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US3277002A - Process for stably dispersing metal compounds - Google Patents

Process for stably dispersing metal compounds Download PDF

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Publication number
US3277002A
US3277002A US124315A US12431561A US3277002A US 3277002 A US3277002 A US 3277002A US 124315 A US124315 A US 124315A US 12431561 A US12431561 A US 12431561A US 3277002 A US3277002 A US 3277002A
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US
United States
Prior art keywords
metal
alkoxide
oil
soluble
cobalt
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 - Lifetime
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US124315A
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English (en)
Inventor
Mack W Hunt
Gerald L Nield
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.)
ConocoPhillips Co
Original Assignee
Continental Oil Co
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Filing date
Publication date
Priority to NL281035D priority Critical patent/NL281035A/xx
Application filed by Continental Oil Co filed Critical Continental Oil Co
Priority to US124315A priority patent/US3277002A/en
Priority to US124389A priority patent/US3141745A/en
Priority to GB22117/62A priority patent/GB997335A/en
Priority to FR903272A priority patent/FR1337804A/fr
Priority to BE636928A priority patent/BE636928Q/fr
Application granted granted Critical
Publication of US3277002A publication Critical patent/US3277002A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/68—Preparation of metal alcoholates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/68—Preparation of metal alcoholates
    • C07C29/685—Preparation of metal alcoholates by converting O-metal groups to other O-metal groups
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    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to a process for the preparation of intermediates utilized in preparing stable dispersions for use as additives for lubricating oils and the like. More particularly, but not by way of limitation, this invention relates to a method of preparing alcohol soluble metal alkoxides and/or alcohol soluble carbonates of such metal alkoxides. In another of its aspects, the invention relates to a process for dispersing basic metal compounds, including metallic carbonates, derived from said metal alkoxides and the carbonates thereof in a nonvolatile carrier.
  • Dispersions containing certain oil-insoluble metal compounds which are dispersed by an oil-soluble dispersing or peptizing agent in a nonvolatile carrier material have recently acquired considerable importance as additives in lubricating oils. Such dispersions have also been highly useful as additives to other materials where the problem of suspending insoluble waste materials formed in the utilization of the material and also the problem of corrosion inhibition are met. For example, in lubricating oils of the heavy-duty detergenttype, such as those used in diesel and similar internal combustion engines, at least two desiderata must be met by such oils.
  • the oil must be capable of neutralizing acidic lacquer precursors which are formed by either oil oxidation, or by interaction of the oil with certain sulfur acids produced from fuel combustion, or by both of these conditions.
  • the oil must possess the power to disperse such insoluble material as is formed by fuel combustion or oil oxidization in order that the abrasive and corrosive effect of said insolubles shall be minimized.
  • lubricating oil compositions which are utilized in marine diesel engines have a high degree of basicity.
  • the requirement of high basicity stems from the use of fuels in such engines which are characterized by high sulfur content which, in turn, means a larger amount of acidic combustion products are produced.
  • the insoluble materials such as sludge, formed in the use of such lubricating oils and the like, it is necessary to also add to the oil some composition which effectively peptizes or disperses insolubles, there-by retaining them in suspension in the lubricant.
  • the present invention provides a process for preparing certain valuable additives for use in internal combustion engine lubricating compositions, which additives are characterized by a high basicity and include an oil-soluble dispersing agent which functions to effectively disperse or peptize such insolubles are formed by fuel combustion, oil oxidization or similar conditions obtaining during the utilization of said composition.
  • the additives are prepared in the form of highly stable dispersions of metal hydroxides or metal carbonates in a nonvolatile carrier.
  • the substantial quantity of basic metal compounds which are present in such dispersions effectively combats the deleterious effect of acidic oxidization products, while the dispersing agent employed effectively prevents the precipitation or accumulation of sludge and insoluble material.
  • compositions which contain large amounts of dispersed cations.
