ES2584285T3 - Procedimiento de preparación de compuestos fluorados - Google Patents
Procedimiento de preparación de compuestos fluorados Download PDFInfo
- Publication number
- ES2584285T3 ES2584285T3 ES10164600.8T ES10164600T ES2584285T3 ES 2584285 T3 ES2584285 T3 ES 2584285T3 ES 10164600 T ES10164600 T ES 10164600T ES 2584285 T3 ES2584285 T3 ES 2584285T3
- Authority
- ES
- Spain
- Prior art keywords
- weight
- dehydrofluorination
- catalyst
- tetrafluoro
- pentafluoropropane
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 12
- 239000003054 catalyst Substances 0.000 abstract 4
- 238000005796 dehydrofluorination reaction Methods 0.000 abstract 4
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 abstract 3
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 229910001868 water Inorganic materials 0.000 abstract 3
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 abstract 2
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical compound FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
Classifications
-
- 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
-
- 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
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Procedimiento de preparación de 2,3,3,3-tetrafluoro-1-propeno que comprende las siguientes etapas: (i) hidrogenación en fase gaseosa de hexafluoropropileno en 1,1,1,2,3,3-hexafluoropropano en presencia de una cantidad sobreestequiométrica de hidrógeno y de un catalizador en un reactor; (ii) deshidrofluoración del 1,1,1,2,3,3-hexafluoropropano obtenido en la etapa precedente en 1,2,3,3,3- pentafluoropropeno-1 en presencia de un catalizador de deshidrofluoración o con la ayuda de una mezcla agua e hidróxido de potasio, estando presente el hidróxido de potasio entre 20 y 75% en peso con relación al peso de la mezcla agua y KOH; (iii) hidrogenación en fase gaseosa del 1,2,3,3,3-pentafluoropropeno-1 obtenido en la etapa precedente en 1,1,1,2,3- pentafluoropropano en presencia de una cantidad sobreestequiométrica de hidrógeno y de un catalizador en un reactor; (iv) purificación del 1,1,1,2,3-pentafluoropropano obtenido en la etapa precedente; (v) deshidrofluoración del 1,1,1,2,3-pentafluoropropano purificado en 2,3,3,3-tetrafluoro-1-propeno en presencia de un catalizador de deshidrofluoración o con la ayuda de una mezcla de agua e hidróxido de potasio, estando presente el hidróxido de potasio entre 20 y 75% en peso con respecto al peso del (vi) purificación del 2,3,3,3-tetrafluoro-1-propeno obtenido en la etapa precedente.
Description
Claims (1)
-
imagen1 imagen2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0955139A FR2948362B1 (fr) | 2009-07-23 | 2009-07-23 | Procede de preparation de composes fluores |
| FR0955139 | 2009-07-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2584285T3 true ES2584285T3 (es) | 2016-09-26 |
Family
ID=41664462
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16165721T Active ES2794784T3 (es) | 2009-07-23 | 2010-06-01 | Procedimiento de preparación de 2,3,3,3-tetrafluoro-1-propeno |
| ES10173804.5T Active ES2525142T3 (es) | 2009-07-23 | 2010-06-01 | Procedimiento de preparación de compuestos fluorados |
| ES10164600.8T Active ES2584285T3 (es) | 2009-07-23 | 2010-06-01 | Procedimiento de preparación de compuestos fluorados |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16165721T Active ES2794784T3 (es) | 2009-07-23 | 2010-06-01 | Procedimiento de preparación de 2,3,3,3-tetrafluoro-1-propeno |
