CN103649264A - 1,3,3,3-四氟丙烯和氨的二元组合物 - Google Patents
1,3,3,3-四氟丙烯和氨的二元组合物 Download PDFInfo
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- CN103649264A CN103649264A CN201280035210.3A CN201280035210A CN103649264A CN 103649264 A CN103649264 A CN 103649264A CN 201280035210 A CN201280035210 A CN 201280035210A CN 103649264 A CN103649264 A CN 103649264A
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IZGCNPIQWCRGSF-PSHIPCJZSA-N trichothecane Chemical compound C([C@@]12C)CC(C)C[C@H]1O[C@H]1[C@@H](C)[C@]2(C)CC1 IZGCNPIQWCRGSF-PSHIPCJZSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OOTXFYSZXCPMPG-BMYLZFHVSA-N ursane Chemical compound C1CCC(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C)[C@H](C)[C@H]5[C@H]4CC[C@@H]3[C@]21C OOTXFYSZXCPMPG-BMYLZFHVSA-N 0.000 description 1
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
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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
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
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- 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
- C08J9/127—Mixtures of organic and inorganic blowing agents
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
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- C09K3/00—Materials not provided for elsewhere
- C09K3/30—Materials not provided for elsewhere for aerosols
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/5068—Mixtures of halogenated and non-halogenated solvents
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- C—CHEMISTRY; METALLURGY
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- 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
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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
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/132—Components containing nitrogen
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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
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/32—The mixture being azeotropic
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dispersion Chemistry (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及1,3,3,3-四氟丙烯和氨的二元组合物及其用途，特别是作为传热流体。
Description
技术领域
本发明涉及1,3,3,3-四氟丙烯的二元组合物及其用途，特别是作为传热流体。
背景技术
基于碳氟化合物的流体广泛地用于通过蒸气压缩来传输热量的系统，特别是空调、热泵、制冷或冷冻装置。这些装置共同点在于它们基于包括如下的热力学循环：在低压下的流体蒸发(其中该流体吸收热量)；该经蒸发的流体的压缩直至高压；在高压下该经蒸发的流体的冷凝以得到液体(其中该流体放出热量)；以及该流体的压力降低以完成该循环。
传热流体(其可为纯化合物或者化合物的混合物)的选择一方面受流体的热力学性质控制，且另一方面受额外的约束条件控制。因此，特别重要的标准是所考虑的流体对环境的影响。具体地说，氯化化合物(氯氟烃和氢氯氟烃)表现出破坏臭氧层的缺点。因此，今后，非氯化化合物例如氢氟烃、氟代醚和氟烯烃相对于氯化化合物通常是优选的。
但是，有必要开发表现出比当前使用的传热流体低的全球增温潜势(GWP)且表现出相等或改善的性能的其它传热流体。
氨作为传热流体的用途是已知的。但是，许多问题与该化合物有关：与氢氟烃相比非常高的压缩机出口温度；不存在回油且需要安装油分离器；由于该产品的毒性，允许的总装料有时受限。