  • Such compositions have a variety of "ice uses, as, for example, homogeneous catalyst systems, corrosion inhibitors, and particularly corrosion inhibitors for vanadium-containing fuels, and fuel additives in general.
  • the advantages of using a basic inorganic compound to react with undesirable acid components in fuel or lubricating oil are both obvious and well known.
  • the basicity of the additive is usually of little concern.
  • the primary concern is the cation available from the additive.
  • the inorganic dispersions of the present invention have a considerable advantage over the oil-soluble neutral salts in that they contain a much greater amount of metal per unit weight or volume. This allows lower treatment levels to be used which in turn results in considerable economies.
  • the process is especially useful in that it permits the excess metal content of the dispersions prepared thereby to be predicted with considerable accuracy. Moreover, the process may be practiced without the requirement of extreme process conditions of time, temperature and pressure.
  • the starting materials utilized in the process are relatively inexpensive, and the particles of the metallic compounds suspended in the final dispersion are uniformly small as contrasted to previous types of dispersions containing various metallic compounds. This constitutes an advantageous features of the dispersions prepared by the present invention in that the development of haze in the lubricating oil is prevented, and the particles of suspended metallic compounds do not reach a size sufficient to abrade the metal bearings with which the lubricating oil comes in contact.
  • Double decomposition reactions similar. to those employed in the process of the present invention have been used previously in the preparation of lubricating oil additives of the alkyl-substituted metal phenolate types. In these particular reactions, a double decomposition reaction is used because the phenol is not strongly enough acidic to react with the less strongly basic metal oxides or hydroxides.
  • the process of the present invention differs from that referred to. In the afore-mentioned process the double decomposition reaction is used to produce phenates, which are essentially neutral and which do not contain excess metal as the desired product.
  • the double decomposition reaction is used to produce alkoxides, or alkoxide-carbonate complexes, as intermediates, which intermediates in turn are used to produce products containing excess basicity, or excess metal content, which is in contrast to the neutral phenates produced by the other process.
  • -It is a particular object of the present invention to prepare a variety of metal alkoxide, or metal alkoxide-carbonate, intermediates which are derived from metals which are not reactive with alcohols, or metals which are only slightly reactive with alcohols, which intermediates may be very conveniently used for preparing a dispersion of basic metallic compounds in a nonvolatile carrier.
  • Another object of the invention is to provide a process by which an overbased dispersion of oil-insoluble basic metallic compounds in a nonvolatile carrier may be easily and inexpensively prepared.
  • a further object of the invention is to provide a process for preparing overbased dispersions having utility as additives for lubricating oil and the like, which dispersions are quite stable and are characterized in having relatively small and uniformly sized particles of metal hydroxides and/or carbonates dispersed therein.
  • a further object of the invention is to increase the number or variety. of metallic hydroxides and/or carbonates which may be incorporated in an overbased dispersion for use in lubricating oils and the like.
  • Another object is to provide a method by which high basicity may be imparted to dispersions useful as lubricating oil additives, and to improve the control which may be maintained over the basicity attained.
  • the present invention comprises a process which involves three reactions in proceeding from the raw materials utilized to the final overbased dispersions discussed above.
  • a sodium alkoxide is first prepared from the reaction between sodium and an alcohol, or by the reaction between sodium hydroxide and an alcohol.
  • the first reaction is the simpler of the two.
  • the sodium-alcohol reaction is more costly than the second method which employs sodium hydroxide and yields sodium alkoxide and water.
  • the Water which is produced is substantially removed from the reaction mixture by azeotropic distillation.
  • the two preparations of the sodium alkoxide are expressed in the following equations:
  • reaction (1) or (2) may be utilized as the initial step in practicing the process of the present invention.
  • the second step in the process is a double decomposition or metathetical reaction which is accomplished by the addition of a metal salt to the alcoholic solution of the sodium alkoxide. position to occur leading to the formation of a metal alkoxide and a sodium salt, the metal salt which is added to the sodium alkoxide solution must be chosen so that the corresponding sodium salt which is produced is less soluble in the alcohol system than is the metal salt.
