GB776455A - Additive compositions for lubricating oils and lubricating compositions containing them - Google Patents
Additive compositions for lubricating oils and lubricating compositions containing themInfo
- Publication number
- GB776455A GB776455A GB23889/54A GB2388954A GB776455A GB 776455 A GB776455 A GB 776455A GB 23889/54 A GB23889/54 A GB 23889/54A GB 2388954 A GB2388954 A GB 2388954A GB 776455 A GB776455 A GB 776455A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- sulphide
- alkaline earth
- earth metal
- phenol
- 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
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- 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
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
- C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/06—Metal compounds
- C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/104—Aromatic fractions
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- C10M2203/106—Naphthenic fractions
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
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- C10M2205/026—Butene
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- C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
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- C10M2205/17—Fisher Tropsch reaction products
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- C10M2205/20—Natural rubber; Natural resins
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- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
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- C10M2207/08—Aldehydes; Ketones
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- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
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- C10M2219/106—Thiadiazoles
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- C10M2219/108—Phenothiazine
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- C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
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- 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
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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- C10M2223/042—Metal salts thereof
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- 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
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- 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
- C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
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- 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
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- 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
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- C10N2010/06—Groups 3 or 13
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
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- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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- 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
- C10N2040/20—Metal working
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
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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)
Abstract
An additive composition suitable for use in lubricating oils comprises a product obtained by forming a mixture of an oil-soluble hydrocarbon sulphonic acid or an alkaline earth metal salt thereof and an alkyl phenol sulphide or alkyl thiophenol sulphide whose alkaline earth metal salts are oil soluble or an alkaline earth metal salt thereof, heating this mixture with a basic reacting inorganic alkaline earth metal compound in an amount in excess of that required to form the normal metal salt of the mixture and contacting the product so formed with an acidic reagent in an amount sufficient to neutralize at least a portion of the titratable basicity of the product. Preferred alkyl phenol sulphide or alkyl thiophenol sulphide starting materials are defined by the formula RAr(XH)-Sx-R1 and the alkaline earth metal salts thereof. Ar represents a benzene nucleus or a plurality of rings, e.g. in biphenyl or a condensed ring system, e.g. derived from alkyl naphthalene or anthracene, R is an alkyl group, X is sulphur or oxygen, x is an integer from 1 to 4 and R1 is an organic group, e.g. an aryl, alkyl, aralkyl or alkylaryl group which may contain substituent atoms or groups such as halogen, nitro, amino, hydroxy, alkoxy, aroxy, mercapto or carboxy. Especially suitable are compounds of the formula RAr(XH)-Sx-Ar(XH)R wherein R represents at least one alkyl radical attached to an aromatic nucleus Ar, the number of carbon atoms in all such radicals attached to each benzene nucleus being at least 5 where the metal complex is to be dissolved in hydrocarbon oils, X is oxygen or sulphur and x is an integer from 1 to 4. Nuclear substituents which may be present include alkyl, cycloalkyl, aralkyl, aryl, carboxyl, hydroxyl, alkoxy, aroxy, sulphydryl, nitro ester (organic and/or inorganic), keto, amino, aldehyde, chlormethyl, aminomethyl, alkyl thiomethyl, alkyl xanthomethyl. Alkaline earth metal compounds of the above may be employed. Lists of other general formul of suitable alkyl phenol- and thiophenol sulphides are furnished. Specific sulphide starting materials mentioned are tert.-octyl phenol sulphide, 2,4-di-tert.-amyl phenol sulphide, tert.-amyl phenol sulphide, 2 - hydroxy - 3,5 - di - tert. - amyl - 41 - diethyl - amino diphenyl sulphide, 2-stearoyl-4-amyl phenol sulphide, C16-C20-branched chain alkyl phenol sulphide and bis-(2,4 - diamyl phenol)-4-amyl phenol dithioether prepared from 2,4-di-tert.-amyl phenol and one mol. of p-tert.-amyl phenol, sulphurized with sulphur chloride. Oil-soluble hydrocarbon sulphonic acid starting materials are prepared by sulphonating alkyl benzenes, naphthalenes, anthracenes or picenes. Preferred sulphonate starting materials are obtained by sulphonating lubricating oils with sulphuric acids and the sulphonates may optionally be neutralized with a basic agent, e.g. sodium hydroxide or carbonate, extracted with aqueous alcohol and converted to an alkaline earth metal salt by double decomposition or the sulphonic acids may be neutralized with an oxide or hydroxide of the desired metal. Preferred sulphonates are those of calcium, strontium, barium and magnesium. The oxides, hydroxides and carbides are specified as basic reacting alkaline earth metal compounds. Acidic reagents mentioned include carbon dioxide, hydrogen halides, acidic nitrogen oxides or sulphur oxides. In examples, additives are produced when a mixture in mineral oil of alkaline calcium-barium sulphonate obtained by treating a calcium petroleum sulphonate with barium hydroxide, and tertiary octyl phenol sulphide, obtained by alkylating phenol with di-isobutylene and treating the product with sulphur dichloride in hexane, is heated with barium hydroxide and the product treated with carbon dioxide whilst heating (I); in similar processes mineral oil mixtures of neutral calcium petroleum sulphonate and an alkyl benzene sulphonate respectively with tert.-octyl phenol sulphide are similarly treated (II). The products are employed as antioxidants and stabilizers, e.g. in lubricating oils (see Group III) and natural and synthetic rubber and asphalts. Specification 744,534 is referred to.ALSO:A lubricating oil composition comprises a major proportion of a lubricating oil and a minor proportion of an additive obtained by forming a mixture of an oil-soluble hydrocarbon sulphonic acid or an alkaline earth metal salt thereof and an alkyl phenol sulphide or alkyl thiophenol sulphide whose alkaline earth metal salts are oil-soluble or an alkaline earth metal salt thereof, heating this mixture with a basic reacting inorganic alkaline earth metal compound in an amount in excess of that required to form the normal metal salt of the mixture and contacting the product so formed with an acidic reagent in an amount sufficient to neutralize at least a portion of the tetratable basicity of the product (see Group IV(b)). Preferred alkyl phenol sulphide or alkyl thiophenol sulphide starting materials are defined by the formula R Ar (XH) - Sx - R1 and the alkaline earth metal salts thereof. Ar in the formula may be a benzene nucleus or may consist of a plurality of rings, e.g. biphenyl, or maybe a condensed nucleus, e.g. derived from naphthalene or anthracene, R is an alkyl group, X is sulphur or oxygen, x is an integer from 1 to 4 and R1 is an organic group, e.g. an aryl, alkyl, aralkyl or alkylaryl group which may contain substituent atoms or groups such as halogen, nitro, amino, hydroxy, alkoxy, aroxy, mercapto or carboxy. Especially suitable are compounds of the formula R Ar (XH) - Sx - Ar (XH) R where R represents at least one alkyl radical attached to an aromatic nucleus Ar, the number of carbon atoms in all such radicals attached to each benzene nucleus being at least 5 where the metal complex is to be dissolved in hydrocarbon oils, X is oxygen or sulphur and x is an integer from 1 to 4. Nucleus substituents which may be present include alkyl, cycloalkyl, aralkyl, aryl, carboxyl, hydroxyl, alkoxy, aroxy, sulphydryl, nitro, ester (organic or inorganic), keto, amino, aldehyde, chlormethyl, aminomethyl, alkyl thiomethyl, and alkyl xanthomethyl. Alkaline earth metal salts of the above compounds may be employed. The starting materials may be alkyl phenol thioethers, alkyl phenol disulphides or polymers thereof. Lists of the general formulae of suitable alkyl phenol sulphides and alky thiophenol sulphides are furnished. In examples: A mixture of an oil-soluble calcium petroleum sulphonate, tertiary octyl phenol sulphide and mineral oil is heated with an excess of barium hydroxide and part of the product is blown with moist carbon dioxide whilst heating at elevated temperatures; water sensitivity and copper and silver corrosion tests are applied to both the carbon dioxide-treated and the untreated product; a similar product is prepared and compared with a product obtained by heating an alkyl benzene sulphonate and tertiary octyl phenol sulphide with barium hydroxide in mineral oil and treating the reacted mixture with moist carbon dioxide. Other specific acidic reagents mentioned include hydrogen halides, acidic nitrogen oxides and sulphur oxides. Base stocks include mineral oils, hydrogenated oils or white oils, synthetic oils prepared by the polymerization of olefines, e.g. polyisobutylenes, or by the reaction of carbon