DE1593128A1 - Verfahren zur Herstellung von Hexafluorbicyclo-(2,2,0)-hexa-2,5-dien und Trifluormethylpentafluorbicyclo-(2,2,0)-hexa-2,5-dien - Google Patents
Verfahren zur Herstellung von Hexafluorbicyclo-(2,2,0)-hexa-2,5-dien und Trifluormethylpentafluorbicyclo-(2,2,0)-hexa-2,5-dienInfo
- Publication number
- DE1593128A1 DE1593128A1 DE19661593128 DE1593128A DE1593128A1 DE 1593128 A1 DE1593128 A1 DE 1593128A1 DE 19661593128 DE19661593128 DE 19661593128 DE 1593128 A DE1593128 A DE 1593128A DE 1593128 A1 DE1593128 A1 DE 1593128A1
- Authority
- DE
- Germany
- Prior art keywords
- hexa
- diene
- trifluoromethylpentafluorobicyclo
- hexafluorobicyclo
- pressure
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- NYGMLGNCZOOGFI-UHFFFAOYSA-N 1,2,3,4,5,6-hexafluorobicyclo[2.2.0]hexa-2,5-diene Chemical compound FC1=C(F)C2(F)C(F)=C(F)C21F NYGMLGNCZOOGFI-UHFFFAOYSA-N 0.000 title claims description 9
- GJXWXDDMYYYZRC-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)bicyclo[2.2.0]hexa-2,5-diene Chemical compound FC(F)(F)C1=C(F)C2(F)C(F)=C(F)C21F GJXWXDDMYYYZRC-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 11
- USPWUOFNOTUBAD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F USPWUOFNOTUBAD-UHFFFAOYSA-N 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GMSLIHFGLPSLSA-UHFFFAOYSA-N 2,3,4,5,6-pentafluoro-1-(trifluoromethyl)bicyclo[2.2.0]hexa-2,5-diene Chemical compound FC1=C(F)C2(F)C(F)=C(F)C21C(F)(F)F GMSLIHFGLPSLSA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002222 fluorine compounds Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 CO 2 Substances 0.000 description 3
- 125000000950 dibromo group Chemical group Br* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WGJMAOSFKMCEHZ-UHFFFAOYSA-N 1,2,3-trifluoro-4-(2,3,4-trifluorocyclohexa-1,3-dien-1-yl)cyclohexa-1,3-diene Chemical compound FC1=C(C(=C(CC1)C1=C(C(=C(CC1)F)F)F)F)F WGJMAOSFKMCEHZ-UHFFFAOYSA-N 0.000 description 2
- VVJKLIVHANPAQV-UHFFFAOYSA-N 5,6-dibromo-2,3-diethoxy-1,4,5,6-tetrafluorobicyclo[2.2.0]hex-2-ene Chemical compound FC1(Br)C(F)(Br)C2(F)C(OCC)=C(OCC)C21F VVJKLIVHANPAQV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PFBBHWYEWLMJPL-UHFFFAOYSA-N FC1=C(C(C(C(=C1F)F)(F)F)(F)F)C1=C(C(=C(C(C1(F)F)(F)F)F)F)F Chemical compound FC1=C(C(C(C(=C1F)F)(F)F)(F)F)C1=C(C(=C(C(C1(F)F)(F)F)F)F)F PFBBHWYEWLMJPL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QBYWGBGZFWZNLY-UHFFFAOYSA-N 1,2-diethoxy-3,4,5,6-tetrafluorobenzene Chemical compound CCOC1=C(F)C(F)=C(F)C(F)=C1OCC QBYWGBGZFWZNLY-UHFFFAOYSA-N 0.000 description 1
- HHJKNGIDEPYUBN-UHFFFAOYSA-N 1,3-diethoxy-2,4,5,6-tetrafluorobenzene Chemical compound CCOC1=C(F)C(F)=C(F)C(OCC)=C1F HHJKNGIDEPYUBN-UHFFFAOYSA-N 0.000 description 1
- WVVPQTTXYYMGIK-UHFFFAOYSA-N 1,4-diethoxy-2,3,5,6-tetrafluorobenzene Chemical compound CCOC1=C(F)C(F)=C(OCC)C(F)=C1F WVVPQTTXYYMGIK-UHFFFAOYSA-N 0.000 description 1
- XQFXHBZEFSZCKX-UHFFFAOYSA-N 2,3,5,6-tetrabromo-1,2,3,4,5,6-hexafluorobicyclo[2.2.0]hexane Chemical compound FC1(Br)C(F)(Br)C2(F)C(F)(Br)C(F)(Br)C21F XQFXHBZEFSZCKX-UHFFFAOYSA-N 0.000 description 1
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
- KQROKFBHENIQSO-UHFFFAOYSA-N CCOC(C(C(C1=CC=CCC1)=C1OCC)F)(C(F)=C1F)F Chemical compound CCOC(C(C(C1=CC=CCC1)=C1OCC)F)(C(F)=C1F)F KQROKFBHENIQSO-UHFFFAOYSA-N 0.000 description 1
- JZBIXYWTHXOWSX-UHFFFAOYSA-N CCOC(C(C(F)=C1F)(F)F)C(C2=CC=CCC2)=C1OCC Chemical compound CCOC(C(C(F)=C1F)(F)F)C(C2=CC=CCC2)=C1OCC JZBIXYWTHXOWSX-UHFFFAOYSA-N 0.000 description 1
- JISJVEUQCWJKGM-UHFFFAOYSA-N CCOC(C(OCC)=C(CC1)F)=C1C(CCC(F)=C1F)=C1F Chemical compound CCOC(C(OCC)=C(CC1)F)=C1C(CCC(F)=C1F)=C1F JISJVEUQCWJKGM-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QLVDOWBJYVLGIP-UHFFFAOYSA-M sodium;methyl sulfite Chemical compound [Na+].COS([O-])=O QLVDOWBJYVLGIP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
-
- 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
- C07C23/26—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with a bicyclo ring system containing six carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1272965 | 1965-12-24 | ||
| IT1791266 | 1966-05-16 | ||
| IT1864866 | 1966-06-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593128A1 true DE1593128A1 (de) | 1970-05-06 |
Family
ID=27272835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593128 Pending DE1593128A1 (de) | 1965-12-24 | 1966-12-23 | Verfahren zur Herstellung von Hexafluorbicyclo-(2,2,0)-hexa-2,5-dien und Trifluormethylpentafluorbicyclo-(2,2,0)-hexa-2,5-dien |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE691744A (en:Method) |
| DE (1) | DE1593128A1 (en:Method) |
| ES (1) | ES335524A1 (en:Method) |
| SE (1) | SE324561B (en:Method) |
-
1966
- 1966-12-22 SE SE1757766A patent/SE324561B/xx unknown
- 1966-12-23 BE BE691744D patent/BE691744A/fr unknown
- 1966-12-23 DE DE19661593128 patent/DE1593128A1/de active Pending
- 1966-12-24 ES ES0335524A patent/ES335524A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE691744A (en:Method) | 1967-06-23 |
| ES335524A1 (es) | 1967-12-01 |
| SE324561B (en:Method) | 1970-06-08 |
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