[go: up one dir, main page]

WO2012142765A1 - Fluide de travail pour cycle de rankine - Google Patents

Fluide de travail pour cycle de rankine Download PDF

Info

Publication number
WO2012142765A1
WO2012142765A1 PCT/CN2011/073132 CN2011073132W WO2012142765A1 WO 2012142765 A1 WO2012142765 A1 WO 2012142765A1 CN 2011073132 W CN2011073132 W CN 2011073132W WO 2012142765 A1 WO2012142765 A1 WO 2012142765A1
Authority
WO
WIPO (PCT)
Prior art keywords
working fluid
heat
rankine cycle
formula
organic rankine
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.)
Ceased
Application number
PCT/CN2011/073132
Other languages
English (en)
Inventor
Jingtao Wang
Bo PANG
Christian Persson
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.)
Emmaljunga Barnvagnsfabrik AB
Original Assignee
Emmaljunga Barnvagnsfabrik AB
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
Application filed by Emmaljunga Barnvagnsfabrik AB filed Critical Emmaljunga Barnvagnsfabrik AB
Priority to EP11863895.6A priority Critical patent/EP2710086A4/fr
Priority to CN201180070205.1A priority patent/CN103717699B/zh
Priority to US14/111,908 priority patent/US20140305125A1/en
Priority to PCT/CN2011/073132 priority patent/WO2012142765A1/fr
Publication of WO2012142765A1 publication Critical patent/WO2012142765A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • 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
    • 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
    • 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
    • C09K2205/132—Components containing nitrogen
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency
    • Y02P20/129—Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines

Definitions

  • the present invention relates to a working fluid for the organic Rankine cycle, having improved energy conversion efficiency, heat exchange characteristics and thermal stability.
  • the present invention also relates to a process for converting thermal energy to mechanical energy, method for power generation, an organic Rankine cycle system and use of a working fluid for transfer of heat or in a mechanical power generation device.
  • the organic Rankine cycle involves an organic fluid with a liquid-vapor phase change occurring at a lower temperature than the water- steam phase change. Due to the organic fluid's low phase change temperature heat recovery from low temperature sources such as industrial waste heat, geothermal heat and solar ponds, is made possible and economical. The low-temperature heat is converted into useful work that can itself be converted into electricity.
  • the working fluid is fed or pumped into a heat exchange relationship with a heat source, e.g. a boiler, where the working fluid is evaporated, thereafter passed through a turbine of some sort and then finally re-condensed.
  • a heat source e.g. a boiler
  • the ORC could be used for waste heat recovery in e.g. industrial and farming processes, hot exhausts from ovens or furnaces, flue gas
  • a general disadvantage of most working fluids made commercial for organic Rankine cycles are the fact that they have been designed specifically for the refrigeration cycle commonly used in air condition systems and heat pump systems.
  • the refrigeration cycle is the anti-cycle of the Carnot cycle to generate power.
  • working fluids for the purpose to generate power from low-grade heat should have distinct features from refrigerants.
  • a pressure-enthalpy graph is shown in Figure 1. The energy conversion process is from point H3 to point H4.
  • the working fluid should influence to decrease the enthalpy difference between H3 and H4 in order to reduce the compressor power.
  • the working fluid should influence to increase the enthalpy difference between H3 and H4 in order to convert more power from heat.
  • Some refrigerants like e.g. R600a are also used as working fluids in the ORC to convert heat to electrical power but the flammability of the R600a is a big problem in most industrial or commercial environments.
  • Isobutane used as a refrigerant in domestic refrigerators may upon leakage into the refrigerator cabinet be ignited by sparks from the electrical system.
  • the use of a flammable gas as a refrigerant is quite dangerous and encompasses a great deal of risk.
  • the normal risks that chlorofluorocarbon compounds (CFC) or other potentially toxic refrigerants would have upon escape, are mainly related to depletion of breathable air and frosting at the point of escape.
  • the ozone depletion potential (ODP) of a chemical compound is the relative amount of degradation of the ozone layer it may cause.
  • ODP of a specific substance is defined as the ratio of global loss of ozone due to given substance over the global loss of ozone due the same mass of trichlorofluoro- methane (R-11 or CFC-11 ) having a fixed ODP of 1.0.
  • R11 has the maximum potential amongst all chlorocarbons due to the presence of three chlorine atoms in the molecule.
  • Chlorodifluoromethane (R-22) has an ODP of 0.05.
  • the ODP can be estimated from the structure of a given substance.
  • Chlorofluorocarbons have ODPs in the vicinity of 1 and hydrochlorofluoro- carbons (HCFC) have ODPs often in the range of 0.005 to 0.2, since the presence of hydrogen causes the compounds to react readily in the troposphere, therefore reducing their chance to reach the stratosphere.
  • HCFC hydrochlorofluoro- carbons
  • Hydrofluorocarbons have no chlorine content, so their ODPs are essentially zero.
  • Some used refrigerants such as CFCs, HCFCs and HFCs, e.g. R11 and R22, show relatively good performance on heat efficiency in the ORC but due to stricter environmental legislations such refrigerants, due to their halogen content, already have been or in the near future probably will be phased out from the market.
  • ORC ORC
  • GWP global warming potential
  • US 2010/139274 discloses chloro- and bromo-fluoro-olefins useful as organic Rankine cycle working fluids for efficiently converting waste heat generated from industrial processes, such as electric power generation from fuel cells, into mechanical energy or further to electric power.
  • WO 2006/014609 discloses a process for recovering heat and a working fluid for an organic Rankine cycle system comprising one or more compounds of Formula (I) (I) CR'y, wherein y is 3 or 4 and each R' is independently H, F, I, Br, substituted or unsubstituted C3 - C9 alkyl, substituted or unsubstituted C2-C9 alkoxy, substituted or unsubstituted fluoropolyether, substituted or unsubstituted C2-C9 alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted C6-C9 alkylaryl, or substituted or unsubstituted C6-C9 alkenyaryl, provided said compound includes at least two carbon atoms, at least one fluorine atom, and no chloride atoms, and further provided that any OH substituted alkyl preferably has at least three carbon atoms.
  • US 4 541 943 discloses a working fluid to be used in a mechanical vapor recompression heat pump system.
  • the working fluid can be either a saturated hydrocarbon or a fluorohydrocarbon ether or a fluorinated amine.
