GB786167A - Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts - Google Patents

Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts

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Publication number
GB786167A
GB786167A GB27853/54A GB2785354A GB786167A GB 786167 A GB786167 A GB 786167A GB 27853/54 A GB27853/54 A GB 27853/54A GB 2785354 A GB2785354 A GB 2785354A GB 786167 A GB786167 A GB 786167A
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United Kingdom
Prior art keywords
acids
oil
basic
polyvalent metal
water
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
Application number
GB27853/54A
Inventor
Glyn Ellis
James Hartley
John Campbell Moseley
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Research Ltd
Original Assignee
Shell Research Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shell Research Ltd filed Critical Shell Research Ltd
Priority to GB27853/54A priority Critical patent/GB786167A/en
Priority to US510502A priority patent/US2865956A/en
Priority to DEN11235A priority patent/DE1086701B/en
Priority to FR1136852D priority patent/FR1136852A/en
Publication of GB786167A publication Critical patent/GB786167A/en
Expired legal-status Critical Current

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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
    • C10M159/00Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12Reaction products
    • C10M159/20Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • 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
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06Well-defined aromatic compounds
    • 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
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102Aliphatic fractions
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/028Overbased salts thereof
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    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/16Naphthenic acids
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    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/26Overbased carboxylic acid salts
    • C10M2207/262Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid 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
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40Fatty vegetable or animal oils
    • C10M2207/402Castor oils
    • 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
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
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    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046Overbasedsulfonic acid salts
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
    • 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
    • C10N2010/02Groups 1 or 11
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    • 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
    • C10N2010/04Groups 2 or 12
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/08Groups 4 or 14
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/14Group 7
    • CCHEMISTRY; METALLURGY
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    • C10N2070/00Specific manufacturing methods for lubricant compositions
    • C10N2070/02Concentrating of additives

