EP0030249B1 - Isolierölzusammensetzungen - Google Patents
Isolierölzusammensetzungen Download PDFInfo
- Publication number
- EP0030249B1 EP0030249B1 EP19790302746 EP79302746A EP0030249B1 EP 0030249 B1 EP0030249 B1 EP 0030249B1 EP 19790302746 EP19790302746 EP 19790302746 EP 79302746 A EP79302746 A EP 79302746A EP 0030249 B1 EP0030249 B1 EP 0030249B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- insulating oil
- oil
- product
- temperature range
- 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 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 60
- 239000003921 oil Substances 0.000 claims description 38
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 28
- 238000009835 boiling Methods 0.000 claims description 13
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000010690 paraffinic oil Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000006384 oligomerization reaction Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- -1 polyethylbenzenes Chemical compound 0.000 claims description 4
- 239000002199 base oil Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000001555 benzenes Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000000704 physical effect Effects 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
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical class CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 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
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 238000002464 physical blending Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-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
- H01B3/22—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
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
- C10G29/205—Organic compounds not containing metal atoms by reaction with hydrocarbons added to the hydrocarbon oil
Definitions
- This invention relates to novel insulating oil compositions comprising a major amount of an insulating oil and a minor amount of a product obtained as a result of a process which comprises reacting benzene with ethylene in the presence of an alkylation catalyst to obtain a reaction mixture containing largely unreacted benzene, ethylbenzene, polyethylbenzenes, 1,1-diphenylethane and heavier material, separating at least benzene, ethylbenzene and polyethylbenzenes from said reaction mixture and thereafter recovering from said heavier material a fraction whose boiling points fall within a temperature range of about 255° to about 420°C as said product.
- Insulating oils for example, transformer oils
- transformer oils are required to have low power factors and high dielectric strengths, and to be able to maintain thermal and oxidative stability toward degradation and oxidation and to possess minimum tendency toward the formation of gas while in use. See, for example, U.S. Patent No. 3,549,537 to Brewster et al. Insulating oils composed largely of naphthenes and/or highly-branched, non-cyclic, paraffins can be used satisfactorily as transformer oils, for example, but unfortunately, they possess the tendency to produce gas during service.
- the insulating oils used herein can be obtained from any naphthenic and/or paraffinic origin.
- naphthenic and/or paraffinic oils we mean to include naturally-derived, or synthetic, stocks containing largely one-ring structures, such as cyclopentane and cyclohexane derivatives, two-ring structures, such as decalin and dicyclohexyl derivatives, three-, four-, and five-membered ring structures, which may be part of the same or different molecule and their mixtures, etc.
- the paraffinic oils are defined as being largely of highly-branched, non-cyclic, compounds. A more useful conventional definition is that developed by E. C. Lane and E.
- oils can be synthetic oils, such as those obtained as the result of the oligomerization of 1-olefins having from six to 14 carbon atoms, preferably from eight to 12 carbon atoms, such as 1- decene, mixtures of 1-decene and 1-octene, 1-dodecene, etc., as described, for example, in US-A-4,045,507 to Cupples et al.
- Mixtures of naphthenic and paraffinic oils, including mixtures of natural and synthetic oils can also be used, for example, in weight ratios of about 99:1 to about 1:99, preferably about 90:10 to about 10:90.
- the insulating oil used herein can be defined in accordance with the parameters set forth in Table I.
- the product is obtained by reacting benzene with ethylene to obtain a reaction mixture containing unreacted benzene, ethylbenzene, polyethylbenzenes, 1,1-diphenylethane and heavier material, separating at least benzene, ethylbenzene, and polyethylbenzenes from said reaction mixture and thereafter recovering from said heavier material the entire fraction, or any portion of said fraction, whose boiling points at atmospheric pressure (ambient pressure) fall within a temperature range of 255° to 420°C, preferably 260° to 400°C, most preferably 268° to 400°C.
- the product that is added to the above insulating oils is the entire fraction, or any portion of said fraction, whose boiling points at atmospheric pressure fall within a temperature range of 275° to 420°C, preferably 280° to 400°C.