  • the heat pumps may operate on reverse Rankine cycle.
  • US 2010/0095703 discloses a working medium for refrigeration processes comprising at least one sorbent material and at least one refrigerant.
  • the sorbent material contains at least one nonvolatile organic salt.
  • a list of suitable anions to be included in the salt is presented.
  • the list of anions includes bis(perfluoroalkylsulfonyl)amides.
  • Suitable ionic liquids are 1- methyl-3-octylimidazolium tetrafluoroborate and butylmethylpyrrolidinium bis(trifluoromethylsulfonyl)-imide.
  • the characteristics for the working fluid according to the present invention is a high thermal efficiency, low or reasonable flammability, low or reasonable toxicity (i.e. low degree of poisoning during operation, no or iow ODP and low or reasonable corrosion on copper (if this material is used for e.g. pipings and/or heat exchanger).
  • the working fluids according to the present invention comprise at least one compound having a structure according to Formula (I):
  • R is fluorinated or non-fluorinated methyl, ethyl, vinyl, or ethynyl
  • N is the element nitrogen
  • connection of R-N is a ring structure (i.e. a heterogeneous ring) or a straight chain structure, and
  • Q is chosen from a hydrogen atom and/or at least one fluorine atom.
  • One embodiment of the present invention relates to an organic Rankine cycle working fluid comprising at least one compound having either the Formula (II):
  • R 1 is fluorinated or non-fluorinated methyl, ethyl, vinyl or ethynyl, and n is 0 or 1 ;
  • R 2 and R 3 are independently chosen from H 2 , F 2 and HF, and
  • p is 0 or 1, preferably 1.
  • R 1 in Formula (II) is a fluorinated or non-fluorinated methyl or ethyl group.
  • said compound according to Formula (II) is chosen from the group consisting of CH 3 NHF, CH 2 FNHF, CHF 2 NHF, CF 3 NHF, CH 3 NF 2 , CH 2 FNF 2l CHF 2 NF 2 , CF 3 NF 2 , C 2 H 5 NHF, CH 2 FCH 2 NHF, CHF 2 CH 2 NHF, CHsCHFNHF, CH 2 FCHFNHF, C 2 H 5 NF 2> CH 2 FCH 2 NF 2 , CH 3 CHFNF 2) and CHF 2 CF 2 NF 2 ; preferably CH 3 NF 2 , CH 2 FNF 2 , CHF 2 NF 2 , and CF 3 NF 2 .
  • R 2 in Formula (III) contains preferably at least one fluorine.
  • the compound according to Formula (III) is preferably tetrafluoroaziridine.
  • the temperature of the working fluid after being brought in contact with a heat source in a) is at most 100°C, preferably said temperature is 25 to 90°C.
  • a working fluid according to the present invention
  • a heat exchanging device containing said working fluid, connected to a heat source, for vaporizing the working fluid
  • an expansion device responsive to said vaporized working fluid for expanding said working fluid vapor resulting in heat depleted working fluid
  • an electric generator driven by said expansion device for producing electrical power
  • a condenser for condensing the heat depleted working fluid and producing condensate
  • the heat source is heat from a boiler or a fuel cell, waste heat from an industrial or farming process, geothermal heat, waste heat from a combustion engine or power plant, or solar heat.
  • the expander is a turbine, screw expander, scroll expander, or piston expander.
  • Still one embodiment relates to use of a working fluid according to the present invention for transfer of heat.
  • Yet another embodiment relates to use of a working fluid according the present invention in a mechanical power generation device adapted to use an organic Rankine cycle or a modification thereof.
  • Another embodiment relates to a method for power generation comprising transfer of heat using a working fluid according to the present invention.
  • One embodiment relates to a method for power generation according to the present invention, using a Rankine cycle or a modification thereof to generate work from heat.
  • Another embodiment relates to a compound having the Formula (IV):
  • Figure 1 shows a pressure-enthalpy graph
  • Figure 2 shows a graph of the entropy and efficiency for known existing working fluids of the ORC for a temperature shift between 20 to 60°C in the system.
  • This temperature cycle in the ORC i.e. 60°C is the evaporating temperature for the working fluid and 20°C is the condensing temperature, is in the following referred to as an ORC 20-60 cycle.
  • Figure 3 shows a schematic drawing of an organic Rankine Cycle system.
  • a heat source supplies heat to an ORC with the aid of a heat exchanging device.
  • the temperature of the working fluid in the ORC in this heat exchanging section can be below 90°C.
  • heat sources suitable for use in the ORC include industrial waste heat or geothermal waste heat.
  • One advantage of the working fluid according to the present invention is that it increases the thermal efficiency in the conversion of heat into work.
  • the heat source is able to give the working fluid in the ORC system a temperature of at most 100°C, preferably at most 90°C, preferably at most 80°C, and at least a temperature of 25°C, preferably 30-75°C, e.g. 40-70°C, 40-65°C, or 50-70°C, in the heat retrieving section (the evaporation section) of the ORC.
  • thermodynamics relates itself to the entropy of a system. It states that the entropy of a pure substance approaches zero as the temperature approaches absolute zero. This law provides a reference point in the calculation of the entropy, where the entropy calculated relative to this point is considered the absolute entropy.
