thermal power into mechanical power, e.g. Rankine, Stirling or solar thermal engines
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E20/00—Combustion technologies with mitigation potential
    • Y02E20/14—Combined heat and power generation [CHP]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Engine Equipment That Uses Special Cycles (AREA)
CA2745762A 2008-12-05 2009-12-04 Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids Active CA2745762C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US12012508P 2008-12-05 2008-12-05
US61/120,125 2008-12-05
US12/351,807 2009-01-09
US12/351,807 US9499729B2 (en) 2006-06-26 2009-01-09 Compositions and methods containing fluorine substituted olefins
US12/630,647 US8820079B2 (en) 2008-12-05 2009-12-03 Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids
US12/630,647 2009-12-03
PCT/US2009/066828 WO2010065895A1 (en) 2008-12-05 2009-12-04 Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids

Publications (2)

Publication Number Publication Date
CA2745762A1 CA2745762A1 (en) 2010-06-10
CA2745762C true CA2745762C (en) 2018-02-27

Family

ID=42229534

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2745762A Active CA2745762C (en) 2008-12-05 2009-12-04 Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids

Country Status (13)

Country Link
US (2) US8820079B2 (enExample)
EP (2) EP2364340B1 (enExample)
JP (4) JP2012511087A (enExample)
KR (2) KR101891798B1 (enExample)
CN (2) CN102307965B (enExample)
CA (1) CA2745762C (enExample)
DK (1) DK2364340T3 (enExample)
ES (1) ES2739674T3 (enExample)
HR (1) HRP20191125T1 (enExample)
IL (1) IL213366A0 (enExample)
MX (1) MX2011005880A (enExample)
WO (1) WO2010065895A1 (enExample)
ZA (1) ZA201104157B (enExample)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130091843A1 (en) * 2008-12-05 2013-04-18 Honeywell International Inc. Fluoro olefin compounds useful as organic rankine cycle working fluids
FR2948679B1 (fr) * 2009-07-28 2011-08-19 Arkema France Procede de transfert de chaleur
EP2609303B1 (en) * 2010-08-26 2023-08-09 Michael Joseph Timlin III The timlin cycle- a binary condensing thermal power cycle
US9157018B2 (en) * 2010-11-25 2015-10-13 Arkema France Compositions of chloro-trifluoropropene and hexafluorobutene
US8378158B2 (en) * 2010-12-03 2013-02-19 Honeywell International Inc. Azeotrope-like compositions of (Z)-1-chloro-3,3,3-trifluoropropene and hydrogen fluoride
JP2014514488A (ja) 2011-03-25 2014-06-19 スリーエム イノベイティブ プロパティズ カンパニー 有機ランキンサイクル作動流体としてのフッ素化オキシラン及びその使用方法
KR101951618B1 (ko) * 2011-05-19 2019-02-25 알케마 인코포레이티드 클로로-트리플루오로프로펜의 불연성 조성물
CA2778101A1 (en) * 2012-05-24 2013-11-24 Jean Pierre Hofman Power generation by pressure differential
US20140260252A1 (en) * 2013-03-15 2014-09-18 Honeywell International Inc. Stabilized hfo and hcfo compositions for use in high temperature heat transfer applications
JP6213194B2 (ja) * 2013-11-29 2017-10-18 セントラル硝子株式会社 熱エネルギーを機械エネルギーへ変換する方法、有機ランキンサイクル装置、及び作動流体を置換える方法
US9957428B2 (en) 2013-12-20 2018-05-01 3M Innovative Properties Company Fluorinated olefins as working fluids and methods of using same
JP5983671B2 (ja) * 2014-03-31 2016-09-06 ダイキン工業株式会社 １−クロロ−３，３，３−トリフルオロプロペン及び１，１，１，３，３−ペンタフルオロプロパンを含有する共沸乃至共沸様組成物
US10302335B2 (en) * 2014-06-10 2019-05-28 Lg Chem, Ltd. Heat recovery apparatus
US10030185B2 (en) 2014-07-16 2018-07-24 3M Innovative Properties Company Hydrofluoroether olefins and methods of using same