- the amounts of said product added to the insulating oil to inhibit the gassing tendency thereof can be varied over a wide limit, but, in general, the amount present, based on the weight of the final insulating composition, will be in the range of five to 20 weight per cent, preferably five to 15 weight per cent. Since the insulating oil and said product are both hydrocarbons and therefore completely miscible one in the other, mixing of the two at ambient temperature and ambient pressure until a homogeneous solution is obtained will suffice.
- the following Table 11 compares the properties of the naphthenic base oil employed herein with the ASTM D-3487 insulating oil specifications for Type I Oil.
- the naturally-derived base oil (naphthenic) was obtained from Interprovincial Pipeline No. 1 and was a mixture of low sulfur, low pour point crudes. After conventional distillation, the fraction consisting of a 50:50 mixture of light vacuum and heavy vacuum oils (Gravity °API 25) was subjected to hydrotreating following the conditions in US-A-3,764,518. The purpose of this treatment was to upgrade the product through hydrocracking, isomerization and saturation.
- the product from the two stage hydrotreatment has the properties shown in Table II.
- the synthetic base oil was prepared in accordance with the procedure of Example 1 of US-A-4,045,507 of Cupples et al, employing 1- decene as feedstock.
- the total product was then passed over a commercial nickel catalyst (Ni0104T, 1/8-inch pellets having a surface area of 125 square meters per gram) at 165°C and 600 pounds per square inch gauge (41 kilograms per square centimeter) of hydrogen pressure at a rate sufficient to effect stabilization of the product through hydrogenation. Distillation under vacuum afforded the synthetic base oil used herein, a dimer fraction boiling in the temperature range of 160°-168°C at 666 Pa (five millimeters of mercury).
- a product for adding to the naphthenic oil was prepared 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) 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 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 as 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 percent 1, 1-diphenylethane and 0.4 weight percent 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.
- the residue so obtained was subjected to distillation to obtain a cut having a boiling point at atmospheric pressure within the temperature range of 275° to 400°C. This cut was the product added to the naphthenic oil and to the paraffinic oil in a later example.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Insulating Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE7979302746T DE2965961D1 (en) | 1979-11-30 | 1979-11-30 | Insulating oil compositions |
| EP19790302746 EP0030249B1 (de) | 1979-11-30 | 1979-11-30 | Isolierölzusammensetzungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19790302746 EP0030249B1 (de) | 1979-11-30 | 1979-11-30 | Isolierölzusammensetzungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0030249A1 EP0030249A1 (de) | 1981-06-17 |
| EP0030249B1 true EP0030249B1 (de) | 1983-07-20 |
Family
ID=8186474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19790302746 Expired EP0030249B1 (de) | 1979-11-30 | 1979-11-30 | Isolierölzusammensetzungen |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0030249B1 (de) |
| DE (1) | DE2965961D1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543207A (en) * | 1982-12-25 | 1985-09-24 | Nippon Petrochemicals Company, Limited | Electrical insulating oil and oil-filled electrical appliances |
| US7531083B2 (en) | 2004-11-08 | 2009-05-12 | Shell Oil Company | Cycloalkane base oils, cycloalkane-base dielectric liquids made using cycloalkane base oils, and methods of making same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036010A (en) * | 1958-07-01 | 1962-05-22 | Exxon Standard Sa | Non-gassing insulating oils |
| FR1243597A (fr) * | 1959-12-10 | 1960-10-14 | Progil | Perfectionnements à l'isolation de l'appareillage électrique |
| GB1052658A (de) * | 1963-07-22 | |||
| US4045507A (en) * | 1975-11-20 | 1977-08-30 | Gulf Research & Development Company | Method of oligomerizing 1-olefins |
| US4111824A (en) * | 1977-07-21 | 1978-09-05 | Gulf Research & Development Co. | Liquid dielectric composition based on a fraction derived from the alkylation product of benzene with ethylene |
-
1979
- 1979-11-30 EP EP19790302746 patent/EP0030249B1/de not_active Expired
- 1979-11-30 DE DE7979302746T patent/DE2965961D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2965961D1 (en) | 1983-08-25 |
| EP0030249A1 (de) | 1981-06-17 |
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