ES2546132T3 - Método y aparato para transferencia de calor con éteres de alquil-perfluoroalqueno - Google Patents
Método y aparato para transferencia de calor con éteres de alquil-perfluoroalqueno Download PDFInfo
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- ES2546132T3 ES2546132T3 ES11741352.6T ES11741352T ES2546132T3 ES 2546132 T3 ES2546132 T3 ES 2546132T3 ES 11741352 T ES11741352 T ES 11741352T ES 2546132 T3 ES2546132 T3 ES 2546132T3
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- heat transfer
- mixtures
- xcf
- cfcf
- temperature
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- 238000000034 method Methods 0.000 title claims abstract description 32
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- 239000000203 mixture Substances 0.000 claims abstract description 55
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical group [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
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- VVMQLAKDFBLCHB-UHFFFAOYSA-N 1,1,1,2,3,4,4,5,5,5-decafluoropent-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(F)C(F)(F)F VVMQLAKDFBLCHB-UHFFFAOYSA-N 0.000 description 2
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- GRAVXMKICSKBIS-UHFFFAOYSA-N 1,1,1,2,3,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-2-methoxyoct-3-ene Chemical compound COC(F)(C(F)(F)F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F GRAVXMKICSKBIS-UHFFFAOYSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
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- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
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- RXTHCRMIJMEURB-UHFFFAOYSA-N 1,1,1,2,3,4,5,5,5-nonafluoro-4-methoxypent-2-ene Chemical compound COC(F)(C(F)(F)F)C(F)=C(F)C(F)(F)F RXTHCRMIJMEURB-UHFFFAOYSA-N 0.000 description 1
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- QNTIPADFCNTBBK-UHFFFAOYSA-N 1,1,1,3,4,4,5,5,5-nonafluoro-2-methoxypent-2-ene Chemical compound COC(C(F)(F)F)=C(F)C(F)(F)C(F)(F)F QNTIPADFCNTBBK-UHFFFAOYSA-N 0.000 description 1
- PBWHQPOHADDEFU-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,5-decafluoropent-1-ene Chemical compound FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F PBWHQPOHADDEFU-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
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- 239000004743 Polypropylene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
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- 230000006835 compression Effects 0.000 description 1
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- 239000002826 coolant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
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- 230000000737 periodic effect Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
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- 239000000243 solution Substances 0.000 description 1
- 239000005437 stratosphere Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
- PPQRADLPLZYEKN-UHFFFAOYSA-N tritylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 PPQRADLPLZYEKN-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US362833P | 2002-03-09 | ||
| US36283310P | 2010-07-09 | 2010-07-09 | |
| PCT/US2011/043301 WO2012006493A1 (en) | 2010-07-09 | 2011-07-08 | Novel alkyl perfluoroalkene ethers and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2546132T3 true ES2546132T3 (es) | 2015-09-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11741352.6T Active ES2546132T3 (es) | 2010-07-09 | 2011-07-08 | Método y aparato para transferencia de calor con éteres de alquil-perfluoroalqueno |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8486295B2 (https=) |
| EP (1) | EP2590928B1 (https=) |
| JP (1) | JP5746338B2 (https=) |
| CN (1) | CN103003226B (https=) |
| ES (1) | ES2546132T3 (https=) |
| MY (1) | MY158294A (https=) |
| SG (1) | SG186965A1 (https=) |
| TW (1) | TWI503408B (https=) |
| WO (1) | WO2012006493A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8399713B2 (en) * | 2009-02-16 | 2013-03-19 | E I Du Pont De Nemours And Company | Alkyl perfluoroalkene ethers |
