EP0000622B1 - Liquid dielectric composition - Google Patents
Liquid dielectric composition Download PDFInfo
- Publication number
- EP0000622B1 EP0000622B1 EP78300089A EP78300089A EP0000622B1 EP 0000622 B1 EP0000622 B1 EP 0000622B1 EP 78300089 A EP78300089 A EP 78300089A EP 78300089 A EP78300089 A EP 78300089A EP 0000622 B1 EP0000622 B1 EP 0000622B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- benzene
- composition
- alkylation
- liquid dielectric
- ethylene
- 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 25
- 239000007788 liquid Substances 0.000 title claims description 16
- 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 31
- 238000005804 alkylation reaction Methods 0.000 claims description 31
- 229940058172 ethylbenzene Drugs 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 12
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- -1 polyethylbenzenes Chemical compound 0.000 claims description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000000463 material Substances 0.000 description 5
- 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
- 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
- 229910052782 aluminium Inorganic materials 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
- 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
- 239000012808 vapor phase Substances 0.000 description 2
- 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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- 150000005195 diethylbenzenes Chemical class 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
- 150000004679 hydroxides Chemical class 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
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 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 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°C to 420°C as said liquid dielectric composition.
- the boiling point of the recovered fraction is more preferably 260°C to 400°C and most preferably 268°C to 400°C.
- 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, 1,1-diphenyiethane, polyethylbenzenes and still higher molecular weight products, separating benzene, ethylbenzene and polyethylbenzenes from said alkylation product and thereafter recovering from the remainder a fraction which contains 1,1-diphenylethane and whose boiling point is in the temperature range of 255°C to 420°C, preferably 260°C to 400°C, most preferably 268°C to 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 vapor 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.
- an alkylation catalyst for example, a Friedel Crafts catalyst, such as aluminum chloride or aluminum bromide or some other organo-aluminum halide; Lewis acids, such as promoted ZnCl 2 , FecI 3 and BF 3 ; and Bronsted acids, including sulfuric acid, sulfonic acid and p-toluene sulfonic 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 that is 170 x 10 4 Pa), preferably about seven to about 200 pounds per square inch
- a Friedel Crafts catalyst such as aluminum chloride or aluminum bromide
- the reactants can be passed over a suitable alkylation catalyst bed containing alkylation catalysts, such as phosphoric acid on kieselguhr, silica or alumina, aluminum silicates, etc. at a convenient hourly space velocity in a temperature range of about 250° to about 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 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, aluminum silicates, etc.
- an alkylation product is obtained containing unreacted benzene, the desired ethylbenzene, polyethylbenzenes, such as diethylbenzenes and triethylbenzene, 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 aluminum 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.) and polyethylbenzenes (B.P. 176°-250°C).
- the heavier product remaining after removal of benzene, ethylbenzene and polyethylbenzenes, 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 the entire fraction recovered whose boiling point at atmospheric pressure (14.7 pounds per square inch or 760 millimeters of mercury that is 10.13 x 10 4 Pa is in the temperature range of about 255° to about 420°C., or preferably the fraction recovered whose boiling point is in the temperature range of about 260° to about 400°C., most preferably about 268° to about 400°C., constitutes the desired and novel liquid dielectric composition. That portion whose boiling point is in the range of about 255° to about 420°C. will contain a maximum of about 20 weight per cent 1,1-diphenylethane, that portion whose boiling point is in the range of about 260° to about 400°C.
- 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 48 x 10 4 Pa) in the presence of AIC1 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 AIcI 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 to 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 tri- ethylbenzenes, 2.1 weight per cent tetra- ethylbenzenes 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, ethyl- benzene and polyalkylated benzenes, 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 0.014 parts for each part of ethylbenzene produced.
- aged aluminum chloride complex the amount of high-boiling residue formed can be increased substantially.
- 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.
- the power factor of the composition claimed herein can be further improved by recovering said composition from the heavier products defined herein by distillation in the presence of basic materials, such as Group I and Group II alkali metals and alkaline earth metals, their oxides and hydroxides, as defined in our copending European Patent Application No. 78300088.8 (publication number 0000621).