  • the double decomposition reaction constituting the second step in the overall process of the invention may be expressed by the following equations:
  • the insoluble sodium salt which is formed in this double decomposition reaction is'removed by filtration or centrifugation. Such removal yields a stable, clear alcoholic solution of the desired metal alkoxide.
  • the carbonation is achieved by passing carbon dioxide gas through the system, and the carbonation reaction can be expressed as follows:
  • n is defined as indicated above, and
  • x is from 0.5 to 5, depending upon the valency of the metal and the solubility of the carbonate which is formed.
  • the third step in the overall process of preparing stable overbased dispersions comprises that of incorporating the metal alkoxide or metal alkoxide-carbonate complex in a nonvolatile carrier -by means of an oil-soluble dispersing agent, and then hydrolyzing the metal alkoxide to the corresponding metal hydroxide.
  • incorporation is accomplished by first mixing a quantity of an oil-soluble dispersing agent, a hydrocarbon nonvolatile carrier and water and then heating such mixture to a predetermined temperature. The metal alkoxide or carbonate complex intermediate is then added to this mixture over a short period of time. Generally, the quantity of water incorporated in the mixture and the conditions of heat.
  • the intermediate has been added to the dispersing agentcarrier-water mixture, the volatile sol-i vents are removed by heating. Since in some cases itis more desirable to provide a metal carbonate in the dispersion than the corresponding metal hydroxide, it will, in such instances, be desirable to blow the dispersion with carbon dioxide in order to form the carbonate from the metal hydroxide.
  • the oil-insoluble, basic metallic com In order for the double decompounds which are suspended in the dispersion are of unifor-mly small particle size.
  • the importance of using a soluble metal containing intermediate to prepare inorganic dispersions in oil is quite important. Such an intermediate permits the controlled precipitation of the inorganic phase as uniformly fine colloidal particles.
  • the resulting colloidal dispersions are indefinitely stable under extreme conditions.
  • the process of the present invention is capable of preparing dispersions containing relatively large amounts of metal compounds.
  • the dispersoid metal compound is basic (e.g., calcium hydroxide)
  • the process is applicable to metals which are amphoteric. A dispersion containing a large amount of an amphoteric metal (e.g., aluminum) will not show a high basicity, even though the metal may be present as the hydroxide.
  • metal alkoxides or metal alkoxide-carbonate complexes wherein the metal or metal oxide is either non-reactive or only slightly reactive with an alcohol.
  • metals which are non-reactive or only slightly reactive with alcohols include: chromium, molybdenum, manganese, iron, cobalt, nickel, copper, zinc, cadmium, tin, lead, vanadium, zirconium, silver, mercury, arsenic, antimony, and bismuth.
  • the metal compound used in the double decomposition reaction must be one in which the corresponding sodium salt which is produced is less soluble in the alcohol system than is the metal salt (or compound).
  • Suitable cations of the metal compounds include the metals of the following groups of the periodic table (according to Deming): LB, II-A, II-B, III-A, I-ILB, IV-A, IVB, V-A, V*B, VI-B, VII-B, and VIII.
  • Particularly suitable cations by reason of availability, economics, or non-reactivity (including slightly reactive) with alcohols, are the following: aluminum, silver, arsenic, barium, bismuth, calcium, cadmium, cobalt, chromium, copper, iron, mercury, magnesium, manganese, molybdenum, nickel, lead, antimony, strontium, tin, vanadium, zinc, and zirconium.
  • Preferred cations by reason of being either non-reactive or only slightly reactive with alcohols, are the following: silver, arsenic, bismuth, cadmium, cobalt, chromium, copper, iron, mercury, manganese, molybdenum, nickle, lead, antimony, tin, vanadium, zinc, and zirconium.
