GB2540427B - Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) - Google Patents
Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf)Info
- Publication number
- GB2540427B GB2540427B GB1512593.3A GB201512593A GB2540427B GB 2540427 B GB2540427 B GB 2540427B GB 201512593 A GB201512593 A GB 201512593A GB 2540427 B GB2540427 B GB 2540427B
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrafluoropropene
- preparation
- 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
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/357—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of zinc, cadmium or mercury
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/132—Halogens; Compounds thereof with chromium, molybdenum, tungsten or polonium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/28—Regeneration or reactivation
- B01J27/32—Regeneration or reactivation of catalysts comprising compounds of halogens
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/12—Treating with free oxygen-containing gas
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/42—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst using halogen-containing material
- B01J38/46—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst using halogen-containing material fluorine-containing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
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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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00539—Pressure
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
- C07C21/185—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine tetrafluorethene
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- 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
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- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1512593.3A GB2540427B (en) | 2015-07-17 | 2015-07-17 | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| CN201680041643.8A CN107848916B (zh) | 2015-07-17 | 2016-07-14 | 用于制备2,3,3,3-四氟丙烯(1234yf)的制程 |
| PCT/GB2016/052145 WO2017013406A1 (en) | 2015-07-17 | 2016-07-14 | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| JP2018502143A JP6688383B2 (ja) | 2015-07-17 | 2016-07-14 | 2,3,3,3−テトラフルオロプロペン(1234yf)の調製プロセス |
| KR1020187004683A KR102676107B1 (ko) | 2015-07-17 | 2016-07-14 | 2,3,3,3-테트라플루오로프로펜(1234yf)의 제조 방법 |
| ES16750478T ES2864023T3 (es) | 2015-07-17 | 2016-07-14 | Proceso para la preparación de 2,3,3,3-tetrafluoropropeno (1234yf) |
| US15/745,505 US10899686B2 (en) | 2015-07-17 | 2016-07-14 | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| EP16750478.6A EP3325435B1 (en) | 2015-07-17 | 2016-07-14 | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1512593.3A GB2540427B (en) | 2015-07-17 | 2015-07-17 | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB201512593D0 GB201512593D0 (en) | 2015-08-26 |
| GB2540427A GB2540427A (en) | 2017-01-18 |
| GB2540427B true GB2540427B (en) | 2017-07-19 |
Family
ID=54013203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1512593.3A Active GB2540427B (en) | 2015-07-17 | 2015-07-17 | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10899686B2 (enExample) |
| EP (1) | EP3325435B1 (enExample) |
| JP (1) | JP6688383B2 (enExample) |
| KR (1) | KR102676107B1 (enExample) |
| CN (1) | CN107848916B (enExample) |
| ES (1) | ES2864023T3 (enExample) |
| GB (1) | GB2540427B (enExample) |
| WO (1) | WO2017013406A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6115550B2 (ja) | 2014-11-17 | 2017-04-19 | ダイキン工業株式会社 | HFC−245cbと(E)−HFO−1234zeとを含有する組成物から両化合物を分離する方法 |
| GB201712775D0 (en) * | 2017-08-09 | 2017-09-20 | Mexichem Fluor Sa De Cv | Compositions and uses thereof |
| US10233137B1 (en) * | 2017-10-13 | 2019-03-19 | Honeywell International Inc. | Method for removing unsaturated halogenated impurities from 2,3,3,3-tetrafluoropropene (HFO-1234yf) |
| US11209196B2 (en) | 2018-10-26 | 2021-12-28 | The Chemours Company Fc, Llc | HFO-1234ZE, HFO-1225ZC and HFO-1234YF compositions and processes for producing and using the compositions |
| BR112021022059A2 (pt) | 2018-10-26 | 2021-12-28 | Chemours Co Fc Llc | Composições de fluoropropeno, métodos de produção de uma mistura e de resfriamento, processos para transferência de calor, para tratamento de uma superfície e para formação de uma composição, sistema de refrigeração, aparelhos de refrigeração, uso da composição de fluoropropeno e método para substituição de um refrigerante |
