ES2705051T3 - Procedimiento para la fabricación de olefinas fluoradas - Google Patents
Procedimiento para la fabricación de olefinas fluoradas Download PDFInfo
- Publication number
- ES2705051T3 ES2705051T3 ES14773255T ES14773255T ES2705051T3 ES 2705051 T3 ES2705051 T3 ES 2705051T3 ES 14773255 T ES14773255 T ES 14773255T ES 14773255 T ES14773255 T ES 14773255T ES 2705051 T3 ES2705051 T3 ES 2705051T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- fluorinated
- stream
- alkane
- 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.)
- Active
Links
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 65
- 239000013067 intermediate product Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 26
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 19
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 19
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 17
- 239000012467 final product Substances 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 9
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 6
- 238000004064 recycling Methods 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims description 139
- 238000005984 hydrogenation reaction Methods 0.000 claims description 59
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 57
- 239000003054 catalyst Substances 0.000 claims description 54
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 49
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 claims description 37
- 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 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 239000002994 raw material Substances 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 claims description 18
- 239000007791 liquid phase Substances 0.000 claims description 12
- 229910052759 nickel Inorganic materials 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052593 corundum Inorganic materials 0.000 claims 2
- 229910001845 yogo sapphire Inorganic materials 0.000 claims 2
- 239000000047 product Substances 0.000 description 43
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 28
- 239000003795 chemical substances by application Substances 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 20
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000005796 dehydrofluorination reaction Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- -1 Ni mesh) Chemical compound 0.000 description 7
- 150000002367 halogens Chemical group 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 239000012808 vapor phase Substances 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 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 description 2
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910004261 CaF 2 Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- NEAPKZHDYMQZCB-UHFFFAOYSA-N N-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]ethyl]-2-oxo-3H-1,3-benzoxazole-6-carboxamide Chemical compound C1CN(CCN1CCNC(=O)C2=CC3=C(C=C2)NC(=O)O3)C4=CN=C(N=C4)NC5CC6=CC=CC=C6C5 NEAPKZHDYMQZCB-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 229910001293 incoloy Inorganic materials 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910001512 metal fluoride Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 1
- 229910016569 AlF 3 Inorganic materials 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000013019 agitation Methods 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
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical class O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 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
- 238000000605 extraction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C17/25—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
-
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/827,302 US9290424B2 (en) | 2013-03-14 | 2013-03-14 | Processes for the hydrogenation of halogenated alkenes and the manufacture of fluorinated olefins |
| PCT/US2014/021482 WO2014159014A1 (en) | 2013-03-14 | 2014-03-07 | Process for the manufacture of fluorinated olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2705051T3 true ES2705051T3 (es) | 2019-03-21 |
