DE1937110B2 - - Google Patents
Info
- Publication number
- DE1937110B2 DE1937110B2 DE1937110A DE1937110A DE1937110B2 DE 1937110 B2 DE1937110 B2 DE 1937110B2 DE 1937110 A DE1937110 A DE 1937110A DE 1937110 A DE1937110 A DE 1937110A DE 1937110 B2 DE1937110 B2 DE 1937110B2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- stream
- compounds
- chromium
- fluorination
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 39
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 34
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 26
- 238000003682 fluorination reaction Methods 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000011651 chromium Substances 0.000 claims description 21
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 claims description 18
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials 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 16
- 229910052804 chromium Inorganic materials 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 14
- 229910052742 iron Inorganic materials 0.000 claims description 14
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 14
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 11
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 150000002816 nickel compounds Chemical class 0.000 claims description 10
- 230000004913 activation Effects 0.000 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- -1 aluminum compound Chemical class 0.000 claims description 7
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 4
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000001845 chromium compounds Chemical class 0.000 claims description 3
- OCMWNPXYDGZWJQ-UHFFFAOYSA-I [Fe+2].[F-].[Al+3].[F-].[F-].[F-].[F-] Chemical compound [Fe+2].[F-].[Al+3].[F-].[F-].[F-].[F-] OCMWNPXYDGZWJQ-UHFFFAOYSA-I 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910000990 Ni alloy Inorganic materials 0.000 description 5
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 4
- 238000007323 disproportionation reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- DASQIKOOFDJYKA-UHFFFAOYSA-N CCIF Chemical compound CCIF DASQIKOOFDJYKA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 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 2
- 239000002245 particle Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005029 sieve analysis Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910016569 AlF 3 Inorganic materials 0.000 description 1
- 241000238633 Odonata Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- RZQIADHNAWHUIG-UHFFFAOYSA-N [AlH]=C Chemical class [AlH]=C RZQIADHNAWHUIG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated 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
- 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
- C07C17/37—Preparation of halogenated hydrocarbons by disproportionation of halogenated hydrocarbons
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
- Fertilizers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1944868 | 1968-07-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1937110A1 DE1937110A1 (de) | 1970-09-10 |
| DE1937110B2 true DE1937110B2 (en:Method) | 1979-11-15 |
| DE1937110C3 DE1937110C3 (de) | 1980-08-14 |
Family
ID=11158082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1937110A Expired DE1937110C3 (de) | 1968-07-25 | 1969-07-22 | Katalysator zur Fluorierung und Chlorfluorierung von Kohlenwasserstoff-Verbindungen in der Gasphase, ein Verfahren zu seiner Herstellung und seine Verwendung |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3650987A (en:Method) |
| JP (1) | JPS5013238B1 (en:Method) |
| AT (1) | AT292024B (en:Method) |
| BE (1) | BE736582A (en:Method) |
| BR (1) | BR6911010D0 (en:Method) |
| CH (1) | CH511056A (en:Method) |
| DE (1) | DE1937110C3 (en:Method) |
| DK (1) | DK126161B (en:Method) |
| ES (1) | ES369847A1 (en:Method) |
| FR (1) | FR2014711A1 (en:Method) |
| GB (1) | GB1274030A (en:Method) |
| IL (1) | IL32648A (en:Method) |
| NL (1) | NL169036C (en:Method) |
| NO (1) | NO125478B (en:Method) |
| SE (1) | SE361134B (en:Method) |
| YU (1) | YU32638B (en:Method) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6226239A (ja) * | 1985-05-28 | 1987-02-04 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | フルオロオレフインの接触ハロゲン交換法 |
| DE3660802D1 (en) | 1985-05-28 | 1988-11-03 | Du Pont | Catalytic fluoroolefin transhalogenations |
