US2229528A - Stabilized hydrocarbon oil - Google Patents
Stabilized hydrocarbon oil Download PDFInfo
- Publication number
- US2229528A US2229528A US197611A US19761138A US2229528A US 2229528 A US2229528 A US 2229528A US 197611 A US197611 A US 197611A US 19761138 A US19761138 A US 19761138A US 2229528 A US2229528 A US 2229528A
- Authority
- US
- United States
- Prior art keywords
- alcoholates
- oils
- lubricating
- thio
- ring sticking
- 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
- 239000004215 Carbon black (E152) Substances 0.000 title description 2
- 229930195733 hydrocarbon Natural products 0.000 title description 2
- 150000002430 hydrocarbons Chemical class 0.000 title description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 11
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 11
- 239000003921 oil Substances 0.000 description 9
- 230000001050 lubricating effect Effects 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- 239000010688 mineral lubricating oil Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- IVSPJKRLTWBHHN-UHFFFAOYSA-N 1-sulfanyloxybutane Chemical compound CCCCOS IVSPJKRLTWBHHN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000013531 gin Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/10—Groups 5 or 15
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
-
- 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
- C10N2040/135—Steam engines or turbines
-
- 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
- This invention relates to improvements in be prepared by treating aluminum with butyl allubricating oils and, in particular, to lubricating cohol in the presence of iodine.
- the reaction oils having improved lubricity, color and sludge which takes place may be illustrated by the folstability and non-rlngsticking properties. lowing equation:
- 5 It is the primary object of this invention to 5 provide viscous mineral oils, such as lubricating l+6C4Ho0H 2Al(0C4Hs):-l-3 Oils Suitable for use in the lubrication of autolm-
- the heavy metal alcoholates or thio alcoholates t ve and Dies l e nes and turbines. whi v may also be prepared by treating the metal halide especially d lubricating P p t e a e highly with sodium alcoholate or thio alcoholate, as
- erties n be imp to ViSoOII-S mineral oils of
- the corresponding thio alcoholates may be prethe type fin d by ddin to such oils from about pared by substituting the corresponding mercap '0-001% to about 5% and prefera ly fr m about tan for the alcohol or alcoholates in the above 15 0.01% to about 1% of the heavy metal alcoholates equations.
- Lubrlcating oils containing small amounts of holates or thio alcoholates have the general the heavy metal alcoholates or thio alcoholates formula M(XR)d in which M is a heavy metal, X are particularly well adapted for use in lubricatis an element selected from the group consisting ing high speed combustion engines, especially en f xy d u R is B radical selected from gines of the Diesel type because of their property the group consisting of alkyl, aryl, aralkyl and of eliminating or materially reducing the tendy 171 c s and n p ese ts e n mber ency to ring sticking.
- Ring sticking is due to the of the effective valences of the metal M.
- the term heavy metal as used herein and in and/or oxidation which are deposited or formed the appended claims includes the elements such in the piston ring grooves. Ring sticking causes as aluminum, zinc, iron, tin, lead, antimony, etc., excessive blow-by resulting in decreased engine and excludes the light metals such as potassium.
- holates and/or thio alcoholates of the type herein A8 Specific examples of the alcoholates or thio described materially improves the efiectiveness alooholalies which may e e v y us d a e!
- the alcoholates or thio a-lcohol y be p leum products such as insulating oils, transformer pared by treating the metal with an alcohol or 11 t mercaptan using iodine or tin tetra chloride as a I lai carrier.