文献WO2007/126414描述了传热化合物的很多种混合物且特别是“包含”1,3,3,3-四氟丙烯(HFO-1234ze)和氨的混合物。没有提供包含这两种化合物(不论具有或不具有额外的化合物)的组合物的实例，而且，没有提出有关这些化合物的任何相对浓度范围。
文献US2006/0243945描述了传热化合物的很多种混合物且特别是包含HFO-1234ze的混合物和包含氨的混合物，但是，没有公开这两种化合物的组合。
文献WO2008/009922描述了传热组合物，特别是通常基于1,2,3,3,3-五氟丙烯(HFO-1225ye)和四氟丙烯(HFO-1234)(优选2,3,3,3-四氟丙烯或HFO-1234yf)的传热组合物，其可包含选自特别包含氨的列表的额外化合物。
文献WO2008/027555描述了传热组合物，特别是基于HFO-1225ye或者基于HFO-1234yf的传热组合物，其可包含可特别地为氨的额外化合物。
但是，仍然需要开发表现出相对低的GWP且能够替代普通传热流体的其它传热流体。
具体地说，希望开发具有低GWP的其它传热流体，其是准共沸的、实际上甚至是共沸的，和/或其表现出与普通传热流体(例如R404A或R410A)相比良好的能量性能。
发明内容
本发明首先涉及1,3,3,3-四氟丙烯和氨的二元组合物。
根据一个实施方式，所述组合物包含：
-40%-99%的氨和1%-60%的1,3,3,3-四氟丙烯；
-优选地，60%-98%的氨和2%-40%的1,3,3,3-四氟丙烯；
-优选地，70%-95%的氨和5%-30%的1,3,3,3-四氟丙烯；
-优选地，75%-90%的氨和10%-25%的1,3,3,3-四氟丙烯；
-优选地，78%-85%的氨和15%-22%的1,3,3,3-四氟丙烯。
根据一个实施方式，所述1,3,3,3-四氟丙烯为顺式形式、或者反式形式、或者顺式形式和反式形式的混合物，而且，优选地，所述1,3,3,3-四氟丙烯的至少80%或至少90%或至少95%或至少98%或至少99%为反式形式。
本发明还涉及上述组合物作为传热流体的用途。
根据一个实施方式，所述组合物是准共沸的，优选共沸的。
本发明还涉及传热组合物，其包含上述组合物以及选自如下的一种或多种添加剂：润滑剂、稳定剂、表面活性剂、示踪剂、荧光剂、气味剂、增溶剂、以及它们的混合物，所述传热组合物优选包含至少一种稳定剂。
本发明还涉及包含蒸气压缩回路的传热装置，所述蒸气压缩回路含有作为传热流体的本发明组合物或者含有本发明的传热组合物。
根据一个实施方式，所述装置选自用于热泵加热、空气调节、制冷或冷冻以及兰金循环的移动或固定设备，且特别是选自机动车辆空调系统。
本发明还涉及借助于包含传热流体的蒸气压缩回路加热或冷却液体或形体的方法，所述方法相继包括传热流体的蒸发、传热流体的压缩、热流体的凝结、以及传热流体的压力降低，其中所述传热流体为本发明的组合物。
根据一个实施方式，所述方法是用于冷却流体或形体(body)的方法，其中所述经冷却的流体或形体的温度为-15℃～15℃、且优选-10℃～10℃、更特别优选-5℃～5℃；或者，所述方法是用于加热流体或形体的方法，其中所述经加热的流体或形体的温度为30℃～90℃、且优选35℃～60℃、更特别优选40℃～50℃。
根据一个实施方式，所述方法是用于冷却流体或形体的方法，其中所述经冷却的流体或形体的温度为-40℃～-10℃、且优选-35℃～-25℃、更特别优选-30℃～-20℃。
根据一个实施方式，所述方法是用于加热流体或形体的方法，其中所述经加热的流体或形体的温度大于90℃、优选大于或等于100℃、或者大于或等于110℃，且优选小于或等于120℃。
本发明还涉及用于降低包含含有初始传热流体的蒸气压缩回路的传热设备的环境影响的方法，所述方法包括用最终传导流体替换所述蒸气压缩回路中的所述初始传热流体的步骤，所述最终传导流体表现出低于所述初始传热流体的GWP，其中最终传热流体为本发明的组合物。
本发明还涉及本发明的组合物作为溶剂的用途。
本发明还涉及本发明的组合物作为发泡剂的用途。
本发明还涉及本发明的组合物作为推进剂、优选用于气溶胶的推进剂的用途。
本发明还涉及本发明的组合物作为清洗剂的用途。
本发明使得可满足现有技术状态中意识到的需要。更具体地说，本发明提供能够(尤其)用作传热流体的低GWP的新型组合物，特别是用作普通传热流体的替代物。
具体地说，本发明提供共沸或准共沸组合物。
在一些实施方式中，本发明提供这样的传热流体，其与普通传热流体相比表现出良好的能量性能。
在一些实施方式中，本发明的组合物特别地表现出与现有技术状态的组合物相比改善的体积容量和/或改善的性能系数。
最后，本发明使得可部分或完全克服常规地与氨有关且在前面列出的问题。
附图说明
图1表示HFO-1234ze和NH3的二元混合物在5℃下的蒸气/液体平衡数据，其证明存在共沸物和准共沸物。在横坐标上示出在0和1(=100%)之间的NH3比例，而且，在纵坐标上示出以巴计的压力。
具体实施方式
现在在下面的说明书中更详细且无隐含限制地描述本发明。
除非另有说明，在整个本专利申请中，所示的化合物比例以摩尔百分数给出。
根据本专利申请，全球增温潜势(GWP)是根据“The Scientific Assessmentof Ozone Depletion,2002,a Report of the World Meteorological Association’sGlobal Ozone Research and Monitoring Project”中表明的方法相对于二氧化碳并且相对于100年的时间定义的。
术语“传热化合物”(相应地“传热流体”(或制冷剂))理解为指在蒸气压缩回路中能够在低温和低压下蒸发时吸收热量并且在高温和高压下凝结时放出热量的化合物(相应地流体)。通常地，传热流体可包含仅一种、两种、三种或超过三种的传热化合物。
术语“传热组合物”理解为是指包含传热流体以及任选的一种或多种添加剂(其不是用于预期应用的传热化合物)的组合物。
所述添加剂可特别地选自润滑剂、稳定剂、表面活性剂、示踪剂、荧光剂、气味剂以及增溶剂。
当存在稳定剂时，其在传热组合物中优选占至多5重量%。
所述稳定剂可尤其选自胺化合物，特别是选自三乙基胺，三丁基胺，二异丙基胺，三异丙基胺，三异丁基胺，对苯二胺，二苯胺，二烷基胺，N-(1-甲基乙基)-2-丙胺，呈现烷基取代基的杂氮环己基(piperidyl)、哌啶基(piperidinyl)、哌嗪酮和烷氧基哌啶基化合物，2,2,6,6-四甲基-4-哌啶酮，2,2,6,6-四甲基-4-哌啶醇，癸二酸双(1,2,2,6,6-五甲基哌啶基)酯，癸二酸二(2,2,6,6-四甲基-4-哌啶基)酯，聚(N-羟乙基-2,2,6,6-四甲基-4-羟基哌啶基琥珀酸酯)，以及这些的组合。这些稳定剂的详细描述出现在例如文献WO2008/042066中。
