JP2017525669A5 - - Google Patents
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- Publication number
- JP2017525669A5 JP2017525669A5 JP2016575837A JP2016575837A JP2017525669A5 JP 2017525669 A5 JP2017525669 A5 JP 2017525669A5 JP 2016575837 A JP2016575837 A JP 2016575837A JP 2016575837 A JP2016575837 A JP 2016575837A JP 2017525669 A5 JP2017525669 A5 JP 2017525669A5
- Authority
- JP
- Japan
- Prior art keywords
- stream
- reactor
- tetrafluoropropene
- supplying
- reaction
- 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.)
- Granted
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- 230000008929 regeneration Effects 0.000 claims 23
- 238000011069 regeneration method Methods 0.000 claims 23
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 22
- 238000006243 chemical reaction Methods 0.000 claims 21
- 238000000034 method Methods 0.000 claims 17
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims 15
- 238000003682 fluorination reaction Methods 0.000 claims 11
- 239000003054 catalyst Substances 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- 239000001301 oxygen Substances 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 238000011084 recovery Methods 0.000 claims 7
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical group FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 4
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 4
- 239000007789 gas Substances 0.000 claims 4
- 239000007800 oxidant agent Substances 0.000 claims 4
- 230000001590 oxidative effect Effects 0.000 claims 4
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical group F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims 3
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 claims 3
- IYFMQUDCYNWFTL-UHFFFAOYSA-N 1,1,2,2,3-pentachloropropane Chemical compound ClCC(Cl)(Cl)C(Cl)Cl IYFMQUDCYNWFTL-UHFFFAOYSA-N 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000012429 reaction media Substances 0.000 claims 3
- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical compound CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 claims 2
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 claims 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims 2
- 230000001172 regenerating effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 claims 1
- IQUPUSQWHHBXAH-UHFFFAOYSA-N 1-chloro-1,2,2-trifluoroethene;prop-1-ene Chemical class CC=C.FC(F)=C(F)Cl IQUPUSQWHHBXAH-UHFFFAOYSA-N 0.000 claims 1
- LDTMPQQAWUMPKS-UHFFFAOYSA-N 1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=CCl LDTMPQQAWUMPKS-UHFFFAOYSA-N 0.000 claims 1
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical group CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 claims 1
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1456303 | 2014-07-02 | ||
| FR1456303A FR3023286B1 (fr) | 2014-07-02 | 2014-07-02 | Procede de fabrication de tetrafluoropropene |
| PCT/FR2015/051653 WO2016001515A1 (fr) | 2014-07-02 | 2015-06-22 | Procede de fabrication de tetrafluoropropene |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019191703A Division JP6847182B2 (ja) | 2014-07-02 | 2019-10-21 | テトラフルオロプロペンの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017525669A JP2017525669A (ja) | 2017-09-07 |