| ES10173804.5T Active ES2525142T3 (es) | 2009-07-23 | 2010-06-01 | Procedimiento de preparación de compuestos fluorados |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8389779B2 (es) |
| EP (3) | EP2289864B1 (es) |
| JP (4) | JP5599658B2 (es) |
| CN (5) | CN107011115B (es) |
| ES (3) | ES2794784T3 (es) |
| FR (2) | FR2948362B1 (es) |
| HU (1) | HUE029613T2 (es) |
| PL (2) | PL2281792T3 (es) |
| WO (1) | WO2011010025A1 (es) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8263816B2 (en) * | 2006-06-27 | 2012-09-11 | E I Du Pont De Nemours And Company | 1,2,3,3,3-Pentafluoropropene production processes |
| US8710282B2 (en) | 2008-03-14 | 2014-04-29 | Honeywell International Inc. | Integrated process for the manufacture of fluorinated olefins |
| FR2935703B1 (fr) * | 2008-09-11 | 2010-09-03 | Arkema France | Procede de preparation de composes fluores. |
| FR2948362B1 (fr) | 2009-07-23 | 2012-03-23 | Arkema France | Procede de preparation de composes fluores |
| US8513474B2 (en) | 2010-06-24 | 2013-08-20 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| FR2962442B1 (fr) | 2010-07-09 | 2016-02-26 | Arkema France | Composition stable de 2,3,3,3-tetrafluoropropene |
| GB2492847A (en) * | 2011-07-15 | 2013-01-16 | Mexichem Amanco Holding Sa | A process for reducing TFMA content in R-1234 |
| IN2014DN06917A (es) * | 2012-02-10 | 2015-05-15 | Haiyou Wang | |
| FR3000096B1 (fr) | 2012-12-26 | 2015-02-20 | Arkema France | Composition comprenant du 2,3,3,3-tetrafluoropropene |
| US9290424B2 (en) * | 2013-03-14 | 2016-03-22 | Honeywell International Inc. | Processes for the hydrogenation of halogenated alkenes and the manufacture of fluorinated olefins |
| CN103449960B (zh) * | 2013-08-06 | 2016-01-20 | 巨化集团技术中心 | 一种1,1,1,2,3-五氟丙烷的制备方法 |
| KR101492871B1 (ko) | 2013-08-07 | 2015-02-13 | 한국과학기술연구원 | 이온성 액체를 이용하여 제조된 탄소에 담지된 팔라듐 촉매 및 이것의 제조방법과, 이를 이용한 수소불화탄소의 수소화 반응 |
| FR3033791B1 (fr) | 2015-03-18 | 2017-04-14 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
| CN104945221B (zh) * | 2015-06-11 | 2017-07-18 | 浙江衢州巨新氟化工有限公司 | 一种联产2,3,3,3‑四氟丙烯和1,3,3,3‑四氟丙烯的方法 |
| CN105061136B (zh) * | 2015-08-18 | 2017-12-22 | 巨化集团技术中心 | 一种氟烯烃的制造方法 |
| KR101756532B1 (ko) | 2015-08-24 | 2017-07-11 | (주)후성 | 플루오로화합물의 제조 방법 |
| KR102844400B1 (ko) * | 2015-09-11 | 2025-08-11 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 히드로클로로플루오로카본의 탈할로겐화수소화 |
| KR20160017661A (ko) | 2016-01-29 | 2016-02-16 | 한국과학기술연구원 | 헥사플루오로프로필렌으로부터 2,3,3,3-테트라플루오로프로펜과 1,3,3,3-테트라플루오로프로펜의 제조방법 |
| KR101914236B1 (ko) | 2017-01-11 | 2018-12-28 | 한국과학기술연구원 | 1,2,3,3,3-펜타플루오로프로펜 제조방법 |
| GB201701099D0 (en) * | 2017-01-23 | 2017-03-08 | Mexichem Fluor Sa De Cv | Process |
| CN107042104B (zh) * | 2017-06-06 | 2019-08-23 | 浙江师范大学 | 用于HFC-245fa裂解制HFO-1234ze的催化剂及其制备方法 |
| FR3096984B1 (fr) | 2017-06-09 | 2023-07-14 | Arkema France | 1,1,1,2,3,3-hexafluoropropane de haute pureté, son procédé de fabrication et utilisation |
| FR3067347B1 (fr) | 2017-06-09 | 2020-07-24 | Arkema France | 1,1,1,2,3,3-hexafluoropropane de haute purete, son procede de fabrication et utilisation |
| FR3068968B1 (fr) | 2017-07-17 | 2019-08-16 | Arkema France | Methode de stockage du 1,1,1,2,3,3-hexafluoropropane et container pour stocker celui-ci.. |
