AU630807B2 - Process for the manufacture of 1,1,1,2-tetra-fluorochloroethane and/or pentafluoroethane - Google Patents
Process for the manufacture of 1,1,1,2-tetra-fluorochloroethane and/or pentafluoroethane Download PDFInfo
- Publication number
- AU630807B2 AU630807B2 AU76053/91A AU7605391A AU630807B2 AU 630807 B2 AU630807 B2 AU 630807B2 AU 76053/91 A AU76053/91 A AU 76053/91A AU 7605391 A AU7605391 A AU 7605391A AU 630807 B2 AU630807 B2 AU 630807B2
- Authority
- AU
- Australia
- Prior art keywords
- process according
- chromium
- catalyst
- tetrafluorochloroethane
- pentafluoroethane
- 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 abstract description 28
- 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 abstract description 8
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 19
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011651 chromium Substances 0.000 claims abstract description 11
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 230000003647 oxidation Effects 0.000 claims abstract description 3
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 4
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 4
- -1 oxyhalide Chemical compound 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- YMRMDGSNYHCUCL-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoroethane Chemical compound FC(Cl)C(F)(F)Cl YMRMDGSNYHCUCL-UHFFFAOYSA-N 0.000 claims 1
- JQZFYIGAYWLRCC-UHFFFAOYSA-N 1-chloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)(F)Cl JQZFYIGAYWLRCC-UHFFFAOYSA-N 0.000 claims 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical group FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 9
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 230000004913 activation Effects 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 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
- 229950011008 tetrachloroethylene Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 229940117975 chromium trioxide Drugs 0.000 description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910001026 inconel Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 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
- 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
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004340 Chloropentafluoroethane Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101100258315 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-1 gene Proteins 0.000 description 1
- JQGGAELIYHNDQS-UHFFFAOYSA-N Nic 12 Natural products CC(C=CC(=O)C)c1ccc2C3C4OC4C5(O)CC=CC(=O)C5(C)C3CCc2c1 JQGGAELIYHNDQS-UHFFFAOYSA-N 0.000 description 1
- 101150093156 Rras gene Proteins 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000019406 chloropentafluoroethane Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000010276 construction Methods 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
- 230000007123 defense Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- 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
- C07C17/093—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
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
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)
- Developing Agents For Electrophotography (AREA)
- Pyrrole Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9005908 | 1990-05-11 | ||
| FR9005908A FR2661906B1 (fr) | 1990-05-11 | 1990-05-11 | Procede de fabrication du 1,1,1,2-tetrafluoro-chloroethane et du pentafluoroethane. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7605391A AU7605391A (en) | 1991-11-14 |
| AU630807B2 true AU630807B2 (en) | 1992-11-05 |
Family