  • silver, arsenic, bismuth, cadmium, cobalt, chromium, copper, iron, mercury, manganese, molybdenum, nickle, lead, antimony, tin, vanadium, zinc, and zirconium are particularly preferred, by reason of availability and economics: cadmium, cobalt, copper, chromium, manganese, nickel, and zinc.
  • Suitable anions of the metal salt include the following: halide, nitrate, sulfate, acetate, ammonium phosphate, bromate, carbonate, citrate, cyanide, dithicnate, formate, iodate, nitrite, oxyla-te, phosphate, silicate, sulfide, sulfite, tartrate, aluminate, antimonate, arsenate, bismuthate, borate, chromate, manganate, molybdate, selen-ate, tungstate, uranate, and vanadate.
  • *Preferred anions of the metal salt include halide, nitrate, and sulfate.
  • suitable metal compounds include the following: aluminum chloride, .barium chloride, cadmium chloride, calcium chloride, cobalt chloride, cupric chloride, magnesium chloride, manganese chloride, nickel chloride, strontium chloride, zinc chloride, tin chloride, chromic chloride, aluminum sulfate, barium nitrate, cadmium nitrate, calcium nitrate, cupric sulfate, magnesium sulfate, manganese sulfate, nickel sulfate, strontium sulfate, zinc sulfate, stannic sulfate and chromic sulfate.
  • the alcohols which are suitable in the process are those in which the metal alkoxide has an appreciable solubility.
  • suitable alcohols to be the following: aliphatic monohydric alcohols having from one to six carbon atoms, monoethers of ethylene glycol containing not more than eight carbon atoms, and monoethers of diethylene glycol containing not more than eight carbon atoms.
  • Preferred glycol ethers are the monoethyl ether of ethylene glycol and the monomethyl ether of ethylene glycol. These materials are available commercially under the trademarks Cellosolve and methyl Cellosolve.
  • the monoethyl ether of diethylene glycol is available commercially under the trademark Carbitol.
  • the monoethers of ethylene glycol are also known as alkoxy alkanols, and more specifically as alkoxy ethanols. These materials have the generic formula, ROCH OH OH, where R is a C to C hydrocarbon group. Similarly, the monoalkylether of diethylene glycol has the generic formula, HOCH CH OCH C-H OR, where R is a C to C hydrocarbon group.
  • azeotroping agent such as benzene or toluene.
  • the use of such a material is necessary only when the alcohol employed does not form a favorable azeotrope with water.
  • favorable azeotrope is meant one which contains a relatively large amount of water.
  • the ethanol-water azeotrope is regarded as unfavorable due to the small amount of water present therein.
  • the glycol ethers form an azeotrope with water and, for that reason, do not require an additional azeotroping agent.
  • nonvolative carriers which may be utilized in our process
  • a Wide variety of materials have been found suitable for such usage.
  • the principal requisites desired in the nonvolatile carrier are that it will dissolve the dispersing agents utilized in the process, and that such solutions will be relatively stable when the basic metallic compounds are peptized in the dispersion by the dispersing agent.
  • nonvolatile carriers examples include mineral lubricating oil obtained by any of the conventional refining procedures; vegetable oils, such as corn oil, cottonseed oil, castor oil, etc.; animal oil, such as lard oil, sperm oil, etc.; and synthetic oils, such as polymers of propylene, 'polyoxyalkylenes, polyoxypropylene, dicarboxylic acid esters, such as esters of adipic and azelaic acids with alcohols such as butyl, 2-ethyl hexyl and dodecyl alcohols, and esters of acids of phosphorus, such as diethyl ester of decanephosphonic acid and tricresyl phosphate.
  • mineral lubricating oil obtained by any of the conventional refining procedures
  • vegetable oils such as corn oil, cottonseed oil, castor oil, etc.
  • animal oil such as lard oil, sperm oil, etc.
