EP0000619B1 - Liquid dielectric composition - Google Patents
Liquid dielectric composition Download PDFInfo
- Publication number
- EP0000619B1 EP0000619B1 EP78300086A EP78300086A EP0000619B1 EP 0000619 B1 EP0000619 B1 EP 0000619B1 EP 78300086 A EP78300086 A EP 78300086A EP 78300086 A EP78300086 A EP 78300086A EP 0000619 B1 EP0000619 B1 EP 0000619B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- benzene
- ethylbenzene
- alkylation
- liquid dielectric
- composition
- 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
- 239000000203 mixture Substances 0.000 title claims description 26
- 239000007788 liquid Substances 0.000 title claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 78
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 40
- 230000029936 alkylation Effects 0.000 claims description 30
- 238000005804 alkylation reaction Methods 0.000 claims description 30
- 238000009835 boiling Methods 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 claims description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 12
- -1 polyethylbenzenes Chemical compound 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 3
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- FEWANSQOXSIFOK-UHFFFAOYSA-N 1,2,3,4-tetraethylbenzene Chemical class CCC1=CC=C(CC)C(CC)=C1CC FEWANSQOXSIFOK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003226 decolorizating effect Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
Definitions
- This invention relates to a liquid dielectric composition obtained from the alkylation product of benzene with ethylene.
- Belgian Patent A-504293 discloses that an oil for use as electrical insulation for cables can be obtained from the product of alkylation of aromatic hydrocarbons by heating the alkylation product which has a molecular weight above 500, for example with an absorbent such as a decolourising earth, silica gel or alumina.
- the present invention provides a liquid dielectric composition obtained as a result of a process which comprises reacting benzene with ethylene in the presence of an alkylation catalyst to obtain an alkylation product containing unreacted benzene, ethylbenzene, polyethylbenzenes, 1, 1-diphenylethane and higher molecular weight products, characterised in that benzene, ethylbenzene, polyethylbenzenes and 1,1-diphenylethane are removed from said alkylation product and thereafter there is recovered from said higher molecular weight products a fraction having a boiling point in the temperature range of 275° to 420°C as said liquid dielectric composition.
- the process employed in obtaining the new liquid dielectric compositions defined and claimed herein comprises reacting benzene with ethylene in the presence of an alkylation catalyst to obtain an alkylation product containing largely unreacted benzene, ethylbenzene, polyethylbenzenes, 1,1-diphenylethane and heavier, still higher-boiling products, separating benzene, ethylbenzene, polyethylbenzenes and 1,1 -diphenylethane from said alkylation product and thereafter recovering from said heavier products a fraction having a boiling point in the temperature range of 275° to 420°C, preferably about 280° to about 400°C, as said liquid dielectric composition.
- the alkylation of benzene with ethylene that can be employed to obtain the new liquid dielectric compositions claimed herein can be any of the processes known in the art for producing a product containing ethylbenzene, for example, either liquid phase alkylation or vapour phase alkylation.
- the molar ratios of benzene to ethylene employed can be, for example, in the range of about 25:1 to about 2:1, preferably about 10:1 to about 3:1.
- the benzene and ethylene together with an alkylation catalyst, for example a Friedel Crafts catalyst, such as aluminium chloride or aluminium bromide or some other organo-aluminium halide; Lewis acids, such as promoted ZnCl 2 , FeCI 3 and BF 3 , and Bronsted acids, including sulfuric acid, sulfonic acid and p-toluenesulfonic acid, hydrofluoric acid, etc., in an amount corresponding to about 0.002 to about 0.050 parts, preferably about 0.005 to about 0.030 parts, relative to ethylbenzene produced, are reacted in a temperature range of about 20° to about 175°C., preferably about 90° to about 150°C, and a pressure in the range of about atmospheric to about 250 pounds per square inch gauge (about atmospheric to about 17.6 kilograms per square centimeter or 170 x 10 4 Pa), preferably about seven to about 200 pounds per square inch gauge (about
- an alkylation catalyst for example
- the reactants can be passed over a suitable alkylation catalyst bed containing alkylation catalysts, such as phosphoric acid on kieselguhr, silica or alumina, aluminium silicates, etc., at a convenient hourly space velocity in a temperature range of about 250° to 450°C, preferably about 300° to about 400°C, and a pressure of about 400 to about 1200 pounds per square inch gauge (about 28 to about 85 kilograms per square centimeter that is, about 265 x 10 4 Pa to about 830 x 10 4 Pa), preferably about 600 to about 1000 pounds per square inch gauge (about 42 to about 70 kilograms per square centimeter that is, about 410 x 10 4 Pa to about 690 x 10 4 Pa).
