FR2489303A1 - Derives 3,3,3-trifluoropropyl du naphtalene ou du methylnaphtalene, procede de preparation et utilisation - Google Patents
Derives 3,3,3-trifluoropropyl du naphtalene ou du methylnaphtalene, procede de preparation et utilisation Download PDFInfo
- Publication number
- FR2489303A1 FR2489303A1 FR8115992A FR8115992A FR2489303A1 FR 2489303 A1 FR2489303 A1 FR 2489303A1 FR 8115992 A FR8115992 A FR 8115992A FR 8115992 A FR8115992 A FR 8115992A FR 2489303 A1 FR2489303 A1 FR 2489303A1
- Authority
- FR
- France
- Prior art keywords
- methylnaphthalene
- naphthalene
- trifluoropropyl
- group
- trifluoropropene
- 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.)
- Granted
Links
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 title claims abstract description 39
- -1 3,3,3-TRIFLUOROPROPYL DERIVATIVES OF NAPHTHALENE Chemical class 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 12
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910015900 BF3 Inorganic materials 0.000 claims abstract description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003377 acid catalyst Substances 0.000 claims abstract description 9
- 239000003989 dielectric material Substances 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 30
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 claims description 29
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 12
- 150000001491 aromatic compounds Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- DDULIRMVYYFHQX-UHFFFAOYSA-N 1-(3,3,3-trifluoropropyl)naphthalene Chemical compound C1=CC=C2C(CCC(F)(F)F)=CC=CC2=C1 DDULIRMVYYFHQX-UHFFFAOYSA-N 0.000 claims description 2
- NHGOUBURBPEFHY-UHFFFAOYSA-N 2-methyl-1-(3,3,3-trifluoropropyl)naphthalene Chemical compound C1=CC=CC2=C(CCC(F)(F)F)C(C)=CC=C21 NHGOUBURBPEFHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- AFISHFRSDWTKKM-UHFFFAOYSA-N 1-methyl-2-(3,3,3-trifluoropropyl)naphthalene Chemical compound C1=CC=C2C(C)=C(CCC(F)(F)F)C=CC2=C1 AFISHFRSDWTKKM-UHFFFAOYSA-N 0.000 claims 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
- 101150035983 str1 gene Proteins 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CBRCQUBDGSXMTD-UHFFFAOYSA-N 1-(4,4,4-trifluorobutan-2-yl)naphthalene Chemical compound C1=CC=C2C(C(CC(F)(F)F)C)=CC=CC2=C1 CBRCQUBDGSXMTD-UHFFFAOYSA-N 0.000 description 1
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- QIMMUPPBPVKWKM-RHRFEJLCSA-N 2-methylnaphthalene Chemical class C1=CC=[14CH]C2=CC(C)=CC=C21 QIMMUPPBPVKWKM-RHRFEJLCSA-N 0.000 description 1
- NLMURJDGDBEMAB-UHFFFAOYSA-N 3,3,3-trifluoropropylbenzene Chemical compound FC(F)(F)CCC1=CC=CC=C1 NLMURJDGDBEMAB-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G4/00—Fixed capacitors; Processes of their manufacture
- H01G4/002—Details
- H01G4/018—Dielectrics
- H01G4/20—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06
- H01G4/22—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06 impregnated
- H01G4/221—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06 impregnated characterised by the composition of the impregnant
- H01G4/222—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06 impregnated characterised by the composition of the impregnant halogenated
-
- 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
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Physics & Mathematics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Organic Insulating Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55120927A JPS5745115A (en) | 1980-09-01 | 1980-09-01 | 3,3,3-trifluoropropylnaphthalene |
| JP55186565A JPS57112339A (en) | 1980-12-29 | 1980-12-29 | Beta-methyl-(3,3,3-trifluoropropyl)naphthalene |
| JP56010642A JPS57126431A (en) | 1981-01-27 | 1981-01-27 | Alpha-methyl-(3,3,3-trifluoropropyl)naphthalene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2489303A1 true FR2489303A1 (fr) | 1982-03-05 |
| FR2489303B1 FR2489303B1 (en:Method) | 1984-11-30 |
Family
ID=27279035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8115992A Granted FR2489303A1 (fr) | 1980-09-01 | 1981-08-20 | Derives 3,3,3-trifluoropropyl du naphtalene ou du methylnaphtalene, procede de preparation et utilisation |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4396785A (en:Method) |
| DE (1) | DE3132501C2 (en:Method) |
| FR (1) | FR2489303A1 (en:Method) |
| GB (1) | GB2083027B (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4956390A (en) * | 1987-08-25 | 1990-09-11 | Air Products And Chemicals, Inc. | Gas transport employing perfluorobutyldecalin |
| US4777304A (en) * | 1987-08-25 | 1988-10-11 | Air Products & Chemicals, Inc. | Perfluorinated butyl derivative compounds |
| US4873315A (en) * | 1987-08-25 | 1989-10-10 | Air Products And Chemicals, Inc. | Perfluorinated propyl derivative compounds |
| US4881682A (en) * | 1987-08-25 | 1989-11-21 | Air Products And Chemicals, Inc. | Vapor phase soldering with perfluorinated butyl derivative compounds |
| US4827053A (en) * | 1988-08-03 | 1989-05-02 | Air Products And Chemicals, Inc. | Perfluorinated Di-isopropylmethyl decalin |
| US4849553A (en) * | 1988-08-03 | 1989-07-18 | Air Products And Chemicals, Inc. | Perfluorinated dibutyl derivatives compounds |
| TWI222433B (en) * | 1998-10-20 | 2004-10-21 | Nippon Catalytic Chem Ind | Method for production of halogen-containing aromatic compound |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2561738A (en) * | 1949-11-04 | 1951-07-24 | Westinghouse Electric Corp | Cooling and insulating electrical apparatus |
-
1981
- 1981-08-07 US US06/290,931 patent/US4396785A/en not_active Expired - Fee Related
- 1981-08-13 GB GB8124768A patent/GB2083027B/en not_active Expired
- 1981-08-18 DE DE3132501A patent/DE3132501C2/de not_active Expired
- 1981-08-20 FR FR8115992A patent/FR2489303A1/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| Néant * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2083027B (en) | 1984-06-20 |
| US4396785A (en) | 1983-08-02 |
| DE3132501C2 (de) | 1983-10-20 |
| GB2083027A (en) | 1982-03-17 |
| FR2489303B1 (en:Method) | 1984-11-30 |
| DE3132501A1 (de) | 1982-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |