ES2490607T3 - Método para producir olefina que contiene flúor - Google Patents
Método para producir olefina que contiene flúor Download PDFInfo
- Publication number
- ES2490607T3 ES2490607T3 ES08852480.6T ES08852480T ES2490607T3 ES 2490607 T3 ES2490607 T3 ES 2490607T3 ES 08852480 T ES08852480 T ES 08852480T ES 2490607 T3 ES2490607 T3 ES 2490607T3
- Authority
- ES
- Spain
- Prior art keywords
- fluorine
- fluorochrome
- oxide
- catalyst
- hfc
- 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
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 56
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 239000011737 fluorine Substances 0.000 title claims abstract description 51
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 27
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 claims abstract description 34
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 11
- 150000002221 fluorine Chemical class 0.000 claims abstract description 10
- 239000001294 propane Substances 0.000 claims abstract description 9
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical group FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 claims description 10
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims description 7
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 12
- 239000013076 target substance Substances 0.000 description 9
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 7
- 229910000423 chromium oxide Inorganic materials 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 6
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 6
- 238000003379 elimination reaction Methods 0.000 description 5
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- DMUPYMORYHFFCT-OWOJBTEDSA-N (e)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(\F)C(F)(F)F DMUPYMORYHFFCT-OWOJBTEDSA-N 0.000 description 3
- 238000004438 BET method Methods 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 3
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- FSRXUMANYPGVTO-UHFFFAOYSA-N 1,1,2,2-tetrachloroethene;hydrofluoride Chemical group F.ClC(Cl)=C(Cl)Cl FSRXUMANYPGVTO-UHFFFAOYSA-N 0.000 description 1
- MWDWMQNTNBHJEI-UHFFFAOYSA-N 1,1,2,3,3-pentafluoropropane Chemical compound FC(F)C(F)C(F)F MWDWMQNTNBHJEI-UHFFFAOYSA-N 0.000 description 1
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical class O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007301542A JP4849058B2 (ja) | 2007-11-21 | 2007-11-21 | 含フッ素オレフィンの製造方法 |
| JP2007301542 | 2007-11-21 | ||
| PCT/JP2008/070467 WO2009066580A1 (ja) | 2007-11-21 | 2008-11-11 | 含フッ素オレフィンの製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2490607T3 true ES2490607T3 (es) | 2014-09-04 |
Family
ID=40667405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08852480.6T Active ES2490607T3 (es) | 2007-11-21 | 2008-11-11 | Método para producir olefina que contiene flúor |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7973202B2 (enExample) |
| EP (1) | EP2223906B1 (enExample) |
| JP (1) | JP4849058B2 (enExample) |
| CN (1) | CN101868436B (enExample) |
| ES (1) | ES2490607T3 (enExample) |
| WO (1) | WO2009066580A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9724684B2 (en) | 2011-02-21 | 2017-08-08 | The Chemours Company Fc, Llc | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
| JP5800562B2 (ja) * | 2011-05-10 | 2015-10-28 | 三菱電機株式会社 | 冷凍空調機の不良原因推定方法 |
| PT3872057T (pt) | 2014-08-14 | 2026-06-23 | The Chemours Co Fc Llc | Processo para a produo de e-1,3,3,3-tetrafluoropropeno (hfc-1234ze) por desidrofluorao |
| PT3018183T (pt) | 2014-09-26 | 2022-12-07 | Daikin Ind Ltd | Composição à base de halo-olefina e sua utilização |
| EP3549995A1 (en) | 2014-09-26 | 2019-10-09 | Daikin Industries, Ltd. | Haloolefin-based composition |
| JP6328589B2 (ja) * | 2015-05-29 | 2018-05-23 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
| JP6623561B2 (ja) * | 2015-05-29 | 2019-12-25 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
| FR3055221B1 (fr) | 2016-08-29 | 2023-12-15 | Arkema France | Compositions de catalyseurs d'oxyfluorure ou de fluorure de chrome, leur preparation et leur utilisation dans des procedes en phase gazeuse |
| FR3068970B1 (fr) | 2017-07-17 | 2019-07-26 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene. |
| CN116143585B (zh) * | 2023-04-04 | 2023-07-14 | 北京宇极科技发展有限公司 | 制备氢卤烯烃的方法和制备含氟炔烃的方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5155082A (en) * | 1991-04-12 | 1992-10-13 | Allied-Signal Inc. | Catalyst for the manufacture of chlorofluorocarbons, hydrochlorofluorocarbons and hydrofluorocarbons |
| US6300531B1 (en) * | 1991-05-24 | 2001-10-09 | Daikin Industries, Ltd. | Fluorination catalyst and process for fluorinating halogenated hydrocarbon |
| JP3412165B2 (ja) | 1991-05-24 | 2003-06-03 | ダイキン工業株式会社 | フッ素化触媒およびハロゲン化炭化水素のフッ素化方法 |
| KR950701896A (ko) | 1992-06-05 | 1995-05-17 | 이노우에 노리유키 | 1,1,1,2,3-펜타플루오로프로펜의 제조방법 및 1,1,1,2,3-펜타플루오로프로판의 제조방법 |
| JP4378779B2 (ja) | 1998-07-17 | 2009-12-09 | ダイキン工業株式会社 | 含フッ素エタンの製造方法 |
| US6124510A (en) | 1998-07-21 | 2000-09-26 | Elf Atochem North America, Inc. | 1234ze preparation |
| US7230146B2 (en) * | 2003-10-27 | 2007-06-12 | Honeywell International Inc. | Process for producing fluoropropenes |
| US8530708B2 (en) * | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
| 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 |
| CA2628463C (en) | 2005-11-03 | 2014-07-08 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| CN101522597B (zh) | 2006-10-03 | 2013-05-29 | 墨西哥化学阿玛科股份有限公司 | 通过脱卤化氢制备c3-c6(氢)氟烯烃的方法 |
-
2007
- 2007-11-21 JP JP2007301542A patent/JP4849058B2/ja not_active Expired - Fee Related
-
2008
- 2008-11-11 ES ES08852480.6T patent/ES2490607T3/es active Active
- 2008-11-11 US US12/743,939 patent/US7973202B2/en active Active
- 2008-11-11 CN CN200880116725.XA patent/CN101868436B/zh active Active
- 2008-11-11 WO PCT/JP2008/070467 patent/WO2009066580A1/ja not_active Ceased
- 2008-11-11 EP EP08852480.6A patent/EP2223906B1/en not_active Revoked
Also Published As
| Publication number | Publication date |
|---|---|
| US20100249469A1 (en) | 2010-09-30 |
| CN101868436B (zh) | 2014-07-16 |
| JP2009126803A (ja) | 2009-06-11 |
| CN101868436A (zh) | 2010-10-20 |
| EP2223906B1 (en) | 2014-07-30 |
| JP4849058B2 (ja) | 2011-12-28 |
| WO2009066580A1 (ja) | 2009-05-28 |
| EP2223906A4 (en) | 2011-02-09 |
| US7973202B2 (en) | 2011-07-05 |
| EP2223906A1 (en) | 2010-09-01 |
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