GB700303A - Improvements in or relating to the preparation of hydrocarbon lubricating oil antioxidants and anticorrosion agents and to hydrocarbon lubricating oil compositions containing the same - Google Patents
Improvements in or relating to the preparation of hydrocarbon lubricating oil antioxidants and anticorrosion agents and to hydrocarbon lubricating oil compositions containing the sameInfo
- Publication number
- GB700303A GB700303A GB30225/50A GB3022550A GB700303A GB 700303 A GB700303 A GB 700303A GB 30225/50 A GB30225/50 A GB 30225/50A GB 3022550 A GB3022550 A GB 3022550A GB 700303 A GB700303 A GB 700303A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lubricating oil
- sulphur
- per cent
- pinene
- concentrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/04—Reaction products of phosphorus sulfur compounds with hydrocarbons
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
-
- 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
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- 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
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- 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
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
-
- 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
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
-
- 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
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing 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
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Abstract
A hydrocarbon lubricating oil antioxidant and anti-corrosion agent is obtained by effecting simultaneous reaction at elevated temperature of a bicyclic terpene, phosphorus pentasulphide, and sulphur, the reactants being employed in the proportion of at least about 4 mols. of the bicyclic terpene and from about 0.5 to about 3 mols. of sulphur for each mol. of phosphorus pentasulphide. Specified bicyclic terpenes are alpha pinene, beta-pinene, camphene, bornylene, a -fenchene, thujene, sabinene and D 3-carene. Commercial grades of turpentine may also be used. A small excess of terpene may be employed, e.g. 6 mols. of terpene per mol. of phosphorus pentasulphide, so as to provide sufficient liquid vehicle to permit easy handling of the reaction product. Any common inert organic solvent can also be used as the liquid vehicle. The reaction temperature should preferably be below 160 DEG C. and is generally from 80 DEG to 90 DEG C. but when reflux equipment is used superatmospheric pressure and more elevated temperatures may be employed. In examples: (1) 0.5 mol. of P2S5 and 1 mol. of sulphur are added to 3 mols. of alpha-pinene and the mixture heated, a SAE 10 grade hydrocarbon lubricating oil and a diatomaceous earth filter aid are then added and the excess terpene stripped off, the oil concentrate is then filtered and an additional amount of the hydrocarbon lubricating oil added to yield a 50 per cent. concentrate of the product in oil; (2) as in (1) except that 0.25 mol. of sulphur is employed, the reaction product being diluted with light grade refined mineral lubricating oil to form a 50 per cent. concentrate; (3) as in (1) using 1.5 mol. of sulphur the reaction product being diluted with hydrocarbon lubricating oil to form a 50 per cent. concentrate; (4) alphapinene, P2S5 and sulphur are reacted as in (1) using various molar proportions of the reactants within the specified range and the products treated as in (1) to yield a 50 per cent. concentrate in lubricating oil; (5) camphene, P2S5 and sulphur are reacted and the product prepared as a 50 per cent. concentrate in oil as in (1); (6) beta-pinene, P2S5 and sulphur are reacted and a 50 per cent. concentrate in oil formed as in (1); (7) steam-distilled turpentine is reacted with P2S5 and sulphur and a 50 per cent. concentrate of the product in oil formed as in (1).ALSO:A hydrocarbon lubricating oil composition comprises a hydrocarbon lubricating oil having dissolved therein a minor proportion by weight of an antioxidant and anticorrosive agent obtained by simultaneously reacting at elevated temperature a bicyclic terpene, phosphorus pentasulphide and sulphur, the reactants being employed in the proportion of at least about 4 mols of the bicyclic terpene and from about 0.5 to about 3 mols of sulphur for each mol of phosphorus pentasulphide (see Group IV (b)). Specified terpenes are alpha-pinene, beta-pinene, camphene, bornylene, a -fenchene, thujene, sabinene and D 3-carene. Commercial