- alkylation catalysts such as phosphoric acid on kieselguhr, silica or alumina, aluminium silicates, etc.
- an alkylation product is obtained containing unreacted benzene, the desired ethylbenzene, polyethylbenzenes, such as diethylbenzens and triethylbenzene, 1,1-diphenylethane and higher-boiling products.
- the alkylation product can be treated in any conventional manner to remove any alkylation catalyst present therein.
- the alkylation product can be sent to a settler wherein the aluminium chloride complex is removed and recycled to the reaction zone and the remaining product can then be water washed and neutralized.
- the resulting alkylation product is then distilled at atmospheric pressure or under vacuum to recover unreacted benzene (B.P. 80°C.), ethylbenzene (B.P. 136°C.), polyethylbenzenes (B.P. 176°-250°C.) and 1,1-diphenylethane (B.P. 270°C.).
- the heavier product remaining after removal of benzene, ethylbenzene, polyethylbenzenes and 1, 1-diphenylethane, as described above, is a dark, viscous, high-boiling material from which the novel liquid dielectric compositions defined and claimed herein are obtained.
- the said heavier product is simply subjected to distillation and those portions recovered having a boiling point at atmospheric pressure (14.7 pounds per square inch or 760 millimeters of mercury that is 10.13 x 10 4 Pa) in the temperature range of about 275° to about 420°C., preferably about 280° to about 400°C., constitute the desired and novel liquid dielectric composition.
- the remaining heavier material or residue is a black asphalt-like material solid at ambient temperature believed, in part, to be polynuclear structure having fuel value only.
- a number of liquid dielectric compositions were prepared from the residue, or heavier products, obtained as a result of the production of ethylbenzene.
- This residue was obtained as follows: Benzene and ethylene in a molar ratio of 9:1 were contacted in the liquid phase, while stirring, in a reactor at a temperature of 130°C. and a pressure of 70 pounds per square inch gauge (4.9 kilograms per square centimeter that is, 49 x 10" Pa) in the presence of AICI 3 catalyst over a period of one hour, which was sufficient to convert all of the ethylene.
- the AICI 3 complex catalyst was prepared by dissolving AICI 3 in a polyethylbenzene cut from a previous run so that after the addition the composition of the catalyst complex was as follows: 31.5 weight per cent AICI 3 . 7.0 weight per cent benzene, 19.3 weight per cent ethylbenzene, 29.8 weight per cent polyalkylated benzenes, 3.4 weight per cent 1,1-diphenylethane and 9.0 weight per cent higher-boiling components.
- the amount of AIC1 3 present in the catalyst mixture amounted to 0.0034 parts by weight per one part by weight of ethylbenzene produced.
- ethyl chloride promoter in an amount corresponding 0.0034 parts by weight per one part by weight of ethylbenzene produced to maintain a high catalyst efficiency.
- Analysis of the alkylation product showed the presence of 49.0 weight per cent benzene, 32.9 weight per cent ethylbenzene, 17.5 weight per cent of polyalkylated benzenes (6.0 weight per cent diethylbenzene, 2.7 weight per cent triethylbenzenes, 2.1 weight per cent tetraethylbenzenes and 6.7 weight per cent other alkylbenzenes), 0.1 weight per cent 1,1 -diphenylethane and 0.4 weight per cent residue.