所述稳定剂还可选自二苯甲酮衍生物且特别地选自2,5-二氟二苯甲酮、2',5'-二羟基苯乙酮、2-氨基二苯甲酮、2-氯二苯甲酮、2-氟二苯甲酮、2-羟基二苯甲酮、2-甲基二苯甲酮、2-氨基-4'-氯二苯甲酮、2-氨基-4'-氟二苯甲酮、2-氨基-5-溴-2'-氯二苯甲酮、2-氨基-5-氯二苯甲酮、2-氨基-5-氯-2'-氟二苯甲酮、2-氨基-5-硝基二苯甲酮、2-氨基-5-硝基-2'-氯二苯甲酮、2-氨基-2',5-二氯二苯甲酮、2-氯-4'-氟二苯甲酮、2-羟基-4-甲氧基二苯甲酮、2-羟基-5-氯二苯甲酮、2-甲基氨基-5-氯二苯甲酮、3-甲基二苯甲酮、3-硝基二苯甲酮、3-硝基-4'-氯-4-氟二苯甲酮、4-氯二苯甲酮、4-氟二苯甲酮、4-羟基二苯甲酮、4-甲氧基二苯甲酮、4-甲基二苯甲酮、4-硝基二苯甲酮、4-苯基二苯甲酮、4-氯-3-硝基二苯甲酮、4-羟基-4'-氯二苯甲酮、2,4-二羟基二苯甲酮、2,4-二甲基二苯甲酮、2,5-二甲基二苯甲酮、3,4-二氨基二苯甲酮、3,4-二氯二苯甲酮、3,4-二氟二苯甲酮、3,4-二羟基二苯甲酮、3,4-二甲基二苯甲酮、4,4'-双(二乙基氨基)二苯甲酮、4,4'-双(二甲基氨基)二苯甲酮、4,4'-二氯二苯甲酮、4,4'-二氟二苯甲酮、4,4'-二羟基二苯甲酮、4,4'-二甲氧基二苯甲酮、以及这些的组合。这些稳定剂的详细描述出现在例如文献WO2008/027596中。
所述稳定剂还可选自酚类化合物且特别地选自2,6-二(叔丁基)-4-甲基苯酚、2,6-二(叔丁基)-4-乙基苯酚、2,4-二甲基-6-(叔丁基)苯酚、生育酚、对苯二酚、叔丁基对苯二酚、4,4'-硫代双(2-甲基-6-(叔丁基)苯酚、4,4'-硫代双(3-甲基-6-(叔丁基)苯酚)、2,2'-硫代双(4-甲基-6-(叔丁基)苯酚)、4,4'-亚甲基双(2,6-二(叔丁基)苯酚)、4,4'-双(2,6-二(叔丁基)苯酚)、2,2'-亚甲基双(4-乙基-6-(叔丁基)苯酚)、2,2'-亚甲基双(4-甲基-6-(叔丁基)苯酚)、4,4’-亚丁基双(3-甲基-6-(叔丁基)苯酚)、4,4’-异亚丙基双(2,6-二(叔丁基)苯酚)、2,2'-亚甲基双(4-甲基-6-壬基苯酚)、2,2'-异亚丁基双(4,6-二甲基苯酚)、2,2'-亚甲基双(4-甲基-6-环己基苯酚)、2,2'-亚甲基双(4-乙基-6-(叔丁基)苯酚)、丁基化羟基甲苯(BHT)、2,6-二(叔-α-二甲基氨基)-对-甲酚、4,4’-硫代双(6-(叔丁基)-间-甲酚)、酰氨基苯酚、2,6-二(叔丁基)-4-(N,N'-二甲基氨甲基)苯酚、双(3-甲基-4-羟基-5-(叔丁基)苯甲基)硫醚、双(3,5-二(叔丁基)-4-羟基苯甲基)硫醚、以及这些的组合。这些稳定剂的详细描述出现在例如文献WO2008/027594中。
所述稳定剂还可选自烷基硅烷化合物且特别地选自式SinR2n+2的经取代的硅烷，其中各R独立地表示H、额外的甲硅烷基、烷基、烷氧基、胺基团、乙烯基或苯基且其中所述基团R可被卤素或胺基团取代。优选双(二甲基氨基)甲基硅烷、三(三甲基甲硅烷基)硅烷、乙烯基三乙氧基硅烷和乙烯基三甲氧基硅烷。这些稳定剂的详细描述出现在例如文献WO2008/027595中。
所述稳定剂还可选自离子液体且特别是包含选自如下的阳离子的离子液体：吡啶
、哒嗪
、嘧啶
、吡嗪、咪唑
、吡唑
、噻唑、
唑
、三唑
、
和铵阳离子，所述阳离子任选地被取代，而且，所述离子液体包含选自如下的阴离子：[CH3CO2]–、[HSO4]–、[CH3OSO3]–、[C2H5OSO3]–、[AlCl4]–、[CO3]2–、[HCO3]–、[NO2]–、[NO3]–、[SO4]2–、[PO4]3–、[HPO4]2–、[H2PO4]–、[HSO3]–、[CuCl2]–、Cl–、Br–、I–、SCN–以及氟化阴离子。这些稳定剂的详细描述出现在例如文献WO2009/042855中。
所述稳定剂还可选自具有下式的氧杂环丁烷：
其中基团R1-R6相同或不同且可选自氢、取代或未取代的烷基、以及取代或未取代的芳基，且所述稳定剂特别地选自3-乙基-3-羟基甲基氧杂环丁烷、3-乙基-3-(苯氧基甲基)氧杂环丁烷和3-乙基-3-((2-乙基己氧基)甲基)氧杂环丁烷。这些稳定剂的详细描述出现在例如文献WO2008/027519中。
所述稳定剂还可选自硫醇且特别地选自甲硫醇、乙硫醇、辅酶A、二巯基琥珀酸、(R)-2-(4-甲基环己烯-3-基)丙烷-2-硫醇、半胱氨酸和硫辛酰胺，和/或选自硫酯，特别是选自苄基苯基硫醚、二苯基硫醚、二苄基硫醚、3,3'-硫代二丙酸双十八烷基酯、3,3'-硫代丙酸双十二烷基酯，以及这些的组合。这些稳定剂的详细描述出现在例如文献WO2008/027517中。
所述稳定剂还可选自抗坏血酸、对苯二甲酸酯(特别是对苯二甲酸二乙烯酯或对苯二甲酸二苯酯)、硝基甲烷、以及这些的组合。这些稳定剂的详细描述出现在例如文献WO2008/027518中。
所述稳定剂还可选自内酯且特别地选自γ-丁内酯、葡萄糖酸δ-内酯、γ-十一烷酸内酯、6,7-二氢-4(5H)-苯并呋喃酮、5,7-双(1,1-二甲基乙基)-3-[2,3(或3,4)-二甲基苯基]-2(3H)-苯并呋喃酮、以及这些的组合。这些稳定剂的详细描述出现在例如文献WO2008/027516中。
所述稳定剂还可选自萜烯、萜烯酯(terpenoide)和富勒烯且特别是选自异戊二烯、月桂烯、别罗勒烯、β-罗勒烯、特惹烯、柠檬烯、视黄醛、蒎烯、薄荷醇、香叶醇、法呢醇、叶绿醇、维生素A、萜品烯、Δ3-蒈烯、萜品油烯、水芹烯、葑烯、番茄红素、β-胡萝卜素、玉米黄质、肝黄质、异维甲酸、松香烷、豚草烷、马兜铃烷、阿替斯烷(atisane)、贝叶烷、没药烷、莰烷、丁香烷、柏木烷、达玛烷、补身烷、艾里莫芬烷、桉叶烷、葑烷、伽马蜡烷、大根香叶烷、赤霉素烷、木藜芦毒烷、愈创木烷、雪松烷、藿烷、律草烷、贝壳杉烷、半日花烷、羊毛甾烷、羽扇烷、对-薄荷烷、齐墩果烷、蛇胞菌烷(ophiobolane)、苦树烷(picrasane)、海松烷、蒎烷、罗汉松烷、原萜烷、玫瑰烷、紫杉烷、苧烷、孢菌烷(trichothecane)、乌散烷、巴克敏斯特富勒烯、[5,6]-富勒烯-C70、富勒烯-C76、富勒烯-C78和富勒烯-C84、以及这些的组合。这些稳定剂的详细描述出现在例如文献WO2008/027514中。
所述稳定剂还可选自芳基烷基醚、聚氧化烯化的芳族化合物或者烷基化的芳族化合物(线型或支化的烷基苯润滑剂)且特别地选自下式的化合物：
