ES2555859T3 - Proceso para la preparación de 3,3,3-trifluoropropeno - Google Patents
Proceso para la preparación de 3,3,3-trifluoropropeno Download PDFInfo
- Publication number
- ES2555859T3 ES2555859T3 ES10717715.6T ES10717715T ES2555859T3 ES 2555859 T3 ES2555859 T3 ES 2555859T3 ES 10717715 T ES10717715 T ES 10717715T ES 2555859 T3 ES2555859 T3 ES 2555859T3
- Authority
- ES
- Spain
- Prior art keywords
- zinc
- catalyst
- approximately
- process according
- compound
- 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
- 238000000034 method Methods 0.000 title claims abstract description 63
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 114
- 239000011701 zinc Substances 0.000 claims abstract description 57
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 54
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 52
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 27
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 23
- 239000011651 chromium Substances 0.000 claims abstract description 23
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000003752 zinc compounds Chemical class 0.000 claims abstract description 17
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- PFFGXVGPSGJOBV-UHFFFAOYSA-N 1,1,1,3-tetrafluoropropane Chemical compound FCCC(F)(F)F PFFGXVGPSGJOBV-UHFFFAOYSA-N 0.000 claims description 6
- VKEIPALYOJMDAC-UHFFFAOYSA-N 3,3,3-trichloroprop-1-ene Chemical compound ClC(Cl)(Cl)C=C VKEIPALYOJMDAC-UHFFFAOYSA-N 0.000 claims description 6
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 claims description 5
- WGABYHBTXHBSEI-UHFFFAOYSA-N 1,3-dichloro-1,1-difluoropropane Chemical compound FC(F)(Cl)CCCl WGABYHBTXHBSEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000012808 vapor phase Substances 0.000 claims description 4
- ZPIFKCVYZBVZIV-UHFFFAOYSA-N 3-chloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CCCl ZPIFKCVYZBVZIV-UHFFFAOYSA-N 0.000 claims description 3
- UQIKKIADJVUSNI-UHFFFAOYSA-N 1,1,3-trichloro-1-fluoropropane Chemical compound FC(Cl)(Cl)CCCl UQIKKIADJVUSNI-UHFFFAOYSA-N 0.000 claims description 2
- FIROAKDNSCQSTG-UHFFFAOYSA-N 3,3-dichloro-3-fluoroprop-1-ene Chemical compound FC(Cl)(Cl)C=C FIROAKDNSCQSTG-UHFFFAOYSA-N 0.000 claims description 2
- AQBMNBSTXOCKKZ-UHFFFAOYSA-N 3-chloro-3,3-difluoroprop-1-ene Chemical compound FC(F)(Cl)C=C AQBMNBSTXOCKKZ-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000003682 fluorination reaction Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000007789 gas Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 238000001354 calcination Methods 0.000 description 6
- -1 trifluoropropene epoxide Chemical class 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000001845 chromium compounds Chemical class 0.000 description 4
- 229910000423 chromium oxide Inorganic materials 0.000 description 4
- 229910001026 inconel Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000002912 waste gas Substances 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000975 co-precipitation Methods 0.000 description 3
- 238000007033 dehydrochlorination reaction Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical compound ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 description 1
