GB715505A - Improvements in or relating to improved additives for hydrocarbon oils and particularly for lubricating oils and production thereof - Google Patents
Improvements in or relating to improved additives for hydrocarbon oils and particularly for lubricating oils and production thereofInfo
- Publication number
- GB715505A GB715505A GB7755/52A GB775552A GB715505A GB 715505 A GB715505 A GB 715505A GB 7755/52 A GB7755/52 A GB 7755/52A GB 775552 A GB775552 A GB 775552A GB 715505 A GB715505 A GB 715505A
- Authority
- GB
- United Kingdom
- Prior art keywords
- barium
- sulphide
- tert
- phenol
- octyl
- 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
- 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
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
- C10L1/2412—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides sulfur bond to an aromatic radical
-
- 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
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
-
- 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
- C10N2010/08—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
- C10N2010/12—Groups 6 or 16
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
A process for the purification of alkylphenol sulphides, whereby they are adapted for use as improved additives for hydrocarbon oils and particularly lubricating oils, either as such or as the corresponding metal salt derivatives, comprises treating a crude alkylphenol sulphide with a basic reacting barium compound and subsequently hydrolysing the product to form an alkyl phenol sulphide substantially free of barium. The crude alkyl phenol sulphide may be prepared, usually in a solvent, by treating an alkyl phenol preferably at above 70 DEG F., e.g. 80 DEG to 95 DEG F., with a sulphur chloride to form a product having 1 to 4 sulphur atoms interconnecting benzene nuclei. Preferably about 2 mols. of the phenol to about 1.5 to 2.0 mols. of sulphur chloride are used. Preferred phenols are those having 4 to 20 carbon atoms in at least one alkyl group. Such alkyl groups are n-butyl, tert.-butyl, tert.-amyl, n-hexyl, tert.-octyl, n-decyl, cetyl, stearyl and wax-alkyl groups. Cycloaliphatic groups may also be present. Generally at least an equivalent of 0.1 mol. and preferably 0.2 to 0.6 mol. of barium for each mol. of -OH radical in the alkyl phenol sulphide is employed, although the alkyl phenol sulphide may be completely neutralized. Treatment with the p barium compound may be effected at about 175 DEG to 300 DEG F. or higher. Specified barium compounds are barium hydroxide penta- and octahydrates, barium oxide and barium carbonate. The partial barium salt may be hydrolysed with excess concentrated mineral acid at ordinary temperatures, inorganic barium salts and excess acid being removed by waterwashing. The treating and hydrolysis steps are preferably effected with an oil solution of the phenol sulphide. The treated and hydrolysed sulphide may be converted to salts, e.g. by reaction in oil at about 175 DEG to 300 DEG F. (with removal of water) with the oxide, hydroxide, hydride, alkoxide of e.g. calcium, barium, magnesium, sodium, potassium, lithium, nickel, cobalt, tin, lead, zinc, copper, cadmium, manganese, chromium, or a mixture of such compounds (e.g. of calcium and barium). In an example: (1) p-tert.-octyl phenol (2 mols.) and sulphur dichloride (1.6 mols.) are reacted in ethylene dichloride. After removal of solvent and HCl vapour, the product, dissolved in oil, is reacted at 250 DEG F. with barium hydroxide octahydrate (0.22 mols. per mol. of -OH in the sulphide), while blowing with nitrogen to remove water. The product is treated with hydrochloric acid and washed, to remove barium. The treated phenol sulphide is converted to its calcium salt by reaction with hydrated lime in the presence of isopropyl alcohol. For comparison there are prepared other products by (D) neutralizing with lime a tert.-octyl phenol/sulphur dichloride reaction product prepared as above; (E) treatment of a tert.-octyl-phenol/sulphur monochloride reaction product prepared as above with lime (0.18 mols. per mol. of -OH radical in the sulphide) followed by removal of the calcium by hydrolysis with water. A table gives results of corrosion tests on the crude and treated p-tert.-octyl phenol sulphide in hydrocarbon oils. The products may be used in lubricating or heating oils and in diesel fuels, with or without other additives.ALSO:A process for the purification of alkylphenol sulphides whereby they are adapted for use as improved additives for hydrocarbon oils and particularly lubricating oils, either as such or as the corresponding metal salt derivatives, comprises treating a crude alkyl phenol sulphide with a basic reacting barium compound and subsequently hydrolysing the product to form an alykyl phenol sulphide substantially free of barium. The crude alkyphenol sulphide may be a product having 1 to 4 sulphur atoms connecting benzene nuclei. Preferred phenols are those having 4 to 20 carbon atoms in at least one alkyl group. Such groups mentioned are n-butyl, tert.-butyl, tert.-amyl, n-hexyl, tert.