TWI708767B - 氫氟烯烴及其使用方法 - Google Patents
氫氟烯烴及其使用方法 Download PDFInfo
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- TWI708767B TWI708767B TW105117675A TW105117675A TWI708767B TW I708767 B TWI708767 B TW I708767B TW 105117675 A TW105117675 A TW 105117675A TW 105117675 A TW105117675 A TW 105117675A TW I708767 B TWI708767 B TW I708767B
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- Prior art keywords
- heat transfer
- hydrofluoroolefin
- composition
- carbon atoms
- working fluid
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- 238000000034 method Methods 0.000 title claims description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 32
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 29
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 239000012530 fluid Substances 0.000 claims description 84
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- 238000012546 transfer Methods 0.000 claims description 22
- 230000007246 mechanism Effects 0.000 claims description 18
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- 238000009826 distribution Methods 0.000 claims description 3
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/24—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/14—Monomers containing only one unsaturated aliphatic radical
- C08F16/24—Monomers containing halogen
-
- 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
- C08J9/0014—Use of organic additives
- C08J9/0019—Use of organic additives halogenated
-
- 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
- C08J9/0014—Use of organic additives
- C08J9/0023—Use of organic additives containing oxygen
-
- 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
- C08J9/0014—Use of organic additives
- C08J9/0028—Use of organic additives containing nitrogen
-
- 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
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- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2101/00—Manufacture of cellular products
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US201562171463P | 2015-06-05 | 2015-06-05 | |
| US62/171,463 | 2015-06-05 |
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| TW201714880A TW201714880A (zh) | 2017-05-01 |
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| EP (1) | EP3303436B1 (OSRAM) |
| JP (1) | JP6738837B2 (OSRAM) |
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| CN (1) | CN107614559B (OSRAM) |
| TW (1) | TWI708767B (OSRAM) |
| WO (1) | WO2016196242A1 (OSRAM) |
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| WO2016196242A1 (en) * | 2015-06-05 | 2016-12-08 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| WO2016196240A1 (en) * | 2015-06-05 | 2016-12-08 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| EP3455322B1 (en) * | 2016-05-09 | 2021-03-03 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| JP7076886B2 (ja) | 2016-08-22 | 2022-05-30 | スリーエム イノベイティブ プロパティズ カンパニー | プロペニルアミン、並びにその製造方法及び使用方法 |
| US10934281B2 (en) * | 2016-08-29 | 2021-03-02 | 3M Innovative Properties Company | Nitrogen and dioxolane-containing hydrofluoroethers and methods of using the same |
| US10934247B2 (en) * | 2016-09-26 | 2021-03-02 | 3M Innovative Properties Company | Nitrogen and/or oxygen-containing hydrofluoroolefins and methods of making and using the same |
| CN113796173B (zh) | 2018-12-21 | 2025-04-08 | 霍尼韦尔国际公司 | 热传递方法、系统和流体 |
| WO2020136533A1 (en) * | 2018-12-26 | 2020-07-02 | 3M Innovative Properties Company | Hydrochlorofluoroolefins and methods of using same |
| JP2022525190A (ja) * | 2019-03-18 | 2022-05-11 | ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． | 低いｇｗｐを有するフッ素化化合物を使用する熱交換方法 |
| KR102853204B1 (ko) * | 2019-06-12 | 2025-08-29 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 플루오르화 방향족 물질 및 이의 사용 방법 |
| US20210376409A1 (en) * | 2020-05-26 | 2021-12-02 | Global Graphene Group, Inc. | Battery cooling and fire protection system and method of operating same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050113609A1 (en) * | 2002-07-03 | 2005-05-26 | Asahi Glass Company Limited | Fluorine-containing unsaturated compound and method for its production |
| TW200838843A (en) * | 2006-12-06 | 2008-10-01 | 3M Innovative Properties Co | Hydrofluoroether compounds and processes for their preparation and use |
