US2141593A - Lubricating oil - Google Patents
Lubricating oil Download PDFInfo
- Publication number
- US2141593A US2141593A US741724A US74172434A US2141593A US 2141593 A US2141593 A US 2141593A US 741724 A US741724 A US 741724A US 74172434 A US74172434 A US 74172434A US 2141593 A US2141593 A US 2141593A
- Authority
- US
- United States
- Prior art keywords
- oil
- viscosity index
- lubricating oil
- lubricating
- synthetic
- 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
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- 239000010687 lubricating oil Substances 0.000 title description 17
- 239000003921 oil Substances 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 239000007859 condensation product Substances 0.000 description 9
- 239000010689 synthetic lubricating oil Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 239000010802 sludge Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- -1 allowing the Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
Definitions
- This invention relates to the manufacture of synthetic lubricating oils, and particularly to synthetic lubricating oils of improved character having an increased viscosity index, and to syn- 5 thetic oils applicable for blending with mineral lubricating oils to improve the character thereof.
- high grade lubricating oils it is well known that a relatively small change in the viscosity of the oilbetween temperatures of say 100 F. and 210 -F., isidesirable.
- the oil it is advantageous for the oil to have a relatively flat iscosity-temperature curve, which means that the oil has a high viscosity index as defined by Dean and Davis in their article in Chemical and Metallurgical Engineering, vol. 36, page, 618.
- Improvement in lubricating oils has heretofore been accomplished by refining, as by the use of selective solvents which are efiective in extracting or separating naphthenic constituents from paraflinic constituents, thereby producin a resulting raflinate of increased viscosity index.
- the present invention relates to the increase in viscosity index of naphthene base or paraffin base lubricating oils, which may or may not have been solvent refined as a primary step, by the ad 85 dition thereto of a material which is active to increase the viscosity index without objectionably affecting other desirable properties thereof. More particularly, the present invention relates to the production of an improved lubricating oil 40 of this type having increased viscosity index, by the addition thereto of a controlled proportion 01 a hydrogenated condensation product of an alkyl halide with an aromatic hydrocarbon. The invention also contemplates the preparation of synt6 thetic lubricating oils by hydrogenation of the condensation-product of an alkyl halide with an (or. av -9) the lower or normally gaseous oieflnes are particularly effective in this-reaction.
- benzene and its homologues such for example as toluene, mesitylene, tertiary butylv benzene, tertiary amyl ben- 5 zene, normal butyl benzene, secondary butyl benzene, and the "like may be employed.
- halogenated derivatives of benzene and its hom-' ologues, such as chlorbenzene are satisfactory.
- the condensation is eflected in the presence of 10 a catalyst of the Friedel-Craft type, such as anhydrous halides of aluminum, iron, boron, manganese, nickel, zinc, antimony, cadmium, tin-"and the like. Very satisfactory resultsare secured with anhydrous aluminum chloride. With proper .15 a catalyst of the Friedel-Craft type, such as anhydrous halides of aluminum, iron, boron, manganese, nickel, zinc, antimony, cadmium, tin-"and the like. Very satisfactory resultsare secured with anhydrous aluminum chloride. With proper .15
- a viscous synthetic lubricating oil may be produced.
- the condensation product may be allowed to stand and stratify into an upper oily layer and a lower sludge layer, 20
- The. upper oily layer is preferably distilled to remove lower boiling liquids including unreacted chemicals, to obtain as a residue a viscous synthetic oil of lubricating character.
- This oil is then hydro- 25 genated in accordance with well known hydrogenation practice, as by heating in the presence of hydrogen under pressure, and with or without a hydrogenation catalyst.
- a resulting synthetic oil of high viscosity index which may be in excess of 100, is thereby obtained.
- This oil itself is useful as a lubricating oil. Or, it may be blended with a petroleum lubricating oil in controlled proportions, to thereby increase the viscosity index of the petroleumlubricating oil.
- proportions of from about 1% to 25% of the hydrogenated synthetic oil may be added to r a naphthene base or paramn base petroleum lubricating ofl to materially increase the viscosity index of the latter.
- proportions of the blend may vary widely, and higher proportions of the synthetic oil up to about or more may be employed. But for economical reasons the lower percentages range mentioned is preferred. so
- a satisfactory product may also be prepared from the lower sludge layer.
- a satisfactory product may also be prepared from the lower sludge layer.
- thetic lubricating oil of high viscosity index and other desirable properties which comprises condensing about five parts by weight of ethylene chloride with about eight parts by weight of benzene in the presence of a Friedel-Craft catalyst of the character of anhydrous aluminum chloride to produce an oily condensation product, separating the oily condensation product from sludge and removing lower boiling constituents therefrom to obtain a synthetic oil within the lubricating oil: boiling range having a viscosity index of about 80 or above, and then hydrogenating the obtained oily productqwithin the lubricating oil boiling range to produce a synthetic lubricating oil having a viscosity index in excess of 100.
- the method in the manufacture of a synthetic lubricating oil of highviscosity indexand other desirable properties which comprises condensing about five parts of ethylene chloride with abouteight parts of benzene in the presence of a Friedel-Craft catalyst of the character of anhydrous aluminum chloride. to produce an oily condensation product, allowing the condensation product to stand to stratify into an upper oily layer and a lower sludge layer, separating the layers, recovering a viscous oil within the lubrieating oil boiling range from the lower sludge layer having a viscosity index in excess of about 100, and then hydrogenating the recovered viscous oil to produce a synthetic lubricating oil having a viscosity. index substantially in excess of 100.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
Patented Dec. 27, 1938 UNITED STATES LUBRICATING on.
Louis a Clarke, Fishkill, and Charles 0. Towno, Poughkeepsie,,N. Y., assignors' to The Texas Company, New York, N. Y., a corporation of llelaware No Drawing.- Application August 27, 1934,- S erial No. 741,724
3 Claims.
This invention relates to the manufacture of synthetic lubricating oils, and particularly to synthetic lubricating oils of improved character having an increased viscosity index, and to syn- 5 thetic oils applicable for blending with mineral lubricating oils to improve the character thereof. In the production of high grade lubricating oils, it is well known that a relatively small change in the viscosity of the oilbetween temperatures of say 100 F. and 210 -F., isidesirable. In other words, it is advantageous for the oil to have a relatively flat iscosity-temperature curve, which means that the oil has a high viscosity index as defined by Dean and Davis in their article in Chemical and Metallurgical Engineering, vol. 36, page, 618. Improvement in lubricating oils has heretofore been accomplished by refining, as by the use of selective solvents which are efiective in extracting or separating naphthenic constituents from paraflinic constituents, thereby producin a resulting raflinate of increased viscosity index.
This procedure involves expensive processing, and results in a reduced yield of finished oil.
The advantage of low pour point of a lubricating oil has long been recognized. Paraflin base and Mid-Continent lubricating oils have been subjected to dewaxing in order to reduce the pour Y point thereof. However, substantially complete removal of wax from suchoils results in a lower- 80 ing in viscosity index.
The present invention relates to the increase in viscosity index of naphthene base or paraffin base lubricating oils, which may or may not have been solvent refined as a primary step, by the ad 85 dition thereto of a material which is active to increase the viscosity index without objectionably affecting other desirable properties thereof. More particularly, the present invention relates to the production of an improved lubricating oil 40 of this type having increased viscosity index, by the addition thereto of a controlled proportion 01 a hydrogenated condensation product of an alkyl halide with an aromatic hydrocarbon. The invention also contemplates the preparation of synt6 thetic lubricating oils by hydrogenation of the condensation-product of an alkyl halide with an (or. av -9) the lower or normally gaseous oieflnes are particularly effective in this-reaction.
Of the aromatic hydrocarbons, benzene and its homologues, such for example as toluene, mesitylene, tertiary butylv benzene, tertiary amyl ben- 5 zene, normal butyl benzene, secondary butyl benzene, and the "like may be employed. Likewise, halogenated derivatives of benzene and its hom-' ologues, such as chlorbenzene," are satisfactory.
