CA3014204C - Use of perfluoroheptenes in power cycle systems - Google Patents
Use of perfluoroheptenes in power cycle systems Download PDFInfo
- Publication number
- CA3014204C CA3014204C CA3014204A CA3014204A CA3014204C CA 3014204 C CA3014204 C CA 3014204C CA 3014204 A CA3014204 A CA 3014204A CA 3014204 A CA3014204 A CA 3014204A CA 3014204 C CA3014204 C CA 3014204C
- Authority
- CA
- Canada
- Prior art keywords
- working fluid
- perfluoroheptene
- heat
- pressure
- cycle
- 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
Links
- CDAVUOSPHHTNBU-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,7,7,7-tetradecafluorohept-1-ene Chemical class FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CDAVUOSPHHTNBU-UHFFFAOYSA-N 0.000 title abstract description 33
- 239000012530 fluid Substances 0.000 claims abstract description 251
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 30
- 230000008569 process Effects 0.000 claims abstract description 23
- 238000010438 heat treatment Methods 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims description 38
- UGHJWZHBCXGSAY-UHFFFAOYSA-N 1,1,1,2,3,4,4,5,5,6,6,7,7,7-tetradecafluorohept-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UGHJWZHBCXGSAY-UHFFFAOYSA-N 0.000 claims description 36
- UAEWLONMSWUOCA-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluorohept-3-ene Chemical compound FC(F)(F)C(F)(F)C(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F UAEWLONMSWUOCA-UHFFFAOYSA-N 0.000 claims description 35
- 239000007788 liquid Substances 0.000 claims description 33
- 238000001816 cooling Methods 0.000 claims description 18
- 230000001351 cycling effect Effects 0.000 claims description 8
- 238000005086 pumping Methods 0.000 claims description 2
- 230000008016 vaporization Effects 0.000 claims description 2
- 230000005611 electricity Effects 0.000 abstract description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000002918 waste heat Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- NOPJRYAFUXTDLX-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-methoxypropane Chemical compound COC(F)(F)C(F)(F)C(F)(F)F NOPJRYAFUXTDLX-UHFFFAOYSA-N 0.000 description 3
- QKAGYSDHEJITFV-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)pentane Chemical compound FC(F)(F)C(F)(F)C(F)(OC)C(F)(C(F)(F)F)C(F)(F)F QKAGYSDHEJITFV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 238000010248 power generation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 description 2
- HHBBIOLEJRWIGU-UHFFFAOYSA-N 4-ethoxy-1,1,1,2,2,3,3,4,5,6,6,6-dodecafluoro-5-(trifluoromethyl)hexane Chemical compound CCOC(F)(C(F)(C(F)(F)F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F HHBBIOLEJRWIGU-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 Methyl Perfluoro-Heptene Ether isomers Chemical class 0.000 description 2
- 238000003491 array Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002440 industrial waste Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 1
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- 101100285408 Danio rerio eng2a gene Proteins 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- NMZZYGAYPQWLGY-UHFFFAOYSA-N pyridin-3-ylmethanol;hydrofluoride Chemical compound F.OCC1=CC=CN=C1 NMZZYGAYPQWLGY-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Engine Equipment That Uses Special Cycles (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662299580P | 2016-02-25 | 2016-02-25 | |
| US62/299,580 | 2016-02-25 | ||
| PCT/US2017/019323 WO2017147400A1 (en) | 2016-02-25 | 2017-02-24 | Use of perfluoroheptenes in power cycle systems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA3014204A1 CA3014204A1 (en) | 2017-08-31 |
| CA3014204C true CA3014204C (en) | 2023-07-18 |
Family