grades of turpentine may also be used. A small excess of terpene may be employed, e.g. 6 mols of terpene per mol of phosphorus pentasulphide, so as to provide sufficient liquid vehicle to permit easy handling of the reaction product. Any common organic solvent can also be used as the liquid vehicle. Ordinarily about 0.5 per cent. to 1.25 per cent. of the additive, by weight, is added to the lubricating oil. The additive may be used alone or in conjunction with other hydrocarbon lubricating oil antioxidants or detergents, e.g. the antioxidants comprising the metal salts of esters of dithiophosphoric acids such as barium dioctyl dithiophosphate, zinc dihexyl dithiophosphate and barium didodecyl dithiophosphate. Suitable detergents include the metal salts of petroleum sulphonic acids such as calcium petroleum sulphonate, alkylated aromatic sulphonates such as calcium or barium dodecyl phenyl sulphonate, and metal salts of phenol sulphides and disulphides such as calcium, barium and zinc salts of dioctyl phenol sulphide, diamyl phenol sulphide, and barium and calcium meta-, ortho-, and paraoctyl phenol sulphides. In examples the antioxidant properties of a product obtained by reacting alpha-pinene, P2 S5 and sulphur are demonstrated by submitting a Mid-Continent base lubricating oil of SAE 30 grade containing 0.4 per cent. by weight of the product with or without 0.04 per cent. of iron naphthenate to the Underwood corrosion test using cadmium-silver alloy bearings as test material. Samples obtained by incorporating amounts of 0.75 per cent. to 1.0 per cent. by weight of additives, obtained by reacting alpha-pinene with various proportions of P2 S5 and sulphur within the specified range, in a Mid-Continent base lubricating oil of SAE grade 30, are also subjected to actual operating conditions in a Chevrolet automobile engine for a continuous run of 36 hours and results showing the bearing corrosion, viscosity increase and Neutralization Number are tabulated, a detergent consisting of a barium salt of an alkylated phenol sulphide being included in some of the samples tested. Bearing corrosion tests for a Mid-Continent base SAE 30 grade lubricating oil containing products obtained by reacting camphene, beta-pinene and steam-distilled turpentine respectively with P2S5 and sulphur are also described.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US132995A US2689846A (en) | 1949-12-14 | 1949-12-14 | Terpene-phosphorous pentasulfidesulfur lubricating oil additive |
Publications (1)
Publication Number | Publication Date |
---|---|
GB700303A true GB700303A (en) | 1953-11-25 |
Family
ID=22456543
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB30225/50A Expired GB700303A (en) | 1949-12-14 | 1950-12-11 | Improvements in or relating to the preparation of hydrocarbon lubricating oil antioxidants and anticorrosion agents and to hydrocarbon lubricating oil compositions containing the same |
Country Status (2)
Country | Link |
---|---|
US (1) | US2689846A (en) |
GB (1) | GB700303A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2798045A (en) * | 1954-09-27 | 1957-07-02 | Shell Dev | Lubricating compositions |
US3850822A (en) * | 1972-07-14 | 1974-11-26 | Exxon Research Engineering Co | Ashless oil additive combination composed of a nitrogen-containing ashless dispersant phosphosulfurized olefin and phosphorothionyl disulfide |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2316087A (en) * | 1941-06-26 | 1943-04-06 | Standard Oil Co | Lubricant |
US2486188A (en) * | 1943-07-14 | 1949-10-25 | Sinclair Refining Co | Lubricant |
US2379453A (en) * | 1944-06-01 | 1945-07-03 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2455668A (en) * | 1945-05-03 | 1948-12-07 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2413648A (en) * | 1945-06-28 | 1946-12-31 | Hercules Powder Co Ltd | Terpene reaction product and method of producing |
US2580430A (en) * | 1946-08-24 | 1952-01-01 | Standard Oil Co | Catalyzed sulfide-hydrocarbon reaction products and method of making same |
US2515222A (en) * | 1947-07-18 | 1950-07-18 | Sinclair Refining Co | Sulfurized condensate of alphapinene and phosphorus pentasulfide |
US2571737A (en) * | 1949-08-18 | 1951-10-16 | Pure Oil Co | Method of sulfurizing terpene hydrocarbons |
-
1949
- 1949-12-14 US US132995A patent/US2689846A/en not_active Expired - Lifetime
-
1950
- 1950-12-11 GB GB30225/50A patent/GB700303A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US2689846A (en) | 1954-09-21 |
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