US3671430A - High alkalinity additives for lubricating oil compositions - Google Patents

High alkalinity additives for lubricating oil compositions Download PDF

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US3671430A
US3671430A US107846A US3671430DA US3671430A US 3671430 A US3671430 A US 3671430A US 107846 A US107846 A US 107846A US 3671430D A US3671430D A US 3671430DA US 3671430 A US3671430 A US 3671430A
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calcium
sulfonate
phenol
reaction
metal
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Jean Corringer
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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    • 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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Definitions

  • metal sulfonate calcium hydroxide, with carbon dioxide in the presence of the metal sulfonate and an alkaline earth metal phenate, there also being present a polar solvent such as benzyl alcohol or tetrahydrofurfuryl alcohol, as well as free phenol in an amount over and above the stoichiometric quantity necessary to form metal phenate by reaction with the metal base.
  • a polar solvent such as benzyl alcohol or tetrahydrofurfuryl alcohol
  • free phenol free phenol in an amount over and above the stoichiometric quantity necessary to form metal phenate by reaction with the metal base.
  • Preformed metal phenate can be used at the beginning of the reaction or the metal phenate can be formed in situ, starting with free phenol.
  • free sulfonic acid can be used initially, with sufficient metal base to convert it to metal sulfonate.
  • This second dispersant which is used with the sulfonate in the proportion of 0.1 to 1 part per part of sulfonate, can be a thioacid of phosphorus, or metal salt thereof, obtained by reaction of a sulfide of phosphorus on a hydrocarbon; an alkyl phenol or alkyl phenol sulfide, or metal salt thereof; or a monocarboxylic or polycarboxylic acid or anhydride, or metal salt thereof, characterized by a long chain hydrocarbon group of from about 20 to 200 carbon atoms, as for example, a polyisobutenyl succinic acid.
  • This invention concerns an improved process for making an overbased alkaline earth metal sulfonate, an improved product, and an improved lubricant containing the product. More particularly, the invention concerns the preparation of a sulfonate of high alkalinity, i.e. an overbased sulfonate wherein a colloidal dispersion of calcium carbonate is formed by the carefully controlled reaction of a calcium base and carbon dioxide in the presence of said sulfonate and a promoter.
  • Overbased metal sulfonates are well known in the art as desirable additives for lubricating oils. See for example, U.S. Pats. Nos. 2,839,470; 2,856,360; 3,057,896; 3,429,8ll, etc. Their desirable functions include suspension of sludge, prevention of deposit formation, and imparting of rust inhibiting properties to lubricants and other oil compositions.
  • an overbased sulfonate is one containing excess metal over that required for complete neutralization of the sulfonic acid.
  • overbasing is accomplished by adding excess metal base, e.g. lime, to the sulfonate or sulfonic acid, and then neutralizing the excess metal base with carbon dioxide.
  • the colloidal dispersion of calcium carbonate or other metal carbonate that is thereby formed is stabilized by the sulfonate, which forms a protective covering around the carbonate to thereby prevent undesirable agglomeration of the colloidal-size carbonate crystals. Otherwise, this agglomeration can lead to precipitation of the carbonate, particularly when making overbased sulfonates of high base number. Frequently, in the overbasing of sulfonates, the excess metal base is added in the presence of a promoter.
  • an oil-soluble alkaline earth metal sulfonate of high alkalinity is prepared by a process in which a mixture of 1) an alkaline earth metal base and a stoichiometric excess of phenol; or a mixture of an alkaline earth metal phenate and phenol, (2) a polar solvent, (3) an alkaline earth metal sulfonate or a purified sulfonic acid is reacted with carbon dioxide and thereafter the reaction mixture is distilled, thereby removing and recovering phenol and solvent, and the product is filtered.
  • a colloidal dispersion of calcium carbonate is prepared by reaction of carbon dioxide with a calcium base in the presence of calcium hydrocarbon sulfonate, in the presence of an amount of phenol in excess of the stoichiometric amount of total calcium base present, and in the presence of a polar solvent.
  • the invention is particularly applicable to the preparation of a high base number calcium hydrocarbon sulfonate.
  • the starting sulfonates used in the present invention may be either neutral sulfonates, i.e. where the sulfonic acid is neutralized with an equal molar equivalent amount of metal base, or they may have been overbased to a mild degree, e.g. to a base number of say 30 or 40.
  • One may also start with a sulfonic acid in which case additional lime will be used to convert the acid to the salt.
  • sulfonic acids are used as starting materials they should be purified, i.e., they should contain no more than about 0.2 wt. percent of sulfuric acid.
  • Petroleum sulfonic acids used in this art are classified generally as either petroleum sulfonic acids or synthetic sulfonic acids.
  • Petroleum sulfonic acids are produced by treating petroleum fractions, usually lubricating oil distillate fractions, the socalled white oil distillates, or other petroleum fractions, e.g.
  • sulfonating agents including sulfur tiioxide, concentrated sulfuric acid and fuming sulfuric acid.
  • Synthetic sulfonic acids are prepared by treating relatively pure synthetic hydrocarbons in the same manner.
  • Synthetic sulfonic acids are usually prepared by sulfonating alkylated aromatic hydrocarbons having alkyl groups totalling about 10 to 33 carbon atoms, e.g. sulfonated products of alkylated aromatics, such as benzene, toluene, xylene, and naphthalene, alkylated with wax hydrocarbons, olefins, olefin polymers, etc.
  • benzene is alkylated with a polymer of propylene or butylene, e.g. butylene trimer, and then sulfonated.
  • the natural or synthetic sulfonic acids used in this invention include alkane sulfonic acids, aromatic sulfonic acids, alkaryl sulfonic acids and aralkyl sulfonic acids. Specific details of the preparation of sulfonic acids need not be given here because the sulfonation of hydrocarbons is well known to the art.
  • the sulfonate or sulfonic acid in the form of a concentrate of from 30 to 50 weight percent in a light mineral oil.
  • a sulfonic acid solution or concentrate it may be an advantage to add to parts of that acid 0.5 to 1 part of an alkaline earth chloride or 1 or 5 parts of an alkaline earth nitrate, in order to avoid the formation of gels.
  • This invention is particularly a plicable to the overbasin g of calcium sulfonates and is especially advantageous for preparing an overbased calcium sulfonate having a total base number of at least 250-300.
  • Base number is defined in numerical terms equivalent to milligrams of KOH per gram of the material. Base number is also frequently referred to as alkalinity index.
  • the importance of overbasing a sulfonate is an economic one; the higher the base number the more benefit one obtains per unit weight of sulfonate.
  • overbased calcium hydrocarbon sulfonates of total base numbers of about 300 to about 320 are obtained when using the metal sulfonate as the dispersant.
  • total base numbers of 400 or greater are obtained by using as the dispersant a combination of metal hydrocarbon sulfonate and a second dispersant, selected from the class consisting of an organic thioacid of phosphorus, an alkyl phenol, an alkyl phenol sulfide, an alkenyl monocarboxylic acid of about 300 to 2,000 molecular weight in the alkenyl group, an alkenyl dicarboxylic acid of about 300 to 2,000 molecular weight in the alkenyl group, or an alkaline earth metal salt of any of the aforementioned compounds.
  • Dispersion of the alkaline earth metal phenate in the sulfonate can be efiected in any manner, either by preparing a dispersion separately by introducing alkaline earth base into a mixture of solvent and phenol and injecting this dispersion into the sulfonate, or by mixing sulfonate, solvent and phenol and treating the whole with the alkaline earth metal base. Although this operation can be performed in the cold, a temperature in the region of 80 C. or so is helpful for obtaining a good dispersion.
  • the preferred alkaline earth metal base is one of calcium; e.g. lime of standard quality, quick or slaked.
  • the solvenm that can be used are polar solvents such as alcohols, ethers, chlorinated hydrocarbons, or nitrohydrocarbons, etc.
  • Solvents which have a boiling point between 160 and 220 C. are preferable for, besides the part they play as dispersing agent for the phenate, they allow the easier elimination of the phenol by distillation.
  • Preferred examples are benzyl alcohol andtetrahydrofurfuryl alcohol, but alternative solvents are cyclohexanol and methylcyclohexanol. Aliphatic alcohols and glycols are not so suitable.
  • a suitable proportion of solvent is from 80 to 150 percent, or better still, from 100 to 120 percent based on the weight of the sulfonate or sulfonic acid, e.g. a 40 percent by weight sulfonate solution in lubricating oil.
  • the proposition of phenol in relation to the alkaline earth metal base should be at least stoichiometric; an excess of 10 percent, i.e. the introduction of about 2.2 mols phenol to 1 mol base is preferable.
  • the suspension obtained with the base, the phenol and solvent can be injected into an oil solution of sulfonic acids, or else the oil solution of sulfonic acids can be mixed with phenol, the polar solvent and the medium thus obtained being treated with alkaline earth metal base.
  • Water is present in the reaction mixture and comes in particular from the reaction of the base or from the slaked lime when the latter is used. However, water can be added to the reaction mixture to further the reaction and the water is easily eliminated by final distilling.
  • the carbon dioxide gas serves on the one hand to displace the phenol and to supply colloidal alkaline earth metal carbonate; on the other hand it helps to remove the phenol and the solvent by serving as a stripping gas.
  • the quantity of Co, to be used should, therefore, exceed the theoretical quantity of one mol of C per mol of alkaline earth metal base or phenate used; in practice two or four times the theoretical quantity is preferable.
  • the reaction according to the invention can be carried out in several stages, two for preference. For instance, it is possible to use half the required quantity of solvent, phenol and base and treat with carbon dioxide gas to displace the phenol; then, after this treatment, the remainder of the quantity of base is added to reconstitute phenate and further treatment by carbon dioxide gas takes place; the solvent and phenol are thus used twice.
  • the finished products may be subjected to a finishing treatment consisting of steam treatment at a temperature between 180 and 230 C.
  • an additive concentrate of colloidally dispersed calcium carbonate is obtained having a calcium content of about 12 to 13 percent by weight and a total base number, or alkalinity index in the approximate range of 300 to 320. If one attempts to increase the total base number by the above procedure, by using larger proportions of base, the products thereby obtained have such a high viscosity that it is impossible to use them. Now it is desirable to improve further the lubrication of engines, in particular the lubrication of certain diesel engines operating under difficult conditions with fuels containing a high proportion of sulfur, and for this purpose additives that are as alkaline and detergent as possible must be created. Accordingly in a modification of this invention it is possible to increase both the alkalinity and the detergency of the products obtained, without their viscosity attaining unacceptable values.
  • This modification or improvement involves the addition to the reaction mixture, within which carbonation is carried out, before or after the introduction of carbon dioxide, but before the distillation of the liberated phenol and the solvent, of a dispersant that is diflerent from the hydrocarbon sulfonic acids and their metal salts.
  • This modification has the quite unexpected result that it is possible to increase the proportion of base used until products are finally obtained whose total base number reaches or exceeds 400 and whose viscosity is acceptable.
  • a solution is made of 1 part phenol dissolved in 1 to 1.5 parts of a solvent (referred to as S) and an alkaline earth base is added in the proportion of 1 mol of base to at most 2.2 mols of phenol. While the base reacts with the phenol at ambient temperature, it is preferable to operate at a temperature of about 70 to C.
  • a temperature of about 70 to C.
  • about 1 mol of water is added per mol of base; conditions that are very favorable to the reaction, but which can nevertheless be departed from considerably, are then obtained by keeping the mixture at about 120 C., with stirring and under a stream of nitrogen which carries off a portion of the water previously added.
  • a further portion of alkaline earth base can be added to the mixture in the proportion of 1 mol at most to 2.2 mols of phenol present so as to form phenate again, then carbonating as before.
  • the second dispersant R is soluble in mineral oils and is preferably used in the process in the form of a concentrate, e.g. 30 to 50 weight percent in oil.
  • R may comprise a thioacid of phosphorus obtained by reaction of 5 to 30 weight percent of a sulfide of phosphorus with a hydrocarbon material such as a terpene, e.g. alphapinen, or a polyolefin, e.g. a polymer of a C, to Q, olefin wherein the polymer has a molecular weight of about 400 to about 100,000, e.g. polyisobutylene of 400 molecular weight or 1,000 molecular weight reacted with a sulfide of phosphorus such as 10 to 20 wt. percent of P 8 Treatment of such polymers with sulfides of phosphorus is well known in the art. Alkaline earth metal salts of such acids can also be used, e.g. the calcium salt of P 8 treated polyisobutylene of about 1,000 average molecular weight.
  • a hydrocarbon material such as a terpene, e.g. alphapinen
  • alkyl phenols or alkyl phenol sulfides include hexyl phenol, nonyl phenol, dodecyl phenol, hexadecyl phenol, the sulfides of any of said phenols, and the alkaline earth metal salts of any of said phenols or their sulfides.
  • R can also be a monocarboxylic acid, dicarb'oxylic acid, or acid anhydride characterized by having a long chain hydrocarbon group with a total molecular weight in the range of about 300 to about 2,800, i.e. having hydrocarbon groups with at least 20 carbon atoms and up to about 200 carbon atoms.
  • Procedures for preparing such acids and anhydrides are well known in the art; see for example US. Pat. No. 3,489,619, columns 2, 3 and 4.
  • the monocarboxylic acids are preferably obtained by causing a carboxylic acid having ethylene unsaturation in the alpha-beta position of the acid function, for instance acrylic or methacrylic acid, to react with a monochlorinated C to C polymer or copolymer, of suitable molecular weight, in particular with a chlorinated polyisobutylene having an average of one chlorine atom per mol.
  • a carboxylic acid having ethylene unsaturation in the alpha-beta position of the acid function for instance acrylic or methacrylic acid
  • a monochlorinated C to C polymer or copolymer of suitable molecular weight, in particular with a chlorinated polyisobutylene having an average of one chlorine atom per mol.
  • the said derivatives are preferably the salts obtained by causing the oxide or hydroxide of an alkaline earth metal to react on alkenyl succinic anhydrides of molecular weight between 300.and 2000, better still between 700 and 1,000, these anhydrides being preferably polyisobutenyl succinic anhydrides.
  • the improved procedure according tothe present invention makes it possible to prepare new additives which are remarkably effective as detergents, as inhibitors of varnish formation and as anti-rust agents.
  • additives in which the alkaline earth metal is calcium are characterized by an alkalinity index between 350 and 450, by a viscosity less than 400 centistokes at 98.9 C and by the fact that they contain, in colloidal solution in a light mineral oil, from 30 to 40 percent calcium carbonate, from 15 to 25 percent calcium hydrocarbon sulfonate having a molecular weight preferably between about 800 and 1,200, and from 2 to percent R.
  • the overbased additive concentrates of this invention can be incorporated into lubricating oil compositions in various proportions, ranging from about 0.5 to about 30 weight percent, and dependent upon the type of lubricant composition and the qualities it is desired to'obtain.
  • the additive concentrate according to the invention can be used in proportions of to 30 percent, or better still, from to percent by weight of the additive concentrate, based on the lubricating composition.
  • the products according to the invention meet in particular needs of diesel engines which call for thermally very stable additives, furnishing little ash, and whose alkalinity index, i.e. total base number attains at least 250.
  • the additive concentrate can be used in proportions of 0.5 to 1 percent by weight.
  • the working proportions of this additive concentrate as dispersing agent and inhibitor in a lubricating oil will be in the region of 3 to 6 percent by weight.
  • EXAMPLE 2 Preparation of Product B The same operations as in Example 1 were performed as before, using a quantity of 368 g of phenol. A distillate of 1,080 g of benzyl alcohol and 368 g of phenol was obtained.
  • EXAMPLE 4 the foregoing sulfonic acid was replaced by a sulfonic acid obtained by sulfonating an alkylate derived by alkylation of Preparation of Product A1 benzene by means of a polypropylene of mean carbon conden-
  • the distillate obtained in Example 1 was added to 900 g sation equal to 24.
  • the final product A4 after filtration, had a neutral calcium sulfonate concentrate containing 50 percent 1 5 calcium content of l2.5 perc n and alinity ind x f 310. sulfonate derived from the sulfonation of polydodecyl benzene. While stirring, 200 g quicklime was admitted at 80 C.
  • Part D Preparation of Metal Salt of Polyisobentenyl Succinic Acid
  • product of type R there was furthermore prepared as follows the calcium salt of polyisobutenyl succinic acids in solution in a light paraffin oil.
  • polyisobutylene having an average molecular weight of 780 was chlorinated at about 100 C. with gaseous chlorine in order to produce a chlorinated polyolefin containing 4.5 percent chlorine.
  • the clear brown product contained 15.7 percent calcium, and had an alkalinity index of 405 and a viscosity of 278 cSt at 989 C.
  • the composition of this product was as follows:
  • EXAMPLE 12 A mixture of 720 g calcium sulfonate product 9-A,180 g calcium polyisobutenyl succinate product 9-D, 1,080 g phenol, 1,440 g benzyl alcohol and g water was heated to 80 C. while stirring. Then 170, g quicklirne was added and the mixture was stirred for 1 hour at C. in a stream of nitrogen, thereby removing 70 g water. Then CO was introduced at a rate of 3 liters per minute for 2 hours while heating the reacting mixture from 120 to C. The temperature was then raised to 250 C.
  • Example 10 The method of operation of Example 10 was repeated, 240 g product 9-A being replaced by 240 g product 9-B. The result was a gelified product, unfilterable and insufficiently carbonated.
  • Example 10 The method of operation of Example 10 was again repeated, omitting the addition of 60 g product 9-B afier carbonation. The result was a solid unfilterable product.
  • Example 11 The method of operation of Example 11 was repeated, the 750 g of product A being replaced by 750V 8 of product C. The result was a cloudy filterable product-having the consistency of a grease.
  • Example 11 The method of operation of Example 11 was again repeated, the 750 g of product 9-A and the 250 g of product 9-C being replaced by 1,000 g of a solution con- 1 l taining the same sulfonate as product 9A, but in a concentration of 50 percent instead of 38 percent. After filtration, the product contained 12.6 percent calcium and had an alkalinity index of 310. The use of a solution of 50 percent sulfonate is necessary in this case to obtain a sufficient colloidal stability.
  • EXAMPLE 13 Two motor oil compositions were prepared as follows: Oil A 10 percent by weight of an oil of viscosity 32 cSt at 37.8 C. and viscosity index 105.
  • Example 1 Oil B (reference) Same base oils 6 percent commercial high alkalinity calcium sulfonates containing 28 percent by weight pure calcium sulfonate, 27 percent by weight colloidal calcium carbonate and 45 percent by weight mineral oil.
  • Example 12 In order to demonstrate the improved anti-rust properties of an additive of higher alkalinity index as compared toone of lower alkalinity index, the product obtained in Example 12 and a high alkalinity additive prepared by the process of Example '7 were subjected to the special tests provided for in military standard MIL-L -2 1 260A.
  • Oil H 1 slight traces of rust (acceptable result)
  • Oil H2 a number of rust spots (poor result)
  • Oil H1 no trace of rust (excellent result)
  • Oil H2 a few corrosion spots (result barely acceptable)
  • Rust test in damp atmosphere ASTM D-l748-602. This test consists of soaking metal test pieces in the oil being tested, keeping them in a constantly ventilated cabinet containing water at its boiling point. The test is halted when the test pieces display incipient corrosion and the antirust properties of an oil are rated by the time the soaked test piece remains in that oil. This test fumished the following results: Oil H1: 2] days; and Oil H2: 14 days.
  • a process for preparing a high alkalinity oil-soluble alkaline earth metal hydrocarbon sulfonate which comprises reacting carbon dioxide with an alkaline earth metal base selected from the group consisting of metal oxide, metal hydroxide and metal phenate in the presence of a sufficient quantity of a dispersant capable of maintaining a colloidal dispersion of the resulting alkaline earth metal carbonate, in the presence of an amount of phenol in excess of the stoichiometric amount thereof needed to convert total alkaline earth metal base present to phenate, and in the presence of a solvent selected from the group consisting of benzyl alcohol, tetrahydrofurfuryl alcohol, cyclohexanol, and methyl cyclohexanol, said dispersant being selected from the group consisting of (A) alkaline earth metal sulfonate and (B) a mixture of alkaline earth metal sulfonate and a second material selected from the group consisting of (a) thio
  • the molar quantity of carbon dioxide used in the reaction exceeding the molar quantity of total alkaline earth metal base, and the quantity of said solvent equalling at least about 80 weight per cent of the amount of phenol involved in the reaction.
  • said second dispersant material is the calcium salt of polyisobutenyl succinic acid.
  • metal hydrocarbon sulfonate is prepared in situ in the reaction mixture by reaction of free sulfonic acid with calcium base.
  • a process for preparing a calcium hydrocarbon sulfonate of high alkalinity which comprises reacting, at a temperature within the range of about 80 to 250 C., carbon dioxide with a calcium base selected from the group consisting of calcium phenate, quicklime, and slaked lime, in the presence of sufficient oil-soluble calcium hydrocarbon sulfonate to maintain said colloidal dispersion, in the presence of an amount of phenol in excess of the stoichiometric amount thereof needed to convert total calcium base present to phenate, and in the presence of a solvent selected from the group consisting of benzyl alcohol, tetrahydrofiirfuryl alcohol, cyclohexanol, and methyl cylohexanol, there being present in said reaction mixture for each part by weight of total calcium base, calculated as quicklime, from 3 to 5 parts by weight of phenol and from 4 to parts by weight of said solvent, the total amount of carbon dioxide used in the reaction exceeding one mol of carbon dioxide per mol
  • a calcium hydrocarbon sulfonate of high alkalinity is prepared by reaction of carbon dioxide with a calcium base selected from the group consisting of quicklime and slaked lime, in the presence of calcium hydrocarbon sulfonate, the improvement which comprises conducting said reaction at a temperature within the range of about 80 to 250 C.

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Cited By (15)

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US4049560A (en) * 1974-07-05 1977-09-20 Exxon Research & Engineering Co. Detergent additives
US4059536A (en) * 1974-03-29 1977-11-22 Institut Francais Du Petrole Improved process for preparing superbasic detergent additives
US4283940A (en) * 1980-01-03 1981-08-18 Exxon Research & Engineering Co. Method for deconditioning an engine used in fuel economy tests
US4775490A (en) * 1987-07-30 1988-10-04 The Lubrizol Corporation Magnesium overbasing process
US4895674A (en) * 1987-03-16 1990-01-23 King Industries, Inc. Thermally stable sulfonate compositions
US5023016A (en) * 1987-03-16 1991-06-11 King Industries, Inc. Thermally stable sulfonate compositions
US5032299A (en) * 1987-07-30 1991-07-16 The Lubrizol Corporation Magnesium overbasing process
US5133900A (en) * 1987-03-16 1992-07-28 King Industries, Inc. Thermooxidatively stable compositions
US5169564A (en) * 1987-03-16 1992-12-08 King Industries, Inc. Thermooxidatively stable compositions
US5384053A (en) * 1988-06-04 1995-01-24 Bp Chemicals (Additives) Limited Production of a lubricating oil additive concentrate