Abstract

A solution of a basic oil-soluble polyvalent metal salt of an organic acid in an oil (i.e. a liquid which is not miscible with water) is prepared by reacting, at a temperature between 20 DEG and 70 DEG C., an oil-soluble polyvalent metal salt of the organic acid, in the presence of the oil and a water-miscible oxygen-containing organic solvent, with a polyvalent metal carbonate which is formed in situ in the reaction mixture. The in situ formation of the polyvalent metal carbonate is defined as either the reaction of a polyvalent metal base such as the oxide or hydroxide or an alkoxide with carbon dioxide or carbonic acid or the interaction of polyvalent metal ions and carbonate ions. The reaction mixture obtained by the process is worked up to remove the oxygen-containing solvent and water. Preferably the reaction mixture contains a small amount not exceeding 10 per cent by volume of water, other than the water formed during the reaction, and is stirred or agitated. The oil-soluble polyvalent metal salt used as starting material is usually formed as a first step in the process by the reaction of the organic acid (or a salt thereof other than a polyvalent metal salt) with a compound of the polyvalent metal, preferably the hydroxide, and this salt may itself be a basic salt. Mixtures of acids may be used as starting materials. Specified polyvalent metals, the salts of which may be prepared by the process, are calcium, barium, strontium, magnesium, copper, zinc, manganese, cobalt and lead. The organic acids which may be used are aliphatic, cycloaliphatic and aromatic acids comprising carboxylic acids, sulphur containing acids such as sulphonic acids and phosphoric acids and the corresponding thio-acids. Phenols and partial esters of sulphur- and phosphorus-containing acids can also be used. Specified acids are alkyl-substituted aromatic, cycloaliphatic and heterocyclic sulphonic acids having at least 12 carbon atoms in the alkyl substituent or substituents such as petroleum sulphonic acids; petroleum naphthene sulphonic acids; aromatic carboxylic acids with an oil-solubilizing radical or radicals having at least about 12 carbon atoms such as mono- or poly-wax substituted benzoic or naphthoic acids or alkyl salicylic acids; naphthenic acids; aliphatic, cycloaliphatic and aromatic phosphoric and thiophosphoric acids having at least 12 carbon atoms per molecule; octyl-, dodecyl-, octadecyl-, diisopropyl- and dihexyl-phenols and the condensation products of phenols with aldehydes or ketones such as the reaction products of octyl phenol and formaldehyde. Specified oils are mineral oils, gasoline, carbon tetrachloride, xylenes, benzene, toluene, cyclohexane, iso-octane and decane. Specified water-miscible oxygen-containing organic solvents are aliphatic alcohols containing not more than 5 carbon atoms such as methanol and ethanol, polyhydric alcohols such as ethylene glycol, ketones containing less than 6 carbon atoms such as acetone, ethers such as diisopropyl ether, methyl and ethyl ethers of ethylene glycol and 1 : 3- and 1 : 4-dioxane and esters such as ethyl lactate. In a preferred procedure, a solution of the organic acid in a hydrocarbon solvent is contacted with the solid material obtained during the working up of the reaction product, and then an excess of polyvalent metal hydroxide over that required to form the salt is added. The oxygen-containing solvent may be present during this first stage or may be added after it. Carbon dioxide is then passed into the reaction mixture and forms the polyvalent metal carbonate in situ. The product of the carbonation stage comprises the basic polyvalent metal salt of the organic acid, the basicity of which depends inter alia on the amount of polyvalent metal hydroxide and the duration of the carbon dioxide treatment, unused polyvalent metal hydroxide and byproduct carbonate both in the solid state and the liquids comprising the hydrocarbon solvent, the oxygen-containing solvent and water. The mixture is clarified, e.g. by centrifuging and the solid material recycled. The clarified material is subjected to phase separation to yield an oxygen-containing solvent phase containing water and a hydrocarbon solvent phase containing the desired basic salt. The hydrocarbon solvent phase may be further worked up by the addition of a light mineral oil followed by steam distillation to remove the hydrocarbon solvent. The resultant mineral oil concentrate of the basic salt, and the basic salts generally, are used as additives for lubricating and fuel oils (see Group III). The process may be carried out batchwise or continuously. In examples: (1) a solution of alkyl salicylic acids in xylene, methanol and an excess of calcium hydroxide were mixed together