  • the thermodynamic property (absolute entropy) in the gaseous state at the 293.15K, 101.325KPa is calculated for all the molecules using density functional theory (DFT) with Gaussian 09 program. Absolute entropy means the increment of entropy when the temperature is increased from OK to 293.15K. All calculations for the molecules were carried out with B3LYP/6-31 G(d) Opt Freq.
  • the working fluids according to the present invention are to be selected from molecule structures which might contribute to less entropy, such as cyclic structures, double bonds, triple bonds, and/or molecules with a low total number of atoms but with proper boiling point.
  • atoms making up the working fluid according to the present invention are four atoms, i.e. C, N, F and H.
  • Workings fluids used in an ORC preferably present characteristics like: a) an isentropic saturation vapor curve, and preferably displaying a small superheating at the exhaust of the evaporator;
  • freezing point should be lower than the lowest temperature in the cycle and maximum temperature of the heat source is limited by the chemical stability of the working fluid
  • ODP ozone depletion potential
  • GWP global warming potential
  • a working fluid according to the present invention comprises at least one compound having a structure according to Formula (I):
  • R is fluorinated or non-fluorinated methyl, ethyl, vinyl, or ethynyl
  • N is the element nitrogen
  • the connection of R-N is a ring structure (i.e. a heterogeneous ring) or a straight chain structure
  • Q is chosen from a hydrogen atom and/or at least one fluorine atom.
  • the working fluid according to the present invention comprises at least one compound having either the Formula (II): wherein
  • R 1 is fluorinated or non-fluorinated methyl, ethyl, vinyl or ethynyl, and n is 0 or 1;
  • R 2 and R 3 are independently chosen from H 2 , F 2 and HF, and
  • p 0 or 1.
  • R 1 may be non-fluorinated, or fully or partially fluorinated.
  • R 1 is a fluorinated or non-fluorinated methyl or ethyl group.
  • Preferred compounds according to Formula (II) are chosen from CH 3 NHF, CH 2 FNHF, CHF 2 NHF, CF3NHF, CH 3 NF 2 , CH2FNF2, CHF2NF2, CF 3 NF2, C 2 H 5 NHF, CH 2 FCH 2 NHF, CHF2CH 2 NHF, CH3CHFNHF,
  • CH 2 FCHFNHF C 2 H 5 NF 2 , CH 2 FCH 2 NF 2 , CH 3 CHFNF 2 , CHF 2 CF 2 NF 2 , in particular CH3NHF, CH 2 FNHF, CHF 2 NHF, CF3NHF, CH3NF2, CH 2 FNF 2 , CHF 2 NF 2 , CF 3 NF 2 , C2H5NHF, CH2FCH 2 NHF, CHF2CH2NHF, CH3CHFNHF, and CH 2 FCHFNHF,
  • R 1 is a fluorinated or non-fluorinated methyl group, and especially in combination with p being 0.
  • the working fluid comprises a compound having a structure according to Formula (III) it is preferred that p is 1.
  • R 2 and R 3 the more fluorine that is present in Formula (III) the better the compound seems to perform in an ORC. Thus, fluorinated aziridines are preferred.
  • the compound according to Formula (I), such as e.g. Formula (II) and/or (III), constitutes 60-100%, by weight of the working fluid, preferably 80- 100%, more preferably 90-100%, most preferably 95-100%, by weight.
  • One of the more preferred compounds having Formula (III) is tetrafluoroaziridine.
  • the synthesis of the tetrafluoroaziridin may be done by the followin reaction steps:
  • Tetrafluoroethene and triethylammoniumazide react in sym-tetrachloro- ethane at -5°C to generate intermediates with one negative charge.
  • the unstable intermediates decompose immediately to produce tetrafluorovinyl- azide.
  • the tetrafluorovinylazide decomposes at a convenient rate at a temperature of 25 to 40°C and lose nitrogen to form 2,3,3-trifluoro-2H- aziridine.
  • 2,3,3-trifluoro-2H-aziridine reacts with hydrogen fluoride at a temperature of 25°C to produce tetrafluoroaziridine.
  • T c " T b /[A T +B T ⁇ ⁇ , ⁇ ,+ ⁇ ( ⁇ njATi) 2 +Dr( ⁇ ⁇ , ⁇ ,) 3 ]
  • ⁇ 0 [0.315 ⁇ b +ln(P c 7l.01325)]/(0.0838(p b Hn T br ' )
  • the Figure 1 shows the principle of the ORC cycle.
  • the total heat absorption process should be from point 1 to point 3.
  • the total heat can be calculated as the efficiency ⁇ then can be written as, . ( 5)
  • the efficiency of new molecules can be estimated by the equation (5), and the useful parameters in the new molecules are calculated by the Group Contribution Method.
  • Table 3 Results from efficiency calculations using group contribution method and final efficiency after calculations using enthalpies, software Refprop and group contribution method. Results from molecules according to the present invention
  • ⁇ is equal to: ( ⁇ GC) - (systematic error)
  • C1 takes the value of 1 or 0 according to whether the molecule is a compound of mono-carbon skeleton or not. However, the methane derivatives that contain CO, COO, CN, or COOH group are treated exceptionally; C1 takes the value of 0 for these compounds.
  • ROE, RCO, RCOO, and RNH denote numbers of ether, carbonyl, ester, and imine groups, respectively, divided by the total number of skeletal carbons.
  • RRNG and RARM denote numbers of aliphatic and aromatic rings, respectively, divided by the total number of skeletal carbons.
  • RUS denotes the total number of unsaturation in the carbon skeleton including aliphatic and aromatic rings divided by the total number of skeletal carbons.
  • RF, RCI, and so on, and RCOOH denote numbers of F, CI, and so on, and COOH, respectively, divided by the total number of hydrogen atoms in the corresponding pure hydrocarbon molecule.

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Engine Equipment That Uses Special Cycles (AREA)

Abstract

La présente invention concerne un fluide de travail pour cycle de Rankine organique, le fluide de travail comprenant au moins un composé de formule (I) : RNQ, où R est un groupe méthyle, éthyle, vinyle ou éthynyle fluoré ou non fluoré, N est un azote, la connexion de R-N est une structure cyclique ou une structure à chaîne linéaire, et Q est un hydrogène et/ou au moins un atome de fluor. L'invention concerne également un procédé de conversion d'énergie thermique en énergie mécanique, un procédé de production d'électricité, un système à cycle de Rankine organique, et l'utilisation du fluide de travail pour effectuer un transfert thermique ou dans un dispositif de production d'énergie mécanique. Le fluide de travail pour cycle de Rankine organique présente un rendement de conversion d'énergie élevé, une faible inflammabilité, une faible toxicité et un pouvoir corrosif faible sur le cuivre.
PCT/CN2011/073132 2011-04-21 2011-04-21 Fluide de travail pour cycle de rankine Ceased WO2012142765A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP11863895.6A EP2710086A4 (fr) 2011-04-21 2011-04-21 Fluide de travail pour cycle de rankine
CN201180070205.1A CN103717699B (zh) 2011-04-21 2011-04-21 用于兰金循环的工作流体
US14/111,908 US20140305125A1 (en) 2011-04-21 2011-04-21 Working fluid for rankine cycle
PCT/CN2011/073132 WO2012142765A1 (fr) 2011-04-21 2011-04-21 Fluide de travail pour cycle de rankine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2011/073132 WO2012142765A1 (fr) 2011-04-21 2011-04-21 Fluide de travail pour cycle de rankine

Publications (1)

Publication Number Publication Date
WO2012142765A1 true WO2012142765A1 (fr) 2012-10-26

Family

ID=47041040

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2011/073132 Ceased WO2012142765A1 (fr) 2011-04-21 2011-04-21 Fluide de travail pour cycle de rankine

Country Status (4)

Country Link
US (1) US20140305125A1 (fr)
EP (1) EP2710086A4 (fr)
CN (1) CN103717699B (fr)
WO (1) WO2012142765A1 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11480074B1 (en) 2021-04-02 2022-10-25 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11486330B2 (en) 2021-04-02 2022-11-01 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
US11493029B2 (en) 2021-04-02 2022-11-08 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11578706B2 (en) 2021-04-02 2023-02-14 Ice Thermal Harvesting, Llc Systems for generating geothermal power in an organic Rankine cycle operation during hydrocarbon production based on wellhead fluid temperature
US11592009B2 (en) 2021-04-02 2023-02-28 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11644014B2 (en) 2021-04-02 2023-05-09 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
US11959466B2 (en) 2021-04-02 2024-04-16 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power in an organic Rankine cycle operation
US12180861B1 (en) 2022-12-30 2024-12-31 Ice Thermal Harvesting, Llc Systems and methods to utilize heat carriers in conversion of thermal energy
US12312981B2 (en) 2021-04-02 2025-05-27 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US12534990B2 (en) 2023-12-15 2026-01-27 Ice Thermal Harvesting, Llc Power generation assemblies for hydraulic fracturing systems and methods

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106528900B (zh) * 2015-09-10 2023-05-05 中国海洋石油总公司 一种朗肯循环系统及其流体工质材料构建方法
CN105781647A (zh) * 2016-04-28 2016-07-20 张家港市华昌新材料科技有限公司 一种低压蒸汽发电的方法
CN108518249B (zh) * 2018-06-12 2023-12-12 匡亚剑 一种竖直排列式汽轮发电机
CN109886339B (zh) * 2019-02-25 2021-10-26 广东电网有限责任公司 一种化学物质的gwp回归预测方法及装置
CN119019986B (zh) * 2024-08-16 2025-10-28 珠海格力电器股份有限公司 复合制冷剂及其制备方法与应用、包含复合制冷剂的制冷装置