| JP2017525669A5 true JP2017525669A5 (OSRAM) | 2018-06-21 |
| JP6677658B2 JP6677658B2 (ja) | 2020-04-08 |
Family
ID=51726670
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016575837A Active JP6677658B2 (ja) | 2014-07-02 | 2015-06-22 | テトラフルオロプロペンの製造方法 |
| JP2019191703A Active JP6847182B2 (ja) | 2014-07-02 | 2019-10-21 | テトラフルオロプロペンの製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019191703A Active JP6847182B2 (ja) | 2014-07-02 | 2019-10-21 | テトラフルオロプロペンの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US10227275B2 (OSRAM) |
| EP (2) | EP3164376B1 (OSRAM) |
| JP (2) | JP6677658B2 (OSRAM) |
| CN (1) | CN106660909B (OSRAM) |
| CA (1) | CA2951023C (OSRAM) |
| FR (2) | FR3023286B1 (OSRAM) |
| MX (1) | MX384336B (OSRAM) |
| WO (1) | WO2016001515A1 (OSRAM) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3023286B1 (fr) | 2014-07-02 | 2018-02-16 | Arkema France | Procede de fabrication de tetrafluoropropene |
| EP3180299B1 (en) | 2014-08-14 | 2018-12-19 | The Chemours Company FC, LLC | Process for the production of e-1,3,3,3-tetrafluoropropene (hfc-1234ze) by dehydrofluorination |
| CN112939731A (zh) | 2014-10-16 | 2021-06-11 | 化学和冶金生产联合体股份公司 | 用于制备高纯度氯化烷烃的方法 |
| WO2017023966A1 (en) * | 2015-08-05 | 2017-02-09 | Arkema Inc. | Chromium oxyfluoride catalysts having high fluorination activity |
| JP6233535B2 (ja) * | 2016-02-03 | 2017-11-22 | ダイキン工業株式会社 | テトラフルオロプロペンの製造方法 |
| FR3048429B1 (fr) * | 2016-03-04 | 2019-09-27 | Arkema France | Composition azeotropique ou quasi-azeotropique comprenant de la trifluoropropyne |
| JP6935423B2 (ja) * | 2016-04-13 | 2021-09-15 | アルケマ フランス | ２，３，３，３−テトラフルオロプロペンの製造方法 |
| JP2017193511A (ja) * | 2016-04-21 | 2017-10-26 | ダイキン工業株式会社 | ハイドロクロロフルオロカーボン及び／又はハイドロフルオロカーボンの製造方法 |
| FR3051468B1 (fr) * | 2016-05-19 | 2019-07-26 | Arkema France | Procede de fabrication de tetrafluoropropene. |
| FR3051469B1 (fr) * | 2016-05-19 | 2018-05-11 | Arkema France | Procede de fabrication de tetrafluoropropene. |
| FR3066926B1 (fr) * | 2017-06-06 | 2020-05-22 | Arkema France | Procede de modification de la distribution en fluor dans un compose hydrocarbure. |
| FR3068970B1 (fr) * | 2017-07-17 | 2019-07-26 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene. |
| US10450248B2 (en) * | 2017-11-22 | 2019-10-22 | Honeywell International Inc. | Method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze) from 1-chloro-3,3,3-trifluoropopene (HCFO-1233zd) |
| FR3078700B1 (fr) | 2018-03-07 | 2020-07-10 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| FR3078698B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2-chloro-3,3,3-trifluoropropene |
| FR3078699B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| EP3540035A1 (en) | 2018-03-13 | 2019-09-18 | The Procter & Gamble Company | Hand dishwashing detergent composition |
| FR3081158B1 (fr) | 2018-05-16 | 2020-07-31 | Arkema France | Procede de production du 1-chloro-3,3,3-trifluoropropene. |
| FR3083232B1 (fr) | 2018-06-27 | 2021-11-12 | Arkema France | Procede de production du 1-chloro-3,3,3-trifluoropropene |
| US11904301B2 (en) * | 2018-09-07 | 2024-02-20 | The Chemours Company Fc, Llc | Fluorine removal from antimony fluorohalide catalyst using chlorocarbons |
| FR3086287B1 (fr) | 2018-09-26 | 2020-09-18 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