US5433871A (en) * 1988-06-14 1995-07-18 Bp Chemicals (Additives) Limited Process for the production of a lubricating oil additive concentrate
US5437803A (en) * 1988-06-14 1995-08-01 Bp Chemicals (Additives) Limited Process for the production of a lubricating oil additive concentrate
US5441652A (en) * 1988-06-14 1995-08-15 Bp Chemicals (Additives) Limited Process for the production of a lubricating oil additive concentrate
US6245571B1 (en) * 1998-01-16 2001-06-12 Elf Antar France Method of characterizing the neutralization capacity of a lubricant and device for the implementation of this method
US20070151526A1 (en) * 2005-12-02 2007-07-05 David Colbourne Diesel engine system

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FR2733165B1 (fr) * 1995-04-20 1997-06-13 Inst Francais Du Petrole Carbonates alcalins ou alcalino-terreux colloidaux contenant un compose de calcium,de phospore et de soufre sous forme miscellisee
US6159912A (en) * 1998-11-05 2000-12-12 Chevron Chemical Company Llc Low viscosity, chloride-free, low overbased alkyl-aryl-sulfonate, its application as an additive for lubricating oil, and methods of preparation

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US2616924A (en) * 1951-03-16 1952-11-04 Lubrizol Corp Organic alkaline earth metal complexes and method of making same
US2695910A (en) * 1951-05-03 1954-11-30 Lubrizol Corp Methods of preparation of superbased salts
US3312618A (en) * 1966-07-15 1967-04-04 Lubrizol Corp Process for preparing an oil soluble highly basic metal salt of an organic acid
US3350308A (en) * 1963-09-16 1967-10-31 Lubrizol Corp Method for preparing calcium sulfonate complexes

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US2616924A (en) * 1951-03-16 1952-11-04 Lubrizol Corp Organic alkaline earth metal complexes and method of making same
US2695910A (en) * 1951-05-03 1954-11-30 Lubrizol Corp Methods of preparation of superbased salts
US3350308A (en) * 1963-09-16 1967-10-31 Lubrizol Corp Method for preparing calcium sulfonate complexes
US3312618A (en) * 1966-07-15 1967-04-04 Lubrizol Corp Process for preparing an oil soluble highly basic metal salt of an organic acid

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4059536A (en) * 1974-03-29 1977-11-22 Institut Francais Du Petrole Improved process for preparing superbasic detergent additives
US4049560A (en) * 1974-07-05 1977-09-20 Exxon Research & Engineering Co. Detergent additives
US4283940A (en) * 1980-01-03 1981-08-18 Exxon Research & Engineering Co. Method for deconditioning an engine used in fuel economy tests
US5133900A (en) * 1987-03-16 1992-07-28 King Industries, Inc. Thermooxidatively stable compositions
US5169564A (en) * 1987-03-16 1992-12-08 King Industries, Inc. Thermooxidatively stable compositions
US4895674A (en) * 1987-03-16 1990-01-23 King Industries, Inc. Thermally stable sulfonate compositions
US5023016A (en) * 1987-03-16 1991-06-11 King Industries, Inc. Thermally stable sulfonate compositions
US5032299A (en) * 1987-07-30 1991-07-16 The Lubrizol Corporation Magnesium overbasing process
US4775490A (en) * 1987-07-30 1988-10-04 The Lubrizol Corporation Magnesium overbasing process
US5384053A (en) * 1988-06-04 1995-01-24 Bp Chemicals (Additives) Limited Production of a lubricating oil additive concentrate
US5433871A (en) * 1988-06-14 1995-07-18 Bp Chemicals (Additives) Limited Process for the production of a lubricating oil additive concentrate
US5437803A (en) * 1988-06-14 1995-08-01 Bp Chemicals (Additives) Limited Process for the production of a lubricating oil additive concentrate
US5441652A (en) * 1988-06-14 1995-08-15 Bp Chemicals (Additives) Limited Process for the production of a lubricating oil additive concentrate
US6245571B1 (en) * 1998-01-16 2001-06-12 Elf Antar France Method of characterizing the neutralization capacity of a lubricant and device for the implementation of this method
US20070151526A1 (en) * 2005-12-02 2007-07-05 David Colbourne Diesel engine system

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