ID=58231783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3014204A Active CA3014204C (en) | 2016-02-25 | 2017-02-24 | Use of perfluoroheptenes in power cycle systems |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US11220932B2 (enExample) |
| EP (1) | EP3420203A1 (enExample) |
| JP (3) | JP6995050B2 (enExample) |
| CN (1) | CN108699921B (enExample) |
| AU (2) | AU2017222606B2 (enExample) |
| BR (1) | BR112018015643B1 (enExample) |
| CA (1) | CA3014204C (enExample) |
| MX (1) | MX2022015424A (enExample) |
| WO (1) | WO2017147400A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11220932B2 (en) * | 2016-02-25 | 2022-01-11 | The Chemours Company Fc, Llc | Use of perfluoroheptenes in power cycle systems |
| JP6941076B2 (ja) * | 2018-06-05 | 2021-09-29 | 株式会社神戸製鋼所 | 発電方法 |
| CN109813001B (zh) * | 2019-01-21 | 2020-12-15 | 东营市浩瀚生化科技有限公司 | 一种免提式利用低温地热流体的方法及地热能提取装置 |
| ES3048489T3 (en) * | 2019-10-28 | 2025-12-10 | Chemours Co Fc Llc | Heat transfer fluids for use in low temperature chiller applications |
| JP2021143212A (ja) * | 2020-03-10 | 2021-09-24 | 三井・ケマーズ フロロプロダクツ株式会社 | 共沸混合物様組成物 |
| JP7620418B2 (ja) * | 2020-11-30 | 2025-01-23 | 三井・ケマーズ フロロプロダクツ株式会社 | フッ素系溶剤組成物 |
| US12060867B2 (en) | 2021-04-02 | 2024-08-13 | Ice Thermal Harvesting, Llc | Systems for generating geothermal power in an organic Rankine cycle operation during hydrocarbon production based on working fluid temperature |
| 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 |
| 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 |
| US11480074B1 (en) | 2021-04-02 | 2022-10-25 | Ice Thermal Harvesting, Llc | Systems and methods utilizing gas temperature as a power source |
| US12312981B2 (en) | 2021-04-02 | 2025-05-27 | Ice Thermal Harvesting, Llc | Systems and methods utilizing gas temperature as a power source |
| US11493029B2 (en) | 2021-04-02 | 2022-11-08 | Ice Thermal Harvesting, Llc | Systems and methods for generation of electrical power at a drilling rig |
| US11644015B2 (en) | 2021-04-02 | 2023-05-09 | Ice Thermal Harvesting, Llc | Systems and methods for generation of electrical power at a drilling rig |
| 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 |
| US11592009B2 (en) | 2021-04-02 | 2023-02-28 | Ice Thermal Harvesting, Llc | Systems and methods for generation of electrical power at a drilling rig |
| CA3228397A1 (en) * | 2021-08-12 | 2023-02-16 | Babak Bob AREFI | Thermal processes and systems for generating electricity utilizing predetermined working fluids |
| WO2023027189A1 (ja) * | 2021-08-27 | 2023-03-02 | セントラル硝子株式会社 | 共沸組成物、共沸様組成物、組成物、洗浄剤、溶媒、エアゾール、及び熱移動媒体 |
| WO2023027188A1 (ja) * | 2021-08-27 | 2023-03-02 | セントラル硝子株式会社 | 溶剤組成物、洗浄剤、洗浄方法、塗膜形成用組成物、塗膜付き基材の製造方法、及びエアゾール |
| CN118251475A (zh) * | 2021-11-23 | 2024-06-25 | 科慕埃弗西有限公司 | 全氟庚烯和氟代醚的共沸和类共沸组合物及其用途 |
| 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 (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1204119A (en) | 1966-09-22 | 1970-09-03 | Nat Res Dev | Improvements in and relating to power generating systems |
| US3584457A (en) * | 1969-06-02 | 1971-06-15 | Cox Ass Edwin | External combustion power generating system |
| NZ183668A (en) | 1976-04-06 | 1979-04-26 | Sperry Rand Corp | Geothermal power plants; working fluid injected into deep well |
| US4926650A (en) * | 1988-05-18 | 1990-05-22 | Pennwalt Corporation | Refrigerant fluid and method of use |
| US5347058A (en) | 1993-12-07 | 1994-09-13 | E. I. Du Pont De Nemours And Company | Process for the production of fluorinated olefins |
| US5762817A (en) * | 1996-04-12 | 1998-06-09 | E. I. Du Pont De Nemours And Company | Decafluoropentane compositions |
| 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 |
| EP1983038A1 (en) | 2007-04-18 | 2008-10-22 | Turboden S.r.l. | Turbo generator (orc) for applications at middle-low temperatures, using a fluid with azeotropic behaviour |
