CA1122597A - Cyclic hydrocarbon perfluorination process - Google Patents
Cyclic hydrocarbon perfluorination processInfo
- Publication number
- CA1122597A CA1122597A CA297,549A CA297549A CA1122597A CA 1122597 A CA1122597 A CA 1122597A CA 297549 A CA297549 A CA 297549A CA 1122597 A CA1122597 A CA 1122597A
- Authority
- CA
- Canada
- Prior art keywords
- reaction zone
- process according
- boiling point
- polycyclic hydrocarbon
- perfluorination
- 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 abstract description 37
- 125000000753 cycloalkyl group Chemical group 0.000 title abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 29
- -1 Perfluorinated polycyclic hydrocarbons Chemical class 0.000 claims abstract description 28
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 17
- 238000009835 boiling Methods 0.000 claims abstract description 14
- 239000012808 vapor phase Substances 0.000 claims abstract description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 23
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 claims description 18
- WZJQNLGQTOCWDS-UHFFFAOYSA-K cobalt(iii) fluoride Chemical compound F[Co](F)F WZJQNLGQTOCWDS-UHFFFAOYSA-K 0.000 claims description 18
- 239000012025 fluorinating agent Substances 0.000 claims description 16
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 claims description 12
- KWVVTSALYXIJSS-UHFFFAOYSA-L silver(ii) fluoride Chemical compound [F-].[F-].[Ag+2] KWVVTSALYXIJSS-UHFFFAOYSA-L 0.000 claims description 8
- 229910021571 Manganese(III) fluoride Inorganic materials 0.000 claims description 6
- SRVINXWCFNHIQZ-UHFFFAOYSA-K manganese(iii) fluoride Chemical compound [F-].[F-].[F-].[Mn+3] SRVINXWCFNHIQZ-UHFFFAOYSA-K 0.000 claims description 6
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims description 5
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 4
- 229910018485 SF4 Inorganic materials 0.000 claims description 4
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 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
- HUCLCMAVGXHPPK-UHFFFAOYSA-N 1-ethyl-3-methyladamantane Chemical compound C1C(C2)CC3CC2(C)CC1(CC)C3 HUCLCMAVGXHPPK-UHFFFAOYSA-N 0.000 claims 1
- LXTHCCWEYOKFSR-UHFFFAOYSA-N 1-ethyladamantane Chemical compound C1C(C2)CC3CC2CC1(CC)C3 LXTHCCWEYOKFSR-UHFFFAOYSA-N 0.000 claims 1
- UZUCFTVAWGRMTQ-UHFFFAOYSA-N 1-methyladamantane Chemical compound C1C(C2)CC3CC2CC1(C)C3 UZUCFTVAWGRMTQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 150000001923 cyclic compounds Chemical class 0.000 abstract 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 abstract 2
- 229910052709 silver Inorganic materials 0.000 abstract 2
- 239000004332 silver Substances 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000007858 starting material Substances 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 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
- 238000006731 degradation reaction Methods 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
- CWNOIUTVJRWADX-UHFFFAOYSA-N 1,3-dimethyladamantane Chemical compound C1C(C2)CC3CC1(C)CC2(C)C3 CWNOIUTVJRWADX-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 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 description 3
- 238000005984 hydrogenation reaction 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
- LMFDJEHVVMZWBT-UHFFFAOYSA-N 2,2-difluoroadamantane Chemical compound C1C(C2)CC3CC1C(F)(F)C2C3 LMFDJEHVVMZWBT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- BEWYHVAWEKZDPP-UHFFFAOYSA-N bornane Chemical compound C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 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
- 230000000593 degrading effect Effects 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
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 150000003048 pinane derivatives Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical class C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 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 description 1
- 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
- HQKASRVURLHPOF-UHFFFAOYSA-N 1,1,2,2,3,3,3a,4,4,5,5,6,6,7,7,8,8,8a-octadecafluoroazulene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C1(F)C(F)(F)C(F)(F)C2(F)F HQKASRVURLHPOF-UHFFFAOYSA-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
- 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
- RXUILBOYECJOBB-UHFFFAOYSA-N 2,3,3-trifluoro-2-(trifluoromethyl)bicyclo[2.2.2]octane Chemical compound C1CC2CCC1C(C(F)(F)F)(F)C2(F)F RXUILBOYECJOBB-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
- JPYIHLUWEIJMHH-UHFFFAOYSA-N 2,3-difluoro-2,3-bis(trifluoromethyl)bicyclo[2.2.1]heptane Chemical compound C1CC2C(C(F)(F)F)(F)C(C(F)(F)F)(F)C1C2 JPYIHLUWEIJMHH-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
- 238000006261 Adler reaction Methods 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XETQTCAMTVHYPO-UHFFFAOYSA-N Isocamphan von ungewisser Konfiguration Natural products C1CC2C(C)(C)C(C)C1C2 XETQTCAMTVHYPO-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 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
- 230000015572 biosynthetic process Effects 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
- 229930006742 bornane Natural products 0.000 description 1
- 150000001636 bornane derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 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
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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 class 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
- 229910052697 platinum Inorganic materials 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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA380,858A CA1129411A (en) | 1977-02-25 | 1981-06-29 | Cyclic hydrocarbon perfluorination process |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77187377A | 1977-02-25 | 1977-02-25 | |
| US771,873 | 1977-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1122597A true CA1122597A (en) | 1982-04-27 |
Family
ID=25093219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA297,549A Expired CA1122597A (en) | 1977-02-25 | 1978-02-23 | Cyclic hydrocarbon perfluorination process |
Country Status (13)
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 |
| DE3778324D1 (de) * | 1986-12-01 | 1992-05-21 | Tokuyama Soda Kk | Verfahren zur herstellung von organischen perfluoro-verbindungen. |
| 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 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
- 1978-02-24 CH CH205178A patent/CH637910A5/de not_active IP Right Cessation
- 1978-02-24 SE SE7802153A patent/SE428206B/sv not_active IP Right Cessation
- 1978-02-24 DE DE19782808112 patent/DE2808112A1/de active Granted
- 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 |
|---|---|
| SE8102878L (sv) | 1981-05-07 |
| FR2381732A1 (fr) | 1978-09-22 |
| IT7820651A0 (it) | 1978-02-24 |
| BE864328A (fr) | 1978-08-28 |
| FI69831C (fi) | 1986-05-26 |
| FR2381732B1 (enrdf_load_stackoverflow) | 1983-11-25 |
| DE2808112A1 (de) | 1978-08-31 |
| NO153965B (no) | 1986-03-17 |
| FI69831B (fi) | 1985-12-31 |
| NO153607C (no) | 1986-04-23 |
| NO780651L (no) | 1978-08-28 |
| NL7802145A (nl) | 1978-08-29 |
| IT1095441B (it) | 1985-08-10 |
| JPS6254088B2 (enrdf_load_stackoverflow) | 1987-11-13 |
| DE2808112C2 (enrdf_load_stackoverflow) | 1989-04-27 |
| NO153965C (no) | 1986-06-25 |
| GB1597914A (en) | 1981-09-16 |
| SE7802153L (sv) | 1978-08-26 |
| SE428206B (sv) | 1983-06-13 |
| FI780610A7 (fi) | 1978-08-26 |
| DK84878A (da) | 1978-08-26 |
| SE448371B (sv) | 1987-02-16 |
| JPS53116359A (en) | 1978-10-11 |
| NO153607B (no) | 1986-01-13 |
| NO841238L (no) | 1978-08-28 |
| CH637910A5 (en) | 1983-08-31 |
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