其中n具有数值1、2或3，而且，R1是包含1-16个碳原子的烷基、或者包含至少一个-CH2CH2O-基团的聚氧化烯基团、以及这些的组合。实例为茴香醚、1,4-二甲氧基苯、1,4-二乙氧基苯和1,3,5-三甲氧基苯。这些稳定剂的详细描述出现在例如文献WO2008/027513中。
所述稳定剂还可选自官能化的全氟聚醚且特别地选自文献WO2008/027512(特别是第20页第1行至第25页第5行)中详细描述的那些。
所述稳定剂还可选自环氧化物且特别地选自1,2-环氧丙烷、1,2-环氧丁烷、丁基苯基缩水甘油醚、戊基苯基缩水甘油醚、己基苯基缩水甘油醚、庚基苯基缩水甘油醚、辛基苯基缩水甘油醚、壬基苯基缩水甘油醚、癸基苯基缩水甘油醚、缩水甘油基甲基苯基醚、1,4-缩水甘油基苯基二醚、4-甲氧基苯基缩水甘油醚、萘基缩水甘油醚、1,4-二缩水甘油基萘基二醚、丁基苯基缩水甘油醚、正丁基缩水甘油醚、异丁基缩水甘油醚、己二醇二缩水甘油醚、烯丙基缩水甘油醚、聚丙二醇二缩水甘油醚、以及这些的组合。
所述稳定剂还可为：
-硫代磷酸酯，特别是如文献WO2008/027512的第25页第7-17行中所述的；
-丁基化的三苯基硫代磷酸酯，特别是如文献WO2008/027512的第25页第18-26行中所述的；
-有机磷酸酯，特别是如文献WO2008/027512的第26页第1行-第27页第2行中所述的；
-亚磷酸酯，特别是如文献WO2008/027512的第26页第3-12行中所述的；
-氟化的环氧化物，特别是如文献WO2008/027512的第31页第6-23行中所述的；
-芳基硫醚，特别地选自苄基苯基硫醚、二苯基硫醚、二苄基硫醚、以及它们的组合。
所述稳定剂还可为来自所有前述不同种类的化合物的组合。
作为润滑剂，可尤其使用矿物来源的油、硅油、天然来源的石蜡、环烷、合成石蜡、烷基苯、聚(α-烯烃)、聚亚烷基二醇、多元醇酯和/或聚乙烯基醚。
作为示踪剂(能够被检测的试剂)，可提及氘代或未氘代的氢氟烃、氘代烃、全氟烃、氟代醚、溴化化合物、碘化化合物、醇、醛、酮、一氧化二氮、以及这些的组合。所述示踪剂不同于构成传热流体的传热化合物。
作为增溶剂，可提及烃、二甲醚、聚氧亚烷基醚、酰胺、酮、腈、氯烃、酯、内酯、芳基醚、氟代醚和1,1,1-三氟烷烃。所述增溶剂不同于构成传热流体的传热化合物。
作为荧光剂，可提及萘二甲酰亚胺、苝、香豆素、蒽、菲、夹氧杂蒽、噻吨(thioxanthene)、苯并夹氧杂蒽、荧光素、以及这些的衍生物和组合。
作为气味剂，可提及丙烯酸烷基酯、丙烯酸烯丙基酯、丙烯酸、丙烯酰基酯(acryl ester)、烷基醚、烷基酯、炔、醛、硫醇、硫醚、二硫化物、异硫氰酸烯丙基酯、链烷酸、胺、降冰片烯、降冰片烯衍生物、环己烯、芳族杂环化合物、驱蛔萜、邻甲氧基(甲基)苯酚、以及这些的组合。
根据本发明的传热方法基于包含含有传热流体的蒸气压缩回路的设备的使用。该传热方法可为其中对流体或形体进行加热或冷却的方法。
含有传热流体的蒸气压缩回路包含至少一个蒸发器、一个压缩机、一个凝结器和一个膨胀装置、以及在这些构件之间的用于输送传热流体的管线。蒸发器和凝结器包含允许传热流体与其它流体或形体之间的热量交换的热交换器。
作为压缩机，可尤其使用单级或多级离心压缩机或者小型离心压缩机。还可使用旋转式压缩机、活塞式压缩机或螺杆式压缩机。压缩机可通过电动机或通过燃气涡轮机(例如通过来自车辆的废气进行进料，用于移动应用)或者通过传动装置驱动。
所述设备可包含用于发电的涡轮机(兰金循环)。
所述设备还可任选地包含至少一个用于在传热流体回路与待加热或冷却的流体或形体之间输送热量(发生或不发生状态变化)的热交换流体回路。
所述设备还可任选地包含两个(或更多个)含有相同或不同传热流体的蒸气压缩回路。例如，蒸气压缩回路可彼此耦合。
蒸气压缩回路根据常规的蒸气压缩循环操作。所述循环包括：在相对低压下传热流体从液相(或液体/蒸气两相体系)到蒸气相的状态变化，然后，压缩蒸气相的流体直至相对高压，在相对高压下传热流体从蒸气相到液相的状态变化(凝结)，以及降低压力以重新开始循环。
在冷却方法的情况下，在传热流体的蒸发期间，传热流体吸收了得自正在被(直接或间接地，通过热交换流体)冷却的流体或形体的热量，这发生在相对于环境的相对低的温度下。所述冷却方法包括空气调节方法(使用移动系统(例如在车辆中的移动系统)或者固定系统)、制冷方法和冷冻方法或低温方法。
在加热方法的情况下，热量被从传热流体(在其凝结期间)赋予(直接或间接地，通过热交换流体)至正在被加热的流体或形体，这发生在相对于环境的相对高的温度下。在该情况下，使得可实施所述传热的设备称为“热泵”。
可采用用于使用本发明的传热流体的任意类型的热交换器，且尤其是同向流动式热交换器，或者，优选地，逆向流动式热交换器。
本发明上下文中所用的传热流体是HFO-1234ze与NH3的二元组合物。
HFO1234ze可为顺式形式、或者反式形式、或者顺式形式和反式形式的混合物，其中，优选地，1,3,3,3-四氟丙烯的至少80%或至少90%或至少95%或至少98%或至少99%为反式形式。
术语“二元组合物”理解为是指由HFO-1234ze和NH3组成的组合物或者基本上包含HFO-1234ze和NH3的组合物，但是，其可包含比例低于1%、优选低于0.5%、优选低于0.1%、优选低于0.05%、且优选低于0.01%的杂质。
根据特定实施方式，传热流体中的HFO-1234ze比例可为：0.1%～5%；或者5%～10%；或者10%～15%；或者15%～20%；或者20%～25%；或者25%～30%；或者30%～35%；或者35%～40%；或者40%～45%；或者45%～50%；或者50%～55%；或者55%～60%；或者60%～65%；或者65%～70%；或者70%～75%；或者75%～80%；或者80%～85%；或者85%～90%；或者90%～95%；或者95%～99.9%。
根据特定实施方式，传热流体中的NH3比例可为：0.1%～5%；或者5%～10%；或者10%～15%；或者15%～20%；或者20%～25%；或者25%～30%；或者30%～35%；或者35%～40%；或者40%～45%；或者45%～50%；或者50%～55%；或者55%～60%；或者60%～65%；或者65%～70%；或者70%～75%；或者75%～80%；或者80%～85%；或者85%～90%；或者90%～95%；或者95%～99.9%。
在作为传热流体的用途的情况下，优选在该混合物中不具有太高比例的NH3，以避免在压缩机出口处过高的温度上升。