The condensation is eflected in the presence of 10 a catalyst of the Friedel-Craft type, such as anhydrous halides of aluminum, iron, boron, manganese, nickel, zinc, antimony, cadmium, tin-"and the like. Very satisfactory resultsare secured with anhydrous aluminum chloride. With proper .15
control of the proportions of the ingredients and the condensation reaction, a viscous synthetic lubricating oil may be produced. The condensation product may be allowed to stand and stratify into an upper oily layer and a lower sludge layer, 20
which are then separated by decantation. The. upper oily layer, is preferably distilled to remove lower boiling liquids including unreacted chemicals, to obtain as a residue a viscous synthetic oil of lubricating character. This oil is then hydro- 25 genated in accordance with well known hydrogenation practice, as by heating in the presence of hydrogen under pressure, and with or without a hydrogenation catalyst. A resulting synthetic oil of high viscosity index, which may be in excess of 100, is thereby obtained. .This oil itself is useful as a lubricating oil. Or, it may be blended with a petroleum lubricating oil in controlled proportions, to thereby increase the viscosity index of the petroleumlubricating oil. For example, proportions of from about 1% to 25% of the hydrogenated synthetic oil may be added to r a naphthene base or paramn base petroleum lubricating ofl to materially increase the viscosity index of the latter. However, the proportions of the blend may vary widely, and higher proportions of the synthetic oil up to about or more may be employed. But for economical reasons the lower percentages range mentioned is preferred. so
As a specific example or the present invention, the following is given:
1000 g. ethylene chloride 'were mixed with 1580 gxof benzene in the presence of 125 g. of anhydrous aluminum chloride. The mix was 50 warmed gently with agitation to about 36 C.,
when reaction set in which continued without further application of heat until a temperature of 45 C. was attained. Further heating ofv the mix to 0. caused additional reaction to set 66 The oil also had a high specific gravity of 1.03
and a low pour test of 25 F. When this oil is subjected to hydrogenation, by passing through a heating coil with hydrogen gas at a temperature'of around 600 F. and under a pressure of approximately 3000 lbs. per square inch, and
passed over a hydrogenation catalyst such as nickel, a further reaction occurs with the production of a more saturated oil of lubricating character having a still higher viscosity index, generally in excess of 100, and lower Conradson carbon. When the resulting hydrogenated oil is blended with a naphthene base oil, asin the proportion of about 25%, an increase in viscosity index of the order of about 30 -50 points is effected. Similarly, a blend of about 25% of this synthetic oil with a paraflln base petroleum lubricating oil results in an increase in viscosity index of the latter of about 2040 points.
A satisfactory product may also be prepared from the lower sludge layer. For example, a
green oil having a viscosity index in excess of 100 was obtained from the sludge layer in the example mentioned above. This oil had a specific gravity of 1.04, a Saybolt viscosity at 100 F. of
403 and at 210 F. of 60, and a pour test of 20 F. When this oil is subjected to hydrogenation in the manner specified above, a still higher viscosity index lubricatingoil is obtained which is very satisfactory for blending with a petroleum lubricating oil in the manner described above.
Obviously many modifications and variations of the invention, as hereinbefore set forth, may
thetic lubricating oil of high viscosity index and other desirable properties, which comprises condensing about five parts by weight of ethylene chloride with about eight parts by weight of benzene in the presence of a Friedel-Craft catalyst of the character of anhydrous aluminum chloride to produce an oily condensation product, separating the oily condensation product from sludge and removing lower boiling constituents therefrom to obtain a synthetic oil within the lubricating oil: boiling range having a viscosity index of about 80 or above, and then hydrogenating the obtained oily productqwithin the lubricating oil boiling range to produce a synthetic lubricating oil having a viscosity index in excess of 100.
2. The method in the manufacture of a. synthetic lubricating oil of high viscosity index and other desirable properties, which comprises condensing about five parts by weight of ethylene chloride with about eight parts by weight of benzene in the presence of a Friedel-Craft catalyst of the type of anhydrous aluminum chloride to produce an oily condensation product, allowing the, condensation product to stand to-stratify into an 'upper oily layer :and a lower sludge layer, separating the layers, removing lower boiling liquids from the upper layer to obtain a residue of a viscous oil within the lubricating oil boiling range having a viscosity index 9f about 80 or over, and then hydrogenating the 'viscous oil so obtained to produce a ,synthetic lubricating oil having a viscosity index of over 100.
