DE2547182A1 - Verfahren zur herstellung von 1,1-difluoraethan - Google Patents
Verfahren zur herstellung von 1,1-difluoraethanInfo
- Publication number
- DE2547182A1 DE2547182A1 DE19752547182 DE2547182A DE2547182A1 DE 2547182 A1 DE2547182 A1 DE 2547182A1 DE 19752547182 DE19752547182 DE 19752547182 DE 2547182 A DE2547182 A DE 2547182A DE 2547182 A1 DE2547182 A1 DE 2547182A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- bismuth
- acetylene
- hydrogen fluoride
- manganese
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 35
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 21
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 14
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 14
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 13
- 229910052797 bismuth Inorganic materials 0.000 claims description 11
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 11
- 150000002696 manganese Chemical class 0.000 claims description 9
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 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 5
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 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 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000001621 bismuth Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000008139 complexing agent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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-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 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
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 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
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- BRCWHGIUHLWZBK-UHFFFAOYSA-K bismuth;trifluoride Chemical compound F[Bi](F)F BRCWHGIUHLWZBK-UHFFFAOYSA-K 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 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
- 239000008188 pellet Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000600 sorbitol Substances 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
- 238000005406 washing 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
- 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
- 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
-
- 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
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752547182 DE2547182A1 (de) | 1975-10-22 | 1975-10-22 | Verfahren zur herstellung von 1,1-difluoraethan |
| CA263,558A CA1067916A (en) | 1975-10-22 | 1976-10-18 | Process for the production of 1,1-difluoro ethane |
| GB43403/76A GB1561535A (en) | 1975-10-22 | 1976-10-19 | Process for producing fluoroalkanes |
| US05/734,212 US4138439A (en) | 1975-10-22 | 1976-10-20 | Method of preparing 1,1-difluoroethane |
| IT51822/76A IT1069585B (it) | 1975-10-22 | 1976-10-20 | Procedimento per la produzione di 1-1 difluoroetano |
| BE171647A BE847456A (fr) | 1975-10-22 | 1976-10-20 | Procede de preparation de 1,1-difluoretane, |
| CH1331076A CH622234A5 (enExample) | 1975-10-22 | 1976-10-21 | |
| SE7611683A SE414763B (sv) | 1975-10-22 | 1976-10-21 | Forfarande vid framstellning av 1,1-difluoretan genom hydrofluorering av acetylen |
| FR7631720A FR2328681A1 (fr) | 1975-10-22 | 1976-10-21 | Procede de preparation de 1,1-difluorethane |
| NL7611664A NL7611664A (nl) | 1975-10-22 | 1976-10-21 | Werkwijze voor het bereiden van 1,1-difluore- thaan. |
| JP51127126A JPS5251304A (en) | 1975-10-22 | 1976-10-22 | Process for preparing 1*11difluoroethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752547182 DE2547182A1 (de) | 1975-10-22 | 1975-10-22 | Verfahren zur herstellung von 1,1-difluoraethan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2547182A1 true DE2547182A1 (de) | 1977-05-05 |
Family
ID=5959720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752547182 Withdrawn DE2547182A1 (de) | 1975-10-22 | 1975-10-22 | Verfahren zur herstellung von 1,1-difluoraethan |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4138439A (enExample) |
| JP (1) | JPS5251304A (enExample) |
| BE (1) | BE847456A (enExample) |
| CA (1) | CA1067916A (enExample) |
| CH (1) | CH622234A5 (enExample) |
| DE (1) | DE2547182A1 (enExample) |
| FR (1) | FR2328681A1 (enExample) |
| GB (1) | GB1561535A (enExample) |
| IT (1) | IT1069585B (enExample) |
| NL (1) | NL7611664A (enExample) |
| SE (1) | SE414763B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4798818A (en) * | 1987-11-27 | 1989-01-17 | Dow Corning Corporation | Catalyst composition and process for its preparation |
| DE3936024A1 (de) * | 1989-10-28 | 1991-05-02 | Bayer Ag | Verfahren zum halogen-fluor-austausch in organischen verbindungen und katalysatoren hierzu |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2063349A1 (en) * | 1969-12-24 | 1971-07-15 | Kureha Kagaku Kogyo Kabushiki Kaisha, Tokio | 1,1-difluoroethane from acetylene and - hydrogen fluoride |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471525A (en) * | 1947-12-19 | 1949-05-31 | Phillips Petroleum Co | Reaction of an acetylene with hf to produce vinyl fluoride and/or difluoroethane andhomologues thereof |