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3834166A (en) * 1973-04-13 1974-09-10 Union Carbide Corp Thermally stable lubricants for external combustion engines
US4430514A (en) * 1982-06-21 1984-02-07 The United States Of America As Represented By The Secretary Of The Navy Novel method for the preparation of CF3 NF2
US20110079043A1 (en) * 2009-10-01 2011-04-07 3M Innovative Properties Company Apparatus including hydrofluoroether with high temperature stability and uses thereof

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4446068A (en) * 1967-04-04 1984-05-01 The United States Of America As Represented By The Secretary Of The Navy N-Substituted fluoroaziridines and process for making
JPS55131096A (en) * 1979-03-30 1980-10-11 Daikin Ind Ltd Working fluid for rankine cycle
FR2483009A1 (fr) * 1980-05-23 1981-11-27 Inst Francais Du Petrole Procede de production d'energie mecanique a partir de chaleur utilisant un melange de fluides comme agent de travail
EP0127365A3 (fr) * 1983-05-20 1988-03-16 Imperial Chemical Industries Plc Pompes à chaleur
JPH04110383A (ja) * 1990-08-30 1992-04-10 Daikin Ind Ltd 熱伝達用流体
JP2765230B2 (ja) * 1992-11-19 1998-06-11 イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー １，１，２−トリフルオロエタンを含む冷媒組成物
JP2000169837A (ja) * 1998-12-04 2000-06-20 Matsushita Electric Ind Co Ltd 混合冷媒、フルオロアミンを含む混合作動流体および同作動流体を用いた冷凍サイクル装置
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
AR053107A1 (es) * 2004-12-21 2007-04-25 Honeywell Int Inc Composiciones estabilizadas de yodocarbono
DE102006035272B4 (de) * 2006-07-31 2008-04-10 Technikum Corporation, EVH GmbH Verfahren und Vorrichtung zur Nutzung von Niedertemperaturwärme zur Stromerzeugung
US7807074B2 (en) * 2006-12-12 2010-10-05 Honeywell International Inc. Gaseous dielectrics with low global warming potentials
US20090139232A1 (en) * 2007-12-03 2009-06-04 Collis Matthew P Ambient Temperature Energy Generating System

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3834166A (en) * 1973-04-13 1974-09-10 Union Carbide Corp Thermally stable lubricants for external combustion engines
US4430514A (en) * 1982-06-21 1984-02-07 The United States Of America As Represented By The Secretary Of The Navy Novel method for the preparation of CF3 NF2
US20110079043A1 (en) * 2009-10-01 2011-04-07 3M Innovative Properties Company Apparatus including hydrofluoroether with high temperature stability and uses thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
See also references of EP2710086A4 *
W. BLUD BETA ET AL.: "Sulfenylaziridine.", CHEMISCHE BERICHTE., vol. 114, no. 4, 1981, pages 1539 - 1541, XP055091152 *