monoxide with hydrogen, or by the hydrogenation of coal, cracking coal tar fractions, coal tar or shale oil fractions, animal, vegetable or fish oils which may be hydrogenated or voltolized, alone or in admixture with mineral oils, and oils of the ester, polyester and polyester types, e.g. di - 2 - ethylhexyl sebacate, diabasic acid esters and polyalkylene oxides. The additives may also be incorporated in diesel fuels and kerosene. Additional additives which may be incorporated include detergents such as metal soaps, phenates, alcoholates, organophosphates, thiophosphates, phosphites, thiophosphites, salicylates, xanthates, thioxanthates, carbamates, amines and derivatives thereof, sulphurized and phospho-sulphurized metal phenates and metal phenol sulphonates, nickel oleate, barium stearate, calcium phenyl stearate, zinc diisopropyl salicylate, aluminium naphthenate, calcium cetyl phosphate, zinc methylcyclohexyl thiophosphate and calcium dichlorostearate dyes, pour depressors, heat-thickened fatty oils, sulphurized fatty oils, organometallic compounds, metallic or other soaps, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, voltolized mineral oils and/or waxes, colloidal solids e.g. graphite, zinc oxide, and assisting agents such as esters, ketones, aldehydes, halogenated or nitrated compounds and alcohols, e.g. alcohols having 8 or more, preferably 12 to 20 carbon atoms, which may be saturated branched chain alcohols such as octyl, lauryl, cetyl and stearyl alcohols. Specification 744,534 is referred to.ALSO:An antioxidant or stabilizing agent for asphalt and rubber is obtained by forming a mixture of an oil soluble hydrocarbon sulphonic acid or an alkaline earth metal salt thereof and an alkyl phenol sulphide or alkyl thiophenol sulphide whose alkaline earth metal salts are oil soluble or an alkaline earth metal salt thereof, heating this mixture with a basic reacting inorganic alkaline earth metal compound in an amount in excess of that required to form the normal metal salt of the mixture and contacting the product so formed with an acidic reagent in an amount sufficient to neutralise at least a portion of the titratable basicity of the product (see Group IV(b)). Lists of starting materials are furnished. Specification 744,534 [Group III] is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US776455XA | 1953-10-29 | 1953-10-29 |
Publications (1)
Publication Number | Publication Date |
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GB776455A true GB776455A (en) | 1957-06-05 |
Family
ID=22139250
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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GB23889/54A Expired GB776455A (en) | 1953-10-29 | 1954-08-17 | Additive compositions for lubricating oils and lubricating compositions containing them |
Country Status (2)
Country | Link |
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FR (1) | FR1112406A (en) |
GB (1) | GB776455A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3041283A (en) * | 1958-05-19 | 1962-06-26 | Shell Oil Co | Lubricating compositions |
US3178368A (en) * | 1962-05-15 | 1965-04-13 | California Research Corp | Process for basic sulfurized metal phenates |
US3180829A (en) * | 1965-04-27 | Penetrating oil | ||
US3436347A (en) * | 1963-05-23 | 1969-04-01 | Mobil Oil Corp | Overbased metal sulfonate complexes and mineral oil compositions containing the same |
CN108473901A (en) * | 2015-12-17 | 2018-08-31 | 路博润公司 | For lubricating composition by shield sulfydryl phenol |
CN115109016A (en) * | 2021-03-17 | 2022-09-27 | 中国科学院大连化学物理研究所 | Method for preparing alkyl naphthalene lubricating oil from biomass platform compound |
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1954
- 1954-08-17 GB GB23889/54A patent/GB776455A/en not_active Expired
- 1954-09-14 FR FR1112406D patent/FR1112406A/en not_active Expired
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3180829A (en) * | 1965-04-27 | Penetrating oil | ||
US3041283A (en) * | 1958-05-19 | 1962-06-26 | Shell Oil Co | Lubricating compositions |
US3178368A (en) * | 1962-05-15 | 1965-04-13 | California Research Corp | Process for basic sulfurized metal phenates |
US3436347A (en) * | 1963-05-23 | 1969-04-01 | Mobil Oil Corp | Overbased metal sulfonate complexes and mineral oil compositions containing the same |
CN108473901A (en) * | 2015-12-17 | 2018-08-31 | 路博润公司 | For lubricating composition by shield sulfydryl phenol |
US20180371351A1 (en) * | 2015-12-17 | 2018-12-27 | The Lubrizol Corporation | Protected mercaptophenols and thiophenols for lubricating compositions |
US10767133B2 (en) * | 2015-12-17 | 2020-09-08 | The Lubrizol Corporation | Protected mercaptophenols and thiophenols for lubricating compositions |
CN108473901B (en) * | 2015-12-17 | 2021-09-17 | 路博润公司 | Protected mercapto phenols for lubricating compositions |
CN115109016A (en) * | 2021-03-17 | 2022-09-27 | 中国科学院大连化学物理研究所 | Method for preparing alkyl naphthalene lubricating oil from biomass platform compound |
CN115109016B (en) * | 2021-03-17 | 2023-11-10 | 中国科学院大连化学物理研究所 | Method for preparing alkyl naphthalene lubricating oil from biomass platform compound |
Also Published As
Publication number | Publication date |
---|---|
FR1112406A (en) | 1956-03-14 |
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