| WO2012087381A1 (en) * | 2010-12-20 | 2012-06-28 | E. I. Du Pont De Nemours And Company | Azeotropic and azeotrope-like compositions of methyl perfluoroheptene ethers and ethanol and uses thereof |
| TWI633179B (zh) * | 2013-06-04 | 2018-08-21 | 杜邦股份有限公司 | 烷基全氟烯醚及其混合物於高溫熱泵的應用 |
| JP6571435B2 (ja) * | 2014-10-01 | 2019-09-04 | 三井・ケマーズ フロロプロダクツ株式会社 | 沸騰冷却装置用媒体 |
| EP3455322B1 (en) * | 2016-05-09 | 2021-03-03 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| CN107674195B (zh) * | 2017-08-18 | 2021-03-23 | 佳化化学（茂名）有限公司 | 一种聚氧化乙烯类聚合物的合成催化剂及其合成方法 |
| KR102739483B1 (ko) * | 2017-12-13 | 2024-12-05 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 하이드로플루오로올레핀 에테르, 조성물, 장치 및 이의 사용 방법 |
| JP7209722B2 (ja) * | 2017-12-13 | 2023-01-20 | スリーエム イノベイティブ プロパティズ カンパニー | 誘電性流体及び電気デバイス中の全フッ素化１－アルコキシプロペン |
| US11629133B2 (en) * | 2018-05-15 | 2023-04-18 | 3M Innovative Properties Company | Perfluoroaminoolefins and methods of making and using the same |
| JP7525481B2 (ja) * | 2018-10-15 | 2024-07-30 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | フッ素化アルコキシビニルエーテル及びフッ素化アルコキシビニルエーテルの調製方法 |
| US11773352B2 (en) * | 2018-12-26 | 2023-10-03 | 3M Innovative Properties Company | Hydrochlorofluoroolefins and methods of using same |
| CA3153966A1 (en) * | 2019-10-28 | 2021-05-06 | The Chemours Company Fc, Llc | Heat transfer fluids for use in low temperature chiller applications |
| CN116283511A (zh) * | 2023-03-25 | 2023-06-23 | 浙江诺亚氟化工有限公司 | 一种全氟壬烯基三氟乙醚及其制备方法与应用 |
| CN117486685B (zh) * | 2023-10-30 | 2025-01-28 | 台州氟乐新材料合伙企业(有限合伙) | 一种高效全氟壬烯基醚的制备方法 |
| CN117486686B (zh) * | 2023-10-30 | 2025-01-28 | 台州氟乐新材料合伙企业(有限合伙) | 六氟丙烯三聚体绿色化学转化制备全氟醚类化合物的方法 |
| CN117486687A (zh) * | 2023-10-30 | 2024-02-02 | 台州氟乐新材料合伙企业(有限合伙) | 一种环保的全氟壬烯基醚的制备方法 |
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|---|---|---|---|---|
| JPS58146567A (ja) | 1982-02-25 | 1983-09-01 | Agency Of Ind Science & Technol | イオノフオアとして有用なポリエ−テル誘導体 |
| US6019909A (en) * | 1993-01-22 | 2000-02-01 | Daikin Industries, Ltd. | Fluorinated hydrocarbon compound and process for its preparation, and refrigerator oil and magnetic recording medium lubricant |
| US6023002A (en) | 1998-01-26 | 2000-02-08 | 3M Innovative Properties Company | Process for preparing hydrofluoroethers |
| US7071154B2 (en) * | 2003-12-18 | 2006-07-04 | 3M Innovative Properties Company | Azeotrope-like compositions and their use |
| US7053253B1 (en) * | 2005-05-02 | 2006-05-30 | 3M Innovative Properties Company | Process for purifying hexafluoropropene dimers |
| US7691282B2 (en) * | 2005-09-08 | 2010-04-06 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| US7708903B2 (en) * | 2005-11-01 | 2010-05-04 | E.I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins and uses thereof |
| US20100025619A1 (en) | 2006-07-12 | 2010-02-04 | Solvay Fluor Gmbh | Method for heating and cooling using fluoroether compounds, compositions suitable therefore and their use |
| CN101553551A (zh) * | 2006-07-12 | 2009-10-07 | 苏威氟有限公司 | 使用氟醚化合物进行加热和冷却的方法、适合其的组合物及它们的用途 |
| US8399713B2 (en) * | 2009-02-16 | 2013-03-19 | E I Du Pont De Nemours And Company | Alkyl perfluoroalkene ethers |
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- 2011-06-28 US US13/170,646 patent/US8486295B2/en active Active
- 2011-07-05 TW TW100123617A patent/TWI503408B/zh active
- 2011-07-08 WO PCT/US2011/043301 patent/WO2012006493A1/en not_active Ceased
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- 2011-07-08 JP JP2013519717A patent/JP5746338B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP5746338B2 (ja) | 2015-07-08 |
| US20120006510A1 (en) | 2012-01-12 |
| EP2590928B1 (en) | 2015-06-10 |
| TW201204823A (en) | 2012-02-01 |
| CN103003226A (zh) | 2013-03-27 |
| SG186965A1 (en) | 2013-02-28 |
| US8486295B2 (en) | 2013-07-16 |
| CN103003226B (zh) | 2016-03-02 |
| JP2013535529A (ja) | 2013-09-12 |
| WO2012006493A1 (en) | 2012-01-12 |
| TWI503408B (zh) | 2015-10-11 |
| MY158294A (en) | 2016-09-30 |
| EP2590928A1 (en) | 2013-05-15 |
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