| 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 |
| GB2580623A (en) * | 2019-01-17 | 2020-07-29 | Mexichem Fluor Sa De Cv | Method |
| FR3115786B1 (fr) * | 2020-11-03 | 2022-11-04 | Arkema France | Procédé de production du trifluoroéthylène |
| CN114644546A (zh) * | 2020-12-17 | 2022-06-21 | 陕西中蓝化工科技新材料有限公司 | 一种氟代烯烃的制备方法 |
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| BE527988A (OSRAM) * | 1953-04-09 | |||
| NL294955A (OSRAM) | 1962-07-06 | |||
| JPH0685878B2 (ja) * | 1988-04-13 | 1994-11-02 | ダイキン工業株式会社 | クロム系フッ素化触媒の賦活方法 |
| US4902838A (en) | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
| GB9007029D0 (en) * | 1990-03-29 | 1990-05-30 | Ici Plc | Chemical process |
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| GB9224594D0 (en) * | 1991-12-10 | 1993-01-13 | Ici Plc | Water separation process |
| US5322597A (en) | 1992-07-30 | 1994-06-21 | Minnesota Mining And Manufacturing Company | Bipolar flow cell and process for electrochemical fluorination |
| US5919728A (en) * | 1996-04-17 | 1999-07-06 | Ausimont S.P.A. | Catalyst for the fluorination of halogenated hydrocarbons |
| DE69909860T2 (de) | 1998-02-26 | 2004-05-27 | Central Glass Co., Ltd., Ube | Verfahren zur Herstellung von fluorierten Propanen |
| FR2808268B1 (fr) | 2000-04-26 | 2002-08-30 | Atofina | Liquides ioniques derives d'acides de lewis a base de titane, niobium, tantale, etain ou antimoine, et leurs applications |
| CN1254460C (zh) * | 2001-08-06 | 2006-05-03 | 昭和电工株式会社 | 六氟乙烷的生产方法及其应用 |
| US8058486B2 (en) | 2004-04-29 | 2011-11-15 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
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| JP5416587B2 (ja) | 2006-10-03 | 2014-02-12 | メキシケム、アマンコ、ホールディング、ソシエダッド、アノニマ、デ、カピタル、バリアブレ | プロセス |
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| FR2916755B1 (fr) | 2007-05-31 | 2009-08-21 | Arkema France | Procede de preparation d'(hydro)(chloro)(fluoro)olefines |
| CN101687731B (zh) | 2007-06-27 | 2013-09-04 | 阿科玛股份有限公司 | 用于制造氢氟烯烃的方法 |
| WO2009105512A1 (en) * | 2008-02-21 | 2009-08-27 | E. I. Du Pont De Nemours And Company | Processes for separation of 2,3,3,3-tetrafluoropropene from hydrogen fluoride by azeotropic distillation |
| FR2929271B1 (fr) | 2008-03-28 | 2010-04-16 | Arkema France | Procede pour la preparation du 1,2,3,3,3-pentafluoropropene- 1 |
| HRP20220650T1 (hr) | 2008-05-07 | 2022-07-08 | The Chemours Company Fc, Llc | Pripravci |
| FR2936806B1 (fr) * | 2008-10-08 | 2012-08-31 | Arkema France | Fluide refrigerant |
| ES2598484T3 (es) | 2009-04-23 | 2017-01-27 | Daikin Industries, Ltd. | Procedimiento para la preparación de 2,3,3,3-tetrafluoropropeno |
| GB0918069D0 (en) * | 2009-10-15 | 2009-12-02 | Ineos Fluor Holdings Ltd | Process |
| CN102686542A (zh) | 2009-12-23 | 2012-09-19 | 阿克马法国公司 | 1233xf到1234yf的催化气相氟化 |
| GB201010958D0 (en) | 2010-06-30 | 2010-08-11 | 3M Innovative Properties Co | Process for manufacturing perfluoroolefins by pyrolysis of perfluorocarbons in the presence of hydrogen |
| JP5747684B2 (ja) * | 2010-09-14 | 2015-07-15 | セントラル硝子株式会社 | ヒドロフルオロカーボンまたはヒドロクロロフルオロカーボンの脱水方法、および該脱水方法を用いた１，３，３，３−テトラフルオロプロペンの製造方法 |
| ES2773202T3 (es) | 2010-10-22 | 2020-07-09 | Arkema France | Proceso para la preparación de 2,3,3,3-tetrafluoropropeno |