- aluminum butylate may 1, Th method of preventing ring sticking in 55 Diesel engines which comprises lubricating said engines with a lubricant comprising a mineral lubricating oil normally having the tendency to cause ring sticking in such engines and a heavy metal alcoholate having the general formula MQKR) in which M is a heavy metal, X is an element selected from the group consisting of oxygen and sulfur, R is a radical selected from the group consisting of alkyl, aryl, aralkyl and hydroaryl radicals and n represents the number Diesel engine which comprises lubricating said engine with a lubricant comprising a mineral lubricating oil normally having the tendency to cause ring sticking in such engine and a small amount oi aluminum lorolate in small but sufllcient quantity to substantially inhibit ring sticking.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented Jan. 21, 1941 2,229,528
v STABILIZED HYDROCABBQN OIL Bernard H. Shoemaker, Hammond, Ind., assignor toStandard Oil Company, Chicago, 11]., a corporation of Indiana No Drawing. Application March 23, 1938, Serial No. 197,611
Claims. (01. 25235) This invention relates to improvements in be prepared by treating aluminum with butyl allubricating oils and, in particular, to lubricating cohol in the presence of iodine. The reaction oils having improved lubricity, color and sludge which takes place may be illustrated by the folstability and non-rlngsticking properties. lowing equation:
5 It is the primary object of this invention to 5 provide viscous mineral oils, such as lubricating l+6C4Ho0H 2Al(0C4Hs):-l-3 Oils Suitable for use in the lubrication of autolm- The heavy metal alcoholates or thio alcoholates t ve and Dies l e nes and turbines. whi v may also be prepared by treating the metal halide especially d lubricating P p t e a e highly with sodium alcoholate or thio alcoholate, as
10 resistant to color and sludge formation and which illustrated by the equation 10 have no tendency to cause ring sticking, e
I have found that these highly desirable propzncli+ u u (0 u u):+2Na
erties n be imp to ViSoOII-S mineral oils of The corresponding thio alcoholates may be prethe type fin d by ddin to such oils from about pared by substituting the corresponding mercap '0-001% to about 5% and prefera ly fr m about tan for the alcohol or alcoholates in the above 15 0.01% to about 1% of the heavy metal alcoholates equations. and th o alooholatese e heavy metal alo Lubrlcating oils containing small amounts of holates or thio alcoholates have the general the heavy metal alcoholates or thio alcoholates formula M(XR)d in which M is a heavy metal, X are particularly well adapted for use in lubricatis an element selected from the group consisting ing high speed combustion engines, especially en f xy d u R is B radical selected from gines of the Diesel type because of their property the group consisting of alkyl, aryl, aralkyl and of eliminating or materially reducing the tendy 171 c s and n p ese ts e n mber ency to ring sticking. Ring sticking is due to the of the effective valences of the metal M. The decomposition or breakdown of the lubricants 25 yl l'floa-l i Pr f y n ntaining at least under high temperatures and pressures to form three carbon atomsinthe radical. sludge and other products of decomposition The term heavy metal as used herein and in and/or oxidation which are deposited or formed the appended claims includes the elements such in the piston ring grooves. Ring sticking causes as aluminum, zinc, iron, tin, lead, antimony, etc., excessive blow-by resulting in decreased engine and excludes the light metals such as potassium. efiiciency, excessive oil consumption and engine 30 S u um, strontium, barium wear. While the addition of heavy metal alcoand the like. holates and/or thio alcoholates of the type herein A8 Specific examples of the alcoholates or thio described materially improves the efiectiveness alooholalies which may e e v y us d a e! 'of Diesel lubricating oils derived from any petro- Aluminum butylate AMOQHQ) 3 leum base oil or synthetic lubricating oils, greater 35 Aluminum laurylate A1 (0C12H25 3 improvement is obtained when the heavy metal Aluminum cycle hexylate Al(o(Cyc1o)C6Hn) alcoholates or thio alcoholates are added to Diesel Aluminum thio butylate A1 SC4H9 3 lubricating oils derived from naphthemc base Zinc amylate zmocsnmz crude oils. These Diesel lubricating oils prefer- 40 Zinc laurylate zmocmflm 2 ably have a viscosity in the range of a S. A. E. 10 40 Zinc tyl t Zn(sC4H9)2 to a. S. A. E. and a viscosity index Of 1101'; Ferric amylate Fe(OC5Hn)3 I Over t or Lead thioamylate PMSCsHlDz In addition to preventing ring sticking the I heavy metal alcoholates and thio alcoholates 45 My invention contemp a e the use of the when added to lubricating oils prevent the deresponding i s f y of the above velopment of color forming bodies and materially pounds and mixtures of the alcoholates and/0r decrease t tendency of lubricating 11 t thio alcoholates, such as for example the lorolates crease i viscosity during use. They are effective which are a mixture of al yl alooholates having in stabilizing viscous hydrocarbon oils aginst color 30 12 to 18 carbon atoms in the alkyl chain but preand ludge formation during storage, They are dominately dodecyl and tet a decyl derivatives also-efiective oxidation inhibitors for other petro- The alcoholates or thio a-lcohol y be p leum products such as insulating oils, transformer pared by treating the metal with an alcohol or 11 t mercaptan using iodine or tin tetra chloride as a I lai carrier. For example, aluminum butylate may 1, Th method of preventing ring sticking in 55 Diesel engines which comprises lubricating said engines with a lubricant comprising a mineral lubricating oil normally having the tendency to cause ring sticking in such engines and a heavy metal alcoholate having the general formula MQKR) in which M is a heavy metal, X is an element selected from the group consisting of oxygen and sulfur, R is a radical selected from the group consisting of alkyl, aryl, aralkyl and hydroaryl radicals and n represents the number Diesel engine which comprises lubricating said engine with a lubricant comprising a mineral lubricating oil normally having the tendency to cause ring sticking in such engine and a small amount oi aluminum lorolate in small but sufllcient quantity to substantially inhibit ring sticking.
