JPS6254088B2 - - Google Patents
Info
- Publication number
- JPS6254088B2 JPS6254088B2 JP53020412A JP2041278A JPS6254088B2 JP S6254088 B2 JPS6254088 B2 JP S6254088B2 JP 53020412 A JP53020412 A JP 53020412A JP 2041278 A JP2041278 A JP 2041278A JP S6254088 B2 JPS6254088 B2 JP S6254088B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction zone
- temperature
- partially fluorinated
- hydrocarbon
- polycyclic
- 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
- 229930195733 hydrocarbon Natural products 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- -1 polycyclic hydrocarbon Chemical class 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000004215 Carbon black (E152) Substances 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 20
- 238000003682 fluorination reaction Methods 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 16
- 239000012025 fluorinating agent Substances 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 6
- 239000012808 vapor phase Substances 0.000 claims description 6
- LPSXSORODABQKT-FIRGSJFUSA-N exo-trimethylenenorbornane Chemical compound C([C@@H]1C2)C[C@@H]2[C@@H]2[C@H]1CCC2 LPSXSORODABQKT-FIRGSJFUSA-N 0.000 claims description 4
- LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical class C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 claims description 4
- 229910018287 SbF 5 Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- LPSXSORODABQKT-YNFQOJQRSA-N (3ar,4r,7s,7as)-rel-octahydro-1h-4,7-methanoindene Chemical compound C([C@H]1C2)C[C@H]2[C@@H]2[C@H]1CCC2 LPSXSORODABQKT-YNFQOJQRSA-N 0.000 claims description 2
- HUCLCMAVGXHPPK-UHFFFAOYSA-N 1-ethyl-3-methyladamantane Chemical compound C1C(C2)CC3CC2(C)CC1(CC)C3 HUCLCMAVGXHPPK-UHFFFAOYSA-N 0.000 claims description 2
- LXTHCCWEYOKFSR-UHFFFAOYSA-N 1-ethyladamantane Chemical compound C1C(C2)CC3CC2CC1(CC)C3 LXTHCCWEYOKFSR-UHFFFAOYSA-N 0.000 claims description 2
- UZUCFTVAWGRMTQ-UHFFFAOYSA-N 1-methyladamantane Chemical compound C1C(C2)CC3CC2CC1(C)C3 UZUCFTVAWGRMTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 3
- ZAUJDUNVDTUNDD-UHFFFAOYSA-N 1a,2,3,3a,4,5,6,7,7a,7b-decahydro-1h-cyclopropa[a]naphthalene Chemical compound C1CCCC2C3CC3CCC21 ZAUJDUNVDTUNDD-UHFFFAOYSA-N 0.000 claims 2
- FTNPDAKMYKMVKB-UHFFFAOYSA-N 1-ethyl-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC2(C)CC1(CC)C3 FTNPDAKMYKMVKB-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 3
- CWNOIUTVJRWADX-UHFFFAOYSA-N 1,3-dimethyladamantane Chemical compound C1C(C2)CC3CC1(C)CC2(C)C3 CWNOIUTVJRWADX-UHFFFAOYSA-N 0.000 description 3
- 238000005698 Diels-Alder reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- LWRNQOBXRHWPGE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluoro-8-(trifluoromethyl)naphthalene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(C(F)(F)F)(F)C(F)(F)C(F)(F)C(F)(F)C21F LWRNQOBXRHWPGE-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- MCKPOIFVFYONAG-UHFFFAOYSA-N exo-tricyclo[6.2.1.0(2.7)]undecane Chemical compound C12CCCCC2C2CCC1C2 MCKPOIFVFYONAG-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- WSJULBMCKQTTIG-OWOJBTEDSA-N (e)-1,1,1,2,3,4,4,4-octafluorobut-2-ene Chemical compound FC(F)(F)C(/F)=C(\F)C(F)(F)F WSJULBMCKQTTIG-OWOJBTEDSA-N 0.000 description 1
- BDTKCOREDQRWGK-UHFFFAOYSA-N 1,2,3,4,5,5-hexafluorocyclopenta-1,3-diene Chemical compound FC1=C(F)C(F)(F)C(F)=C1F BDTKCOREDQRWGK-UHFFFAOYSA-N 0.000 description 1
- IKCKSJMRBNNSOZ-UHFFFAOYSA-N 1,3-dimethyl-5,7-bis(trifluoromethyl)adamantane Chemical compound C1C(C2)(C)CC3(C(F)(F)F)CC1(C)CC2(C(F)(F)F)C3 IKCKSJMRBNNSOZ-UHFFFAOYSA-N 0.000 description 1
- 238000007115 1,4-cycloaddition reaction Methods 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- QBPHDYRTHRJISH-UHFFFAOYSA-N 2,2,4,4,6,6,8,8,9,9,10,10-dodecafluoro-1,3,5,7-tetrakis(trifluoromethyl)adamantane Chemical compound FC1(F)C(C2(F)F)(C(F)(F)F)C(F)(F)C3(C(F)(F)F)C(F)(F)C1(C(F)(F)F)C(F)(F)C2(C(F)(F)F)C3(F)F QBPHDYRTHRJISH-UHFFFAOYSA-N 0.000 description 1
- LMFDJEHVVMZWBT-UHFFFAOYSA-N 2,2-difluoroadamantane Chemical compound C1C(C2)CC3CC1C(F)(F)C2C3 LMFDJEHVVMZWBT-UHFFFAOYSA-N 0.000 description 1
- JBOVEUMPNNXQMP-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)bicyclo[2.2.1]hepta-1,3-diene Chemical compound C1CC2=C(C(F)(F)F)C(C(F)(F)F)=C1C2 JBOVEUMPNNXQMP-UHFFFAOYSA-N 0.000 description 1
- UJSSMDIYYJRWDD-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2C(C(F)(F)F)C(C(F)(F)F)C1C2 UJSSMDIYYJRWDD-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- KGFHKUZOSKDAKW-UHFFFAOYSA-N 5,7-dimethyladamantane-1,3-dicarboxylic acid Chemical compound C1C(C2)(C)CC3(C(O)=O)CC1(C)CC2(C(O)=O)C3 KGFHKUZOSKDAKW-UHFFFAOYSA-N 0.000 description 1
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- LBVBDLCCWCJXFA-UHFFFAOYSA-N adamantane-1,2-dicarboxylic acid Chemical compound C1C(C2)CC3CC1C(C(=O)O)C2(C(O)=O)C3 LBVBDLCCWCJXFA-UHFFFAOYSA-N 0.000 description 1
- IYKFYARMMIESOX-UHFFFAOYSA-N adamantanone Chemical compound C1C(C2)CC3CC1C(=O)C2C3 IYKFYARMMIESOX-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- RGWHHWWMFUXNAX-UHFFFAOYSA-N bis(1-adamantyl)methanone Chemical class C1C(C2)CC(C3)CC2CC13C(=O)C1(C2)CC(C3)CC2CC3C1 RGWHHWWMFUXNAX-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WZJQNLGQTOCWDS-UHFFFAOYSA-K cobalt(iii) fluoride Chemical compound F[Co](F)F WZJQNLGQTOCWDS-UHFFFAOYSA-K 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000005594 diketone group Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- WBCLXFIDEDJGCC-UHFFFAOYSA-N hexafluoro-2-butyne Chemical compound FC(F)(F)C#CC(F)(F)F WBCLXFIDEDJGCC-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NHCREQREVZBOCH-UHFFFAOYSA-N methyldecalin Natural products C1CCCC2C(C)CCCC21 NHCREQREVZBOCH-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LRMQIJUOLGKFKS-UHFFFAOYSA-N perfluoro-1,3-dimethyladamantane Chemical compound FC1(F)C(C2(F)F)(F)C(F)(F)C3(F)C(F)(F)C1(C(F)(F)F)C(F)(F)C2(C(F)(F)F)C3(F)F LRMQIJUOLGKFKS-UHFFFAOYSA-N 0.000 description 1
- FRZFEPXEUZSBLA-UHFFFAOYSA-N perfluoroadamantane Chemical compound FC1(F)C(C2(F)F)(F)C(F)(F)C3(F)C(F)(F)C1(F)C(F)(F)C2(F)C3(F)F FRZFEPXEUZSBLA-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 150000003048 pinane derivatives Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JADWVCVCIIYHSB-UHFFFAOYSA-N tetracyclo[8.1.1.01,10.02,7]dodecane Chemical compound C12CCCCC2CCC23CC12C3 JADWVCVCIIYHSB-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/18—Polycyclic halogenated hydrocarbons
- C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
- C07C23/38—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with three condensed rings
-
- 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/18—Polycyclic halogenated hydrocarbons
- C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/18—Polycyclic halogenated hydrocarbons
- C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
- C07C23/32—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with a bicyclo ring system containing eight carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77187377A | 1977-02-25 | 1977-02-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53116359A JPS53116359A (en) | 1978-10-11 |
| JPS6254088B2 true JPS6254088B2 (no) | 1987-11-13 |