| NL301860A (enExample) * | 1962-12-28 | |||
| US3395187A (en) * | 1965-05-03 | 1968-07-30 | Du Pont | Process for preparing vinyl fluoride and 1, 1-difluoroethane |
| DE2000200C3 (de) * | 1970-01-03 | 1980-01-24 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen |
| US3904701A (en) * | 1969-01-03 | 1975-09-09 | Dynamit Nobel Ag | Process for the catalytic hydrofluorination of halogenated hydrocarbons |
| US3720722A (en) * | 1971-02-18 | 1973-03-13 | Daikin Ind Ltd | Novel aluminum fluoride catalyst and process for hydrofluorinating acetylene using same |
| BE787410A (fr) * | 1971-08-10 | 1973-02-12 | Bayer Ag | Procede de preparation du 1,1-difluorethane |
-
1975
- 1975-10-22 DE DE19752547182 patent/DE2547182A1/de not_active Withdrawn
-
1976
- 1976-10-18 CA CA263,558A patent/CA1067916A/en not_active Expired
- 1976-10-19 GB GB43403/76A patent/GB1561535A/en not_active Expired
- 1976-10-20 BE BE171647A patent/BE847456A/xx unknown
- 1976-10-20 IT IT51822/76A patent/IT1069585B/it active
- 1976-10-20 US US05/734,212 patent/US4138439A/en not_active Expired - Lifetime
- 1976-10-21 CH CH1331076A patent/CH622234A5/de not_active IP Right Cessation
- 1976-10-21 SE SE7611683A patent/SE414763B/xx unknown
- 1976-10-21 NL NL7611664A patent/NL7611664A/xx not_active Application Discontinuation
- 1976-10-21 FR FR7631720A patent/FR2328681A1/fr active Granted
- 1976-10-22 JP JP51127126A patent/JPS5251304A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2063349A1 (en) * | 1969-12-24 | 1971-07-15 | Kureha Kagaku Kogyo Kabushiki Kaisha, Tokio | 1,1-difluoroethane from acetylene and - hydrogen fluoride |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7611664A (nl) | 1977-04-26 |
| CA1067916A (en) | 1979-12-11 |
| BE847456A (fr) | 1977-02-14 |
| FR2328681A1 (fr) | 1977-05-20 |
| FR2328681B1 (enExample) | 1982-11-12 |
| JPS5251304A (en) | 1977-04-25 |
| CH622234A5 (enExample) | 1981-03-31 |
| IT1069585B (it) | 1985-03-25 |
| SE7611683L (sv) | 1977-04-23 |
| US4138439A (en) | 1979-02-06 |
| GB1561535A (en) | 1980-02-20 |
| SE414763B (sv) | 1980-08-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1910529C3 (de) | Verfahren zur katalytischen Hydrofluorierung von bestimmten gesattigten und ungesättigten halogenierten Kohlenwasserstoffen | |
| DE3150205C2 (de) | Verfahren zur Herstellung eines Silberkatalysators für die Produktion von Ethylenoxid | |
| DE2341363C3 (de) | Verfahren zur Herstellung eines Katalysators zur Zersetzung von Hydrazin und seinen Derivaten | |
| DE69407690T2 (de) | Verfahren zur Metathese von Olefinen in dem ein verbesserter Rheniumkatalysator verwendet wird | |
| DE2215019A1 (de) | Verfahren zur Herstellung von 1,1-Difluoräthan | |
| DE2441109A1 (de) | Verfahren zur katalytischen oxydation von tert.-butylalkohol in der dampfphase | |
| DE1542327B2 (de) | Verfahren zur Herstellung von Katalysatoren | |
| EP0475173A1 (de) | Verfahren zur katalytischen Zersetzung von reinem oder in Gasgemischen enthaltenem Distickstoffmonoxid | |
| DE1262997B (de) | Verfahren zur Herstellung von Acrylsaeurenitril oder Methacrylsaeurenitril durch Umsetzung von Propylen oder Isobutylen mit Ammoniak und Sauerstoff | |
| DE2457158A1 (de) | Verfahren zur herstellung eines alicyclischen diketons | |
| DE2547182A1 (de) | Verfahren zur herstellung von 1,1-difluoraethan | |
| DE1900241C3 (de) | Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen | |
| DE2000200C3 (de) | Verfahren zur Herstellung von fluorierten aliphatischen Kohlenwasserstoffen mit zwei und mehr C-Atomen oder von fluorierten cycloaliphatischen Kohlenwasserstoffen | |
| DE2738010C3 (de) | Verfahren zur Herstellung von Hexafluoraceton | |
| DE2108951C3 (de) | Verfahren zur Herstellung von Halogenfluorkohlenwasserstoffen | |
| DE2555189A1 (de) | Verfahren zur herstellung eines vanadiumkatalysators | |
| DE2624349C3 (de) | Verfahren zur Herstellung von Hexafluoraceton | |
| DE1518702B2 (enExample) | ||
| DE2141657C3 (de) | Verfahren zur Herstellung von Alkoxybenzonitrilen | |
| DE2061538B2 (de) | Verfahren zur herstellung von kobalt (iii)-bis-salicylaldehydaethylendiiminat -komplexen | |
| DE2037975C (de) | Verfahren zur Herstellung von Distickstoffoxid | |
| DE2412162C3 (de) | Trägerkatalysator | |
| DE880133C (de) | Verfahren zur Herstellung von ungesättigten Aldehyden | |
| DE1108197B (de) | Verfahren zur Herstellung von AEthylenoxyd | |
| DD139940A3 (de) | Verfahren zur herstellung von fluorchlorkohlenwasserstoffverbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8136 | Disposal/non-payment of the fee for publication/grant |