4. The method of preventing ring sticking in a Diesel engine which comprises lubricating said engine with a lubricant comprising a mineral lubricating oil normally having the tendency to cause ring sticking in such engine and a small amount of zinc octylate in small but suflicient quantity to'substantially inhibit ring sticking.
5. The method of preventing ring sticking in a Diesel engine which comprises lubricating said engine with a lubricant comprising a mineral lubricating oil normally having the tendency to cause ring sticking in such engines and a small amount of aluminum thioamylate in small but suilicient quantity to substantially inhibit ring sticking. BERNARD H. SHOEMAKER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US197611A US2229528A (en) | 1938-03-23 | 1938-03-23 | Stabilized hydrocarbon oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US197611A US2229528A (en) | 1938-03-23 | 1938-03-23 | Stabilized hydrocarbon oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2229528A true US2229528A (en) | 1941-01-21 |
Family
ID=22730070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US197611A Expired - Lifetime US2229528A (en) | 1938-03-23 | 1938-03-23 | Stabilized hydrocarbon oil |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2229528A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2461335A (en) * | 1938-12-16 | 1949-02-08 | Standard Oil Dev Co | Organometallic compound |
| US2472504A (en) * | 1939-12-30 | 1949-06-07 | Standard Oil Dev Co | Organometallic compound |
| US2493986A (en) * | 1939-12-27 | 1950-01-10 | Standard Oil Dev Co | Heavy metal salts of alkyl phenol sulfides and method of making same |
| US2493987A (en) * | 1939-12-27 | 1950-01-10 | Standard Oil Dev Co | Aluminum salts of alkylated phenol sulfides |
| US2581493A (en) * | 1945-10-01 | 1952-01-08 | Phillips Petroleum Co | Purification of mercaptans |
| US2613162A (en) * | 1952-10-07 | Coating compositions containing | ||
| DE931972C (en) * | 1951-12-23 | 1955-08-22 | Albert Ag Chem Werke | Process for the improvement of autoxidizable oils |
| US2877248A (en) * | 1952-12-18 | 1959-03-10 | Hoechst Ag | Aluminum compounds soluble in organic solvents and process of preparing them |
| US2963434A (en) * | 1957-11-05 | 1960-12-06 | Pure Oil Co | Method of preparing zing mercaptides and method of preparing a greases containing zinc mercaptides |
| US3277002A (en) * | 1961-07-17 | 1966-10-04 | Continental Oil Co | Process for stably dispersing metal compounds |
| US3487095A (en) * | 1967-12-28 | 1969-12-30 | Pennwalt Corp | Octa-mu3-halo and alkoxy hexamolybdenum(ii) alkoxides |
| US4745204A (en) * | 1986-06-05 | 1988-05-17 | International Business Machines Corporation | Process for producing aluminum alkoxide or aluminum aryloxide |
| US4751318A (en) * | 1986-05-09 | 1988-06-14 | Stauffer Chemical Company | Method of making organic solvent soluble zinc alkoxy alkoxides |
| US4835298A (en) * | 1986-09-24 | 1989-05-30 | Union Carbide Corporation | Method for producing liquid alkoxides of mixed metals |
| US4946976A (en) * | 1986-09-24 | 1990-08-07 | Union Carbide Corporation | Cordierite composition and method of production |
| US5139976A (en) * | 1986-09-24 | 1992-08-18 | Union Carbide Coatings Service Technology Corporation | Cordierite composition and method of production |
-
1938
- 1938-03-23 US US197611A patent/US2229528A/en not_active Expired - Lifetime
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2613162A (en) * | 1952-10-07 | Coating compositions containing | ||
| US2461335A (en) * | 1938-12-16 | 1949-02-08 | Standard Oil Dev Co | Organometallic compound |
| US2493986A (en) * | 1939-12-27 | 1950-01-10 | Standard Oil Dev Co | Heavy metal salts of alkyl phenol sulfides and method of making same |
| US2493987A (en) * | 1939-12-27 | 1950-01-10 | Standard Oil Dev Co | Aluminum salts of alkylated phenol sulfides |
| US2472504A (en) * | 1939-12-30 | 1949-06-07 | Standard Oil Dev Co | Organometallic compound |
| US2581493A (en) * | 1945-10-01 | 1952-01-08 | Phillips Petroleum Co | Purification of mercaptans |
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| US4946976A (en) * | 1986-09-24 | 1990-08-07 | Union Carbide Corporation | Cordierite composition and method of production |
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