在上述组合物中，一些具有共沸或准共沸的优点。例如，在5℃(±1℃)的温度下和在5.6巴(±0.5巴)的压力下，对于约81摩尔%(±4%)的NH3比例获得对于二元混合物HFO-1234ze/NH3的共沸物。
术语“准共沸”表示在恒温下，液体饱和压力和蒸汽饱和压力基本上相同(相对于液体饱和压力，最大压力差为10%，或甚至有利地为5%)的组合物。
对于“共沸”组合物，在恒温下，最大压力差在0%附近。
这些传热流体具有容易使用的优点。在无明显偏移(glide)的情况下，循环组成没有明显变化，并且在泄漏的情况下，组成同样没有明显变化。
另外，一些本发明的组合物表现出与一些已知传热流体相比改善的性能，特别是对于中温冷却方法，即，其中经冷却的流体或形体的温度为-15℃～15℃，优选-10℃～10℃、更特别优选-5℃～5℃(理想地约0℃)的那些。
此外，一些本发明的组合物表现出与一些已知传热流体相比改善的性能，特别是对于中温加热方法，即，其中经加热的流体或形体的温度为30℃～80℃、优选35℃～55℃、或者特别优选40℃～50℃(理想地约45℃)的那些。
在前述“中温冷却或加热”方法中，蒸发器处的传热流体的入口温度优选是-20℃～10℃、特别是-15℃～5℃、更特别优选-10℃～0℃、且例如约-5℃；而且，凝结器中的传热流体的凝结开始温度优选是25℃～90℃、特别是30℃～70℃、更特别优选35℃～55℃、且例如约50℃。这些方法可为制冷方法、空气调节方法或加热方法。
一些组合物还适用于高温加热方法，即，其中经加热的流体或形体的温度大于90℃、例如大于或等于100℃、或者大于或等于110℃、且优选小于或等于120℃的那些。
一些本发明的组合物表现出与一些已知传热流体相比改善的性能，特别是对于低温制冷方法，即，其中经冷却的流体或形体的温度为-40℃～-10℃、优选-35℃～-25℃、更特别优选-30℃～-20℃(理想地约-25℃)的那些。
在前述“低温制冷”方法中，蒸发器处的传热流体的入口温度优选是-45℃～-15℃、特别是-40℃～-20℃、更特别优选-35℃～-25℃、且例如约-30℃；而且，凝结器中的传热流体的凝结开始温度优选是25℃～80℃、特别是30℃～60℃、更特别优选35℃～55℃、且例如约40℃。
更通常地，本发明的组合物可用于替代任意传热应用例如机动车辆空气调节中的任意传热流体。例如，本发明的组合物可用于替代：
-1,1,1,2-四氟乙烷(R134a)；
-1,1-二氟乙烷(R152a)；
-1,1,1,3,3-五氟丙烷(R245fa)；
-五氟乙烷(R125)、1,1,1,2-四氟乙烷(R134a)和异丁烷(R600a)的混合物，即R422产品；
-二氟一氯甲烷(R22)；
-51.2%的五氟氯乙烷(R115)和48.8%的二氟一氯甲烷(R22)的混合物，即R502；
-任何烃；
-20%的二氟甲烷(R32)、40%的五氟乙烷(R125)和40%的1,1,1,2-四氟乙烷(R134a)的混合物，即R407A；
-23%的二氟甲烷(R32)、25%的五氟乙烷(R125)和52%的1,1,1,2-四氟乙烷(R134a)的混合物，即R407C；
-30%的二氟甲烷(R32)、30%五氟乙烷(R125)和40%的1,1,1,2-四氟乙烷(R134a)的混合物，即R407F；
-R1234yf(2,3,3,3-四氟丙烯)；
-R1234ze(1,3,3,3-四氟丙烯)。
本发明的组合物除了作为传热流体的用途外，它们还可用作发泡剂、推进剂(例如用于气溶胶)、清洗剂或溶剂。
作为推进剂，本发明的组合物可单独使用或者与已知推进剂组合使用。所述推进剂包含本发明的组合物、优选由本发明的组合物组成。必须被喷射的活性物质可与推进剂和惰性化合物、溶剂或其它添加剂混合，以形成待喷射的组合物。优选地，待喷射的组合物为气溶胶。
作为发泡剂，本发明的组合物可被包含在发泡组合物中，所述发泡组合物优选包含一种或多种能够在适宜的条件下反应并形成泡沫或蜂窝状结构体的其它化合物，这是本领域技术人员已知的。
具体地说，本发明提供膨胀的热塑性产品的制备方法，包括：首先制备聚合物发泡组合物。典型地，聚合物发泡组合物通过使聚合物树脂增塑并且在初始压力下混合在发泡剂组合物的化合物中而制备。聚合物树脂的增塑可在热的作用下进行，加热聚合物树脂以使其充分地软化以混合在发泡剂组合物中。通常地，增塑温度接近于结晶聚合物的熔点或玻璃化转变温度。
本发明的组合物的其它用途包括作为溶剂、清洗剂等的用途。例如，可提及蒸气脱脂、精密清洗、电子电路清洗、干洗、喷砂清洗(abrasive cleaning)、用于润滑剂和脱模剂的沉积的溶剂、以及其它溶剂或表面处理。
实施例
下述实施例说明本发明，而非对其进行限制。
实施例1-共沸或准共沸组合物
使用油浴将装备有蓝宝石管的真空室冷却至5℃。一旦已经到达热平衡，用HFO-1234ze装填所述室，并且记录达到平衡时的压力。将一定量的NH3引入所述室中，并且将内容物混合以加速平衡。在平衡下，从气相和液相中取出最小量的样品用于具有热探测器的气相色谱法分析。
用HFO-1234ze和NH3的不同组合物获得的平衡数据示于图1中。
Claims (17)
1.1,3,3,3-四氟丙烯和氨的二元组合物。
2.权利要求1的组合物，包含：
○40%-99%的氨和1%-60%的1,3,3,3-四氟丙烯；
○优选地，60%-98%的氨和2%-40%的1,3,3,3-四氟丙烯；
○优选地，70%-95%的氨和5%-30%的1,3,3,3-四氟丙烯；
○优选地，75%-90%的氨和10%-25%的1,3,3,3-四氟丙烯；
○优选地，78%-85%的氨和15%-22%的1,3,3,3-四氟丙烯。
3.权利要求1或2的组合物，其中，所述1,3,3,3-四氟丙烯为顺式形式、或者反式形式、或者顺式形式和反式形式的混合物，且其中，优选地，所述1,3,3,3-四氟丙烯的至少80%或至少90%或至少95%或至少98%或至少99%为反式形式。
4.权利要求1-3之一的组合物作为传热流体的用途。
5.权利要求4的用途，其中，所述组合物是准共沸的，优选共沸的。
6.传热组合物，包含权利要求1-3之一的组合物以及选自如下的一种或多种添加剂：润滑剂、稳定剂、表面活性剂、示踪剂、荧光剂、气味剂、增溶剂、以及它们的混合物，所述传热组合物优选包含至少一种稳定剂。
7.包含蒸气压缩回路的传热设备，所述蒸气压缩回路含有作为传热流体的权利要求1-3之一的组合物或者含有权利要求6的传热组合物。
8.权利要求7的设备，选自用于热泵加热、空气调节、制冷或冷冻以及兰金循环的移动或固定设备，且特别地选自机动车辆空气调节系统。
9.借助于包含传热流体的蒸气压缩回路加热或冷却液体或形体的方法，所述方法相继包括传热流体的蒸发、传热流体的压缩、热流体的凝结、以及传热流体的压力降低，其中所述传热流体为权利要求1-3之一的组合物。