- the alkylation product was subjected to distillation to recover unreacted benzene, ethylbenzene, polyalkylated benzenes and 1,1-diphenyiethane, and the benzene and polyalkylated benzenes were recycled to the reaction zone.
- the residue remaining was a dark, viscous, high-boiling material, and was produced in an amount corresponding to 0.012 parts for each part of ethylbenzene produced.
- aged aluminium chloride complex the amount of high-boiling residue formed can be increased substantially.
- compositions defined and claimed herein are useful as liquid dielectric compositions, particularly for use in capacitors.
- compositions can be further treated, if desired, for example, to further improve their properties for a particular purpose, for example, to improve their flash point, interfacial tension, pour point, viscosity, oxidation stability, corrosion resistance, etc.
- Our Copending European Patent Application No. 78 300 089.6 (Publication No. 0 000 622) relates to a similar process which comprises reacting benzene with ethylene in the presence of an alkylation catalyst to obtain an alkylation product containing unreacted benzene, ethylbenzene, polyethylbenzenes, 1,1-diphenylethane and higher molecular weight products, characterised in that benzene, ethylbenzene and polyethylbenzenes are removed from said alkylation product and thereafter there is recovered by distillation from the residual alkylation product a fraction containing 1,1-diphenylethane and whose boiling point is in the temperature range of 255° to 420°C as said liquid dielectric composition.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Insulating Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/817,695 US4111825A (en) | 1977-07-21 | 1977-07-21 | Liquid dielectric composition based on a fraction derived from the alkylation product of benzene with ethylene |
| US817695 | 1977-07-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000619A1 EP0000619A1 (en) | 1979-02-07 |
| EP0000619B1 true EP0000619B1 (en) | 1981-03-11 |
Family
ID=25223668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78300086A Expired EP0000619B1 (en) | 1977-07-21 | 1978-06-27 | Liquid dielectric composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4111825A (enrdf_load_stackoverflow) |
| EP (1) | EP0000619B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5423088A (enrdf_load_stackoverflow) |
| CA (1) | CA1082908A (enrdf_load_stackoverflow) |
| DE (1) | DE2860515D1 (enrdf_load_stackoverflow) |
| IT (1) | IT1099571B (enrdf_load_stackoverflow) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5210543A (en) * | 1975-07-15 | 1977-01-26 | Matsushita Electric Ind Co Ltd | Constant voltage circuit |
| US4228024A (en) * | 1978-10-25 | 1980-10-14 | Gulf Research & Development Company | Insulating oil compositions containing a fraction derived from the alkylation product of benzene with ethylene |
| US4347169A (en) * | 1980-06-30 | 1982-08-31 | Nippon Petrochemicals Company, Limited | Electrical insulating oil and oil-filled electrical appliances |
| IT1135418B (it) * | 1981-02-11 | 1986-08-20 | Caffaro Spa Ind Chim | Fluido isolante dielettrico in particolare atto all'impiego in condensatori elettrici,e condensatore contenente detto fluido |
| US4420791A (en) * | 1981-12-28 | 1983-12-13 | Emhart Industries, Inc. | Dielectric fluid |