EP3197945B1 (en) 2014-09-23 2020-10-21 3M Innovative Properties Company Nitrogen containing hydrofluoroethers and methods of using same
CN107614559B (zh) 2015-06-05 2020-08-04 3M创新有限公司 氢氟烯烃及其使用方法
US10738001B2 (en) 2015-06-05 2020-08-11 3M Innovative Properties Company Hydrofluoroolefins and methods of using same
US10093601B2 (en) 2015-06-29 2018-10-09 The Boeing Company Fire retardant compounds
JP6699112B2 (ja) * 2015-08-28 2020-05-27 Ａｇｃ株式会社 溶剤組成物
CN108290823B (zh) 2015-12-02 2021-01-22 3M创新有限公司 烯丙基封端的不饱和氢氟胺和烯丙基封端的不饱和氢氟醚化合物以及其使用方法
WO2017165225A1 (en) * 2016-03-24 2017-09-28 The Chemours Company Fc, Llc AZEOTROPIC AND AZEOTROPE-LIKE COMPOSITIONS OF Z-1233zd
KR102374272B1 (ko) 2016-05-09 2022-03-15 쓰리엠 이노베이티브 프로퍼티즈 컴파니 하이드로플루오로올레핀 및 이의 사용 방법
WO2018039096A1 (en) 2016-08-22 2018-03-01 3M Innovative Properties Company Propenylamines and methods of making and using same
WO2018044613A1 (en) 2016-08-29 2018-03-08 3M Innovative Properties Company Nitrogen and dioxolane-containing hydrofluoroethers and methods of using the same
JP7043489B2 (ja) 2016-09-26 2022-03-29 スリーエム イノベイティブ プロパティズ カンパニー 窒素及び／又は酸素含有ヒドロフルオロオレフィン、並びにその製造方法及び使用方法
WO2018116159A1 (en) 2016-12-21 2018-06-28 3M Innovative Properties Company Hydrofluoroolefins and methods of using same
JP6693916B2 (ja) * 2017-07-14 2020-05-13 株式会社ニューギン 遊技機
WO2019067113A1 (en) 2017-09-28 2019-04-04 3M Innovative Properties Company HYDROFLUOROCABOXIMIDATE, METHODS OF MAKING AND USING THE SAME
JP6941076B2 (ja) * 2018-06-05 2021-09-29 株式会社神戸製鋼所 発電方法
WO2020065492A1 (en) 2018-09-26 2020-04-02 3M Innovative Properties Company Hydrofluoroethers and methods of using same
WO2021237013A1 (en) * 2020-05-21 2021-11-25 Johnson Ip Holding, Llc Halogen-based thermo-electrochemical converter
US11255315B1 (en) 2021-04-02 2022-02-22 Ice Thermal Harvesting, Llc Controller for controlling generation of geothermal power in an organic Rankine cycle operation during hydrocarbon production
US11326550B1 (en) 2021-04-02 2022-05-10 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11486370B2 (en) 2021-04-02 2022-11-01 Ice Thermal Harvesting, Llc Modular mobile heat generation unit for generation of geothermal power in organic Rankine cycle operations
US12312981B2 (en) 2021-04-02 2025-05-27 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11421663B1 (en) 2021-04-02 2022-08-23 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power in an organic Rankine cycle operation
US11493029B2 (en) 2021-04-02 2022-11-08 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11293414B1 (en) 2021-04-02 2022-04-05 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power in an organic rankine cycle operation
US11644015B2 (en) 2021-04-02 2023-05-09 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11480074B1 (en) 2021-04-02 2022-10-25 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11592009B2 (en) 2021-04-02 2023-02-28 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
WO2023281421A1 (en) 2021-07-07 2023-01-12 3M Innovative Properties Company Hydrofluoroolefins and uses thereof
WO2023002341A1 (en) 2021-07-20 2023-01-26 3M Innovative Properties Company Hydrofluoroolefins and uses thereof
US12534990B2 (en) 2022-12-29 2026-01-27 Ice Thermal Harvesting, Llc Power generation assemblies for hydraulic fracturing systems and methods
US12180861B1 (en) 2022-12-30 2024-12-31 Ice Thermal Harvesting, Llc Systems and methods to utilize heat carriers in conversion of thermal energy