  • synthetic oils such as polymers of propylene, 'polyoxy
  • the preferred nonvolatile carriers are liquid lubricating oils, either mineral or synethetic. If desired, the nonvolatile carriers may be diluted with a solvent to reduce the viscosity. Suitable solvents include petroleum naphtha or hydrocarbons, such as hexane, heptane, octane, benzene, toluene, or xylene.
  • oil-soluble dispersing agents may be used.
  • suitable dispersing agents include the oil-soluble sulfonic acids, carboxylic acids, phosphorus sulfide-treated olefins, phenolic organic compounds, and metal salts thereof.
  • Preferred dispersing agents include the oil-soluble sulfonic acids, carboxylic acids, and metal salts thereof.
  • Sulfonates which are suitable are oil-soluble and include .alkyl sulfonates, alkaryl sulfonates, the so-called mahogany or natural soaps, and the like.
  • the mahogany soaps include, particularly, the oil-soluble aromatic sulfonates from petroleum. Many of the aromatic sulfonates have cycloalkyl (i.e., naphthenic) groups in the side chains attached to the benzene ring.
  • the mahogany soaps may include nonaromatic sulfonates produced in conventional sulfuric acid refining of lubricating oil distillates and from the industrial use of fuming sulfuric acid in the refining of petroleum.
  • oil-soluble mahogany sulfonates from petroleum is well understood in the art and is described in the literature.
  • the alkyl sulfonates require about 24 carbon atoms for oil solubility.
  • the alkaryl sulfonates require an alkyl portion totaling only about 18 carbon atoms.
  • the hydrocarbonportion of the sulfonate have a molecular weight between about 350 and 1,000.
  • this molecular weight is between 400 and 700.
  • Particularly useful sulfonates include diwaxbenzene sulfonates, diwaxtoluene sulfonates, and postdodecylbenzene sulfonates.
  • Postdodecylbenzene which consists of monoalkylbenzenes anddialkylbenzenes in the approximate mole ratio of 2 to 3, has typical properties as follows:
  • the wax used in making the wax aromatic sulfonate is obtained from different sources of crude petroleum oil.
  • Various grades of parafim wax are made with different melting points.
  • the 126128 F. (52.253.3 C.) melting point wax is a mixture of organic compounds with the molecular weight averaging in the range of 330-340. The average number of carbon atoms in this mixture of organic compound will be around 24. As the melting point of the wax decreases, the carbon content of the mixture will average as low as 18 or a little lower.
  • sulfonates which may be used in the process of this invention include, for example, monoand poly-wax substituted naphthalene sulfonates, dinonyl naphthalene sulfonates, diphenyl ether sulfonates, naphthalene disulfide sulfonates, diphenyl amine sulfonates, dicetyl thianthrene sulfonates, dilauryl beta-naphthol sulfonates, dicapryl nitro-naphthalene sulfonates, unsaturated paraffin wax sulfonates, hydroxy substituted paraffin wax sulfonates, tetra-amylene sulfonates, monoand poly-chloro substituted parafiin wax sulfonates, nitrosoparafiin wax sulfonates; cycloaliphatic sulfonates, such as lauryl
  • Suitable carboxylic acids include naphthenic acids such as the substituted cyclopentane monocarboxylic acids, the substituted cyclohexane monocarboxylic acids and the substituted aliphatic polycyclic monocarboxylic acids containing at least 15 carbon atoms.
  • Specific examples include cetyl cyclohexane carboxylic acids, dioctyl cyclopentane carboxylic acids, dilauryl decahydronaphthalene suitable.
  • sulfonates in- I stead of using the foregoing carboxylic acid soap as such, we may form those soaps in situ by adding the corresponding carboxylic acid to the mixture.
  • the phosphorus sulfide treated olefins (by the term olefins we mean to include also olefin polymers, e.g., polyisobutylene) and their oil-soluble metal salts which are suitable for use include, those customarily used in lubricating oil formulations as corrosion inhibitors and/ or detergents. Specifically, they include the potassium-polyisobutylene-phosphorus sulfide products described by U.S. Patent 2,316,080, issued on April 6, 1943, to Loane and Gaynor, and a similar material containing no metal made by addition of a phosphorus sulfide to wax olefins, as described in U.S. Patent 2,516,119, issued on July 25,
  • the phenolic organic compounds which may be used are the free oil-soluble phenolic compounds or the metal phenates thereof. Oil-solubility is imparted to such phenolic compounds by the presence in the molecule of at least nine aliphatic carbon atoms.
  • alkaryl substituted phenols such as alkyl-phenyl phenols
  • polyhydroxy alkyl- I aromatic compounds such as 20-carbon alkyl resorcinol, or poly-hydroxy alkyl-benzenes, such as, for example, octyl catechol, triiso-butyl pyrogallol, and the like
  • monohydroxy alkyl-naphthalenes such as 12-carbon alkyl alpha naphthol, and the like.
  • Alkyl substituted phenol sulfides containing at least S-alkyl carbon atoms such as iso amyl or nonyl phenol disulfide and the like may be used. Dinonyl phenol and nonyl phenol disulfide have been found to be preferred materials.
  • the amount of water which is incorporated in the dispersion mixture initially will be determined by (a) the amount which is stoichiometrically required to hydrolyze the metal alk-. oxide or 'alkoxide-carbonate complex to the correspond ing metal hydroxide, and (b) the amount of water in $X-.
  • the overbasing step (that is, the addition of the metal alkoxide intermediate to the dispersing agent solution) is conducted over a wide range of temperatures, generally at about 25 C. to about 100 C., and more preferably in the range of about 35 C. to about 65 C. Temperatures outside the broad range (25 C. to 100 C.) are generally not used, since they can lead to gel formation or to the formation of inorganic insoluble materials.
  • the volatile materials are removed by distillation from the reaction mixture.
  • gas blowing When it is desired to convert the majority of the metal hydroxide to the corresponding carbonate as previously explained, carbon :dioxide is used for blowing.
  • an inert gas such as nitrogen or helium is used for stripping purposes. The removal of the volatile solvent leaves -a bright fluid product which requires no additional filtration or centrifugation.
  • the relative amounts of the different components employed in the process are dependent upon the desired percent aotives and upon the base numbers desired in the final compositions. (The term percent active refers to the amount of the dispersing agent present in the composition.)
  • This amount of water corresponds to over 98 percent of the amount which should theoretically be yielded by the sodium hydroxide methyl Cellosolve reaction.
  • To the alcoholic sodium alcoholate solution was then added 55 grams of calcium chloride. This mixture was then refluxed for two hours, allowed to cool, and 22 grams of carbon dioxide was added to it by bubbling the gas through the reaction mixture over a twenty-minute period. The carbon dioxide was added as a gas below the surface of the liquid with stirring. The benzene was then removed from the mixture by distillation, and the calcium allcoxide solution was filtered. Three hundred and fifty-three grams of the filtrate was recovered and was a clear, light yellow liquid containing 5.66 percent calcium. This intermediate contained only 0.1 percent chloride and represents a conversion of over percent of the calcium chloride to calcium methoxy ethoxide-carbonate.
  • EXAMPLE 4 Preparation of magnesium methoxy ethoxide-carbonate The preparation of this product was carried out in the same manner as in Example 3, except that an equivalent amount of magnesium chloride was used instead of the calcium chloride. This yielded 381 grams of a clear, light yellow liquid which contained 3.01 percent magnesium and less than 0.1 percent chloride.
  • EXAMPLE 5 Preparation of zinc methoxy ethoxide The preparation of this product was carried out in the same manner as in Example 3, except that an equivalent amount of zinc chloride was used instead of calcium chloride and that the alkoxide was not converted to the carbonate. Also, the benzene was not stripped from the reaction mixture. This yielded 455 grams of a clear, pale yellow liquid containing 7.03 percent zinc.