ID=9396524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU76053/91A Ceased AU630807B2 (en) | 1990-05-11 | 1991-04-29 | Process for the manufacture of 1,1,1,2-tetra-fluorochloroethane and/or pentafluoroethane |
Country Status (15)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU672210B2 (en) * | 1992-06-10 | 1996-09-26 | Ineos Fluor Holdings Limited | Production of hydrofluoroalkanes |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9007029D0 (en) * | 1990-03-29 | 1990-05-30 | Ici Plc | Chemical process |
| FR2669022B1 (fr) * | 1990-11-13 | 1992-12-31 | Atochem | Procede de fabrication du tetrafluoro-1,1,1,2-ethane. |
| ES2128354T3 (es) * | 1991-05-06 | 1999-05-16 | Du Pont | Procedimiento para la preparacion de pentafluoroetano. |
| ZA923274B (en) * | 1991-05-06 | 1993-11-08 | Du Pont | Process for the manufacture of pentafluoroethane |
| DK0513823T3 (da) * | 1991-05-17 | 1996-02-05 | Hoechst Ag | Fremgangsmåde til fremstilling af pentafluorethan (R 125) |
| FR2684567B1 (fr) * | 1991-12-09 | 1994-11-04 | Atochem | Catalyseurs massiques a base d'oxydes de chrome et de nickel, et leur application a la fluoration d'hydrocarbures halogenes. |
| US5395999A (en) * | 1992-11-06 | 1995-03-07 | E. I. Du Pont De Nemours And Company | Catalytic chlorofluorination process for producing CHClFCF3 and CHF2 CF3 |
| EP0687660B2 (en) † | 1993-03-05 | 2006-05-17 | Daikin Industries, Limited | Process for producing 1,1,1,2,2-pentafluoroethane, process for producing 2,2-dichloro-1,1,1-trifluoroethane, and method of purifying 1,1,1,2,2-pentafluoroethane |
| GB9325756D0 (en) * | 1993-12-16 | 1994-02-16 | Ici Plc | Production of pentafluoroethane |
| US5475167A (en) * | 1995-02-17 | 1995-12-12 | E. I. Du Pont De Nemours And Company | Process for the manufacture of pentafluoroethane |
| CA2213579C (en) * | 1995-02-24 | 2007-04-17 | Daikin Industries Ltd. | Process for producing pentafluoroethane and tetrafluorochloroethane |
| JP3853397B2 (ja) * | 1995-05-11 | 2006-12-06 | イネオス フラウアー ホールデイングス リミテッド | ペンタフルオロエタンの製造方法及びペンタフルオロエタンに転化するのに適当な組成物 |
| FR2754815B1 (fr) * | 1996-10-18 | 1998-12-04 | Atochem Elf Sa | Purification du pentafluoroethane |
| FR2764883B1 (fr) * | 1997-06-18 | 1999-07-16 | Atochem Elf Sa | Procede de fabrication d'hydrofluoroalcanes |
| 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 |
| RU2179885C1 (ru) * | 2001-04-24 | 2002-02-27 | Открытое акционерное общество "Галоген" | Катализатор для синтеза хладонов |
| FR2828193B1 (fr) | 2001-08-03 | 2004-04-02 | Atofina | Nouveau procede de preparation du 1,1,1,-trifluoro-2,2-dichloroethane |
| US20070191652A1 (en) * | 2004-03-29 | 2007-08-16 | Hiromoto Ohno | Process for production of 1,1,1,2- tetrafluoroethane and/or pentafluorethane and applications of the same |
| GB0525701D0 (en) | 2005-12-17 | 2006-01-25 | Ineos Fluor Holdings Ltd | Process |
| GB0525699D0 (en) | 2005-12-17 | 2006-01-25 | Ineos Fluor Holdings Ltd | Process |
| GB0525700D0 (en) | 2005-12-17 | 2006-01-25 | Ineos Fluor Holdings Ltd | Process |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU609529B2 (en) * | 1987-10-22 | 1991-05-02 | E.I. Du Pont De Nemours And Company | Improved process for the manufacture of 1,1,1- trifluorodichloroethane and 1,1,1,2-tetrafluorochloroethane |
| AU612857B2 (en) * | 1988-06-29 | 1991-07-18 | E.I. Du Pont De Nemours And Company | Gas-phase hydrofluorination process |
| AU8779991A (en) * | 1990-11-13 | 1992-05-14 | Atochem | Process for the manufacture of 1,1,1,2-tetrafluoroethane |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB468447A (en) * | 1936-01-03 | 1937-07-05 | Fred Davison Leicester | Improvements in or relating to the manufacture of fluorine derivatives of aliphatic hydrocarbons |