| WO2015013155A1 (en) * | 2013-07-25 | 2015-01-29 | 3M Innovative Properties Company | Nitrogen containing hydrofluoroethers and methods of making same |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0170445U (OSRAM) | 1987-10-28 | 1989-05-10 | ||
| JPS6470445A (en) | 1988-07-23 | 1989-03-15 | Agency Ind Science Techn | Novel perfluoroalkenylamine and production thereof |
| US6203944B1 (en) | 1998-03-26 | 2001-03-20 | 3M Innovative Properties Company | Electrode for a lithium battery |
| WO2001003444A2 (en) | 1999-07-07 | 2001-01-11 | Rossides Michael T | Expected value methods and systems for paying and qualifying |
| JPWO2004005231A1 (ja) * | 2002-07-03 | 2005-11-04 | 旭硝子株式会社 | 含フッ素不飽和化合物およびその製造方法 |
| RU2245319C1 (ru) | 2003-08-04 | 2005-01-27 | Открытое акционерное общество "Галоген" | Способ получения фторсодержащих олефинов |
| US9499729B2 (en) * | 2006-06-26 | 2016-11-22 | Honeywell International Inc. | Compositions and methods containing fluorine substituted olefins |
| US7691282B2 (en) * | 2005-09-08 | 2010-04-06 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| US8820079B2 (en) | 2008-12-05 | 2014-09-02 | Honeywell International Inc. | Chloro- and bromo-fluoro olefin compounds useful as organic rankine cycle working fluids |
| CN103596915B (zh) * | 2011-06-10 | 2016-08-24 | 3M创新有限公司 | 部分氟化酮及其制备和使用方法 |
| WO2015095285A1 (en) * | 2013-12-20 | 2015-06-25 | 3M Innovative Properties Company | Fluorinated olefins as working fluids and methods of using same |
| KR102411949B1 (ko) * | 2014-07-16 | 2022-06-22 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 하이드로플루오로에테르 올레핀 및 이의 사용 방법 |
| US10308592B2 (en) * | 2014-09-23 | 2019-06-04 | 3M Innovative Properties Company | Nitrogen containing hydrofluoroethers and methods of using same |
| WO2016064585A1 (en) * | 2014-10-24 | 2016-04-28 | 3M Innovative Properties Company | Segregated fluorinated esters |
| WO2016196242A1 (en) * | 2015-06-05 | 2016-12-08 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| WO2016196240A1 (en) * | 2015-06-05 | 2016-12-08 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| JP6868623B2 (ja) * | 2015-12-02 | 2021-05-12 | スリーエム イノベイティブ プロパティズ カンパニー | アリル末端不飽和ヒドロフルオロアミン及びアリル末端不飽和ヒドロフルオロエーテル化合物並びにこれらの使用方法 |
| US10703833B2 (en) * | 2015-12-17 | 2020-07-07 | 3M Innovative Properties Company | Amine-containing polymers, dispersions thereof and methods of making and using the same |
| US10344006B2 (en) * | 2016-03-11 | 2019-07-09 | 3M Innovative Properties Company | Amine-containing acyclic hydrofluoroethers and methods of using the same |
| EP3455322B1 (en) * | 2016-05-09 | 2021-03-03 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
-
2016
- 2016-05-27 WO PCT/US2016/034516 patent/WO2016196242A1/en not_active Ceased
- 2016-05-27 KR KR1020187000401A patent/KR102617084B1/ko active Active
- 2016-05-27 CN CN201680031415.2A patent/CN107614559B/zh active Active
- 2016-05-27 EP EP16804089.7A patent/EP3303436B1/en active Active
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- 2016-05-27 US US15/578,278 patent/US10266472B2/en active Active
- 2016-06-03 TW TW105117675A patent/TWI708767B/zh active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050113609A1 (en) * | 2002-07-03 | 2005-05-26 | Asahi Glass Company Limited | Fluorine-containing unsaturated compound and method for its production |
| TW200838843A (en) * | 2006-12-06 | 2008-10-01 | 3M Innovative Properties Co | Hydrofluoroether compounds and processes for their preparation and use |
| WO2015013155A1 (en) * | 2013-07-25 | 2015-01-29 | 3M Innovative Properties Company | Nitrogen containing hydrofluoroethers and methods of making same |
Also Published As
| Publication number | Publication date |
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| US10266472B2 (en) | 2019-04-23 |
| EP3303436A4 (en) | 2019-02-20 |
| CN107614559A (zh) | 2018-01-19 |
| EP3303436A1 (en) | 2018-04-11 |
| JP2018524291A (ja) | 2018-08-30 |
| KR102617084B1 (ko) | 2023-12-21 |
| US20180141887A1 (en) | 2018-05-24 |
| TW201714880A (zh) | 2017-05-01 |
| CN107614559B (zh) | 2020-08-04 |
| JP6738837B2 (ja) | 2020-08-12 |
| WO2016196242A1 (en) | 2016-12-08 |
| KR20180017083A (ko) | 2018-02-20 |
| EP3303436B1 (en) | 2020-12-09 |
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