10.权利要求9的方法，其为用于冷却流体或形体的方法，其中经冷却的流体或形体的温度为-15℃～15℃、且优选-10℃～10℃、更特别优选-5℃～5℃；或者其为用于加热流体或形体的方法，其中经加热的流体或形体的温度为30℃～90℃、且优选35℃～60℃、更特别优选40℃～50℃。
11.权利要求9的方法，其为用于冷却流体或形体的方法，其中经冷却的流体或形体的温度为-40℃～-10℃、且优选-35℃～-25℃、更特别优选-30℃～-20℃。
12.权利要求9的方法，其为用于加热流体或形体的方法，其中经加热的流体或形体的温度大于90℃、优选大于或等于100℃、或者大于或等于110℃，且优选小于或等于120℃。
13.用于降低包含含有初始传热流体的蒸气压缩回路的传热设备的环境影响的方法，所述方法包括用最终传导流体替换所述蒸气压缩回路中的所述初始传热流体的步骤，所述最终传导流体表现出低于所述初始传热流体的GWP，其中最终传热流体为权利要求1-3之一的组合物。
14.权利要求1-3之一的组合物作为溶剂的用途。
15.权利要求1-3之一的组合物作为发泡剂的用途。
16.权利要求1-3之一的组合物作为推进剂、优选用于气溶胶的推进剂的用途。
17.权利要求1-3之一的组合物作为清洗剂的用途。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR11.54945 | 2011-06-07 | ||
| FR1154945A FR2976289B1 (fr) | 2011-06-07 | 2011-06-07 | Compositions binaires de 1,3,3,3-tetrafluoropropene et d'ammoniac |
| PCT/FR2012/051069 WO2012168607A1 (fr) | 2011-06-07 | 2012-05-14 | Compositions binaires de 1,3,3,3-tetrafluoropropene et d'ammoniac |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103649264A true CN103649264A (zh) | 2014-03-19 |
| CN103649264B CN103649264B (zh) | 2016-08-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280035210.3A Expired - Fee Related CN103649264B (zh) | 2011-06-07 | 2012-05-14 | 1,3,3,3-四氟丙烯和氨的二元组合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8951432B2 (zh) |
| EP (1) | EP2718388B1 (zh) |
| JP (1) | JP5890010B2 (zh) |
| KR (2) | KR20150043519A (zh) |
| CN (1) | CN103649264B (zh) |
| AU (1) | AU2012266111B2 (zh) |
| ES (1) | ES2637112T3 (zh) |
| FR (1) | FR2976289B1 (zh) |
| WO (1) | WO2012168607A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109187808A (zh) * | 2018-10-23 | 2019-01-11 | 重庆鹏凯精细化工有限公司 | 检测羟丙基甲基纤维素生产工艺回收气体中有机物的方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2957083B1 (fr) | 2010-03-02 | 2015-12-11 | Arkema France | Fluide de transfert de chaleur pour compresseur centrifuge |
| FR2959999B1 (fr) | 2010-05-11 | 2012-07-20 | Arkema France | Fluides de transfert de chaleur et leur utilisation dans des echangeurs de chaleur a contre-courant |
| FR2959997B1 (fr) | 2010-05-11 | 2012-06-08 | Arkema France | Fluides de transfert de chaleur et leur utilisation dans des echangeurs de chaleur a contre-courant |
| FR2964976B1 (fr) | 2010-09-20 | 2012-08-24 | Arkema France | Composition a base de 1,3,3,3-tetrafluoropropene |
| FR2964975B1 (fr) | 2010-09-20 | 2012-08-24 | Arkema France | Composition a base de 2,3,3,3-tetrafluoropropene |
| FR2964977B1 (fr) | 2010-09-20 | 2013-11-01 | Arkema France | Composition a base de 3,3,3-tetrafluoropropene |
| FR3003569B1 (fr) | 2013-03-20 | 2015-12-25 | Arkema France | Composition comprenant hf et 1,3,3,3-tetrafluoropropene |
| FR3079359B1 (fr) * | 2018-03-22 | 2020-10-09 | Arkema France | Utilisation du 1-chloro-2,3,3,3-tetrafluoropropene pour l'isolation ou l'extinction d'arcs electriques |
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| US20060243945A1 (en) * | 2005-03-04 | 2006-11-02 | Minor Barbara H | Compositions comprising a fluoroolefin |
| WO2007126414A2 (en) * | 2006-03-30 | 2007-11-08 | E. I. Du Pont De Nemours And Company | Compositions comprising a fluoroolefin |
| US20100186432A1 (en) * | 2007-07-27 | 2010-07-29 | E.I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins |
| WO2010148003A1 (en) * | 2009-06-15 | 2010-12-23 | Honeywell International Inc. | Compositions and methods comprising trifluoronitromethane |
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| US5387357A (en) * | 1992-09-25 | 1995-02-07 | E. I. Du Pont De Nemours And Company | Azeotropic or azeotrope-like compositions of ammonia and hydrofluorocarbons |
| JPH10130685A (ja) * | 1996-10-30 | 1998-05-19 | Daikin Ind Ltd | 冷凍装置 |
| JPH11351774A (ja) * | 1998-06-05 | 1999-12-24 | Matsushita Electric Ind Co Ltd | 空調冷凍装置 |
| JP2007145922A (ja) * | 2005-11-25 | 2007-06-14 | Japan Petroleum Exploration Co Ltd | 冷媒組成物 |
| GB0614080D0 (en) | 2006-07-17 | 2006-08-23 | Ineos Fluor Holdings Ltd | Heat transfer compositions |
| WO2008027513A2 (en) | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Aryl-alkyl ether, polyoxyalkylated aromatic, and alkylated aromatic stabilizers for fluoroolefins |
| JP2010513827A (ja) * | 2006-09-01 | 2010-04-30 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 閉ループ・サイクル中の選択された伝熱流体の循環方法 |
| WO2008027516A1 (en) | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Lactones for fluoroolefins |
| EP2069455A1 (en) | 2006-09-01 | 2009-06-17 | E.I. Du Pont De Nemours And Company | Terpene, terpenoid, and fullerene stabilizers for fluoroolefins |
| EP2057246A1 (en) | 2006-09-01 | 2009-05-13 | E.I. Du Pont De Nemours And Company | Thiol and thioether stabilizers for fluoroolefins |
| WO2008027596A2 (en) | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Benzophenone derivative stabilizers for fluoroolefins |
| WO2008027595A1 (en) | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Alkyl silane stabilizers for fluoroolefins |
| EP2057248A2 (en) | 2006-09-01 | 2009-05-13 | E.I. Du Pont De Nemours And Company | Phenol stabilizers for fluoroolefins |
| WO2008027519A1 (en) | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Oxetane stabilizers for fluoroolefins |
| EP2057247B1 (en) | 2006-09-01 | 2016-04-13 | E. I. du Pont de Nemours and Company | Ascorbic acid stabilizers for fluoroolefins |
| WO2008027512A2 (en) | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Functionalized perfluoropolyether stabilizers for fluoroolefins |
| WO2008042066A1 (en) | 2006-09-01 | 2008-04-10 | E.I. Du Pont De Nemours And Company | Amine stabilizers for fluoroolefins |