| GB745818A (en) * | 1952-06-12 | 1956-03-07 | Nat Smelting Co Ltd | Improvements in or relating to a process for producing fluorohalo-derivatives of saturated aliphatic hydrocarbons |
| DE1568614A1 (de) * | 1962-01-13 | 1970-03-05 | Hoechst Ag | Verfahren zur Herstellung fluorhaltiger aliphatischer Verbindungen |
| CA931978A (en) * | 1968-01-24 | 1973-08-14 | Frank J. Christoph, Jr. | Process for preparing trichlorotrifluoroethane and dichlorotetrafluoroethane |
| US3632834A (en) * | 1968-10-23 | 1972-01-04 | Du Pont | Process for preparing trichlorotrifluoroethane and dichlorotetrafluoroethane |
| US4129603A (en) * | 1978-02-07 | 1978-12-12 | Imperial Chemical Industries Limited | Manufacture of halogenated compounds |
| JPS6012910B2 (ja) * | 1979-08-04 | 1985-04-04 | ダイキン工業株式会社 | フツ素化触媒 |
| JPS59225131A (ja) * | 1983-06-06 | 1984-12-18 | Showa Denko Kk | ジフルオロメタンの製造方法 |
| US4766260A (en) * | 1987-07-07 | 1988-08-23 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
-
1990
- 1990-05-11 FR FR9005908A patent/FR2661906B1/fr not_active Expired - Fee Related
-
1991
- 1991-04-03 CA CA002039646A patent/CA2039646C/fr not_active Expired - Fee Related
- 1991-04-12 NO NO911442A patent/NO172796C/no unknown
- 1991-04-29 DE DE69101025T patent/DE69101025T2/de not_active Expired - Fee Related
- 1991-04-29 EP EP91401136A patent/EP0456552B1/fr not_active Expired - Lifetime
- 1991-04-29 AT AT91401136T patent/ATE100430T1/de not_active IP Right Cessation
- 1991-04-29 ES ES91401136T patent/ES2048569T3/es not_active Expired - Lifetime
- 1991-04-29 AU AU76053/91A patent/AU630807B2/en not_active Ceased
- 1991-05-07 KR KR1019910007372A patent/KR930010404B1/ko not_active Expired - Fee Related
- 1991-05-08 PT PT97608A patent/PT97608A/pt not_active Application Discontinuation
- 1991-05-09 TW TW080103611A patent/TW258725B/zh active
- 1991-05-10 IE IE161591A patent/IE911615A1/en unknown
- 1991-05-10 FI FI912296A patent/FI912296A7/fi not_active Application Discontinuation
- 1991-05-10 JP JP3106017A patent/JPH06102631B2/ja not_active Expired - Lifetime
-
1993
- 1993-05-24 US US08/065,422 patent/US5354928A/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU609529B2 (en) * | 1987-10-22 | 1991-05-02 | E.I. Du Pont De Nemours And Company | Improved process for the manufacture of 1,1,1- trifluorodichloroethane and 1,1,1,2-tetrafluorochloroethane |
| AU612857B2 (en) * | 1988-06-29 | 1991-07-18 | E.I. Du Pont De Nemours And Company | Gas-phase hydrofluorination process |
| AU8779991A (en) * | 1990-11-13 | 1992-05-14 | Atochem | Process for the manufacture of 1,1,1,2-tetrafluoroethane |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU672210B2 (en) * | 1992-06-10 | 1996-09-26 | Ineos Fluor Holdings Limited | Production of hydrofluoroalkanes |
Also Published As
| Publication number | Publication date |
|---|---|
| PT97608A (pt) | 1992-01-31 |
| JPH04226927A (ja) | 1992-08-17 |
| TW258725B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-10-01 |
| US5354928A (en) | 1994-10-11 |
| KR930010404B1 (ko) | 1993-10-23 |
| FR2661906A1 (fr) | 1991-11-15 |
| AU7605391A (en) | 1991-11-14 |
| NO172796B (no) | 1993-06-01 |
| FI912296A0 (fi) | 1991-05-10 |
| ES2048569T3 (es) | 1994-03-16 |
| EP0456552A1 (fr) | 1991-11-13 |
| FI912296L (fi) | 1991-11-12 |
| CA2039646A1 (fr) | 1991-11-12 |
| DE69101025D1 (de) | 1994-03-03 |
| FI912296A7 (fi) | 1991-11-12 |
| NO172796C (no) | 1993-09-08 |
| EP0456552B1 (fr) | 1994-01-19 |
| NO911442L (no) | 1991-11-12 |
| FR2661906B1 (fr) | 1993-10-01 |
| DE69101025T2 (de) | 1994-07-28 |
| ATE100430T1 (de) | 1994-02-15 |
| KR910019941A (ko) | 1991-12-19 |
| IE911615A1 (en) | 1991-11-20 |
| JPH06102631B2 (ja) | 1994-12-14 |
| CA2039646C (fr) | 1996-10-22 |
| NO911442D0 (no) | 1991-04-12 |
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