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4760705A (en) 1983-05-31 1988-08-02 Ormat Turbines Ltd. Rankine cycle power plant with improved organic working fluid
ES2102759T3 (es) 1990-07-26 1997-08-01 Du Pont Mezclas casi azeotropicas para uso como refrigerantes.
JPH04110388A (ja) 1990-08-31 1992-04-10 Daikin Ind Ltd 熱伝達用流体
US5611210A (en) 1993-03-05 1997-03-18 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
DE69409813T2 (de) 1993-08-09 1999-01-07 Livien Domien Antwerpen Ven Dampfkraftmaschine
DE69506550D1 (de) 1994-07-14 1999-01-21 Du Pont Kühlzusammensetzungen
AU4052097A (en) * 1996-08-14 1998-03-06 Allied-Signal Inc. Pentafluoropropanes and hexafluoropropanes as working fluids for power generation
US5710352A (en) * 1996-09-19 1998-01-20 Alliedsignal Inc. Vapor phase process for making 1,1,1,3,3-pentafluoropropane and 1-chloro-3,3,3-trifluoropropene
US6013846A (en) * 1998-03-05 2000-01-11 Elf Atochem North America, Inc. Azeotrope of HF and 1233zd
US6035643A (en) * 1998-12-03 2000-03-14 Rosenblatt; Joel H. Ambient temperature sensitive heat engine cycle
US6176102B1 (en) 1998-12-30 2001-01-23 Praxair Technology, Inc. Method for providing refrigeration
US6374629B1 (en) 1999-01-25 2002-04-23 The Lubrizol Corporation Lubricant refrigerant composition for hydrofluorocarbon (HFC) refrigerants
US6783691B1 (en) 1999-03-22 2004-08-31 E.I. Du Pont De Nemours And Company Compositions of difluoromethane, pentafluoroethane, 1,1,1,2-tetrafluoroethane and hydrocarbons
US6589355B1 (en) 1999-10-29 2003-07-08 Alliedsignal Inc. Cleaning processes using hydrofluorocarbon and/or hydrochlorofluorocarbon compounds
AU2001275932A1 (en) 2000-07-17 2002-01-30 Honeywell International Inc. Supported catalyst systems
US6516837B2 (en) 2000-09-27 2003-02-11 Honeywell International Inc. Method of introducing refrigerants into refrigeration systems
US6991744B2 (en) 2000-12-08 2006-01-31 E. I. Du Pont De Nemours And Company Refrigerant compositions containing a compatibilizer
US6551469B1 (en) * 2001-11-27 2003-04-22 Honeywell International Photochlorination of 1,1,1,3,3-pentafluoropropane
US9005467B2 (en) * 2003-10-27 2015-04-14 Honeywell International Inc. Methods of replacing heat transfer fluids
US20040089839A1 (en) 2002-10-25 2004-05-13 Honeywell International, Inc. Fluorinated alkene refrigerant compositions
PT2277972T (pt) 2002-10-25 2019-06-11 Honeywell Int Inc Composições contendo olefinas substituídas por flúor
US6844475B1 (en) * 2003-08-08 2005-01-18 Honeywell International Business Machines Low temperature production of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd)
US9499729B2 (en) 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US7428816B2 (en) * 2004-07-16 2008-09-30 Honeywell International Inc. Working fluids for thermal energy conversion of waste heat from fuel cells using Rankine cycle systems
EP1846534B1 (en) * 2004-12-21 2011-07-06 Honeywell International Inc. Stabilized iodocarbon compositions
US20060266976A1 (en) 2005-05-27 2006-11-30 Minor Barbara H Compositions comprising bromofluoro-olefins and uses thereof
KR20090027771A (ko) * 2006-07-12 2009-03-17 솔베이 플루오르 게엠베하 플루오로에테르 화합물을 이용한 가열 및 냉각 방법, 이에 적당한 조성물 및 그들의 용도
US20080157023A1 (en) * 2006-11-14 2008-07-03 Samuels George J Fluorocarbon stabilizers
WO2008065011A1 (en) * 2006-11-29 2008-06-05 Solvay Fluor Gmbh Compositions comprising unsaturated hydrofluorocarbon compounds, and methods for heating and cooling using the compositions
WO2008121783A1 (en) * 2007-03-29 2008-10-09 Arkema Inc. Blowing agent composition of hydrochlorofluoroolefin
US7438826B1 (en) * 2008-03-07 2008-10-21 Arkema Inc. Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and methyl acetate
US7442321B1 (en) * 2008-03-07 2008-10-28 Arkema Inc. Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and trans-1,2-dichloroethylene
US7438825B1 (en) * 2008-03-07 2008-10-21 Arkema Inc. Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and dimethoxymethane
ES2727525T3 (es) * 2008-03-07 2019-10-16 Arkema Inc Composiciones de transferencia térmica de alqueno halogenado con retorno de aceite mejorado
US9994751B2 (en) * 2008-04-30 2018-06-12 Honeywell International Inc. Absorption refrigeration cycles using a LGWP refrigerant
FR2937906B1 (fr) 2008-11-03 2010-11-19 Arkema France Procede de chauffage et/ou climatisation d'un vehicule.
FR2948679B1 (fr) 2009-07-28 2011-08-19 Arkema France Procede de transfert de chaleur