  • EXAMPLE 6 Preparation of copper methoxy ethoxide The preparation of this product was carried out in the same manner as in Example 3 except that the alkoxide was not converted to the carbonate and that an equivalent 11 amount of cupric chloride was used instead of calcium chloride. A dark green liquid was obtained which contained 2.34 percent copper as the copper methoxy ethoxide.
  • EXAMPLE 7 Preparation of barium methoxy ethoxide The preparation of the barium methoxy ethoxide product was carried out in the same manner as in Example 3 except that the alkoxide was not converted to the car-' bonate and that an equivalent amount of barium chloride was used instead of calcium chloride. Three hundred and forty grams of a dark colored liquid containing 11.7 percent barium as the methoxy ethoxide was yielded.
  • EXAMPLE 8 Preparation of aluminum methoxy ethoxide
  • nickel methoxy ethoxide To a one-liter flask equipped for azeotropic distillation were charged 30.9 grams of sodium hydroxide, 400 milliliters'of methyl Celloso'lve and 150 milliliters of benzene. A total of 27.3 milliliters of benzene insoluble liquid was removed from the reaction mixture by azeotropic distillation. The reaction mixture was cooled slightly, and then 59.7 grams of nickel sulfate were added, and the mixture was refluxed for four hours. The insoluble solids were removed by filtration to yield a greenish-brown solution containing 3.04 percent nickel.
  • EXAMPLE 10 Preparation of nickel methoxy ethoxide To a 12-liter flask equipped with a fritted tube and an azeotropic distillation trap were charged 4800 milliliters of methyl Cellosolve and 1800 milliliters of benzene. Nitrogen was blown through the fritted tube to purge the system of oxygen. Five hundred grams of sodium hydroxide were then added to the benzene-alcohol mixture and the system was heated to reflux. A benzene insoluble liquid in the amount of 450 milliliters was removed by azeotropic distillation. The reaction mixture was then cooled while purging with nitrogen to maintain the light color of the sodium alkoxide solution.
  • EXAMPLE 11 Preparation of cobalt methoxy ethoxide-carbonate To a one-liter flask equipped for azeotropic distillation were added 30.9 grams of sodium hydroxide, 400 milliliters of methyl Cellosolve, and 150 milliliters of benzene. A total of 27.3 milliliters of benzene insoluble liquid was removed from the mixture of azeotropic distillation. The reaction mixture was then cooled and 59 grams of cobalt chloride were added. The reaction mixture was held at reflux temperature overnight and was then filtered to remove insoluble solids. A deep blue solution, weighing 451.4 grams and containing 5.08 percent cobalt, was recovered.
  • EXAMPLE 12 Preparation of cobalt methoxy ethoxide-carbonate To a one-liter flask equipped with a mechanical stirrer and equipped for azeotropic distillation were added 30.9 grams of sodium hydroxide, 108.2 grams of hydrated cobalt chloride (CoCl -6H O), 400 milliliters of methyl Cellosolve, and 1500 milliliters of benzene. The reactants were stirred and heated, and 82 milliliters of ben-' zene insoluble liquid were removed by azeotropic distillation. The product was filtered through Hyflo to. yield 341.5 grams of a bright blue solution. Solids began to form immediately, but the solution was stabilized by blowing with carbon dioxide to form the deep violetcolored cobalt methoxy ethoxide-carbonate which contained 1.32 percent cobalt.
  • CoCl -6H O hydrated cobalt chloride
  • EXAMPLE 13 Preparation of manganese methoxy ethoxide To a 500-milliliter flask equipped with mechanical stirrer, dropping funnel, thermometer, and reflux condenser were charged 30.6 grams of manganous sulfate and 50 milliliters of methyl Cellosolve. The contents of the flask were then heated to between C., and 207.6 grams of sodium methoxy ethoxide containing 4.5 percent sodium were added over a period of about two hours. The
  • the flask contents were held at the reflux temperature for thirty minutes before solvent removal.
