US2419153A - Lubricant and the like - Google Patents
Lubricant and the like Download PDFInfo
- Publication number
- US2419153A US2419153A US482491A US48249143A US2419153A US 2419153 A US2419153 A US 2419153A US 482491 A US482491 A US 482491A US 48249143 A US48249143 A US 48249143A US 2419153 A US2419153 A US 2419153A
- Authority
- US
- United States
- Prior art keywords
- phosphorus
- boiling point
- product
- reaction
- reaction products
- Prior art date
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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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
-
- 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
Definitions
- This invention relates to lubricants, and more particularly lubricants which are subject to severe usage conditions and in high temperature; and it is among the objects of the invention to provide lubricants having greater stability and resistance against change and having greater film strength than characteristic of usual petroleum lubricants.
- the organic oxygen-containing compound employed is desirably of rather high molecular weight, and preferably of at least 300 F. boiling point, and involves esters, components thereof, ketones, and amino or halogen derivatives of these, -The esters are alkyl or cycloparafiin or aryl esters, of the organic acids.
- Illustrative of some conveniently applicable materials are: octyl laurate, butyl stearate, ethyl lactate, methyl oleate, butyl ricinoleate, dibutyl phthalate, methyl stearate, methyl dichlorostearate, methyl chloronaphthalenate, diohloropalmltic acid, sperm oil, degras, beeswax, lanolin,
- cocoanut oil other fatty oils
- reaction sets in at rather low temperatures, and a product of the general range of temperature, as for instance 340 to around 400 F., or at least such as to involve the,
- a. final excess of phosphorus pentasui-- phide may be easily eliminated by filtering on. For example thus, 300 parts of dichlorostearic acid may be reacted with 110 parts of phosphorus pentasulphide for minutes.
- tion product as foregoing may be further reacted, or at least partially neutralized, with a base, which may be an amine, ammonia or oxides or hydroxides of metals, for example aluminum, lead, tin, calcium, barium, sodium, po tassium, etc. This reaction occurs readily at temperatures in the range of F. to 200 F.
- a base which may be an amine, ammonia or oxides or hydroxides of metals, for example aluminum, lead, tin, calcium, barium, sodium, po tassium, etc. This reaction occurs readily at temperatures in the range of F. to 200 F.
- reaction products may be employed as such in certain usages, as for instance gear lubrication, or they may be incorporated in an oil of lubricating viscosity, asfor instance in oils ,of 40 to 3000, viscosity Saybolt Universal at F.,
- a lubricant comprising the product of reaction of an unpolymerized organic oxygen-containing compound forming oil-soluble metal phosphorus sulfide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation. and in turn converted into a barium phosphorus sulphide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide at a temperature above action of an unpolymerized organic oxygen-containing compound forming oil-soluble metal phosphorus sulphide reaction products and having aboiling point not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation, and in turn converted into a metal compound.
- a lubricant comprising the product of reaction of an unpolymerized organic oxygen-containing compound forming oil-soluble .metal phosphorus sulphide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide and converted in turn to a metal compound.
- a lubricant comprising the product of reaction of. an unpolymerized aliphatic oxygencontaining compound forming oil-soluble phosphorus sulphide reaction products having a boiling point of not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation.
- a lubricant comprising the product of reaction of an unpolymerized aliphatic oxygen-containing compound forming oil-soluble phosphorus sulphide reaction products having a boiling point of not less than 300 F. with phosphorus pentasulphide at a, temperature above phosphate formation and in calculated proportions to form a phosphorus-containing sludge separable from said reaction product.
- Jomr ivr. I IVIUSSELMAN. HERMAN P. LANKELMA.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
. Patented Apr. 15, 1947 LUBRICANT AND THE LIKE John M, Musselman, South Euclid, and Herman r. Lankelma, Shaker Heights, Ohio, assignorl to The Standard Oil Company, Cleveland, Ohio, a corporation of Ohio I No Drawing. Application April 9,-1943,
Serial No. 482,491 r 14 Claims.