| US9340473B2 (en) * | 2011-01-21 | 2016-05-17 | Arkema France | Catalytic gas phase fluorination |
| CN103313960B (zh) * | 2011-01-21 | 2016-06-08 | 阿克马法国公司 | 催化气相氟化 |
| FR2980474B1 (fr) | 2011-09-27 | 2013-08-30 | Arkema France | Procede de fabrication du 2,3,3,3-tetrafluoropropene |
| JP5992532B2 (ja) * | 2011-12-14 | 2016-09-14 | アルケマ フランス | ２，３，３，３−テトラフルオロプロペンを調製する方法 |
| FR2986525B1 (fr) | 2012-02-03 | 2014-02-14 | Arkema France | Procede de production de 2,3,3,3-tetrafluoropropene |
| WO2013154059A1 (ja) * | 2012-04-09 | 2013-10-17 | 旭硝子株式会社 | 共沸または共沸様組成物、および２，３，３，３－テトラフルオロプロペンまたはクロロメタンの製造方法 |
| JP2013241390A (ja) * | 2012-04-27 | 2013-12-05 | Asahi Glass Co Ltd | フルオロオレフィンの精製方法、およびフルオロオレフィンの製造方法 |
| FR2991598B1 (fr) | 2012-06-08 | 2015-08-07 | Arkema France | Regeneration de catalyseur par injection de gaz chauffe |
| JP6107466B2 (ja) * | 2012-06-28 | 2017-04-05 | セントラル硝子株式会社 | トランス−１，３，３，３−テトラフルオロプロペンの精製方法 |
| US9708234B2 (en) * | 2012-07-10 | 2017-07-18 | Daikin Industries, Ltd. | Process for producing fluorine-containing olefin |
| CN104520259B (zh) * | 2012-08-08 | 2016-08-24 | 大金工业株式会社 | 用于制造2,3,3,3-四氟丙烯的方法 |
| FR3013606B1 (fr) | 2013-11-28 | 2015-11-13 | Arkema France | Procede de purification d'acide chlorhydrique |
| US9255045B2 (en) | 2014-01-13 | 2016-02-09 | Arkema France | E-1-chloro-3,3,3-trifluoropropene production process from 1,1,3,3-tetrachloropropene |
| FR3023286B1 (fr) | 2014-07-02 | 2018-02-16 | Arkema France | Procede de fabrication de tetrafluoropropene |
| FR3036398B1 (fr) | 2015-05-22 | 2019-05-03 | Arkema France | Compositions a base de 1,1,3,3-tetrachloropropene |
| JP6935423B2 (ja) | 2016-04-13 | 2021-09-15 | アルケマ フランス | ２，３，３，３−テトラフルオロプロペンの製造方法 |
| FR3078700B1 (fr) | 2018-03-07 | 2020-07-10 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| FR3078699B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| FR3078698B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2-chloro-3,3,3-trifluoropropene |
| FR3081158B1 (fr) | 2018-05-16 | 2020-07-31 | Arkema France | Procede de production du 1-chloro-3,3,3-trifluoropropene. |
| FR3083232B1 (fr) | 2018-06-27 | 2021-11-12 | Arkema France | Procede de production du 1-chloro-3,3,3-trifluoropropene |
| FR3086287B1 (fr) | 2018-09-26 | 2020-09-18 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
-
2014
- 2014-07-02 FR FR1456303A patent/FR3023286B1/fr active Active
-
2015
- 2015-06-22 EP EP15738402.5A patent/EP3164376B1/fr active Active
- 2015-06-22 EP EP19153219.1A patent/EP3495340A1/fr active Pending
- 2015-06-22 CA CA2951023A patent/CA2951023C/fr active Active
- 2015-06-22 MX MX2016015875A patent/MX384336B/es unknown
- 2015-06-22 CN CN201580035389.6A patent/CN106660909B/zh not_active Expired - Fee Related
- 2015-06-22 JP JP2016575837A patent/JP6677658B2/ja active Active
- 2015-06-22 WO PCT/FR2015/051653 patent/WO2016001515A1/fr not_active Ceased
- 2015-06-22 US US15/321,462 patent/US10227275B2/en active Active
-
2017
- 2017-12-11 FR FR1761894A patent/FR3059999B1/fr active Active
-
2019
- 2019-01-17 US US16/250,141 patent/US11459285B2/en active Active
- 2019-10-21 JP JP2019191703A patent/JP6847182B2/ja active Active
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