DE1900241C3 - Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen - Google Patents
Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen KohlenwasserstoffenInfo
- Publication number
- DE1900241C3 DE1900241C3 DE1900241A DE1900241A DE1900241C3 DE 1900241 C3 DE1900241 C3 DE 1900241C3 DE 1900241 A DE1900241 A DE 1900241A DE 1900241 A DE1900241 A DE 1900241A DE 1900241 C3 DE1900241 C3 DE 1900241C3
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- hydrogen fluoride
- fluorinated
- hydrocarbons
- bismuth
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 4
- 229930195733 hydrocarbon Natural products 0.000 title claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 38
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 25
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000008282 halocarbons Chemical class 0.000 claims description 11
- 150000001621 bismuth Chemical class 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 229910052797 bismuth Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 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
- -1 salts Aluminum oxide Chemical class 0.000 claims description 5
- 239000012266 salt solution Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000007423 decrease Effects 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 238000003682 fluorination reaction Methods 0.000 claims description 2
- 238000005470 impregnation Methods 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000012467 final product Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000002791 soaking Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000008139 complexing agent Substances 0.000 description 3
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 3
- 239000008246 gaseous mixture Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 2
- KDWQLICBSFIDRM-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical compound CCC(F)(F)F KDWQLICBSFIDRM-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- JVWLUVNSQYXYBE-UHFFFAOYSA-N Ribitol Natural products OCC(C)C(O)C(O)CO JVWLUVNSQYXYBE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- B01J23/18—Arsenic, antimony or bismuth
-
- 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
- B01J23/32—Manganese, technetium or rhenium
- B01J23/34—Manganese
-
- 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
- B01J23/90—Regeneration or reactivation
- B01J23/92—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
-
- 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
- B01J27/08—Halides
- B01J27/12—Fluorides
-
- 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
- B01J27/28—Regeneration or reactivation
- B01J27/32—Regeneration or reactivation of catalysts comprising compounds of halogens
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/22—Halogenating
- B01J37/26—Fluorinating
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1900241A DE1900241C3 (de) | 1969-01-03 | 1969-01-03 | Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen |
| JP702028A JPS5117544B1 (enrdf_load_stackoverflow) | 1969-01-03 | 1969-12-27 | |
| CH1933669A CH528457A (de) | 1969-01-03 | 1969-12-29 | Verfahren zur Herstellung von fluorierten Kohlenwasserstoffen |
| FR6945742A FR2027735A1 (enrdf_load_stackoverflow) | 1969-01-03 | 1969-12-31 | |
| BE743933D BE743933A (enrdf_load_stackoverflow) | 1969-01-03 | 1969-12-31 | |
| GB305/70A GB1261501A (en) | 1969-01-03 | 1970-01-02 | Improvements in or relating to catalysts used in the preparation of fluorinated hydrocarbons |
| NL7000012A NL7000012A (enrdf_load_stackoverflow) | 1969-01-03 | 1970-01-02 | |
| CA071,332A CA972741A (en) | 1969-01-03 | 1970-01-02 | Process for catalytic hydro-fluoration of halogenated hydrocarbons |
| AT5470A AT301502B (de) | 1969-01-03 | 1970-01-05 | Verfahren zur Herstellung von fluorierten aliphatischen oder cycloaliphatischen Kohlenwasserstoffen oder Halogenfluorkohlenwasserstoffen |
| NL7019071A NL7019071A (en) | 1969-01-03 | 1970-12-31 | Bismuth and manganese contg catalyst for - fluorinated hydrocarbon production |
| US344673A US3904701A (en) | 1969-01-03 | 1973-03-26 | Process for the catalytic hydrofluorination of halogenated hydrocarbons |
| US05/586,839 US3965038A (en) | 1969-01-03 | 1975-06-13 | Regeneration of bismuth containing catalyst used in the hydrofluorination of halogenated hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1900241A DE1900241C3 (de) | 1969-01-03 | 1969-01-03 | Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1900241A1 DE1900241A1 (de) | 1970-07-30 |
| DE1900241B2 DE1900241B2 (de) | 1978-02-09 |
| DE1900241C3 true DE1900241C3 (de) | 1978-09-21 |
Family
ID=5721713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1900241A Expired DE1900241C3 (de) | 1969-01-03 | 1969-01-03 | Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5117544B1 (enrdf_load_stackoverflow) |
