AU663816B2 - Process for the manufacture of 1,1,1,2-tetrafluoro-2- chloroethane and of pentafluoroethane - Google Patents
Process for the manufacture of 1,1,1,2-tetrafluoro-2- chloroethane and of pentafluoroethane Download PDFInfo
- Publication number
- AU663816B2 AU663816B2 AU53951/94A AU5395194A AU663816B2 AU 663816 B2 AU663816 B2 AU 663816B2 AU 53951/94 A AU53951/94 A AU 53951/94A AU 5395194 A AU5395194 A AU 5395194A AU 663816 B2 AU663816 B2 AU 663816B2
- Authority
- AU
- Australia
- Prior art keywords
- process according
- nickel
- chromium
- catalyst
- chloroethane
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 33
- 230000008569 process Effects 0.000 title claims description 32
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 title claims description 5
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000003054 catalyst Substances 0.000 claims description 36
- 238000003682 fluorination reaction Methods 0.000 claims description 33
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 26
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 23
- 239000011651 chromium Substances 0.000 claims description 20
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910052804 chromium Inorganic materials 0.000 claims description 19
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 18
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 230000003197 catalytic effect Effects 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical group FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229960003750 ethyl chloride Drugs 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 230000004913 activation Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 6
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 5
- 229950011008 tetrachloroethylene Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229910000423 chromium oxide Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- -1 chromium halides Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- PLHASFSAGNOMLM-UHFFFAOYSA-N nickel(2+);oxido-(oxido(dioxo)chromio)oxy-dioxochromium Chemical compound [Ni+2].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O PLHASFSAGNOMLM-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- MHTDCCPJYMZHSK-UHFFFAOYSA-N 1,1-dibromo-1,2,2-trifluoroethane Chemical compound FC(F)C(F)(Br)Br MHTDCCPJYMZHSK-UHFFFAOYSA-N 0.000 description 1
- YMRMDGSNYHCUCL-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoroethane Chemical compound FC(Cl)C(F)(F)Cl YMRMDGSNYHCUCL-UHFFFAOYSA-N 0.000 description 1
- RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 description 1
- JQZFYIGAYWLRCC-UHFFFAOYSA-N 1-chloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)(F)Cl JQZFYIGAYWLRCC-UHFFFAOYSA-N 0.000 description 1
- YUQQQYGEDJGUCI-UHFFFAOYSA-N 2,2-dibromo-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Br)Br YUQQQYGEDJGUCI-UHFFFAOYSA-N 0.000 description 1
- 229910016569 AlF 3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004340 Chloropentafluoroethane Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N R-12-HOA Natural products CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- XAGFODPZIPBFFR-IGMARMGPSA-N aluminium-27 atom Chemical compound [27Al] XAGFODPZIPBFFR-IGMARMGPSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 235000019406 chloropentafluoroethane Nutrition 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
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/125—Halogens; Compounds thereof with scandium, yttrium, aluminium, gallium, indium or thallium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/866—Nickel and chromium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/132—Halogens; Compounds thereof with chromium, molybdenum, tungsten or polonium
-
- 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
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
- C07C19/12—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/85—Chromium, molybdenum or tungsten
- C07C2523/86—Chromium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/132—Compounds comprising a halogen and chromium, molybdenum, tungsten or polonium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9300780 | 1993-01-27 | ||
| FR9300780A FR2700770B1 (fr) | 1993-01-27 | 1993-01-27 | Procédé de fabrication du 1,1,1,2-tétrafluoro-2-chloroéthane et du pentafluoroéthane. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5395194A AU5395194A (en) | 1994-08-18 |
| AU663816B2 true AU663816B2 (en) | 1995-10-19 |
Family
ID=9443387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU53951/94A Ceased AU663816B2 (en) | 1993-01-27 | 1994-01-21 | Process for the manufacture of 1,1,1,2-tetrafluoro-2- chloroethane and of pentafluoroethane |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5616820A (enExample) |
| EP (1) | EP0609124B1 (enExample) |
| JP (1) | JP2510126B2 (enExample) |
| KR (1) | KR970000398B1 (enExample) |
| CN (1) | CN1035323C (enExample) |
| AU (1) | AU663816B2 (enExample) |
| BR (1) | BR9400338A (enExample) |
| CA (1) | CA2113511C (enExample) |
| DE (1) | DE69400342T2 (enExample) |
| ES (1) | ES2091097T3 (enExample) |
| FR (1) | FR2700770B1 (enExample) |
| GR (1) | GR3021203T3 (enExample) |
| TW (1) | TW258727B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2700766B1 (fr) * | 1993-01-27 | 1995-03-24 | Atochem Elf Sa | Procédé de fluoration de perchloréthylène ou du pentachloréthane. |
| IT1270959B (it) * | 1993-08-13 | 1997-05-26 | Ausimont Spa | Processo per la preparazione di pentafluoroetano |
| JPH10113562A (ja) * | 1996-04-17 | 1998-05-06 | Ausimont Spa | ハロゲン化炭化水素の弗素化用触媒 |
| FR2771027B1 (fr) | 1997-11-20 | 2000-01-14 | Atochem Elf Sa | Catalyseur mixte de fluoration |
| US6187976B1 (en) * | 1998-04-09 | 2001-02-13 | Alliedsignal Inc. | Process for the preparation of fluorine containing hydrohalocarbons |
| IT1303074B1 (it) | 1998-05-07 | 2000-10-23 | Ausimont Spa | Catalizzatore per la fluorurazione di composti organici alogenati |
| FR2805534B1 (fr) * | 2000-02-29 | 2002-05-17 | Atofina | Procede de preparation du 1,1,1-trifluoro-2,2-dichloroethane |
| FR2828193B1 (fr) | 2001-08-03 | 2004-04-02 | Atofina | Nouveau procede de preparation du 1,1,1,-trifluoro-2,2-dichloroethane |
| EP1502906A1 (en) * | 2003-07-31 | 2005-02-02 | Solvay Solexis S.p.A. | Process for activation of AIF3 based catalysts and process for isomerising hydrochlorofluorocarbons |
| CN100338001C (zh) * | 2004-11-17 | 2007-09-19 | 浙江莹光化工有限公司 | 一种同时制备1,1,1,2－四氟乙烷和五氟乙烷的方法 |
| KR100680766B1 (ko) * | 2005-09-23 | 2007-02-09 | 울산화학주식회사 | 펜타플루오로에탄 제조용 촉매의 제조방법 |
| CN115624981A (zh) * | 2022-11-30 | 2023-01-20 | 北京宇极科技发展有限公司 | 金属氟化物、制备方法及其应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU612857B2 (en) * | 1988-06-29 | 1991-07-18 | E.I. Du Pont De Nemours And Company | Gas-phase hydrofluorination process |
| AU641292B2 (en) * | 1990-11-13 | 1993-09-16 | Atochem | Process for the manufacture of 1,1,1,2-tetrafluoroethane |
| AU5397094A (en) * | 1993-01-27 | 1994-08-18 | Elf Atochem S.A. | Process for fluorination of perchloroethylene or of pentachloroethane |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435551A (en) * | 1944-04-20 | 1948-02-03 | Standard Oil Dev Co | Production of hydrocarbons from carbon monoxide and hydrogen |
| US2900423A (en) * | 1957-12-13 | 1959-08-18 | Allied Chem | Manufacture of perfluoropropene |
| SE361134B (enExample) * | 1968-07-25 | 1973-10-22 | Montedison Spa | |
| DK138673B (da) * | 1968-10-10 | 1978-10-16 | Montedison Spa | Katalysator til fremstilling af chlorfluorerede ethaner. |
| US3661805A (en) * | 1969-11-21 | 1972-05-09 | Universal Oil Prod Co | Method of manufacturing an extruded catalyst composition |
| SE374675B (enExample) * | 1970-06-10 | 1975-03-17 | Montedison Spa | |
| FR2135473B1 (enExample) * | 1971-05-06 | 1973-05-11 | Rhone Progil | |
| US4131616A (en) * | 1974-06-24 | 1978-12-26 | E. I. Du Pont De Nemours And Company | Methanation catalyst |
| FR2407021A1 (fr) * | 1977-10-26 | 1979-05-25 | Anvar | Nouveaux derives metalliques, leur preparation et leur application en tant que catalyseurs, en particulier pour la fabrication de nitriles par ammoxydation d'alcanes a l'aide de monoxyde d'azote |
| FR2501062A1 (fr) * | 1980-12-29 | 1982-09-10 | Ugine Kuhlmann | Catalyseurs de fluoruration en phase gazeuse de derives chlores aliphatiques, a base de microbilles d'oxyde de chrome, et procedes de fluoruration utilisant ces catalyseurs |
| EP0128510A3 (en) * | 1983-06-07 | 1985-05-15 | Showa Denko Kabushiki Kaisha | Process for producing difluoromethane |
| US4912270A (en) * | 1987-03-13 | 1990-03-27 | Allied-Signal Inc. | Chromia aerogel, method of producing same and fluorination process utilizing same |
| US4766260A (en) * | 1987-07-07 | 1988-08-23 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
| CA1310335C (en) * | 1988-02-12 | 1992-11-17 | Leo E. Manzer | Gas-phase fluorination process |
| JP2764980B2 (ja) * | 1988-12-28 | 1998-06-11 | 旭硝子株式会社 | パークロロエチレンのフッ素化方法 |
| DE3930507A1 (de) * | 1989-09-13 | 1991-03-21 | Hoechst Ag | Verfahren zur herstellung von 1,1,1,2-tetrafluorethan |
| US5300710A (en) * | 1991-03-20 | 1994-04-05 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 2-chloro-1,1,1,2-tetrafluoroethane and pentafluoroethane |
| EP0513823B1 (de) * | 1991-05-17 | 1995-10-04 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Pentafluorethan (R 125) |
-
1993
- 1993-01-27 FR FR9300780A patent/FR2700770B1/fr not_active Expired - Fee Related
-
1994
- 1994-01-14 CA CA002113511A patent/CA2113511C/fr not_active Expired - Fee Related
- 1994-01-21 AU AU53951/94A patent/AU663816B2/en not_active Ceased
- 1994-01-21 TW TW083100495A patent/TW258727B/zh not_active IP Right Cessation
- 1994-01-24 EP EP94400140A patent/EP0609124B1/fr not_active Expired - Lifetime
- 1994-01-24 ES ES94400140T patent/ES2091097T3/es not_active Expired - Lifetime
- 1994-01-24 DE DE69400342T patent/DE69400342T2/de not_active Expired - Lifetime
- 1994-01-26 BR BR9400338A patent/BR9400338A/pt not_active IP Right Cessation
- 1994-01-26 JP JP6007031A patent/JP2510126B2/ja not_active Expired - Fee Related
- 1994-01-27 CN CN94101164A patent/CN1035323C/zh not_active Expired - Lifetime
- 1994-01-27 KR KR94001484A patent/KR970000398B1/ko not_active Expired - Lifetime
-
1995
- 1995-06-28 US US08/496,052 patent/US5616820A/en not_active Expired - Lifetime
-
1996
- 1996-09-30 GR GR960402558T patent/GR3021203T3/el unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU612857B2 (en) * | 1988-06-29 | 1991-07-18 | E.I. Du Pont De Nemours And Company | Gas-phase hydrofluorination process |
| AU641292B2 (en) * | 1990-11-13 | 1993-09-16 | Atochem | Process for the manufacture of 1,1,1,2-tetrafluoroethane |
| AU5397094A (en) * | 1993-01-27 | 1994-08-18 | Elf Atochem S.A. | Process for fluorination of perchloroethylene or of pentachloroethane |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2510126B2 (ja) | 1996-06-26 |
| DE69400342D1 (de) | 1996-09-05 |
| AU5395194A (en) | 1994-08-18 |
| ES2091097T3 (es) | 1996-10-16 |
| CA2113511A1 (fr) | 1994-07-28 |
| US5616820A (en) | 1997-04-01 |
| FR2700770B1 (fr) | 1995-03-24 |
| CA2113511C (fr) | 1999-01-12 |
| BR9400338A (pt) | 1994-08-16 |
| EP0609124A1 (fr) | 1994-08-03 |
| CN1035323C (zh) | 1997-07-02 |
| KR970000398B1 (en) | 1997-01-09 |
| TW258727B (enExample) | 1995-10-01 |
| CN1101337A (zh) | 1995-04-12 |
| FR2700770A1 (fr) | 1994-07-29 |
| KR940018341A (ko) | 1994-08-16 |
| GR3021203T3 (en) | 1996-12-31 |
| JPH06247883A (ja) | 1994-09-06 |
| EP0609124B1 (fr) | 1996-07-31 |
| DE69400342T2 (de) | 1997-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU663818B2 (en) | Process for fluorination of perchloroethylene or of pentachloroethane | |
| EP0968161B1 (en) | Process for the manufacture of 1,1,1,3,3-pentafluoropropane | |
| US5731481A (en) | Process for the manufacture of 1,1,1,2-Tetrafluoroethane | |
| RU2007380C1 (ru) | Способ получения 1,1,1-трифтордихлорэтана и 1,1,1,2-тетрафторхлорэтана | |
| EP2417086B1 (en) | Process for preparing 3,3,3-trifluoropropene | |
| US5354928A (en) | Process for the manufacture of 1,1,1,2-tetrafluorochloroethane and of pentafluoroethane | |
| EP0455748B2 (en) | Manufacture of 1,1,1,2-tetrafluoroethane | |
| US5919728A (en) | Catalyst for the fluorination of halogenated hydrocarbons | |
| AU663816B2 (en) | Process for the manufacture of 1,1,1,2-tetrafluoro-2- chloroethane and of pentafluoroethane | |
| US20020155947A1 (en) | Bulk catalysts based on chromium and on nickel for the gas-phase fluorination of halogenated hydrocarbons | |
| EP0576581B1 (en) | Process for the manufacture of 2,2-dichloro-1,1,1-trifluoroethane, 2-chloro-1,1,1,2-tetrafluoroethane and pentafluoroethane | |
| WO1994013609A1 (en) | Process for reducing the fluorine content of hydrofluorocarbons and hydrohalofluorocarbons | |
| JP3675959B2 (ja) | ジフルオロメタンの製造法 | |
| US6297411B1 (en) | Mixed fluorination catalyst | |
| JPH08108073A (ja) | クロム系フッ素化触媒、その製法及びフッ素化方法 | |
| US5008475A (en) | Gas-phase fluorination process | |
| AU714842B2 (en) | Synthesis of difluoromethane | |
| KR101343660B1 (ko) | 펜타플루오로에탄 제조 방법 | |
| HK29096A (en) | Gas-phase fluorination process | |
| Cho et al. | Catalytic fluorination of HCFC-133a (1, 1, 1-trifluoro-2-chloroethane) | |
| JPH0761944A (ja) | フッ素化触媒およびフッ素化方法 | |
| HK1167135B (en) | Process for preparing 3,3,3-trifluoropropene |