Also Published As

Publication number Publication date
ZA201104157B (en) 2012-09-26
JP2018204015A (ja) 2018-12-27
EP2364340B1 (en) 2019-03-20
CA2745762A1 (en) 2010-06-10
JP6100827B2 (ja) 2017-03-22
JP6637551B2 (ja) 2020-01-29
KR101744878B1 (ko) 2017-06-08
CN105462562A (zh) 2016-04-06
JP2012511087A (ja) 2012-05-17
CN105462562B (zh) 2020-03-10
KR20170066683A (ko) 2017-06-14
EP2364340A1 (en) 2011-09-14
CN102307965B (zh) 2016-01-06
EP2364340A4 (en) 2011-09-14
HRP20191125T1 (hr) 2019-09-20
WO2010065895A1 (en) 2010-06-10
IL213366A0 (en) 2011-07-31
US20100139274A1 (en) 2010-06-10
US20140366540A1 (en) 2014-12-18
DK2364340T3 (da) 2019-06-24
KR101891798B1 (ko) 2018-08-27
US8820079B2 (en) 2014-09-02
MX2011005880A (es) 2011-07-29
KR20110099715A (ko) 2011-09-08
JP6363748B2 (ja) 2018-07-25
JP2015221896A (ja) 2015-12-10
EP3572479A1 (en) 2019-11-27
CN102307965A (zh) 2012-01-04
JP2017137495A (ja) 2017-08-10
ES2739674T3 (es) 2020-02-03

Similar Documents

Publication Publication Date Title
US8820079B2 (en) Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids
US20180128131A1 (en) Fluoro olefin compounds useful as organic rankine cycle working fluids
US9797273B2 (en) Method for converting thermal energy into mechanical energy, organic rankine cycle device, and method for replacing working fluid
JP6071552B2 (ja) 熱伝達方法
US10215455B2 (en) Heat transmission method and high-temperature heat pump device
CA2784484C (en) Azeotrope-like compositions of cis-1,1,1,4,4,4-hexafluoro-2-butene
JP2013087187A (ja) 熱サイクル用作動媒体
KR20140031226A (ko) 유기 랜킨 사이클 작동 유체로서의 플루오르화 옥시란 및 이의 사용 방법
JP6468331B2 (ja) 熱エネルギーを機械エネルギーへ変換する方法、有機ランキンサイクル装置、及び作動流体を置換える方法
US20050188697A1 (en) Fluorinated ketone and fluorinated ethers as working fluids for thermal energy conversion
JP2013100805A (ja) 熱サイクル用作動媒体

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20141127

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 15TH ANNIV.) - STANDARD

Year of fee payment: 15

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241125

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20241125

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241125

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 16TH ANNIV.) - STANDARD

Year of fee payment: 16

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251112

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20251112

R11 Change to the name of applicant or owner or transfer of ownership requested

Free format text: ST27 STATUS EVENT CODE: A-4-4-R10-R11-R127 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TRANSFER RECORDAL REQUEST OR RESPONSE

Effective date: 20260319

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W111 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CORRESPONDENT DETERMINED COMPLIANT

Effective date: 20260319

R14 Transfer of ownership recorded

Free format text: ST27 STATUS EVENT CODE: A-4-4-R10-R14-R129 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TRANSFER REQUIREMENTS DETERMINED COMPLIANT

Effective date: 20260501

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260729