This invention relates to lubricants, and more particularly lubricants which are subject to severe usage conditions and in high temperature; and it is among the objects of the invention to provide lubricants having greater stability and resistance against change and having greater film strength than characteristic of usual petroleum lubricants. I
To the accomplishment of the foregoing and related ends, the invention, then, comprises the features hereinafter fully described, and particularly pointed out in the claims, the following description setting forth in detail certain illustrative embodiments of the invention, these being indicative however, of but a. few of the various ways in which the principle of the invention may be employed. a
We have found that by reacting phosphorus pentasulphide with an organic oxygen-containing compound, products result which have peculiar utilities. The organic oxygen-containing compound employed is desirably of rather high molecular weight, and preferably of at least 300 F. boiling point, and involves esters, components thereof, ketones, and amino or halogen derivatives of these, -The esters are alkyl or cycloparafiin or aryl esters, of the organic acids. Illustrative of some conveniently applicable materials are: octyl laurate, butyl stearate, ethyl lactate, methyl oleate, butyl ricinoleate, dibutyl phthalate, methyl stearate, methyl dichlorostearate, methyl chloronaphthalenate, diohloropalmltic acid, sperm oil, degras, beeswax, lanolin,
. and other waxes, cocoanut oil, other fatty oils,
ethylene glycol mono ethers, diglycol chlorohydrin, isophorone, stearic acid, oleic acid, pahnitic acid, myristic acid, naphthalic. acid, benzoic acid, naphthoic acids, naphthenic acids, hydroxy stearate acids, dihydroxy benzoic acids, hydroxy naphthenic acids, dihydroxy stearic acids, chloro benzoic acids, dichloro stearic acids, oxidized petroleum fatty acids, lactones, oxidized oil, dichloro benzoic acid, dichloro dihydroxy stearic acid, etc.
On heating the organic compound and the phosphorus sulphide a reaction sets in at rather low temperatures, and a product of the general range of temperature, as for instance 340 to around 400 F., or at least such as to involve the,
type of reaction above phosphate formation, and
resulting in compounds in which higher'percentages of sulphur are combined, and usually not Usually ,a reaction time of a halfto an hour orsom'ewhat more is suflicient. The materials may be taken in calculated or molecular proportions,
however, a. final excess of phosphorus pentasui-- phide may be easily eliminated by filtering on. For example thus, 300 parts of dichlorostearic acid may be reacted with 110 parts of phosphorus pentasulphide for minutes.
With particular further advantage, tion product as foregoing, may be further reacted, or at least partially neutralized, with a base, which may be an amine, ammonia or oxides or hydroxides of metals, for example aluminum, lead, tin, calcium, barium, sodium, po tassium, etc. This reaction occurs readily at temperatures in the range of F. to 200 F.
- The reaction products may be employed as such in certain usages, as for instance gear lubrication, or they may be incorporated in an oil of lubricating viscosity, asfor instance in oils ,of 40 to 3000, viscosity Saybolt Universal at F.,
and the amounts may be for instance 0.0540 per cent.
This application is a continuation, in part, and as to common subject matter, of our appli-v cation Serial No. 397,178, filed September 29, 1939, now issued as Patent No. 2,361,957 of November 7, 1944.
Other modes of applying the principle of the invention maybe employed, change being made as regards the-details described, provided the features stated in anyof the following claims, or the equivalent of such, be employed.
We therefore particularly point out and distinctly claim as our invention: 1
1. In a process of preparing lubricants, reacting an unpo'lymerized organic oxygen-containing compound forming oil-soluble metal phosphorus sulfide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation, and converting the product into a. barium compound. 7
2. In a, process of preparing lubricants, reacting an unpolymerized organic oxy en-containing compound forming oil-soluble metal phosphorus sulfide reaction products and having a boiling point not less than 300 F. with phosphorus the reacpentasuiphide at a temperature above phosphate formation, and converting the product, into a calcium compound. v
3. In a process of preparing lubricants, reacting an unpolymerized organic oxygen-containing compound forming oil-soluble metal phosphorus sulfide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation, and converting the product into an aluminum compound.
4. In a process of preparing lubricants, reacting an unpolymerized organic oxygen-containing compound forming oil-soluble metal phosphorus sulfide reaction products and having a boiling point vnot less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation, and converting the product into a metal compound.
5. In a process of preparing, lubricants, reacting an unpolymerized organic oxygen-containing compound forming oil-soluble metal phosphorus sulfide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide, and converting the product into a metal compound.
6. In a process of preparing lubricants, reacting an unpolymerized aliphatic oxygen-containin compound forming oil-soluble phosphorus sulphide reaction products and having a boiling point of not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation.
7. In a process of preparing lubricants, mixing an unpolymerized aliphatic oxygen-containin compound forming oil-soluble phosphorus sulphide reaction products and having a boiling point of not less than 300 F. with phosphorus pentasulphide. and reacting said compound with said sulphide at a temperature above phosphate formation, said compound and said sulphide being mixed in calculated proportions to form a reaction product and a phosphorus-containing sludge at said reaction temperature, and separating the reaction product from the sludge.
8. A lubricant comprising the product of reaction of an unpolymerized organic oxygen-containing compound forming oil-soluble metal phosphorus sulfide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation. and in turn converted into a barium phosphorus sulphide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide at a temperature above action of an unpolymerized organic oxygen-containing compound forming oil-soluble metal phosphorus sulphide reaction products and having aboiling point not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation, and in turn converted into a metal compound.
12. A lubricant comprising the product of reaction of an unpolymerized organic oxygen-containing compound forming oil-soluble .metal phosphorus sulphide reaction products and having a boiling point not less than 300 F. with phosphorus pentasulphide and converted in turn to a metal compound.
13. A lubricant comprising the product of reaction of. an unpolymerized aliphatic oxygencontaining compound forming oil-soluble phosphorus sulphide reaction products having a boiling point of not less than 300 F. with phosphorus pentasulphide at a temperature above phosphate formation.
14. A lubricant comprising the product of reaction of an unpolymerized aliphatic oxygen-containing compound forming oil-soluble phosphorus sulphide reaction products having a boiling point of not less than 300 F. with phosphorus pentasulphide at a, temperature above phosphate formation and in calculated proportions to form a phosphorus-containing sludge separable from said reaction product.
Jomr" ivr. I IVIUSSELMAN. HERMAN P. LANKELMA.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,316,085, Kelso et al Apr. 6, 1943 2,242,260 Prutton May 20, 1941 2,142,998 Chittick Jan. 10, 1939 2,167,867 Benning Aug. 1, 1939 2,331,923 Musselman Oct. 19, 1943 2,252,985 Rutherford et al. Aug. 19, 1941 2,252,984 Rutherford et al. Aug. 19, 1941 2,169,634 Cantrell et a1 Aug. 15, 1939
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US482491A US2419153A (en) | 1943-04-09 | 1943-04-09 | Lubricant and the like |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US482491A US2419153A (en) | 1943-04-09 | 1943-04-09 | Lubricant and the like |
Publications (1)
Publication Number | Publication Date |
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US2419153A true US2419153A (en) | 1947-04-15 |
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US482491A Expired - Lifetime US2419153A (en) | 1943-04-09 | 1943-04-09 | Lubricant and the like |
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Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2459090A (en) * | 1945-07-25 | 1949-01-11 | Socony Vacuum Oil Co Inc | Products obtained by reacting phosphorus pentasulfide with sulfurized ketones |
US2482762A (en) * | 1947-02-04 | 1949-09-27 | Shell Dev | Lubricating compositions |
US2489249A (en) * | 1947-03-31 | 1949-11-29 | Shell Dev | Lubricant |
US2502408A (en) * | 1947-10-24 | 1950-04-04 | Shell Dev | Lubricating composition |
US2506572A (en) * | 1946-04-19 | 1950-05-09 | Standard Oil Co | Lubricant composition |
US2511630A (en) * | 1947-02-04 | 1950-06-13 | Shell Dev | Liquid hydrocarbon lubricant, an additive therefor, and a process of making the additive |
US2542982A (en) * | 1946-07-03 | 1951-02-27 | Standard Oil Co | Unsaturated amine-sulfur reaction products as lubricant additives and lubricating oils containing same |
US2553587A (en) * | 1946-07-11 | 1951-05-22 | Standard Oil Co | Preparation of metallic derivatives of the reaction products of phosphorus sulfide and esters or amines by the use of metal carbides |
US2553586A (en) * | 1946-07-11 | 1951-05-22 | Standard Oil Co | Preparation of metallic derivatives of the reaction products of phosphorus sulfide and esters or amines by the use of metal cyanamides |
US2553588A (en) * | 1946-08-27 | 1951-05-22 | Standard Oil Co | Mineral oil lubricant containing alkyl ketone-p2s5 reaction product |
US3097170A (en) * | 1962-07-05 | 1963-07-09 | Sinclair Research Inc | Phosphosulfurized material and extreme pressure lubricant containing the same |
US3501413A (en) * | 1968-03-06 | 1970-03-17 | Sinclair Research Inc | Phosphosulfurized partial ester-partial metal salts of unsaturated dicarboxylic aliphatic acids and lubricating oils containing the partial ester-partial salts |
US3573401A (en) * | 1968-02-21 | 1971-04-06 | Electro Voice | Microphone stand |
US3957745A (en) * | 1974-07-25 | 1976-05-18 | Universal Oil Products Company | Flavoring and fragrance compositions |
US4028259A (en) * | 1975-05-29 | 1977-06-07 | Mobil Oil Corporation | Process for preparing a metal salt of an oxidized, phosphosulfurized hydrocarbon and lubricant compositions containing same |
US4069163A (en) * | 1976-06-30 | 1978-01-17 | The United States Of America As Represented By The Secretary Of Agriculture | Lubricant composition |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2142998A (en) * | 1934-08-24 | 1939-01-10 | Pure Oil Co | Extreme pressure lubricants and method of preparing same |
US2167867A (en) * | 1936-05-07 | 1939-08-01 | Du Pont | Lubricant |
US2169634A (en) * | 1936-09-17 | 1939-08-15 | Gulf Oil Corp | Lubricating oil compositions, inhibitors therefor, and methods of manufacturing the same |
US2242260A (en) * | 1937-01-22 | 1941-05-20 | Lubri Zol Dev Corp | Lubricating composition |
US2252985A (en) * | 1939-05-06 | 1941-08-19 | Standard Oil Co | Compounded oil |
US2252984A (en) * | 1939-05-06 | 1941-08-19 | Standard Oil Co | Compounded hydrocarbon oil |
US2316085A (en) * | 1941-03-24 | 1943-04-06 | Standard Oil Co | Lubricant |
US2331923A (en) * | 1941-01-30 | 1943-10-19 | Standard Oil Co | Preparation of compounds for lubricants, etc. |
-
1943
- 1943-04-09 US US482491A patent/US2419153A/en not_active Expired - Lifetime
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2142998A (en) * | 1934-08-24 | 1939-01-10 | Pure Oil Co | Extreme pressure lubricants and method of preparing same |
US2167867A (en) * | 1936-05-07 | 1939-08-01 | Du Pont | Lubricant |
US2169634A (en) * | 1936-09-17 | 1939-08-15 | Gulf Oil Corp | Lubricating oil compositions, inhibitors therefor, and methods of manufacturing the same |
US2242260A (en) * | 1937-01-22 | 1941-05-20 | Lubri Zol Dev Corp | Lubricating composition |
US2252985A (en) * | 1939-05-06 | 1941-08-19 | Standard Oil Co | Compounded oil |
US2252984A (en) * | 1939-05-06 | 1941-08-19 | Standard Oil Co | Compounded hydrocarbon oil |
US2331923A (en) * | 1941-01-30 | 1943-10-19 | Standard Oil Co | Preparation of compounds for lubricants, etc. |
US2316085A (en) * | 1941-03-24 | 1943-04-06 | Standard Oil Co | Lubricant |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2459090A (en) * | 1945-07-25 | 1949-01-11 | Socony Vacuum Oil Co Inc | Products obtained by reacting phosphorus pentasulfide with sulfurized ketones |
US2506572A (en) * | 1946-04-19 | 1950-05-09 | Standard Oil Co | Lubricant composition |
US2542982A (en) * | 1946-07-03 | 1951-02-27 | Standard Oil Co | Unsaturated amine-sulfur reaction products as lubricant additives and lubricating oils containing same |
US2553586A (en) * | 1946-07-11 | 1951-05-22 | Standard Oil Co | Preparation of metallic derivatives of the reaction products of phosphorus sulfide and esters or amines by the use of metal cyanamides |
US2553587A (en) * | 1946-07-11 | 1951-05-22 | Standard Oil Co | Preparation of metallic derivatives of the reaction products of phosphorus sulfide and esters or amines by the use of metal carbides |
US2553588A (en) * | 1946-08-27 | 1951-05-22 | Standard Oil Co | Mineral oil lubricant containing alkyl ketone-p2s5 reaction product |
US2511630A (en) * | 1947-02-04 | 1950-06-13 | Shell Dev | Liquid hydrocarbon lubricant, an additive therefor, and a process of making the additive |
US2482762A (en) * | 1947-02-04 | 1949-09-27 | Shell Dev | Lubricating compositions |
US2489249A (en) * | 1947-03-31 | 1949-11-29 | Shell Dev | Lubricant |
US2502408A (en) * | 1947-10-24 | 1950-04-04 | Shell Dev | Lubricating composition |
US3097170A (en) * | 1962-07-05 | 1963-07-09 | Sinclair Research Inc | Phosphosulfurized material and extreme pressure lubricant containing the same |
US3573401A (en) * | 1968-02-21 | 1971-04-06 | Electro Voice | Microphone stand |
US3501413A (en) * | 1968-03-06 | 1970-03-17 | Sinclair Research Inc | Phosphosulfurized partial ester-partial metal salts of unsaturated dicarboxylic aliphatic acids and lubricating oils containing the partial ester-partial salts |
US3957745A (en) * | 1974-07-25 | 1976-05-18 | Universal Oil Products Company | Flavoring and fragrance compositions |
US4028259A (en) * | 1975-05-29 | 1977-06-07 | Mobil Oil Corporation | Process for preparing a metal salt of an oxidized, phosphosulfurized hydrocarbon and lubricant compositions containing same |
US4069163A (en) * | 1976-06-30 | 1978-01-17 | The United States Of America As Represented By The Secretary Of Agriculture | Lubricant composition |
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