| KR101992230B1 (ko) | 2017-08-08 | 2019-06-25 | (주)후성 | 기상 촉매를 이용한 1,1,1-트리플루오로-2-클로로프로펜과 1,1,1,2-테트라플루오로프로펜의 동시 제조 방법 |
| FR3076553B1 (fr) | 2018-01-08 | 2020-07-31 | Arkema France | Procede de purification du 1,1,1,2,3-pentafluoropropane et utilisation de celui-ci pour l'obtention de 2,3,3,3-tetrafluoropropene de haute purete. |
| FR3077572B1 (fr) | 2018-02-05 | 2021-10-08 | Arkema France | Composition azeotropique ou quasi-azeotropique ternaire comprenant hf, 2,3,3,3-tetrafluoropropene et 1,1,1,2,2,-pentafluoropropane. |
| FR3077072B1 (fr) | 2019-01-22 | 2021-08-06 | Arkema France | Procédé de purification du 1,1,1,2,3-pentafluoropropane et utilisation de celui-ci pour l’obtention de 2,3,3,3-tétrafluoropropène de haute pureté |
| FR3093721A1 (fr) | 2019-03-12 | 2020-09-18 | Arkema France | Procédé de production de fluorooléfines |
| JP7495430B2 (ja) | 2019-04-17 | 2024-06-04 | バード・アクセス・システムズ,インコーポレーテッド | 長尺状医療部材を安定させるための固定装置およびカテーテルアセンブリの固定方法 |
| CN111253211B (zh) * | 2020-03-16 | 2022-08-05 | 天津绿菱气体有限公司 | 一种高纯电子级四氟丙烯HFO-1234yf的分离纯化方法 |
| FR3137845B1 (fr) | 2022-07-12 | 2025-07-18 | Arkema France | Procédé de purification du 1,1,1,2,3,3-hexafluoropropane |
| WO2024126607A1 (en) | 2022-12-14 | 2024-06-20 | Basf Se | Process for preparing at least one polyisocyanate from co2 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5679875A (en) | 1992-06-05 | 1997-10-21 | Daikin Industries, Ltd. | Method for manufacturing 1,1,1,2,3-pentafluoropropene 1,1,1,2,3-pentafluoropropane |
| US5396000A (en) | 1993-05-24 | 1995-03-07 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,2,3,-pentafluoropropane |
| US6524496B2 (en) * | 2001-03-21 | 2003-02-25 | Honeywell International Inc. | Azeotrope-like composition of 1,1,1,3,3-pentafluoropropane and 1-chloro-1,1,3,3,3-pentafluoropropane |
| US8530708B2 (en) * | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
| US20060243944A1 (en) * | 2005-03-04 | 2006-11-02 | Minor Barbara H | Compositions comprising a fluoroolefin |
| US7476771B2 (en) | 2005-11-01 | 2009-01-13 | E.I. Du Pont De Nemours + Company | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| US7560602B2 (en) * | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
| US7902410B2 (en) * | 2005-11-03 | 2011-03-08 | Honeywell International Inc. | Process for the manufacture of fluorinated alkanes |
| US8766020B2 (en) | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| CA2628463C (en) | 2005-11-03 | 2014-07-08 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8071825B2 (en) * | 2006-01-03 | 2011-12-06 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| RU2445302C2 (ru) * | 2006-06-27 | 2012-03-20 | Е.И. Дюпон Де Немур Энд Компани | Способы получения тетрафторпропена |
| US7833434B2 (en) | 2006-06-27 | 2010-11-16 | E. I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| US7803975B2 (en) * | 2006-07-13 | 2010-09-28 | E.I. Du Pont De Nemours And Company | Process for separating a fluoroolefin from HF by liquid-liquid extraction |
| EP2066605B1 (en) * | 2006-09-05 | 2013-12-25 | E.I. Du Pont De Nemours And Company | Process to manufacture 2,3,3,3-tetrafluoropropene |
| GB0625214D0 (en) * | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
| US9079818B2 (en) * | 2007-10-15 | 2015-07-14 | Honeywell International Inc. | Process for synthesis of fluorinated olefins |