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 |
|---|---|---|---|
| US817693 | 1977-07-21 | ||
| US05/817,693 US4111824A (en) | 1977-07-21 | 1977-07-21 | Liquid dielectric composition based on a fraction derived from the alkylation product of benzene with ethylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000622A1 EP0000622A1 (en) | 1979-02-07 |
| EP0000622B1 true EP0000622B1 (en) | 1981-02-04 |
Family
ID=25223662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78300089A Expired EP0000622B1 (en) | 1977-07-21 | 1978-06-27 | Liquid dielectric composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4111824A (enrdf_load_stackoverflow) |
| EP (1) | EP0000622B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5423086A (enrdf_load_stackoverflow) |
| CA (1) | CA1084693A (enrdf_load_stackoverflow) |
| DE (1) | DE2860389D1 (enrdf_load_stackoverflow) |
| IT (1) | IT1099582B (enrdf_load_stackoverflow) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPS561414A (en) * | 1979-06-19 | 1981-01-09 | Nippon Petrochemicals Co Ltd | Oillfilled power cable |
| EP0030249B1 (en) * | 1979-11-30 | 1983-07-20 | Gulf Research & Development Company | Insulating oil compositions |
| US4347169A (en) * | 1980-06-30 | 1982-08-31 | Nippon Petrochemicals Company, Limited | Electrical insulating oil and oil-filled electrical appliances |
| US4420791A (en) * | 1981-12-28 | 1983-12-13 | Emhart Industries, Inc. | Dielectric fluid |
| US4474989A (en) * | 1982-07-01 | 1984-10-02 | Gulf Research & Development Company | Process for preparing dinitrobenzophenones |
| EP0281162B1 (en) * | 1982-12-25 | 1996-06-12 | Nippon Petrochemicals Company, Limited | Method for improving the electrical insulating characteristics of a fraction, electrical insulating substance, and electrical appliances containing the same |
| JPS6116410A (ja) * | 1984-06-29 | 1986-01-24 | 日本石油化学株式会社 | 電気絶縁油 |
| JPH06101245B2 (ja) * | 1984-08-03 | 1994-12-12 | 日本石油化学株式会社 | 電気絶縁油の製造方法 |
| JPS6261943A (ja) * | 1985-09-11 | 1987-03-18 | Nippon Petrochem Co Ltd | ３−エチルベンゾフエノンの製造法 |
| JPS6261942A (ja) * | 1985-09-11 | 1987-03-18 | Nippon Petrochem Co Ltd | ３−エチルベンゾフエノンの製造法 |
| JPH0770423B2 (ja) * | 1986-09-17 | 1995-07-31 | 日本石油化学株式会社 | 油浸コンデンサ− |
| 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 |
| 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 |
| SA112330278B1 (ar) | 2011-02-18 | 2015-10-09 | ستيم سينتركس، انك. | مواد ضابطة جديدة وطرق للاستخدام |
Family Cites Families (9)
| 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 | ||
| 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 US05/817,693 patent/US4111824A/en not_active Expired - Lifetime
-
1978
- 1978-06-06 CA CA304,857A patent/CA1084693A/en not_active Expired
- 1978-06-27 DE DE7878300089T patent/DE2860389D1/de not_active Expired
- 1978-06-27 EP EP78300089A patent/EP0000622B1/en not_active Expired
- 1978-07-20 IT IT25916/78A patent/IT1099582B/it active
- 1978-07-20 JP JP8779178A patent/JPS5423086A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2860389D1 (en) | 1981-03-19 |
| EP0000622A1 (en) | 1979-02-07 |
| IT1099582B (it) | 1985-09-18 |
| IT7825916A0 (it) | 1978-07-20 |
| US4111824A (en) | 1978-09-05 |
| CA1084693A (en) | 1980-09-02 |
| JPS5423086A (en) | 1979-02-21 |
| JPS6258083B2 (enrdf_load_stackoverflow) | 1987-12-04 |
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