- NLMURJDGDBEMAB-UHFFFAOYSA-N 3,3,3-trifluoropropylbenzene Chemical compound FC(F)(F)CCC1=CC=CC=C1 NLMURJDGDBEMAB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- JOSWYUNQBRPBDN-UHFFFAOYSA-P ammonium dichromate Chemical compound [NH4+].[NH4+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O JOSWYUNQBRPBDN-UHFFFAOYSA-P 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical class [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004334 fluoridation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- YVWGMAFXEJHFRO-UHFFFAOYSA-N halopropane Chemical compound FC(F)C(F)(F)CBr YVWGMAFXEJHFRO-UHFFFAOYSA-N 0.000 description 1
- 229950000188 halopropane Drugs 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C17/093—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| GB0906191 | 2009-04-09 | ||
| GBGB0906191.2A GB0906191D0 (en) | 2009-04-09 | 2009-04-09 | Process |
| PCT/GB2010/000725 WO2010116150A1 (en) | 2009-04-09 | 2010-04-09 | Process for preparing 3,3,3-trifluoropropene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2555859T3 true ES2555859T3 (es) | 2016-01-11 |
Family
ID=40750388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10717715.6T Active ES2555859T3 (es) | 2009-04-09 | 2010-04-09 | Proceso para la preparación de 3,3,3-trifluoropropeno |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9096489B2 (enExample) |
| EP (1) | EP2417086B1 (enExample) |
| JP (1) | JP5816612B2 (enExample) |
| KR (1) | KR101731565B1 (enExample) |
| CN (1) | CN102388006B (enExample) |
| BR (1) | BRPI1008987A2 (enExample) |
| ES (1) | ES2555859T3 (enExample) |
| GB (1) | GB0906191D0 (enExample) |
| MX (1) | MX339991B (enExample) |
| PL (1) | PL2417086T3 (enExample) |
| WO (1) | WO2010116150A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102001912A (zh) * | 2010-10-24 | 2011-04-06 | 浙江衢化氟化学有限公司 | 一种合成3,3,3-三氟丙烯的方法 |
| CN103717560B (zh) * | 2011-07-26 | 2016-04-27 | 大金工业株式会社 | 用于制备2,3,3,3-四氟丙烯的方法 |
| CN104428273B (zh) * | 2012-07-10 | 2018-09-14 | 大金工业株式会社 | 用于制造含氟烯烃的方法 |
| CN104844415A (zh) * | 2015-05-26 | 2015-08-19 | 南京都乐制冷设备有限公司 | 一种三氟丙烯回收装置及回收方法 |
| GB201509323D0 (en) * | 2015-05-29 | 2015-07-15 | Mexichem Fluor Sa De Cv | Process |
| GB2540428B (en) * | 2015-07-17 | 2017-09-13 | Mexichem Fluor Sa De Cv | Process for preparing 3,3,3-trifluoropropene |
| GB2540427B (en) | 2015-07-17 | 2017-07-19 | Mexichem Fluor Sa De Cv | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| GB2559056B (en) | 2015-07-17 | 2019-09-11 | Mexichem Fluor Sa De Cv | Process for preparing 245cb and 1234yf from 243db |
| 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 |
| JP2024515192A (ja) * | 2021-04-19 | 2024-04-05 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | ３，３，３－トリフルオロプロペン（１２４３ｚｆ）を含有する組成物並びに当該組成物の製造及び使用方法 |
| TW202504879A (zh) * | 2023-07-17 | 2025-02-01 | 美商科慕Ｆｃ有限責任公司 | 生產１，１－二氟丙烯（ＨＦＯ－１２５２ｚｃ）、其組成物及中間物之程序 |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2889379A (en) | 1957-02-06 | 1959-06-02 | Dow Chemical Co | Preparation of 3, 3, 3-trifluoropropene |
| US2918501A (en) | 1958-02-27 | 1959-12-22 | Du Pont | Internally unsaturated perfluoroolefins and preparation thereof |
| US3000979A (en) | 1958-11-12 | 1961-09-19 | Du Pont | Isomerization of fluoroolefins |
| US2931840A (en) | 1958-11-25 | 1960-04-05 | Du Pont | Process for preparing 2, 3, 3, 3-tetrafluoropropene |
| DE1140928B (de) * | 1959-04-14 | 1962-12-13 | Dow Chemical Co | Verfahren zur Herstellung von 3,3,3-Trifluorpropen |
| US2996555A (en) | 1959-06-25 | 1961-08-15 | Dow Chemical Co | Preparation of 2, 3, 3, 3-tetrafluoropropene |
| US3398204A (en) | 1965-08-26 | 1968-08-20 | Dow Chemical Co | Isomerization process |
| US3674665A (en) | 1970-05-28 | 1972-07-04 | Du Pont | Photosynthesis of cyclopropyl compounds from allylic compounds |
| NL171235C (nl) | 1970-06-10 | 1983-03-01 | Montedison Spa | Werkwijze voor het bereiden van katalysatoren die in hoofdzaak uit aluminiumfluoride bestaan en werkwijze voor het bereiden van gefluoreerde of gechloorfluoreerde koolwaterstoffen met behulp van een dergelijke katalysator. |
| US3739036A (en) | 1971-09-30 | 1973-06-12 | Dow Corning | Method of preparing 3,3,3-trifluoropropene-1 |
| GB1407696A (en) | 1972-03-28 | 1975-09-24 | Bp Chem Int Ltd | Isomerisation process |
| JPS52108911A (en) | 1976-03-05 | 1977-09-12 | Central Glass Co Ltd | Isomerization of hexafluoropropene oligomers |
| US4220608A (en) * | 1979-06-06 | 1980-09-02 | E. I. Du Pont De Nemours And Company | Preparation of 3,3,3-trifluoropropene-1 |
| US4465786A (en) | 1982-09-27 | 1984-08-14 | General Electric Company | Catalyst composition for the preparation of 3,3,3-trifluoropropene |
| US4781807A (en) | 1986-11-28 | 1988-11-01 | National Distillers And Chemical Corporation | Efficient cis-to-trans isomerization of 1,4-dihalobutene-2 |
| US4798818A (en) | 1987-11-27 | 1989-01-17 | Dow Corning Corporation | Catalyst composition and process for its preparation |
| US5072063A (en) | 1990-01-09 | 1991-12-10 | Dowelanco | Process for rearranging allylic geminal dihalogen compounds |
| GB9104775D0 (en) | 1991-03-07 | 1991-04-17 | Ici Plc | Fluorination catalyst and process |
| US5316690A (en) | 1991-04-18 | 1994-05-31 | Allied Signal Inc. | Hydrochlorofluorocarbons having OH rate constants which do not contribute substantially to ozone depletion and global warming |
| BR9306493A (pt) | 1992-06-05 | 1998-09-15 | Daikin Ind Ltd | Método para a manufatura de 1,1,1,2,3-pentafluoropropeno e método para a manufatura de 1,1,1,2,3-pentafluoropropano |
| MX9800871A (es) | 1995-08-01 | 1998-04-30 | Du Pont | Proceso para la manufactura de halocarburos y compuestos seleccionados y azeotropos con hf. |
| 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 |
| US6111150A (en) | 1996-06-20 | 2000-08-29 | Central Glass Company, Limited | Method for producing 1,1,1,3,3,-pentafluoropropane |
| CA2263711A1 (en) * | 1996-09-10 | 1998-03-19 | Imperial Chemical Industries Plc | Fluorination catalyst and process |
| US5945573A (en) | 1997-01-31 | 1999-08-31 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,3,3-pentafluoropropane |
| US5986151A (en) | 1997-02-05 | 1999-11-16 | Alliedsignal Inc. | Fluorinated propenes from pentafluoropropane |
| JP2001513083A (ja) | 1997-02-19 | 2001-08-28 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | １，１，１，３，３−ペンタフルオロプロペン、２−クロロ−ペンタフルオロプロペンおよびこれらの飽和誘導体を含む組成物の製造方法 |