Family
ID=51530199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14773255T Active ES2705051T3 (es) | 2013-03-14 | 2014-03-07 | Procedimiento para la fabricación de olefinas fluoradas |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9290424B2 (enExample) |
| EP (1) | EP2970056B1 (enExample) |
| JP (1) | JP6549553B2 (enExample) |
| CN (1) | CN105189422B (enExample) |
| ES (1) | ES2705051T3 (enExample) |
| MX (1) | MX2015012245A (enExample) |
| WO (1) | WO2014159014A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9290424B2 (en) * | 2013-03-14 | 2016-03-22 | Honeywell International Inc. | Processes for the hydrogenation of halogenated alkenes and the manufacture of fluorinated olefins |
| FR3098216B1 (fr) * | 2020-07-03 | 2023-01-13 | Arkema France | Procédé de production de 2,3,3,3-tétrafluoropropène et installation pour la mise en œuvre de celui-ci |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3158440B2 (ja) | 1992-06-05 | 2001-04-23 | ダイキン工業株式会社 | １，１，１，２，３−ペンタフルオロプロペンの製造方法及び１，１，１，２，３−ペンタフルオロプロパンの製造方法 |
| JP3407379B2 (ja) | 1993-06-10 | 2003-05-19 | ダイキン工業株式会社 | １，１，１，３，３−ペンタフルオロプロパンの製造方法 |
| US5847018A (en) | 1995-07-03 | 1998-12-08 | Exxon Chemical Patents Inc. | Method of producing rigid foams and products produced therefrom |
| US7560602B2 (en) | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
| US8766020B2 (en) | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8013194B2 (en) | 2008-03-14 | 2011-09-06 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| US8044250B2 (en) | 2007-11-16 | 2011-10-25 | Honeywell International Inc. | Manufacture of 1,1,1,2,3,3-hexafluoropropane and 1,1,1,2-tetrafluoropropane via catalytic hydrogenation |
| GB0801209D0 (en) | 2008-01-23 | 2008-02-27 | Ineos Fluor Holdings Ltd | Process |
| 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 |
| FR2932799B1 (fr) | 2008-06-18 | 2010-08-13 | Arkema France | Procede de preparation de composes fluores |
| FR2935703B1 (fr) | 2008-09-11 | 2010-09-03 | Arkema France | Procede de preparation de composes fluores. |
| CN101456787B (zh) * | 2009-01-04 | 2013-03-13 | 浙江鹏友化工有限公司 | 一种氟化氢加成反应催化剂及含氟烷烃的制备方法 |
| FR2946645B1 (fr) * | 2009-06-12 | 2011-07-01 | Arkema France | Procede de fabrication du hexafluoropropane. |
| FR2946644B1 (fr) | 2009-06-12 | 2011-10-14 | Arkema France | Procede de fabrication du pentafluoropropane. |
| FR2948362B1 (fr) | 2009-07-23 | 2012-03-23 | Arkema France | Procede de preparation de composes fluores |
| CN101628850B (zh) | 2009-08-14 | 2012-09-19 | 西安近代化学研究所 | Z-1,2,3,3,3-五氟丙烯的制备方法 |
| CN101628851B (zh) | 2009-08-14 | 2012-10-10 | 西安近代化学研究所 | 1,2,3,3,3-五氟丙烯的制备方法 |
| CN101628849B (zh) | 2009-08-14 | 2012-10-10 | 西安近代化学研究所 | Z-1,2,3,3,3-五氟丙烯的制备方法 |
| US9290424B2 (en) * | 2013-03-14 | 2016-03-22 | Honeywell International Inc. | Processes for the hydrogenation of halogenated alkenes and the manufacture of fluorinated olefins |
-
2013
- 2013-03-14 US US13/827,302 patent/US9290424B2/en not_active Expired - Fee Related
-
2014
- 2014-03-07 EP EP14773255.6A patent/EP2970056B1/en not_active Not-in-force
- 2014-03-07 ES ES14773255T patent/ES2705051T3/es active Active
- 2014-03-07 WO PCT/US2014/021482 patent/WO2014159014A1/en not_active Ceased
- 2014-03-07 JP JP2016500772A patent/JP6549553B2/ja not_active Expired - Fee Related
- 2014-03-07 CN CN201480027547.9A patent/CN105189422B/zh active Active
- 2014-03-07 MX MX2015012245A patent/MX2015012245A/es unknown
-
2016
- 2016-03-21 US US15/076,191 patent/US10364201B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014159014A1 (en) | 2014-10-02 |
| MX2015012245A (es) | 2015-12-01 |
| EP2970056A4 (en) | 2016-10-05 |
| EP2970056A1 (en) | 2016-01-20 |
| US20140275645A1 (en) | 2014-09-18 |
| US20160340277A1 (en) | 2016-11-24 |
| US10364201B2 (en) | 2019-07-30 |
| JP6549553B2 (ja) | 2019-07-24 |
| CN105189422A (zh) | 2015-12-23 |
| EP2970056B1 (en) | 2018-10-10 |
| US9290424B2 (en) | 2016-03-22 |
| CN105189422B (zh) | 2018-10-19 |
| JP2016510818A (ja) | 2016-04-11 |
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