Family
ID=25093219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2041278A Granted JPS53116359A (en) | 1977-02-25 | 1978-02-25 | Improved method of perfluorating cyclic hydrocarbon |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS53116359A (no) |
| BE (1) | BE864328A (no) |
| CA (1) | CA1122597A (no) |
| CH (1) | CH637910A5 (no) |
| DE (1) | DE2808112A1 (no) |
| DK (1) | DK84878A (no) |
| FI (1) | FI69831C (no) |
| FR (1) | FR2381732A1 (no) |
| GB (1) | GB1597914A (no) |
| IT (1) | IT1095441B (no) |
| NL (1) | NL7802145A (no) |
| NO (2) | NO153607C (no) |
| SE (2) | SE428206B (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5821628A (ja) * | 1981-07-29 | 1983-02-08 | Dainippon Ink & Chem Inc | ノルボルナジエン誘導体およびその製造方法 |
| US4929317A (en) * | 1986-12-01 | 1990-05-29 | Tokuyama Soda Kabushiki Kaisha | Process for preparation of perfluoro organic compounds |
| JP2010215524A (ja) * | 2009-03-13 | 2010-09-30 | Fujifilm Corp | フルオロビシクロ［２．２．２］オクタン化合物、その製造方法、及びその用途 |
| JP2010215523A (ja) * | 2009-03-13 | 2010-09-30 | Fujifilm Corp | フルオロビシクロ［２．２．２］−２−オクテン化合物、その製造方法、及びその用途 |
| RU2451006C1 (ru) * | 2011-05-05 | 2012-05-20 | Общество с ограниченной ответственностью "ГалоПолимер Кирово-Чепецк" (ООО "ГалоПолимер Кирово-Чепецк") | Способ получения перфторциклоалканов |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641167A (en) * | 1965-03-17 | 1972-02-08 | Sun Oil Co | Highly fluorinated alkyladamantanes |
| US4041086A (en) * | 1972-02-07 | 1977-08-09 | Sun Ventures, Inc. | Process of manufacture of flourinated alkyladamantanes |
-
1978
- 1978-02-23 FI FI780610A patent/FI69831C/fi not_active IP Right Cessation
- 1978-02-23 CA CA297,549A patent/CA1122597A/en not_active Expired
- 1978-02-24 DE DE19782808112 patent/DE2808112A1/de active Granted
- 1978-02-24 SE SE7802153A patent/SE428206B/sv not_active IP Right Cessation
- 1978-02-24 CH CH205178A patent/CH637910A5/de not_active IP Right Cessation
- 1978-02-24 IT IT20651/78A patent/IT1095441B/it active
- 1978-02-24 DK DK84878A patent/DK84878A/da not_active Application Discontinuation
- 1978-02-24 NO NO780651A patent/NO153607C/no unknown
- 1978-02-25 JP JP2041278A patent/JPS53116359A/ja active Granted
- 1978-02-27 BE BE185487A patent/BE864328A/xx not_active IP Right Cessation
- 1978-02-27 FR FR7805528A patent/FR2381732A1/fr active Granted
- 1978-02-27 GB GB7727/78A patent/GB1597914A/en not_active Expired
- 1978-02-27 NL NL7802145A patent/NL7802145A/xx not_active Application Discontinuation
-
1981
- 1981-05-07 SE SE8102878A patent/SE448371B/sv not_active IP Right Cessation
-
1984
- 1984-03-28 NO NO841238A patent/NO153965C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI69831C (fi) | 1986-05-26 |
| GB1597914A (en) | 1981-09-16 |
| FI69831B (fi) | 1985-12-31 |
| IT1095441B (it) | 1985-08-10 |
| BE864328A (fr) | 1978-08-28 |
| NO153965B (no) | 1986-03-17 |
| NO153607C (no) | 1986-04-23 |
| NO780651L (no) | 1978-08-28 |
| SE448371B (sv) | 1987-02-16 |
| CH637910A5 (en) | 1983-08-31 |
| JPS53116359A (en) | 1978-10-11 |
| CA1122597A (en) | 1982-04-27 |
| SE8102878L (sv) | 1981-05-07 |
| NO153607B (no) | 1986-01-13 |
| IT7820651A0 (it) | 1978-02-24 |
| FR2381732B1 (no) | 1983-11-25 |
| NO153965C (no) | 1986-06-25 |
| DE2808112A1 (de) | 1978-08-31 |
| DK84878A (da) | 1978-08-26 |
| FI780610A (fi) | 1978-08-26 |
| SE428206B (sv) | 1983-06-13 |
| NO841238L (no) | 1978-08-28 |
| DE2808112C2 (no) | 1989-04-27 |
| SE7802153L (sv) | 1978-08-26 |
| FR2381732A1 (fr) | 1978-09-22 |
| NL7802145A (nl) | 1978-08-29 |
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