and carbon dioxide passed in, the product being worked up as described above to give an oil solution of basic calcium alkyl salicylates; (2) as in (1) but using carbon dioxide diluted with air and working up the reaction product by centrifuging to remove the solids and distilling off the methanol, water and xylene to give the basic salt; (3) as in (1) but water added and a carbon dioxide/air mixture used; (4) as in (2) but using acetone instead of methanol and working up the basic salt as an oil solution; (5) as in 1 but using a solution of naphthenic acids in xylene; (6) as in (5) but using barium oxide, the product being a solution of the basic barium naphthenate in xylene; (7) an acid oil obtained by the sulphonation of a lubricating oil was mixed with an excess of a slurry of calcium hydroxide in methanol, carbon dioxide was passed through and the mixture filtered to give a mineral oil solution of basic calcium petroleum sulphonates; (8) a mixture of basic calcium petroleum sulphonates and alkyl salicylates was dissolved in xylene, a slurry of calcium hydroxide in methanol added, carbon dioxide passed in and the product worked up as a mineral oil solution of the mixed basic salts. Specifications 734,598, 734,622 and 738,359 are referred to.ALSO:Basic oil-soluble polyvalent metal salts of organic acids, which are used as additives for lubricating oils, are prepared in solution in an oil (i.e. a liquid which is not miscible with water) by reacting at a temperature between 20 DEG and 70 DEG C., an oil-soluble polyvalent metal salt of the organic acid, in the presence of the oil and a water-miscible oxygen-containing organic solvent, with a polyvalent metal carbonate which is formed in situ in the reaction mixture (see Group IV (b)). The basic salts are preferably further worked up as solutions in oils of relatively high viscosity such as mineral lubricating oils or synthetic lubricants for use as additives. Specified oils of relatively high viscosity are polymerized olefins, alkylated aromatic hydrocarbons, liquid polysiloxanes or fluorocarbons, ester lubricants, such as di(2-ethylhexyl) sebacate or adipate and trioctyl phosphate or a fatty oil such as castor oil. Specified polyvalent metals the salts of which may be prepared by the process are calcium, barium, strontium, magnesium, copper, zinc, manganese, cobalt and lead. The organic acids which may be used are aliphatic, cycloaliphatic and aromatic acids comprising carboxylic acids, sulphur-containing acids such as sulphonic acids, and phosphoric acids and the corresponding thio-acids. Phenols and partial esters of sulphur- and phosphorus-containing acids can also be used. Specified acids are alkyl-substituted aromatic, cycloaliphatic, and heterocyclic sulphonic acids having at least 12 carbon atoms in the alkyl substituent or substituents, such as petroleum sulphonic acids; petroleum naphthene sulphonic acids; aromatic carboxylic acids with an oil-solubilizing radical or radicals having at least about 12 carbon atoms such as mono- or poly-wax substituted benzoic or naphthoic acids or alkyl salicylic acids; naphthenic acids; aliphatic, cycloaliphatic and aromatic phosphoric and thiophosphoric acids having at least 12 carbon atoms per molecule; octyl-, dodecyl-, octadecyl-, diisopropyl- and dihexyl-phenols and the condensation products of phenols with aldehydes or ketones such as the reaction products of octyl phenol and formaldehyde. Specified additional ingredients in the lubricating oil compositions are octyl formol and Anglamol 304 (the word "Anglamol" is a Registered Trade Mark). In examples, spindle oil solutions of basic calcium alkyl salicylates and mineral oil solutions of a basic calcium naphthenate and of a mixture of basic calcium alkyl salicyates and petroleum sulphonates are prepared.
GB27853/54A 1954-09-27 1954-09-27 Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts Expired GB786167A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB27853/54A GB786167A (en) 1954-09-27 1954-09-27 Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts
US510502A US2865956A (en) 1954-09-27 1955-05-23 Preparation of basic polyvalent metal salts of organic acids
DEN11235A DE1086701B (en) 1954-09-27 1955-09-26 Process for the production of oil-soluble basic salts of polyvalent metals and organic sulfonic or carboxylic acids or their solutions in a hydrocarbon oil
FR1136852D FR1136852A (en) 1954-09-27 1955-09-27 Improvements relating to the preparation of basic salts of polyvalent metals soluble in oil of organic acids and solutions of these basic salts in oils and salts resulting therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB27853/54A GB786167A (en) 1954-09-27 1954-09-27 Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts

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GB786167A true GB786167A (en) 1957-11-13

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Country Status (4)

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US (1) US2865956A (en)
DE (1) DE1086701B (en)
FR (1) FR1136852A (en)
GB (1) GB786167A (en)

Cited By (32)

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US2994661A (en) * 1958-04-09 1961-08-01 Sinclair Refining Co Preparation of diester oil solutions of mineral oil-free basic alkaline earth metal mahogany sulfonates
DE1119270B (en) * 1955-04-22 1961-12-14 Bataafsche Petroleum Process for the production of oil-soluble basic salts of organic carboxylic or sulfonic acids
US3052630A (en) * 1960-04-18 1962-09-04 Shell Oil Co Lubricating oil compositions
DE1154219B (en) * 1960-03-28 1963-09-12 Iashellia Res Ltd Lubricating oil
US3182019A (en) * 1959-12-15 1965-05-04 Exxon Research Engineering Co Process for preparing petroleum oil additives
US3213019A (en) * 1962-02-15 1965-10-19 Socony Mobil Oil Co Inc High barium-content carbonated salts of phosphorus sulfide-hydrocarbon products and method for preparing the same
US3251885A (en) * 1961-12-06 1966-05-17 Monsanto Chemicals Process for preparing complex carbonated metal salts of alkyl phenol sulfides
US3471403A (en) * 1967-03-07 1969-10-07 Lubrizol Corp Basic metal carboxylate complex
DE2227325A1 (en) * 1971-06-07 1972-12-21 Continental Oil Co Process for the production of highly basic oil-soluble preparations
DE2431241A1 (en) * 1973-07-02 1975-01-23 Witco Chemical Corp PROCESS FOR PRODUCING A STRONG BASIC MAGNESIUM-CONTAINING DISPERSION
DE2653717A1 (en) * 1975-12-15 1977-06-16 Karonite Chemical Co PROCESS FOR MANUFACTURING AN OVERBASED ADDITIVE TO LUBRICATING OILS
DE3441439A1 (en) * 1983-11-15 1985-05-30 Shell Internationale Research Maatschappij B.V., Den Haag BASIC METAL SALT MODIFIED WITH BOR, A LUBRICANT OIL COMPOSITION CONTAINING IT, AND METHOD FOR PRODUCING THE METAL SALT
EP0168110A1 (en) * 1984-07-06 1986-01-15 Shell Internationale Researchmaatschappij B.V. Process for the preparation of sulphurized overbased salicylates
EP0168111A1 (en) * 1984-07-06 1986-01-15 Shell Internationale Researchmaatschappij B.V. Process for the preparation of sulphurized salicylates
EP0168880A1 (en) * 1984-07-06 1986-01-22 Shell Internationale Researchmaatschappij B.V. Process for the preparation of sulphurized overbased salicylates
EP0248465A1 (en) * 1986-06-06 1987-12-09 Shell Internationale Researchmaatschappij B.V. Process for the preparation of a basic salt, such a salt and lubricating oil compositions containing such a salt
EP0267658A2 (en) * 1986-11-13 1988-05-18 Shell Internationale Researchmaatschappij B.V. Process for the preparation of a basic salt, salt thus prepared and lubricating oil compositions containing such a salt
EP0279493A2 (en) * 1987-02-16 1988-08-24 Shell Internationale Researchmaatschappij B.V. Process for the preparation of a basic salt, salt thus prepared and oil compositions containing such a salt
US4869837A (en) * 1987-07-09 1989-09-26 Shell Oil Company Preparation of a basic salt
US4876020A (en) * 1987-06-25 1989-10-24 Shell Oil Company Lubricating oil composition
EP0354621A1 (en) * 1988-08-12 1990-02-14 Shell Internationale Researchmaatschappij B.V. Overbased sulphonates and their use as additives
US5089158A (en) * 1989-09-05 1992-02-18 Shell Oil Company Additives for lubricating oils and processes for producing them
US7163911B2 (en) 2003-05-22 2007-01-16 Chevron Oronite Company Llc Carboxylated detergent-dispersant additive for lubricating oils
EP2308953A1 (en) 2009-09-29 2011-04-13 Chevron Oronite Technology B.V. System oil formulation for marine two-stroke engines containing alkyl salicylates
EP2322591A1 (en) 2005-07-29 2011-05-18 Chevron Oronite S.A. Overbased alkaline earth metal alkylhydroxybenzoates having low crude sediment
US7951760B2 (en) 2005-07-29 2011-05-31 Chevron Oronite S.A. Overbased alkali metal alkylhydroxybenzoates having low crude sediment
US8188020B2 (en) 2003-12-22 2012-05-29 Chevron Oronite S.A. Lubricating oil composition containing an alkali metal detergent
US8399388B2 (en) 2009-07-01 2013-03-19 Chevron Oronite Company Llc Low temperature performance lubricating oil detergents and method of making the same
US8618029B2 (en) 2003-12-22 2013-12-31 Chevron Oronite S.A. Overbased detergents for lubricating oil applications
US8778856B2 (en) 2009-12-02 2014-07-15 Chevron Oronite Company Llc Low temperature performance lubricating oil detergents and method of making the same
US8993499B2 (en) 2007-12-28 2015-03-31 Chevron Oronite Company Llc Low temperature performance lubricating oil detergents and method of making the same
EP3144372A1 (en) 2015-09-16 2017-03-22 Infineum International Limited Additive concentrates for the formulation of lubricating oil compositions

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FR1136852A (en) 1957-05-21
US2865956A (en) 1958-12-23
DE1086701B (en) 1960-08-11

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