DE3106168C2 - 3,3,3-Trifluorpropylderivate von Aryl- oder Aralkylbenzolen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende dielektrische Materialien - Google Patents
3,3,3-Trifluorpropylderivate von Aryl- oder Aralkylbenzolen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende dielektrische MaterialienInfo
- Publication number
- DE3106168C2 DE3106168C2 DE3106168A DE3106168A DE3106168C2 DE 3106168 C2 DE3106168 C2 DE 3106168C2 DE 3106168 A DE3106168 A DE 3106168A DE 3106168 A DE3106168 A DE 3106168A DE 3106168 C2 DE3106168 C2 DE 3106168C2
- Authority
- DE
- Germany
- Prior art keywords
- trifluoropropyl
- phenyl
- reaction
- catalyst
- formula
- 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
- -1 aralkyl benzenes Chemical class 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 title claims description 22
- 239000003989 dielectric material Substances 0.000 title claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 52
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 35
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 27
- 239000004305 biphenyl Substances 0.000 claims description 23
- 235000010290 biphenyl Nutrition 0.000 claims description 23
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical group FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 16
- 229910015900 BF3 Inorganic materials 0.000 claims description 16
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 16
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 16
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 10
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 8
- 229940073608 benzyl chloride Drugs 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- HRYIBMGJUNTTMI-UHFFFAOYSA-N 1-(1-phenylethyl)-2-(3,3,3-trifluoropropyl)benzene Chemical compound C=1C=CC=C(CCC(F)(F)F)C=1C(C)C1=CC=CC=C1 HRYIBMGJUNTTMI-UHFFFAOYSA-N 0.000 claims description 2
- 229910021536 Zeolite Inorganic materials 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
- 239000007789 gas Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 24
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 14
- 238000000862 absorption spectrum Methods 0.000 description 13
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 11
- NLMURJDGDBEMAB-UHFFFAOYSA-N 3,3,3-trifluoropropylbenzene Chemical compound FC(F)(F)CCC1=CC=CC=C1 NLMURJDGDBEMAB-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 150000001491 aromatic compounds Chemical class 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 150000005481 1,2-diphenylethanes Chemical class 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- MKPKEPNIOGINET-UHFFFAOYSA-N 1-phenyl-2-(3,3,3-trifluoropropyl)benzene Chemical group FC(F)(F)CCC1=CC=CC=C1C1=CC=CC=C1 MKPKEPNIOGINET-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 3
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IUYHQGMDSZOPDZ-UHFFFAOYSA-N 2,3,4-trichlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 IUYHQGMDSZOPDZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- IWDSRIHZWYDMFC-UHFFFAOYSA-N 1,1,1-trifluoro-3-(3,3,3-trifluoropropoxy)propane Chemical compound FC(F)(F)CCOCCC(F)(F)F IWDSRIHZWYDMFC-UHFFFAOYSA-N 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JOMOHOSZHDWOSR-UHFFFAOYSA-N (4,4,4-trichloro-1-phenylbutyl)benzene Chemical compound C=1C=CC=CC=1C(CCC(Cl)(Cl)Cl)C1=CC=CC=C1 JOMOHOSZHDWOSR-UHFFFAOYSA-N 0.000 description 1