3. The method in the manufacture of a synthetic lubricating oil of highviscosity indexand other desirable properties, which comprises condensing about five parts of ethylene chloride with abouteight parts of benzene in the presence of a Friedel-Craft catalyst of the character of anhydrous aluminum chloride. to produce an oily condensation product, allowing the condensation product to stand to stratify into an upper oily layer and a lower sludge layer, separating the layers, recovering a viscous oil within the lubrieating oil boiling range from the lower sludge layer having a viscosity index in excess of about 100, and then hydrogenating the recovered viscous oil to produce a synthetic lubricating oil having a viscosity. index substantially in excess of 100.
LOUIS A. CLARKE. CHARLES C. TOWNE.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US741724A US2141593A (en) | 1934-08-27 | 1934-08-27 | Lubricating oil |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US741724A US2141593A (en) | 1934-08-27 | 1934-08-27 | Lubricating oil |
Publications (1)
Publication Number | Publication Date |
---|---|
US2141593A true US2141593A (en) | 1938-12-27 |
Family
ID=24981904
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US741724A Expired - Lifetime US2141593A (en) | 1934-08-27 | 1934-08-27 | Lubricating oil |
Country Status (1)
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2425747A (en) * | 1940-07-06 | 1947-08-19 | Standard Oil Dev Co | Lubricating oil composition |
US2439729A (en) * | 1942-03-10 | 1948-04-13 | Melle Usines Sa | Oil for industrial purposes and manufacture thereof |
US2502390A (en) * | 1945-03-02 | 1950-03-28 | Socony Vacuum Oil Co Inc | Wax-substituted polyalkylthiophene |
US2518529A (en) * | 1947-09-12 | 1950-08-15 | Standard Francaise Petroles | Process for producing synthetic lubricants |
US2570407A (en) * | 1948-01-05 | 1951-10-09 | Phillips Petroleum Co | Reactions involving the use of hydrogen halides |
US2879223A (en) * | 1955-09-21 | 1959-03-24 | Texas Co | Method for producing a lubricating oil |
US2912383A (en) * | 1956-06-01 | 1959-11-10 | Sun Oil Co | Compression refrigeration working fluid |
US3114781A (en) * | 1958-12-23 | 1963-12-17 | Ici Ltd | Alkylation of aromatic compounds |
US3169928A (en) * | 1959-02-24 | 1965-02-16 | Herold Bernd | Compression refrigeration working fluid |
US3173965A (en) * | 1961-06-28 | 1965-03-16 | Exxon Research Engineering Co | Aromatic lubricants and their method of preparation |
-
1934
- 1934-08-27 US US741724A patent/US2141593A/en not_active Expired - Lifetime
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2425747A (en) * | 1940-07-06 | 1947-08-19 | Standard Oil Dev Co | Lubricating oil composition |
US2439729A (en) * | 1942-03-10 | 1948-04-13 | Melle Usines Sa | Oil for industrial purposes and manufacture thereof |
US2502390A (en) * | 1945-03-02 | 1950-03-28 | Socony Vacuum Oil Co Inc | Wax-substituted polyalkylthiophene |
US2518529A (en) * | 1947-09-12 | 1950-08-15 | Standard Francaise Petroles | Process for producing synthetic lubricants |
US2570407A (en) * | 1948-01-05 | 1951-10-09 | Phillips Petroleum Co | Reactions involving the use of hydrogen halides |
US2879223A (en) * | 1955-09-21 | 1959-03-24 | Texas Co | Method for producing a lubricating oil |
US2912383A (en) * | 1956-06-01 | 1959-11-10 | Sun Oil Co | Compression refrigeration working fluid |
US3114781A (en) * | 1958-12-23 | 1963-12-17 | Ici Ltd | Alkylation of aromatic compounds |
US3169928A (en) * | 1959-02-24 | 1965-02-16 | Herold Bernd | Compression refrigeration working fluid |
US3173965A (en) * | 1961-06-28 | 1965-03-16 | Exxon Research Engineering Co | Aromatic lubricants and their method of preparation |
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