| US6172270B1 (en) | 1997-04-23 | 2001-01-09 | Asahi Glass Company, Ltd. | Process for producing halogenated hydrocarbons |
| US5895825A (en) * | 1997-12-01 | 1999-04-20 | Elf Atochem North America, Inc. | Preparation of 1,1,1,3,3-pentafluoropropane |
| US5811603A (en) | 1997-12-01 | 1998-09-22 | Elf Atochem North America, Inc. | Gas phase fluorination of 1230za |
| DE69909860T2 (de) | 1998-02-26 | 2004-05-27 | Central Glass Co., Ltd., Ube | Verfahren zur Herstellung von fluorierten Propanen |
| DE69923839T2 (de) | 1998-05-29 | 2005-08-25 | GTC Technology, Inc., Houston | Verfahren zur reindarstellung von terephthalsäure und isophthalsäure aus xylolgemischen |
| CN1178883C (zh) | 1998-06-02 | 2004-12-08 | 纳幕尔杜邦公司 | 六氟丙烯和任选地其他含氟卤代碳氢化合物的制备方法 |
| CN1488614A (zh) * | 2002-10-13 | 2004-04-14 | 浙江三环化工有限公司 | 3，3，3－三氟丙烯的制备方法 |
| US8530708B2 (en) | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
| US7592494B2 (en) | 2003-07-25 | 2009-09-22 | Honeywell International Inc. | Process for the manufacture of 1,3,3,3-tetrafluoropropene |
| US20050038302A1 (en) | 2003-08-13 | 2005-02-17 | Hedrick Vicki E. | Systems and methods for producing fluorocarbons |
| US20050049443A1 (en) | 2003-08-28 | 2005-03-03 | Vulcan Chemicals A Business Group Of Vulcan Materials Company | Method for producing 1,1,1,3-tetrachloropropane and other haloalkanes using a copper catalyst |
| US7435700B2 (en) * | 2003-10-14 | 2008-10-14 | E.I. Du Pont De Nemars And Company | Chromium oxide compositions containing zinc, their preparation and their use as catalysts and catalyst precursors |
| US7285690B2 (en) | 2003-10-14 | 2007-10-23 | E.I. Du Pont De Nemours And Company | Process for the preparation of 1,1,1,3,3-pentafluoropropane and 1,1,1,3,3,3-hexafluoropropane |
| KR101125312B1 (ko) | 2003-10-14 | 2012-03-27 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 1,1,1,3,3-펜타플루오로프로판 및1,1,1,2,3-펜타플루오로프로판의 제조 방법 |
| US8084653B2 (en) | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US7674939B2 (en) | 2004-04-29 | 2010-03-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| CA2564991C (en) | 2004-04-29 | 2013-03-19 | Honeywell International Inc. | Processes for synthesis of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene |
| US8067649B2 (en) | 2004-04-29 | 2011-11-29 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US7102041B2 (en) | 2004-12-08 | 2006-09-05 | Honeywell International Inc. | Continuous process for preparing halogenated compounds |
| CN100372607C (zh) * | 2004-12-23 | 2008-03-05 | 西安近代化学研究所 | 氟化催化剂及其制造方法和用途 |
| US7569170B2 (en) * | 2005-03-04 | 2009-08-04 | E.I. Du Pont De Nemours And Company | Compositions comprising a fluoroolefin |
| GB0507139D0 (en) | 2005-04-08 | 2005-05-18 | Ineos Fluor Holdings Ltd | Catalyst |
| ES2400732T3 (es) | 2005-11-03 | 2013-04-11 | Honeywell International Inc. | Método para la producción de compuestos orgánicos fluorados |
| EP3336074B1 (en) | 2006-01-03 | 2025-07-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US7420094B2 (en) | 2006-09-05 | 2008-09-02 | E.I. Du Pont De Nemours And Company | Catalytic isomerization processes of 1,3,3,3-tetrafluoropropene for making 2,3,3,3-tetrafluoropropene |
| 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 |