- WXAQHHJWFHEHQI-UHFFFAOYSA-N (4,4,4-trifluoro-1-phenylbutyl)benzene Chemical compound C=1C=CC=CC=1C(CCC(F)(F)F)C1=CC=CC=C1 WXAQHHJWFHEHQI-UHFFFAOYSA-N 0.000 description 1
- 150000001833 1,1-diphenylethanes Chemical group 0.000 description 1
- SRNZLHQGZFTLQR-UHFFFAOYSA-N 1,2,3,4-tetrakis(3,3,3-trifluoropropyl)benzene Chemical compound FC(F)(F)CCC1=CC=C(CCC(F)(F)F)C(CCC(F)(F)F)=C1CCC(F)(F)F SRNZLHQGZFTLQR-UHFFFAOYSA-N 0.000 description 1
- WSMWNUSBEOXWLY-UHFFFAOYSA-N 1,2,3-tris(3,3,3-trifluoropropyl)benzene Chemical compound FC(F)(F)CCC1=CC=CC(CCC(F)(F)F)=C1CCC(F)(F)F WSMWNUSBEOXWLY-UHFFFAOYSA-N 0.000 description 1
- QPJKRLGCBNZNDM-UHFFFAOYSA-N 1,2-bis(3,3,3-trifluoropropyl)benzene Chemical compound FC(F)(F)CCC1=CC=CC=C1CCC(F)(F)F QPJKRLGCBNZNDM-UHFFFAOYSA-N 0.000 description 1
- MNJDBFLEFFSBTF-UHFFFAOYSA-N 1-(2-phenylethyl)-2-(3,3,3-trifluoropropyl)benzene Chemical compound FC(F)(F)CCC1=CC=CC=C1CCC1=CC=CC=C1 MNJDBFLEFFSBTF-UHFFFAOYSA-N 0.000 description 1
- BUVKQQKZKQXQSX-UHFFFAOYSA-N 1-(2-phenylethyl)-4-(3,3,3-trifluoropropyl)benzene Chemical compound C1=CC(CCC(F)(F)F)=CC=C1CCC1=CC=CC=C1 BUVKQQKZKQXQSX-UHFFFAOYSA-N 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- HKTCLPBBJDIBGF-UHFFFAOYSA-N 1-phenyl-2-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC=C1C1=CC=CC=C1 HKTCLPBBJDIBGF-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- CGYQTQNHOFGYBP-UHFFFAOYSA-N FC(CCC1=CC=C(C=C1)C1=CC=C(C=C1)CCC(F)(F)F)(F)F Chemical group FC(CCC1=CC=C(C=C1)C1=CC=C(C=C1)CCC(F)(F)F)(F)F CGYQTQNHOFGYBP-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000006840 diphenylmethane group Chemical group 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 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
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JLQFVGYYVXALAG-CFEVTAHFSA-N yasmin 28 Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C([C@]12[C@H]3C[C@H]3[C@H]3[C@H]4[C@@H]([C@]5(CCC(=O)C=C5[C@@H]5C[C@@H]54)C)CC[C@@]31C)CC(=O)O2 JLQFVGYYVXALAG-CFEVTAHFSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
- H01B3/24—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils containing halogen in the molecules, e.g. halogenated oils
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
- C07C22/08—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2109080A JPS5852968B2 (ja) | 1980-02-22 | 1980-02-22 | ３，３，３−トリフルオロプロピルビフエニル |
| JP2109380A JPS56118022A (en) | 1980-02-22 | 1980-02-22 | Di 3,3,3-trifluoropropyl derivative of 1,2-diphenylethane |
| JP2109480A JPS56118023A (en) | 1980-02-22 | 1980-02-22 | Preparation of aromatic compound containing fluorine |
| JP2109280A JPS56118021A (en) | 1980-02-22 | 1980-02-22 | 1-phenyl-2-(3',3',3'-trifluoropropylphenyl)ethane |
| JP2109180A JPS5852969B2 (ja) | 1980-02-22 | 1980-02-22 | ジ（３，３，３−トリフルオロプロピル）ビフエニル |
| JP55120928A JPS5745116A (en) | 1980-09-01 | 1980-09-01 | Benzyl-(3,3,3-trifluoropropyl)benzene |
| JP16443480A JPS5788132A (en) | 1980-11-21 | 1980-11-21 | 1-phenyl-1-(3',3',3'-trifluoropropylphenyl)ethane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3106168A1 DE3106168A1 (de) | 1982-01-07 |
| DE3106168C2 true DE3106168C2 (de) | 1983-12-01 |
Family
ID=27563928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3106168A Expired DE3106168C2 (de) | 1980-02-22 | 1981-02-19 | 3,3,3-Trifluorpropylderivate von Aryl- oder Aralkylbenzolen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende dielektrische Materialien |
Country Status (4)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4356335A (en) * | 1980-02-22 | 1982-10-26 | Kureha Kagaku Kogyo Kabushiki Kaisha | Aryl- or aralkylbenzene having two benzene rings at least one of which is substituted by at least one 3,3,3-trifluoropropyl group |
| DE3151365A1 (de) * | 1981-12-24 | 1983-07-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von teilweise neuen alkylbenzotrifluoriden |
| US5114777B2 (en) | 1985-08-05 | 1997-11-18 | Wangner Systems Corp | Woven multilayer papermaking fabric having increased stability and permeability and method |
| US4835319A (en) * | 1987-11-09 | 1989-05-30 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,4-bis(4-phenoxybenzoyl)benzene with a zeolite catalyst |
| WO2000020364A1 (en) * | 1998-10-07 | 2000-04-13 | Great Lakes Chemical Corporation | Novel bromine-containing 1,2-bis(phenyl)difluoromethanes and method of imparting flame retardancy to flammable materials |
| DE10326917A1 (de) * | 2003-06-16 | 2005-02-10 | Bayer Chemicals Ag | Herstellung von fluorhaltigen Acetophenonen |
| USD749671S1 (en) * | 2014-02-12 | 2016-02-16 | Samsung Electronics Co., Ltd. | Multifunction printer |
| TWI797212B (zh) * | 2017-12-13 | 2023-04-01 | 美商3M新設資產公司 | 在介電流體及電裝置中之全氟化１-烷氧基丙烯 |
| JP7295858B2 (ja) | 2017-12-13 | 2023-06-21 | スリーエム イノベイティブ プロパティズ カンパニー | ハイドロフルオロオレフィンエーテル、組成物、これらを使用するための装置及び方法 |
| CN111479900B (zh) | 2017-12-13 | 2022-03-29 | 3M创新有限公司 | 全氟化1-烷氧基丙烯、组合物、及其使用方法和设备 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2680770A (en) * | 1951-11-28 | 1954-06-08 | Sprague Electric Co | Fluorinated biphenyl derivatives |
| US2978517A (en) * | 1959-01-14 | 1961-04-04 | American Cyanamid Co | Bis-(alphahalotolyl) alkanes |
| US3106587A (en) * | 1959-12-17 | 1963-10-08 | Koninklijke Pharma Fab Nv | 2-trifluoromethyldi-phenylcarbinol |
| US3080428A (en) * | 1960-07-20 | 1963-03-05 | Du Pont | Polyhalopropyl ethers and process for making them |
| GB1359644A (en) * | 1970-09-29 | 1974-07-10 | Biorex Laboratories Ltd | 1,2-diphenyl-ethane derivatives |
| US4356335A (en) * | 1980-02-22 | 1982-10-26 | Kureha Kagaku Kogyo Kabushiki Kaisha | Aryl- or aralkylbenzene having two benzene rings at least one of which is substituted by at least one 3,3,3-trifluoropropyl group |
-
1981
- 1981-02-12 US US06/233,715 patent/US4356335A/en not_active Expired - Fee Related
- 1981-02-19 DE DE3106168A patent/DE3106168C2/de not_active Expired
- 1981-02-20 FR FR8103391A patent/FR2476640A1/fr active Granted
- 1981-02-20 GB GB8105490A patent/GB2070012B/en not_active Expired
-
1982
- 1982-02-10 US US06/347,727 patent/US4405824A/en not_active Expired - Fee Related
- 1982-02-10 US US06/347,728 patent/US4423259A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| US4423259A (en) | 1983-12-27 |
| US4356335A (en) | 1982-10-26 |
| GB2070012B (en) | 1984-06-06 |
| US4405824A (en) | 1983-09-20 |
| FR2476640B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-02-18 |
| FR2476640A1 (fr) | 1981-08-28 |
| GB2070012A (en) | 1981-09-03 |
| DE3106168A1 (de) | 1982-01-07 |
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