| JPS6116410A (ja) * | 1984-06-29 | 1986-01-24 | 日本石油化学株式会社 | 電気絶縁油 |
| JPH088015B2 (ja) * | 1986-11-08 | 1996-01-29 | 日本石油化学株式会社 | 改良された電気絶縁油組成物 |
| US4902841A (en) * | 1987-03-11 | 1990-02-20 | Nippon Petrochemicals Company, Ltd. | Method for producing electrical insulating oil composition |
| JPH0788319B2 (ja) * | 1987-09-09 | 1995-09-27 | 日本石油化学株式会社 | ｍ−ベンジルトルエンの製造方法 |
| JPH0810566B2 (ja) * | 1988-03-09 | 1996-01-31 | 日本石油化学株式会社 | 改良された留分からなる電気絶縁油 |
| US5003119A (en) * | 1988-05-09 | 1991-03-26 | Lummus Crest, Inc. | Manufacture of alkylbenzenes |
| JPH0798946B2 (ja) * | 1988-08-13 | 1995-10-25 | 日本石油化学株式会社 | 副生油の処理方法 |
| US5877362A (en) * | 1996-09-12 | 1999-03-02 | Nippon Petrochemicals Company, Limited | Method for producing diphenylmethane |
| US5880322A (en) * | 1996-12-16 | 1999-03-09 | Nippen Petrochemicals Company, Limited | Method for producing diarylmethane |
| US6207866B1 (en) | 1997-07-11 | 2001-03-27 | Nippon Petrochemicals Company, Limited | Method for producing diarylmethane or its derivatives |
| JP2000016952A (ja) | 1998-07-01 | 2000-01-18 | Nippon Petrochem Co Ltd | 炭化水素の製造方法 |
| JP4376367B2 (ja) | 1999-09-20 | 2009-12-02 | 新日本石油株式会社 | 炭化水素溶剤およびそれを用いた感圧複写材料 |
| US6515235B2 (en) | 2001-05-30 | 2003-02-04 | Ericsson, Inc. | Liquid dielectric tuning of an integrated circuit |
| JP6130143B2 (ja) | 2010-02-23 | 2017-05-17 | ベー．エル．アー．ハー．エム．エス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 少量の体液試料中のマーカーを判定する方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE504293A (enrdf_load_stackoverflow) * | ||||
| US2385187A (en) * | 1942-08-22 | 1945-09-18 | Standard Oil Dev Co | Synthesis of ethyl benzene |
| US2403785A (en) * | 1943-10-07 | 1946-07-09 | Dow Chemical Co | Alkylation method |
| US2653979A (en) * | 1948-11-05 | 1953-09-29 | American Cyanamid Co | Preparation of diarylethanes |
| GB732900A (en) | 1950-07-12 | 1955-06-29 | Karl Brinkmann | Improvements in the production of electric cables |
| DE2014895C3 (de) * | 1969-03-28 | 1974-12-19 | Kureha Kagaku Kogyo K.K., Tokio | Verfahren zur Herstellung von hydrierten alkylierten Hochtemperaturcrackrückstandsölen |
| JPS5115523B2 (enrdf_load_stackoverflow) * | 1971-10-02 | 1976-05-18 | ||
| JPS5427960B2 (enrdf_load_stackoverflow) * | 1972-03-27 | 1979-09-13 | ||
| JPS4931652A (enrdf_load_stackoverflow) * | 1972-07-20 | 1974-03-22 | ||
| US4011274A (en) * | 1973-01-13 | 1977-03-08 | Asahi-Dow Limited | 1,1-diphenyl ethane process |
| US4033854A (en) * | 1974-12-02 | 1977-07-05 | Nippon Oil Company, Ltd. | Electrical insulating oils |
-
1977
- 1977-07-21 US US05/817,695 patent/US4111825A/en not_active Expired - Lifetime
-
1978
- 1978-06-14 CA CA305,491A patent/CA1082908A/en not_active Expired
- 1978-06-27 DE DE7878300086T patent/DE2860515D1/de not_active Expired
- 1978-06-27 EP EP78300086A patent/EP0000619B1/en not_active Expired
- 1978-07-20 IT IT25918/78A patent/IT1099571B/it active
- 1978-07-20 JP JP8779378A patent/JPS5423088A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1082908A (en) | 1980-08-05 |
| EP0000619A1 (en) | 1979-02-07 |
| IT7825918A0 (it) | 1978-07-20 |
| IT1099571B (it) | 1985-09-18 |
| US4111825A (en) | 1978-09-05 |
| JPS5423088A (en) | 1979-02-21 |
| JPS6319962B2 (enrdf_load_stackoverflow) | 1988-04-26 |
| DE2860515D1 (en) | 1981-04-09 |
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