| GB0806422D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| CN103553871A (zh) | 2006-10-31 | 2014-02-05 | 纳幕尔杜邦公司 | 氟丙烷、卤代丙烯以及2-氯-3,3,3-三氟-1-丙烯与hf的共沸组合物和1,1,1,2,2-五氟丙烷与hf的共沸组合物的制备方法 |
| CN101535222B (zh) | 2006-10-31 | 2013-02-06 | 纳幕尔杜邦公司 | 氟丙烷和卤代丙烯的制备方法 |
| GB0625214D0 (en) | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
| CN100500626C (zh) * | 2007-04-11 | 2009-06-17 | 西安近代化学研究所 | 3,3,3-三氟丙烯的制备方法 |
| GB0806389D0 (en) | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
| GB0806419D0 (en) * | 2008-04-09 | 2008-05-14 | Ineos Fluor Holdings Ltd | Process |
-
2009
- 2009-04-09 GB GBGB0906191.2A patent/GB0906191D0/en not_active Ceased
-
2010
- 2010-04-09 WO PCT/GB2010/000725 patent/WO2010116150A1/en not_active Ceased
- 2010-04-09 JP JP2012504075A patent/JP5816612B2/ja not_active Expired - Fee Related
- 2010-04-09 PL PL10717715T patent/PL2417086T3/pl unknown
- 2010-04-09 US US13/256,077 patent/US9096489B2/en active Active
- 2010-04-09 BR BRPI1008987A patent/BRPI1008987A2/pt not_active Application Discontinuation
- 2010-04-09 KR KR1020117023530A patent/KR101731565B1/ko not_active Expired - Fee Related
- 2010-04-09 CN CN201080011409.3A patent/CN102388006B/zh not_active Expired - Fee Related
- 2010-04-09 MX MX2011009426A patent/MX339991B/es active IP Right Grant
- 2010-04-09 EP EP10717715.6A patent/EP2417086B1/en not_active Not-in-force
- 2010-04-09 ES ES10717715.6T patent/ES2555859T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| GB0906191D0 (en) | 2009-05-20 |
| CN102388006A (zh) | 2012-03-21 |
| KR20120026030A (ko) | 2012-03-16 |
| KR101731565B1 (ko) | 2017-05-11 |
| EP2417086B1 (en) | 2015-11-04 |
| JP5816612B2 (ja) | 2015-11-18 |
| US20120071699A1 (en) | 2012-03-22 |
| BRPI1008987A2 (pt) | 2016-03-22 |
| MX2011009426A (es) | 2011-09-28 |
| CN102388006B (zh) | 2016-01-13 |
| US9096489B2 (en) | 2015-08-04 |
| WO2010116150A1 (en) | 2010-10-14 |
| JP2012523402A (ja) | 2012-10-04 |
| MX339991B (es) | 2016-06-21 |
| PL2417086T3 (pl) | 2016-04-29 |
| EP2417086A1 (en) | 2012-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2555859T3 (es) | Proceso para la preparación de 3,3,3-trifluoropropeno | |
| ES2601893T3 (es) | Proceso para la preparación de 2,3,3,3,-tetrafluoropropeno | |
| ES2395146T3 (es) | Proceso de preparación de 1,1,1-trifluoro-2,3-dicloropropano | |
| CA2721124C (en) | Process | |
| ES2616232T3 (es) | Fluoración catalítica en fase gaseosa de 1233XF hasta 1234YF | |
| ES2740848T3 (es) | Fluoración catalítica en fase gaseosa | |
| ES2551244T3 (es) | Procedimiento para producir 2,3,3,3-tetrafluoropropeno | |
| ES2561095T3 (es) | Procedimiento de fabricación del 2,3,3,3-tetrafluoropropeno | |
| ES2864023T3 (es) | Proceso para la preparación de 2,3,3,3-tetrafluoropropeno (1234yf) | |
| EP2154122A1 (en) | Method for producing 2,3,3,3-tetrafluoropropene | |
| WO2016128763A1 (en) | Production of 1,1,1 -trifluoro-2,3-dichloropropane (243bd) by catalytic chlorination of 3,3,3-trifluoropropene (1243zf) | |
| ES2567178T5 (es) | Procedimiento para producir un alqueno que contiene flúor | |
| ES2447366T3 (es) | Procedimiento para la preparación de 2-cloro-1,1,1,2,3,3,3-heptafluoropropano | |
| GB2559056A (en) | Process | |
| HK1167135B (en) | Process for preparing 3,3,3-trifluoropropene |