| EP2145150B8 (en) * | 2007-05-11 | 2016-08-10 | The Chemours Company FC, LLC | Method for exchanging heat in a vapor compression heat transfer system and a vapor compression heat transfer system comprising an intermediate heat exchanger with a dual-row evaporator or condenser |
| US20100200799A1 (en) | 2007-09-28 | 2010-08-12 | E.I. Du Pont De Nemours And Company | Ionic liquid stabilizer compositions |
| JP5592597B2 (ja) * | 2008-03-17 | 2014-09-17 | Ｊｘ日鉱日石エネルギー株式会社 | 冷凍機油及び冷凍機用作動流体組成物 |
| JP5390995B2 (ja) * | 2009-08-28 | 2014-01-15 | Ｊｘ日鉱日石エネルギー株式会社 | 冷凍機油および冷凍機用作動流体組成物 |
-
2011
- 2011-06-07 FR FR1154945A patent/FR2976289B1/fr not_active Expired - Fee Related
-
2012
- 2012-05-14 AU AU2012266111A patent/AU2012266111B2/en not_active Ceased
- 2012-05-14 EP EP12728678.9A patent/EP2718388B1/fr not_active Not-in-force
- 2012-05-14 KR KR20157008159A patent/KR20150043519A/ko not_active Ceased
- 2012-05-14 CN CN201280035210.3A patent/CN103649264B/zh not_active Expired - Fee Related
- 2012-05-14 WO PCT/FR2012/051069 patent/WO2012168607A1/fr active Application Filing
- 2012-05-14 ES ES12728678.9T patent/ES2637112T3/es active Active
- 2012-05-14 US US14/123,819 patent/US8951432B2/en not_active Expired - Fee Related
- 2012-05-14 JP JP2014514128A patent/JP5890010B2/ja not_active Expired - Fee Related
- 2012-05-14 KR KR1020137032443A patent/KR101538260B1/ko not_active Expired - Fee Related
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| US20060243945A1 (en) * | 2005-03-04 | 2006-11-02 | Minor Barbara H | Compositions comprising a fluoroolefin |
| WO2007126414A2 (en) * | 2006-03-30 | 2007-11-08 | E. I. Du Pont De Nemours And Company | Compositions comprising a fluoroolefin |
| CN101415793A (zh) * | 2006-03-30 | 2009-04-22 | 纳幕尔杜邦公司 | 包含氟烯烃的组合物 |
| US20100186432A1 (en) * | 2007-07-27 | 2010-07-29 | E.I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins |
| WO2010148003A1 (en) * | 2009-06-15 | 2010-12-23 | Honeywell International Inc. | Compositions and methods comprising trifluoronitromethane |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109187808A (zh) * | 2018-10-23 | 2019-01-11 | 重庆鹏凯精细化工有限公司 | 检测羟丙基甲基纤维素生产工艺回收气体中有机物的方法 |
| CN109187808B (zh) * | 2018-10-23 | 2021-09-03 | 重庆鹏凯精细化工有限公司 | 检测羟丙基甲基纤维素生产工艺回收气体中有机物的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101538260B1 (ko) | 2015-07-20 |
| CN103649264B (zh) | 2016-08-17 |
| ES2637112T3 (es) | 2017-10-10 |
| JP5890010B2 (ja) | 2016-03-22 |
| FR2976289B1 (fr) | 2013-05-24 |
| KR20150043519A (ko) | 2015-04-22 |
| WO2012168607A1 (fr) | 2012-12-13 |
| AU2012266111A1 (en) | 2014-01-23 |
| KR20140015530A (ko) | 2014-02-06 |
| FR2976289A1 (fr) | 2012-12-14 |
| US20140110623A1 (en) | 2014-04-24 |
| US8951432B2 (en) | 2015-02-10 |
| EP2718388B1 (fr) | 2017-07-12 |
| JP2014520183A (ja) | 2014-08-21 |
| AU2012266111B2 (en) | 2015-05-14 |
| EP2718388A1 (fr) | 2014-04-16 |
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