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11905934B2 (en) 2021-04-02 2024-02-20 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11680541B2 (en) 2021-04-02 2023-06-20 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
US11493029B2 (en) 2021-04-02 2022-11-08 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11542888B2 (en) 2021-04-02 2023-01-03 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11549402B2 (en) 2021-04-02 2023-01-10 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11572849B1 (en) 2021-04-02 2023-02-07 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11578706B2 (en) 2021-04-02 2023-02-14 Ice Thermal Harvesting, Llc Systems for generating geothermal power in an organic Rankine cycle operation during hydrocarbon production based on wellhead fluid temperature
US11592009B2 (en) 2021-04-02 2023-02-28 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11598320B2 (en) 2021-04-02 2023-03-07 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11624355B2 (en) 2021-04-02 2023-04-11 Ice Thermal Harvesting, Llc Modular mobile heat generation unit for generation of geothermal power in organic Rankine cycle operations
US11644014B2 (en) 2021-04-02 2023-05-09 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
US11668209B2 (en) 2021-04-02 2023-06-06 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11879409B2 (en) 2021-04-02 2024-01-23 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11732697B2 (en) 2021-04-02 2023-08-22 Ice Thermal Harvesting, Llc Systems for generating geothermal power in an organic Rankine cycle operation during hydrocarbon production based on wellhead fluid temperature
US11761433B2 (en) 2021-04-02 2023-09-19 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power in an organic Rankine cycle operation
US11761353B2 (en) 2021-04-02 2023-09-19 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11486330B2 (en) 2021-04-02 2022-11-01 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11773805B2 (en) 2021-04-02 2023-10-03 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US11971019B2 (en) 2021-04-02 2024-04-30 Ice Thermal Harvesting, Llc Systems for generating geothermal power in an organic Rankine cycle operation during hydrocarbon production based on wellhead fluid temperature
US11933279B2 (en) 2021-04-02 2024-03-19 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11933280B2 (en) 2021-04-02 2024-03-19 Ice Thermal Harvesting, Llc Modular mobile heat generation unit for generation of geothermal power in organic Rankine cycle operations
US11946459B2 (en) 2021-04-02 2024-04-02 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US11959466B2 (en) 2021-04-02 2024-04-16 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
US12049875B2 (en) 2021-04-02 2024-07-30 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power in an organic Rankine cycle operation
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
US12104553B2 (en) 2021-04-02 2024-10-01 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US12110878B2 (en) 2021-04-02 2024-10-08 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US12135016B2 (en) 2021-04-02 2024-11-05 Ice Thermal Harvesting, Llc Systems for generating geothermal power in an organic Rankine cycle operation during hydrocarbon production based on wellhead fluid temperature
US12140124B2 (en) 2021-04-02 2024-11-12 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power at a drilling rig
US12146475B2 (en) 2021-04-02 2024-11-19 Ice Thermal Harvesting, Llc Systems and methods for generation of electrical power in an organic rankine cycle operation
US12163485B2 (en) 2021-04-02 2024-12-10 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US12454896B2 (en) 2021-04-02 2025-10-28 Ice Thermal Harvesting, Llc Systems and methods utilizing gas temperature as a power source
US12305624B2 (en) 2021-04-02 2025-05-20 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
US12385474B2 (en) 2021-04-02 2025-08-12 Ice Thermal Harvesting, Llc Systems for generating geothermal power in an organic Rankine cycle operation during hydrocarbon production based on working fluid temperature
US12180861B1 (en) 2022-12-30 2024-12-31 Ice Thermal Harvesting, Llc Systems and methods to utilize heat carriers in conversion of thermal energy
US12534990B2 (en) 2023-12-15 2026-01-27 Ice Thermal Harvesting, Llc Power generation assemblies for hydraulic fracturing systems and methods

Also Published As

Publication number Publication date
EP2710086A4 (fr) 2015-03-11
CN103717699B (zh) 2016-10-12
CN103717699A (zh) 2014-04-09
US20140305125A1 (en) 2014-10-16
EP2710086A1 (fr) 2014-03-26

Similar Documents

Publication Publication Date Title
EP2710086A1 (fr) Fluide de travail pour cycle de rankine
JP6637551B2 (ja) 有機ランキンサイクル作動流体として有用なクロロ−及びブロモ−フルオロオレフィン化合物
JP2017129146A (ja) 有機ランキンサイクル作動流体として有用なフルオロオレフィン化合物
CN101155893B (zh) 使用离子液体作为工作流体的吸收循环
JP7113803B2 (ja) テトラフルオロプロペン及びテトラフルオロエタンを含む組成物、動力サイクルにおけるその使用、並びに動力サイクル装置
CN101018931A (zh) 采用兰金循环系统对来自燃料电池的废热进行热能转换所用的工作流体
CN105154014A (zh) 包含(e)-1,1,1,4,4,4-六氟丁-2-烯的制冷剂
Zhang et al. Vapor-liquid equilibrium measurements and assessments of Low-GWP absorption working pairs (R32+ DMETEG, R152a+ DMETEG, and R161+ DMETEG) for absorption refrigeration systems
US20050188697A1 (en) Fluorinated ketone and fluorinated ethers as working fluids for thermal energy conversion
Demenay et al. Predictions of the ideal gas properties of refrigerant molecules
Minor et al. Nonflammable low GWP working fluid for organic Rankine cycles
WO2024247437A1 (fr) Système à cycle thermique et procédé à cycle thermique
Shahinfard Regression Analysis of Organic Working Medium for Low Temperature Rankine Cycle

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11863895

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2011863895

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 14111908

Country of ref document: US