| US20130091843A1 (en) | 2008-12-05 | 2013-04-18 | Honeywell International Inc. | Fluoro olefin compounds useful as organic rankine cycle working fluids |
| US20100154419A1 (en) * | 2008-12-19 | 2010-06-24 | E. I. Du Pont De Nemours And Company | Absorption power cycle system |
| ES2989330T3 (es) | 2011-08-19 | 2024-11-26 | Chemours Co Fc Llc | Proceso de ciclos de Rankine orgánicos para generar energía mecánica a partir de calor |
| TW201829721A (zh) * | 2013-06-04 | 2018-08-16 | 美商杜邦股份有限公司 | 烷基全氟烯醚及其混合物於高溫熱泵的應用 |
| ES2928678T3 (es) * | 2013-11-22 | 2022-11-21 | Chemours Co Fc Llc | Uso de composiciones que comprenden tetrafluoropropeno y tetrafluoroetano en ciclos de potencia; y aparatos de ciclo de potencia |
| WO2015095285A1 (en) * | 2013-12-20 | 2015-06-25 | 3M Innovative Properties Company | Fluorinated olefins as working fluids and methods of using same |
| KR102433038B1 (ko) | 2014-06-03 | 2022-08-18 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 광가교결합된 플루오로중합체를 포함하는 패시베이션 층 |
| CN104469160A (zh) | 2014-12-19 | 2015-03-25 | 宇龙计算机通信科技(深圳)有限公司 | 一种图像的获取及处理方法、系统及终端 |
| US11220932B2 (en) * | 2016-02-25 | 2022-01-11 | The Chemours Company Fc, Llc | Use of perfluoroheptenes in power cycle systems |
-
2017
- 2017-02-24 US US16/073,675 patent/US11220932B2/en active Active
- 2017-02-24 WO PCT/US2017/019323 patent/WO2017147400A1/en not_active Ceased
- 2017-02-24 JP JP2018542190A patent/JP6995050B2/ja not_active Expired - Fee Related
- 2017-02-24 CN CN201780012986.6A patent/CN108699921B/zh active Active
- 2017-02-24 EP EP17709310.1A patent/EP3420203A1/en not_active Withdrawn
- 2017-02-24 AU AU2017222606A patent/AU2017222606B2/en not_active Ceased
- 2017-02-24 CA CA3014204A patent/CA3014204C/en active Active
- 2017-02-24 BR BR112018015643-4A patent/BR112018015643B1/pt active IP Right Grant
-
2018
- 2018-07-27 MX MX2022015424A patent/MX2022015424A/es unknown
-
2021
- 2021-09-27 JP JP2021156648A patent/JP2022023850A/ja active Pending
- 2021-12-07 US US17/544,827 patent/US11732618B2/en active Active
-
2022
- 2022-08-11 AU AU2022215233A patent/AU2022215233A1/en not_active Abandoned
-
2023
- 2023-05-09 JP JP2023077230A patent/JP2023090893A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN108699921B (zh) | 2022-12-23 |
| AU2017222606A1 (en) | 2018-08-02 |
| EP3420203A1 (en) | 2019-01-02 |
| US20200131943A1 (en) | 2020-04-30 |
| WO2017147400A1 (en) | 2017-08-31 |
| BR112018015643A2 (pt) | 2018-12-26 |
| MX2022015424A (es) | 2023-01-11 |
| US11220932B2 (en) | 2022-01-11 |
| JP2022023850A (ja) | 2022-02-08 |
| CA3014204A1 (en) | 2017-08-31 |
| JP6995050B2 (ja) | 2022-01-14 |
| CN108699921A (zh) | 2018-10-23 |
| AU2017222606B2 (en) | 2022-08-04 |
| JP2023090893A (ja) | 2023-06-29 |
| US11732618B2 (en) | 2023-08-22 |
| JP2019512061A (ja) | 2019-05-09 |
| US20220090521A1 (en) | 2022-03-24 |
| AU2022215233A1 (en) | 2022-09-01 |
| BR112018015643B1 (pt) | 2023-12-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11732618B2 (en) | Use of perfluoroheptenes in power cycle systems | |
| US10975279B2 (en) | Use of (2E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene in power cycles | |
| EP2744981B1 (en) | Process for organic rankine cycles for generating mechanical energy from heat | |
| CN104039916A (zh) | 包含1，1，1，2，3-五氟丙烷和任选的z-1，1，1，4，4，4-六氟-2-丁烯的组合物在动力循环中的用途 | |
| EP2995668A1 (en) | Use of compositions comprising e-1,1,1,4,4,5,5,5-octafluoro-2-pentene in power cycles | |
| US20180215979A1 (en) | Use of 1,3,3,4,4,4-hexafluoro-1-butene in power cycles |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20200819 |
|
| EEER | Examination request |
Effective date: 20200819 |
|
| EEER | Examination request |
Effective date: 20200819 |
|
| EEER | Examination request |
Effective date: 20200819 |
|
| EEER | Examination request |
Effective date: 20200819 |