| IT1202652B (it) * | 1987-03-09 | 1989-02-09 | Ausimont Spa | Processo per la preparazione di 1,1,1-trifluoro-2,2-dicloroetano mediante idrofluorurazione in presenza di catalizzatori |
| US5262574A (en) * | 1987-03-09 | 1993-11-16 | Ausimont S.P.A. | Process for preparing 1,1,1-trifluoro-2,2-dichloroethane by hydrofluorination in the presence of catalysts |
| US5276224A (en) * | 1987-03-09 | 1994-01-04 | Ausimont S.P.A. | Process for preparing 1,1,1-trifluoro-2,2-dichloroethane by hydrofluorination in the presence of catalysts |
| US4766260A (en) * | 1987-07-07 | 1988-08-23 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
| US4766259A (en) * | 1987-08-13 | 1988-08-23 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
| US4798818A (en) * | 1987-11-27 | 1989-01-17 | Dow Corning Corporation | Catalyst composition and process for its preparation |
| US4922037A (en) * | 1988-02-24 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
| US4996379A (en) * | 1988-05-30 | 1991-02-26 | Central Glass Company, Limited | Method of preparing 1,1,1,2-tetrafluoroethane from 1,1-dichloro-1,2,2,2-tetrafluoroethane |
| US4902838A (en) * | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
| FR2669022B1 (fr) * | 1990-11-13 | 1992-12-31 | Atochem | Procede de fabrication du tetrafluoro-1,1,1,2-ethane. |
| US5177273A (en) * | 1991-02-01 | 1993-01-05 | E. I. Du Pont De Nemours And Company | Process for the manufacture of halogen-substituted propanes containing hydrogen and at least five fluorine substituents |
| US5243106A (en) * | 1991-06-03 | 1993-09-07 | E. I. Du Pont De Nemours And Company | Processes using aluminum fluoride catalyst compositions for preparing 1,1-dichloro-1,2,2,2-tetrafluoroethane |
| US5243108A (en) * | 1991-06-03 | 1993-09-07 | E. I. Du Pont De Nemours And Company | Aluminum fluoride catalyst compositions and use thereof in a chlorofluorination process for preparing 1,1-dichloro-1,2,2,2-tetrafluoroethane |
| FR2700770B1 (fr) * | 1993-01-27 | 1995-03-24 | Atochem Elf Sa | Procédé de fabrication du 1,1,1,2-tétrafluoro-2-chloroéthane et du pentafluoroéthane. |
| FR2700766B1 (fr) * | 1993-01-27 | 1995-03-24 | Atochem Elf Sa | Procédé de fluoration de perchloréthylène ou du pentachloréthane. |
| US5866730A (en) * | 1993-04-02 | 1999-02-02 | E. I. Du Pont De Nemours And Company | Process for enriching 1,2-dichloro-1,1,2,2-tetrafluoroethane from a mixture of dichlorotetrafluoroethane isomers |
-
1969
- 1969-07-17 NL NLAANVRAGE6911020,A patent/NL169036C/xx not_active IP Right Cessation
- 1969-07-17 NO NO2982/69A patent/NO125478B/no unknown
- 1969-07-17 DK DK387569AA patent/DK126161B/da not_active IP Right Cessation
- 1969-07-17 SE SE10123/69A patent/SE361134B/xx unknown
- 1969-07-18 IL IL32648A patent/IL32648A/en unknown
- 1969-07-18 US US843232A patent/US3650987A/en not_active Expired - Lifetime
- 1969-07-21 YU YU1886/69A patent/YU32638B/xx unknown
- 1969-07-21 FR FR6924711A patent/FR2014711A1/fr not_active Withdrawn
- 1969-07-22 DE DE1937110A patent/DE1937110C3/de not_active Expired
- 1969-07-24 BR BR211010/69A patent/BR6911010D0/pt unknown
- 1969-07-24 ES ES369847A patent/ES369847A1/es not_active Expired
- 1969-07-24 AT AT716269A patent/AT292024B/de not_active IP Right Cessation
- 1969-07-24 JP JP44058681A patent/JPS5013238B1/ja active Pending
- 1969-07-24 GB GB37228/69A patent/GB1274030A/en not_active Expired
- 1969-07-25 CH CH1142569A patent/CH511056A/de not_active IP Right Cessation
- 1969-07-25 BE BE736582D patent/BE736582A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK126161B (da) | 1973-06-18 |
| FR2014711A1 (en:Method) | 1970-04-17 |
| BR6911010D0 (pt) | 1973-04-12 |
| NL169036B (nl) | 1982-01-04 |
| NL6911020A (en:Method) | 1970-01-27 |
| BE736582A (en:Method) | 1970-01-26 |
| DE1937110C3 (de) | 1980-08-14 |
| SE361134B (en:Method) | 1973-10-22 |
| CH511056A (de) | 1971-08-15 |
| DE1937110A1 (de) | 1970-09-10 |
| AT292024B (de) | 1971-08-10 |
| YU32638B (en) | 1975-04-30 |
| NO125478B (en:Method) | 1972-09-18 |
| JPS5013238B1 (en:Method) | 1975-05-17 |
| GB1274030A (en) | 1972-05-10 |
| ES369847A1 (es) | 1971-07-16 |
| YU188669A (en) | 1974-10-31 |
| US3650987A (en) | 1972-03-21 |
| IL32648A (en) | 1972-11-28 |
| IL32648A0 (en) | 1969-09-25 |
| NL169036C (nl) | 1982-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |