US2419153A - Lubricant and the like - Google Patents

Lubricant and the like Download PDF

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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
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United States
Prior art keywords
phosphorus
boiling point
product
reaction
reaction products
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Expired - Lifetime
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US482491A
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John M Musselman
Herman P Lankelma
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Standard Oil Co
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Standard Oil Co
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04Phosphate esters
    • C10M137/10Thio derivatives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/06Groups 3 or 13
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/08Groups 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
US482491A 1943-04-09 1943-04-09 Lubricant and the like Expired - Lifetime US2419153A (en)

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Cited By (16)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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.

Patent Citations (8)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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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