| AT (1) | AT301502B (enrdf_load_stackoverflow) |
| BE (1) | BE743933A (enrdf_load_stackoverflow) |
| CA (1) | CA972741A (enrdf_load_stackoverflow) |
| CH (1) | CH528457A (enrdf_load_stackoverflow) |
| DE (1) | DE1900241C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2027735A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1261501A (enrdf_load_stackoverflow) |
| NL (1) | NL7000012A (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USB23046I5 (enrdf_load_stackoverflow) * | 1970-03-26 | 1975-01-28 | ||
| US4178316A (en) * | 1976-12-31 | 1979-12-11 | Dynamit Nobel Aktiengesellschaft | Method of preparing 1,1-difluoroethylene from acetylene |
| DE2712732C2 (de) * | 1977-03-23 | 1986-03-13 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von Oktafluorpropan |
| DE3435093A1 (de) * | 1984-09-25 | 1986-04-03 | Süddeutsche Kühlerfabrik Julius Fr. Behr GmbH & Co KG, 7000 Stuttgart | Waermetauscher mit einem in einem gehaeuse angeordneten rohrbuendel |
| DE3936024A1 (de) * | 1989-10-28 | 1991-05-02 | Bayer Ag | Verfahren zum halogen-fluor-austausch in organischen verbindungen und katalysatoren hierzu |
| DE3936023A1 (de) * | 1989-10-28 | 1991-05-02 | Bayer Ag | Verfahren zur herstellung von polychlor-fluor-cyclopentenen |
-
1969
- 1969-01-03 DE DE1900241A patent/DE1900241C3/de not_active Expired
- 1969-12-27 JP JP702028A patent/JPS5117544B1/ja active Pending
- 1969-12-29 CH CH1933669A patent/CH528457A/de not_active IP Right Cessation
- 1969-12-31 FR FR6945742A patent/FR2027735A1/fr not_active Withdrawn
- 1969-12-31 BE BE743933D patent/BE743933A/xx unknown
-
1970
- 1970-01-02 NL NL7000012A patent/NL7000012A/xx not_active Application Discontinuation
- 1970-01-02 GB GB305/70A patent/GB1261501A/en not_active Expired
- 1970-01-02 CA CA071,332A patent/CA972741A/en not_active Expired
- 1970-01-05 AT AT5470A patent/AT301502B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1261501A (en) | 1972-01-26 |
| CA972741A (en) | 1975-08-12 |
| FR2027735A1 (enrdf_load_stackoverflow) | 1970-10-02 |
| AT301502B (de) | 1972-09-11 |
| JPS5117544B1 (enrdf_load_stackoverflow) | 1976-06-03 |
| DE1900241A1 (de) | 1970-07-30 |
| BE743933A (enrdf_load_stackoverflow) | 1970-05-28 |
| NL7000012A (enrdf_load_stackoverflow) | 1970-07-07 |
| CH528457A (de) | 1972-09-30 |
| DE1900241B2 (de) | 1978-02-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69909860T2 (de) | Verfahren zur Herstellung von fluorierten Propanen | |
| DE69105924T2 (de) | Verfahren zur Herstellung von 1,1,1,2-Tetrafluorethan. | |
| DE69407870T2 (de) | Fluorierungskatalysator und Fluorierungsverfahren | |
| DE69521968T2 (de) | Katalysator für die Gewinnung von Chlor aus Salzsäure | |
| DE1910529C3 (de) | Verfahren zur katalytischen Hydrofluorierung von bestimmten gesattigten und ungesättigten halogenierten Kohlenwasserstoffen | |
| DE3874231T2 (de) | Katalysator und verfahren zur herstellung von 1,1,1,2-tetrafluoraethan in der dampfphase. | |
| DE69228242T2 (de) | Verfahren zur herstellung von pentafluorethan | |
| DE69829678T2 (de) | Verfahren zur herstellung von perhalogenierten cyclopentenen | |
| DE69304987T2 (de) | Verfahren zur Herstellung von Pentafluorethan durch Disproportionierung von Tetrafluor-Chlorethan | |
| DE1900241C3 (de) | Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen | |
| DE1245935B (de) | Verfahren zur Ruckgewinnung von Brom aus dem bei der Umsetzung von Fluor- bzw Fluorchlorkohlewasserstoffen mit Brom entstandenen Bromwasserstoff | |
| DE1246703B (de) | Verfahren zur Herstellung von Fluor- bzw. Fluorkohlenwasserstoffen der C-Reihe | |
| DE1542132B1 (de) | Verfahren zur Herstellung eines Kupfersilikat enthaltenden Katalysators fuer Oxychlorierungs-,Deacon- und Dehydro- chlorierungsreaktionen | |
| DE69810884T2 (de) | Fluorierungsmischkatalysator | |
| DE69612610T2 (de) | Verfahren zur herstellung von 1,1,1,3,3-pentafluoropropan | |
| DE60010034T2 (de) | Verfahren zum Behandeln von 1,1,1,3,3-Pentafluorpropan | |
| DE69624759T2 (de) | Synthese von Difluormethan | |
| DE2000200C3 (de) | Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen | |
| DE2257107A1 (de) | Verfahren zur herstellung von vinylidenchlorid | |
| DE2738010C3 (de) | Verfahren zur Herstellung von Hexafluoraceton | |
| DE69216682T2 (de) | Verfahren zur Herstellung von Chlortrifluorethylen | |
| DE69417562T2 (de) | Fluorierungskatalysator auf der grundlage von chrom, verfahren zu dessen herstellung und fluorierungsverfahren. | |
| DE1768486C3 (de) | Verfahren zur Herstellung von 1,1,2,2-Tetrachloräthan neben 1,2-Dichloräthan | |
| EP0425888B1 (de) | Verfahren zur Herstellung von Polychlor-fluor-cyclopentenen | |
| DE2108951B2 (de) | Verfahren zur Herstellung von Halogenfluorkohlenwasserstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |