EP0422986B1 - Procédé de synthèse de fluides diélectriques - Google Patents
Procédé de synthèse de fluides diélectriques Download PDFInfo
- Publication number
- EP0422986B1 EP0422986B1 EP90402722A EP90402722A EP0422986B1 EP 0422986 B1 EP0422986 B1 EP 0422986B1 EP 90402722 A EP90402722 A EP 90402722A EP 90402722 A EP90402722 A EP 90402722A EP 0422986 B1 EP0422986 B1 EP 0422986B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- aromatic
- condensation
- dielectric
- toluene
- distillation
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000012530 fluid Substances 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 16
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000005406 washing Methods 0.000 claims abstract description 15
- -1 aromatic halides Chemical class 0.000 claims abstract description 14
- 238000009833 condensation Methods 0.000 claims abstract description 14
- 230000005494 condensation Effects 0.000 claims abstract description 14
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 61
- 239000000047 product Substances 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 15
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical group ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 13
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 12
- 229940073608 benzyl chloride Drugs 0.000 claims description 11
- 239000007859 condensation product Substances 0.000 claims description 6
- 230000003750 conditioning effect Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000001577 simple distillation Methods 0.000 description 4
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IOXAUPNPMJKSKQ-UHFFFAOYSA-N 1-benzyl-2,3-dimethylbenzene Chemical compound CC1=CC=CC(CC=2C=CC=CC=2)=C1C IOXAUPNPMJKSKQ-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003613 toluenes Chemical class 0.000 description 2
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-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
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- 0 C1C2(C3)C1*3(C1)C1C2 Chemical compound C1C2(C3)C1*3(C1)C1C2 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000032677 cell aging Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 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
- H01B3/22—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 hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/02—Well-defined hydrocarbons
- C10M105/06—Well-defined hydrocarbons aromatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
- C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
Definitions
- the present invention relates to a process for the synthesis of dielectric fluids and more particularly to an improvement of the processes comprising a condensation of the FRIEDEL and CRAFTS type catalyzed by ferric chloride.
- dielectric liquids of the formula have been described in which n, x, y and z have the value 1 or 2.
- These products can be prepared by condensation of: in which n, x, y and z have the same meaning as above in the presence of a catalyst from FRIEDEL and CRAFTS. After the condensation, the catalyst is destroyed, for example by adding a dilute aqueous solution of hydrochloric acid followed by washing the organic phase.
- Patent application EP 136230 describes dielectric fluids which are polyarylalkane oligomers obtained by condensation of benzyl chloride C6H5CH2Cl and benzylidene chloride C6H5CHCl2 on toluene in the presence of a FRIEDEL and CRAFTS catalyst.
- the Applicant has made the same observation as for the process of the EP 8251 application cited above, that is to say that by using ferric chloride, it is possible to omit the washing step and yet produce a fluid capable of dielectric.
- the Applicant has found a particularly simple process for synthesizing dielectric fluids by condensation of the FRIEDEL and CRAFTS type.
- step a is a reaction of FRIEDEL and CRAFTS.
- Aromatic halides denote, for example, alkylbenzene or (polyalkyl) benzene having at least one halogen in the benzyl position on the alkyl chain
- the benzated nucleus nique can, in addition to halogenated alkyl chains, be substituted by halogens, alkyls having up to three carbon atoms or nitrile or NO2 groups.
- the alkyl chains which carry at least one halogen can be identical or different and contain up to three carbon atoms.
- aromatic halides can be, for example, the products of formulas: the nucleus can be substituted by 1 or 2 chlorine the nucleus can be substituted by 1 or 2 chlorine
- aromatic halides are condensed with aromatic compounds.
- aromatic compounds denote, for example, benzene which can be substituted by one or more identical or different alkyl groups and having up to 8 carbon atoms, halogens or nitrile or NO2 groups.
- aromatic compounds can be, for example, benzene, toluene, xylene, products of formula:
- the condensation of the step takes place in practice at a temperature between 50 ° C and 150 ° C.
- the amount of ferric chloride is usually between 50 ppm and 1% by weight of the reaction mass.
- an excess of the aromatic halide or an excess of the aromatic compound can be used.
- different condensation products are obtained, which are themselves mixtures. Most often, it may be necessary to distill the excess reagents (step c ) because these products, even in admixture with the condensation products do not have dielectric properties or cannot be used as dielectrics because of their too much volatility.
- step d all or at least one of the condensation products is recovered. Indeed, during the condensation (step a ), a mixture of products is often obtained.
- an oligomer A which is a mixture of isomers of formula where n1 and n2 are 0, 1 or 2 and n1 + n2 is less than or equal to 3.
- MBT benzyltoluene
- DBT dibenzyltoluene
- oligomer B which is a mixture of isomers of formula: where n′1, n ⁇ 1 and n4 are 0, 1 or 2, n′2, n ⁇ 2, n3, n′3 and n5 are 0 or 1, and knowing that the sum n′1 + n ⁇ 1 + n′2 + n ⁇ 2 + n3 + n′3 + n4 + n5 is less than or equal to 2.
- stage d the desired isomers or mixtures of isomers are distilled off, then they are conditioned into dielectric fluid.
- the packaging of products for dielectric use is known per se, it is recalled on page 4 in patent application EP 8251. It consists of a preliminary purification treatment with alkalis such as NaoH, Na2Co3 or compounds similar to calcium or potassium at a temperature ranging from 20 to 350 ° C. Sometimes further distillation can be advantageous.
- the next purification phase consists in using bleaching earth or activated alumina either alone or as a mixture according to the specific techniques known in the dielectric fluids sector.
- stabilizers of the epoxide or other type such as, for example, tetraphenyltin or anthraquinone compounds.
- aromatic halides are derived from the aromatic compounds in question, for example benzyl chloride and toluene or methyl benzyl chloride (CH3C6H4CH2Cl) and xylene, then it is possible to carry out upstream of the step to the partial halogenation of the aromatic compound. A mixture of aromatic halide and aromatic compound is thus obtained in which it suffices to add ferric chloride to carry out step a of the process.
- the dielectric properties have been determined and are listed in the table of Example 7, column 7.1.
- Example 3 is repeated, but replacing the ferric chloride with 35 g of aluminum chloride at the Friedel and Crafts reaction. The reaction medium is then subjected to distillation. The same difficulties are encountered as those observed in Example 2, which leads to a product unsuitable for dielectric application.
- 1500 g are obtained under a vacuum of 15 mm of mercury vacuum with a vapor temperature of 260 to 280 ° C. It is a slightly yellow liquid containing less than 1 ppm of iron. This product is ideal for dielectric application.
- the filtered samples were placed in tan ⁇ measuring cells (2 cells per sample). These cells were placed in an oven at 100 ° C and the tan ⁇ was followed for 500 hours.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Insulating Materials (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Inorganic Insulating Materials (AREA)
- Lubricants (AREA)
- Oxygen, Ozone, And Oxides In General (AREA)
- Compounds Of Iron (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT90402722T ATE80176T1 (de) | 1989-10-13 | 1990-10-02 | Verfahren zur herstellung von dielektrischen fluessigkeiten. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8913451A FR2653134B1 (fr) | 1989-10-13 | 1989-10-13 | Procede de synthese de fluides dielectriques. |
| FR8913451 | 1989-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0422986A1 EP0422986A1 (fr) | 1991-04-17 |
| EP0422986B1 true EP0422986B1 (fr) | 1992-09-02 |
Family
ID=9386400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90402722A Expired - Lifetime EP0422986B1 (fr) | 1989-10-13 | 1990-10-02 | Procédé de synthèse de fluides diélectriques |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5186864A (es) |
| EP (1) | EP0422986B1 (es) |
| JP (1) | JP2569214B2 (es) |
| KR (1) | KR930005531B1 (es) |
| CN (1) | CN1029005C (es) |
| AT (1) | ATE80176T1 (es) |
| CA (1) | CA2027445C (es) |
| DE (1) | DE69000288T2 (es) |
| DK (1) | DK0422986T3 (es) |
| ES (1) | ES2034844T3 (es) |
| FI (1) | FI97478C (es) |
| FR (1) | FR2653134B1 (es) |
| GR (1) | GR3006387T3 (es) |
| IE (1) | IE64608B1 (es) |
| NO (1) | NO904393L (es) |
| PT (1) | PT95588B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5977422A (en) * | 1997-06-09 | 1999-11-02 | The Dow Chemical Company | Organoaluminum catalysis of alkylation reactions |
| US20060100466A1 (en) * | 2004-11-08 | 2006-05-11 | Holmes Steven A | Cycloalkane base oils, cycloalkane-base dielectric liquids made using cycloalkane base oils, and methods of making same |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2012302A (en) * | 1933-04-04 | 1935-08-27 | Gen Electric | Halogenated material and process of preparing the same |
| US2556880A (en) * | 1945-08-17 | 1951-06-12 | Solar Mfg Corp | Synthetic oils and resins and methods of producing same |
| BE533352A (es) * | 1953-11-17 | 1954-12-15 | ||
| US3006972A (en) * | 1959-08-21 | 1961-10-31 | Standard Oil Co | Coupling of aromatic rings |
| US4197417A (en) * | 1977-09-28 | 1980-04-08 | Imperial Chemical Industries Limited | Process for the manufacture of o-benzyl toluenes |
| EP0008251B1 (fr) * | 1978-07-27 | 1982-02-17 | P C U K Produits Chimiques Ugine Kuhlmann | Nouveaux diélectriques liquides, procédé de préparation et applications |
| IT1138101B (it) * | 1981-07-24 | 1986-09-17 | Caffaro Ind Chimica Ed Elettro | Fluido dielettrico per trasformatori e procedimento per la sua preparazione |
| FR2552423B1 (fr) * | 1983-09-23 | 1985-10-25 | Ugine Kuhlmann | Compositions d'oligomeres de polyarylalcanes et leur procede de fabrication |
| DE3836780A1 (de) * | 1988-10-28 | 1990-05-03 | Bayer Ag | Verfahren zur herstellung von gegebenenfalls substituierten benzylbenzolen |
-
1989
- 1989-10-13 FR FR8913451A patent/FR2653134B1/fr not_active Expired - Lifetime
-
1990
- 1990-10-02 AT AT90402722T patent/ATE80176T1/de active
- 1990-10-02 DE DE9090402722T patent/DE69000288T2/de not_active Expired - Fee Related
- 1990-10-02 ES ES199090402722T patent/ES2034844T3/es not_active Expired - Lifetime
- 1990-10-02 DK DK90402722.4T patent/DK0422986T3/da active
- 1990-10-02 EP EP90402722A patent/EP0422986B1/fr not_active Expired - Lifetime
- 1990-10-11 NO NO90904393A patent/NO904393L/no unknown
- 1990-10-12 JP JP2275155A patent/JP2569214B2/ja not_active Expired - Lifetime
- 1990-10-12 FI FI905033A patent/FI97478C/fi not_active IP Right Cessation
- 1990-10-12 CA CA002027445A patent/CA2027445C/fr not_active Expired - Fee Related
- 1990-10-12 PT PT95588A patent/PT95588B/pt not_active IP Right Cessation
- 1990-10-12 KR KR1019900016202A patent/KR930005531B1/ko not_active IP Right Cessation
- 1990-10-13 CN CN90108455A patent/CN1029005C/zh not_active Expired - Fee Related
- 1990-10-15 IE IE369290A patent/IE64608B1/en not_active IP Right Cessation
- 1990-10-15 US US07/597,030 patent/US5186864A/en not_active Expired - Fee Related
-
1992
- 1992-11-30 GR GR920402760T patent/GR3006387T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE903692A1 (en) | 1991-04-24 |
| FI97478C (fi) | 1996-12-27 |
| FI905033A0 (fi) | 1990-10-12 |
| US5186864A (en) | 1993-02-16 |
| GR3006387T3 (es) | 1993-06-21 |
| PT95588B (pt) | 1997-08-29 |
| FR2653134A1 (fr) | 1991-04-19 |
| DK0422986T3 (da) | 1992-10-05 |
| ES2034844T3 (es) | 1993-04-01 |
| CN1050894A (zh) | 1991-04-24 |
| PT95588A (pt) | 1991-09-13 |
| KR910008113A (ko) | 1991-05-30 |
| JP2569214B2 (ja) | 1997-01-08 |
| CA2027445C (fr) | 1994-03-22 |
| KR930005531B1 (ko) | 1993-06-22 |
| ATE80176T1 (de) | 1992-09-15 |
| EP0422986A1 (fr) | 1991-04-17 |
| FR2653134B1 (fr) | 1991-12-13 |
| NO904393D0 (no) | 1990-10-11 |
| CN1029005C (zh) | 1995-06-21 |
| NO904393L (no) | 1991-04-15 |
| CA2027445A1 (fr) | 1991-04-14 |
| JPH03134095A (ja) | 1991-06-07 |
| DE69000288D1 (de) | 1992-10-08 |
| DE69000288T2 (de) | 1993-03-18 |
| FI97478B (fi) | 1996-09-13 |
| IE64608B1 (en) | 1995-08-23 |
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