| CN109438170B (zh) * | 2018-11-27 | 2022-02-01 | 浙江三美化工股份有限公司 | 一种2,3,3,3-四氟丙烯的制备方法 |
| GB2582364A (en) * | 2019-03-21 | 2020-09-23 | Mexichem Fluor Sa De Cv | Methods |
| JP7287965B2 (ja) | 2019-11-13 | 2023-06-06 | フジアン ヨンジン テクノロジー カンパニー リミテッド | 2,3,3,3-テトラフルオロプロペン(1234yf)および2,3-ジクロロ-1,1,1-トリフルオロプロパン(243db)の新しい合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070100175A1 (en) * | 2005-11-01 | 2007-05-03 | Miller Ralph N | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| WO2010059493A1 (en) * | 2008-11-19 | 2010-05-27 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
| WO2010123154A2 (en) * | 2009-04-23 | 2010-10-28 | Daikin Industries, Ltd. | Process for preparation of 2,3,3,3-tetrafluoropropene |
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| GB9104775D0 (en) | 1991-03-07 | 1991-04-17 | Ici Plc | Fluorination catalyst and process |
| FR2740994B1 (fr) | 1995-11-10 | 1997-12-05 | Atochem Elf Sa | Catalyseurs massiques a base d'oxyde de chrome, leur procede de preparation et leur application a la fluoration d'hydrocarbures halogenes |
| CA2263711A1 (en) | 1996-09-10 | 1998-03-19 | Imperial Chemical Industries Plc | Fluorination catalyst and process |
| TW499363B (en) | 1998-06-26 | 2002-08-21 | Sinco Ricerche Spa | Recyclable multi-layer material in polyester resin |
| US8058486B2 (en) | 2004-04-29 | 2011-11-15 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
| US7897823B2 (en) | 2004-10-29 | 2011-03-01 | E. I. Du Pont De Nemours And Company | Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes |
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| GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| KR101394583B1 (ko) | 2006-10-03 | 2014-05-12 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
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| FR2980474B1 (fr) | 2011-09-27 | 2013-08-30 | Arkema France | Procede de fabrication du 2,3,3,3-tetrafluoropropene |
| CN104169245B (zh) | 2011-11-04 | 2016-09-21 | 塞尔马·贝克特什维克 | 用于制造2,3,3,3-四氟丙烯的方法 |
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| CN103998405B (zh) * | 2011-12-14 | 2016-06-08 | 阿克马法国公司 | 2,3,3,3-四氟丙烯的制备方法 |
| EP4098644A1 (en) | 2012-02-29 | 2022-12-07 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| GB201207666D0 (en) | 2012-05-02 | 2012-06-13 | Mexichem Amanco Holding Sa | Process |
| WO2013184865A1 (en) | 2012-06-06 | 2013-12-12 | E.I. Du Pont De Nemours And Company | PROCESS FOR THE REDUCTION OF RfCCX IMPURITIES IN FLUOROOLEFINS |
| CN103055643A (zh) | 2012-12-11 | 2013-04-24 | 上海巴安水务股份有限公司 | 一种多管微旋流过滤分离器 |
-
2015
- 2015-07-17 GB GB1512593.3A patent/GB2540427B/en active Active
-
2016
- 2016-07-14 KR KR1020187004683A patent/KR102676107B1/ko active Active
- 2016-07-14 WO PCT/GB2016/052145 patent/WO2017013406A1/en not_active Ceased
- 2016-07-14 US US15/745,505 patent/US10899686B2/en active Active
- 2016-07-14 CN CN201680041643.8A patent/CN107848916B/zh active Active
- 2016-07-14 JP JP2018502143A patent/JP6688383B2/ja active Active
- 2016-07-14 EP EP16750478.6A patent/EP3325435B1/en active Active
- 2016-07-14 ES ES16750478T patent/ES2864023T3/es active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070100175A1 (en) * | 2005-11-01 | 2007-05-03 | Miller Ralph N | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| WO2010059493A1 (en) * | 2008-11-19 | 2010-05-27 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
| WO2010123154A2 (en) * | 2009-04-23 | 2010-10-28 | Daikin Industries, Ltd. | Process for preparation of 2,3,3,3-tetrafluoropropene |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2540427A (en) | 2017-01-18 |
| WO2017013406A1 (en) | 2017-01-26 |
| JP2018524376A (ja) | 2018-08-30 |
| CN107848916A (zh) | 2018-03-27 |
| GB201512593D0 (en) | 2015-08-26 |
| EP3325435A1 (en) | 2018-05-30 |
| US10899686B2 (en) | 2021-01-26 |
| EP3325435B1 (en) | 2021-02-24 |
| JP6688383B2 (ja) | 2020-04-28 |
| KR20180030188A (ko) | 2018-03-21 |
| KR102676107B1 (ko) | 2024-06-18 |
| CN107848916B (zh) | 2021-09-14 |
| US20200165179A1 (en) | 2020-05-28 |
| ES2864023T3 (es) | 2021-10-13 |
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