-octyl, n-decyl, cetyl, stearyl, and wax-alkyl groups. Cycloaliphatic groups may also be present. The treated sulphide may be used as its salts with, e.g. calcium, barium, magnesium, sodium, potassium, lithium, nickel, cobalt, tin, lead, zinc, copper, cadmium, manganese, or chromium, or a mixture of such salts may be used. The products may be added to lubricating oils in amount 0.01 to 10 per cent. or to heating oils in amount 0.002 to 0.1 per cent. by weight based on the total composition and also to automotive and diesel fuels. Other additives such as antioxidants, metal deactivators or oil soluble petroleum sulphonates may also be present. A table gives results of corrosion tests in the p-tert.-octyl-phenol sulphide which has been barium-treated as described above, and its calcium salts, and also, for comparison, on the crude tert.-octyl-phenol sulphide, its calcium salt, and the corresponding calcium-treated compound, the sulphide being dissolved in diesel-type lubricant and in a solvent-extracted Mid-Continent base oil. The preparation and treatment of such sulphides is described (see Group IV (b)).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US254188A US2673881A (en) | 1951-10-31 | 1951-10-31 | Lubricant additives and production thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
GB715505A true GB715505A (en) | 1954-09-15 |
Family
ID=22963267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7755/52A Expired GB715505A (en) | 1951-10-31 | 1952-03-26 | Improvements in or relating to improved additives for hydrocarbon oils and particularly for lubricating oils and production thereof |
Country Status (2)
Country | Link |
---|---|
US (1) | US2673881A (en) |
GB (1) | GB715505A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3352695A (en) * | 1965-01-18 | 1967-11-14 | Gorham Corp | Silver polish containing di-n-hexadecyl disulfide |
US3365312A (en) * | 1965-03-08 | 1968-01-23 | Hollingshead Corp | Metal cleaner, article and method |
CN105601547A (en) * | 2015-12-24 | 2016-05-25 | 上海微谱化工技术服务有限公司 | Separation and detection methods of heavy metal ion passivator in PVC (polyvinyl chloride) cable material |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2974103A (en) * | 1957-04-10 | 1961-03-07 | Texaco Inc | Stabilization of wax acid greases by means of diphenol sulfides |
US4211663A (en) * | 1978-05-01 | 1980-07-08 | Mobil Oil Corporation | Alkali metal containing transition metal complexes of thiobis (alkylphenols) as stabilizers for various organic media |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2362289A (en) * | 1938-12-16 | 1944-11-07 | Standard Oil Dev Co | Lubricating compositions |
US2409303A (en) * | 1941-04-26 | 1946-10-15 | Texas Co | Lubricating oil |
US2581919A (en) * | 1946-01-26 | 1952-01-08 | Firestone Tire & Rubber Co | Aromatic hydroxy sulfides |
-
1951
- 1951-10-31 US US254188A patent/US2673881A/en not_active Expired - Lifetime
-
1952
- 1952-03-26 GB GB7755/52A patent/GB715505A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3352695A (en) * | 1965-01-18 | 1967-11-14 | Gorham Corp | Silver polish containing di-n-hexadecyl disulfide |
US3365312A (en) * | 1965-03-08 | 1968-01-23 | Hollingshead Corp | Metal cleaner, article and method |
CN105601547A (en) * | 2015-12-24 | 2016-05-25 | 上海微谱化工技术服务有限公司 | Separation and detection methods of heavy metal ion passivator in PVC (polyvinyl chloride) cable material |
CN105601547B (en) * | 2015-12-24 | 2017-10-17 | 上海微谱化工技术服务有限公司 | The separation of heavy metal ion passivator and detection method in PVC cable material |
Also Published As
Publication number | Publication date |
---|---|
US2673881A (en) | 1954-03-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3471404A (en) | Lubricating compositions containing polysulfurized olefin | |
US3178368A (en) | Process for basic sulfurized metal phenates | |
US2695910A (en) | Methods of preparation of superbased salts | |
US3829381A (en) | Boron-and calcium-containing compositions and process | |
US2518379A (en) | Metal-containing organic compound | |
US2688612A (en) | Preparation of phosphorus sulfidehydrocarbon reaction products and removal of inorganic phosphorous acids therefrom | |
US2362624A (en) | Lubricant | |
US3474035A (en) | Lubricating oil containing overbased sulfurized calcium alkylphenolate | |
US3182019A (en) | Process for preparing petroleum oil additives | |
GB715505A (en) | Improvements in or relating to improved additives for hydrocarbon oils and particularly for lubricating oils and production thereof | |
US3256183A (en) | Lubricant having improved oxidation resistance | |
US3044960A (en) | Lubricating oil containing metal salts derived from hydrogenated bridged phenols andlow molecular weight acids | |
GB748137A (en) | Improvements in or relating to lubricating oil compositions | |
US2806022A (en) | Preparation of metal salts of phosphorus sulfide-hydrocarbon reaction products | |
US3761414A (en) | Sulfurized calcium alkylphenolate lubricants | |
GB894650A (en) | Metal salts of phenols and low molecular weight acids | |
US3130160A (en) | Oil compositions containing metal salt of phenol and low molecular weight acid | |
US2281401A (en) | Lubricating oil composition | |
US3194761A (en) | Preparation of overbased sulphurized calcium alkylphenate lubricant additives | |
US2856361A (en) | Superbasic alkaline earth metal sulfonates | |
US2856359A (en) | Superbasic alkaline earth metal sulfonates | |
US3377282A (en) | Production of oil additives | |
GB1392248A (en) | Preparation of highly basic sulphurized alkylphenols | |
US3065179A (en) | Metal salts of phenols and low molecular weight acids | |
US2392252A (en) | Lubricant |