| EP2292574B1 (en) * | 2007-12-27 | 2015-05-06 | Arkema France | Process for producing 2,3,3,3-tetrafluoropropene |
| FR2929272B1 (fr) * | 2008-03-28 | 2010-04-09 | Arkema France | Procede pour la preparation du 2,3,3,3-tetrafluoro-1-propene |
| GB0808836D0 (en) * | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
| FR2935703B1 (fr) * | 2008-09-11 | 2010-09-03 | Arkema France | Procede de preparation de composes fluores. |
| FR2948362B1 (fr) | 2009-07-23 | 2012-03-23 | Arkema France | Procede de preparation de composes fluores |
-
2009
- 2009-07-23 FR FR0955139A patent/FR2948362B1/fr active Active
-
2010
- 2010-05-03 FR FR1053395A patent/FR2948363B1/fr active Active
- 2010-06-01 EP EP10173804.5A patent/EP2289864B1/fr active Active
- 2010-06-01 ES ES16165721T patent/ES2794784T3/es active Active
- 2010-06-01 ES ES10173804.5T patent/ES2525142T3/es active Active
- 2010-06-01 EP EP16165721.8A patent/EP3072870B1/fr active Active
- 2010-06-01 HU HUE10164600A patent/HUE029613T2/en unknown
- 2010-06-01 EP EP10164600.8A patent/EP2281792B9/fr active Active
- 2010-06-01 PL PL10164600.8T patent/PL2281792T3/pl unknown
- 2010-06-01 PL PL10173804T patent/PL2289864T3/pl unknown
- 2010-06-01 WO PCT/FR2010/051053 patent/WO2011010025A1/fr not_active Ceased
- 2010-06-01 ES ES10164600.8T patent/ES2584285T3/es active Active
- 2010-06-11 JP JP2010133593A patent/JP5599658B2/ja active Active
- 2010-07-23 US US12/842,737 patent/US8389779B2/en active Active
- 2010-07-23 CN CN201611043448.7A patent/CN107011115B/zh active Active
- 2010-07-23 CN CN201611043447.2A patent/CN107011114B/zh active Active
- 2010-07-23 CN CN201510114349.2A patent/CN104829417A/zh active Pending
- 2010-07-23 CN CN201610363285.4A patent/CN106167446A/zh active Pending
- 2010-07-23 CN CN2010102373412A patent/CN101962314A/zh active Pending
-
2013
- 2013-11-13 JP JP2013234894A patent/JP2014088383A/ja active Pending
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2015
- 2015-03-13 JP JP2015050323A patent/JP2015145385A/ja active Pending
-
2017
- 2017-10-05 JP JP2017194850A patent/JP6722628B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2281792A1 (fr) | 2011-02-09 |
| HUE029613T2 (en) | 2017-03-28 |
| CN104829417A (zh) | 2015-08-12 |
| EP3072870A1 (fr) | 2016-09-28 |
| FR2948363B1 (fr) | 2012-03-16 |
| EP2281792B9 (fr) | 2018-03-28 |
| CN107011114B (zh) | 2020-03-31 |
| US8389779B2 (en) | 2013-03-05 |
| US20110021849A1 (en) | 2011-01-27 |
| EP2289864A1 (fr) | 2011-03-02 |
| EP2281792B1 (fr) | 2016-04-27 |
| JP2014088383A (ja) | 2014-05-15 |
| CN107011115B (zh) | 2020-03-31 |
| CN106167446A (zh) | 2016-11-30 |
| ES2525142T3 (es) | 2014-12-18 |
| EP2289864B1 (fr) | 2014-10-15 |
| CN107011115A (zh) | 2017-08-04 |
| EP3072870B1 (fr) | 2020-04-22 |
| ES2794784T3 (es) | 2020-11-19 |
| JP6722628B2 (ja) | 2020-07-15 |
| FR2948362B1 (fr) | 2012-03-23 |
| WO2011010025A1 (fr) | 2011-01-27 |
| CN101962314A (zh) | 2011-02-02 |
| JP2018070595A (ja) | 2018-05-10 |
| JP5599658B2 (ja) | 2014-10-01 |
| JP2015145385A (ja) | 2015-08-13 |
| JP2011026297A (ja) | 2011-02-10 |
| FR2948362A1 (fr) | 2011-01-28 |
| FR2948363A1 (fr) | 2011-01-28 |
| PL2289864T3 (pl) | 2015-03-31 |
| PL2281792T3 (pl) | 2016-11-30 |
| CN107011114A (zh) | 2017-08-04 |
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