  • the solvents were removed while heating the flask contents up to 150 C., whereupon carbon dioxide blowing was commenced while maintaining the temperature at approximately 150 C.
  • the bright, green-brown fluid obtained weighed 93.7 grams, was 30 percent active as nickel sulfonate and, by analysis, contained 7.34 percent nickel and had an acetic base number of 102.
  • EXAMPLE 17 Preparation of an oil soluble dispersion containing a basic nickel compound as the dispersoid
  • a tall oil fatty acid (3.39 milliequivalents of acid per gram)
  • 54.5 grams of 100 pale oil 45 grams
  • benzene 45 grams
  • 3.24 grams of water This amount of water was 1.1 times the theoretical amount required to completely hydrolyze the nickel which was available for over-basing.
  • the benzene was present as a process solvent.
  • the reaction mixture was heated to 50 C., and 266 grams of nickel methoxy ethoxide containing 2.74 percent nickel were added.
  • the flask was equipped for distillation, and the solvents were removed to a flask content temperature of 150 C. Carbon dioxide blowing was then used to carbonate the overbasing material and assist in solvent removal.
  • the bright green product weighed 93.3 grams and contained 7.74 percent nickel. This corresponds theoretically to the anticipated 30 percent active, 100 base number product.
  • EXAMPLE 18 Preparation of an oil-soluble dispersion containing basic zinc compounds
  • a total of 167 grams of zinc methoxy ethoxide containing 7.02 percent zinc were added over a twenty-five minute period at a temperature of 47 C.
  • the mixture was heated to 150 C. and the volatile solvents removed.
  • the product was then blown with carbon dioxide for about twenty minutes at 150 C.
  • the product was a bright fluid and had a light yellow color.
  • This procedure produced a 30 percent zinc sulfonate dispersion with a base number of 50, which contained 6.1 percent zinc.
  • the particle size as determined by electron microscope of the zinc sulfonate was less than 0.1 micron.
  • EXAMPLE 19 Preparation of an oil-soluble dispersion containing basic nickel compound as the dispersoid
  • To a one-liter flask equipped as described in Example 16 were charged 25 grams of 2-ethyl hexanoic acid, 12.5 grams of pale oil, 100 milliliters of benzene, and 1.95 grams of water. This amount of water was 1.1 times the theoretical amount required to completely hydrolyze the nickel which was available for overbasing.
  • the benzene served as a process solvent.
  • the reaction mixture was heated to 51 C., and 153.7 grams of nickel methoxy ethoxide containing 5.19 percent nickel were added.
  • the flask was equipped for distillation, and the solvents were removed to a flask content temperature of C.
  • Nitrogen blowing was used to assist in solvent removal.
  • the flask contents were then lowered to 153 C. and carbon dioxide blowing was utilized to carbonate the overbasing material.
  • 35 milliliters of isopropanol were added to improve the fluidity.
  • the 81.2 grams of product were filtered through Hyfio, and the bright green product containing 10.14 percent nickel, This corresponds to a theoretical 63 base number product.
  • the particles in the dispersons produced by the present invention have been described as being colloidal in size. This term is meant to include particles in the range of 0.001 to 1.0 micron.
  • step (a) being characterized further in that the cobalt alkoxide-carbonate complex and the metal alkoxide of step (a) are prepared by a process comprising:
  • step (i) reacting an alcohol solution of an alkali metal alkoxide, wherein the alkoxide radical is selected from the group consisting of alkoxide radicals derived from monoethers of ethylene glycol containing not more than 8 carbon atoms and alkoxide radicals derived from monoethers of diethylene glycol containing not more than 8 carbon atoms, with a metal salt, wherein the metal of said metal salt is selected from the group consisting of cobalt and the metals defined in step (a) above, to form an alkoxide of the metal of said metal salt, said metal salt being characterized further in that the corresponding alkali metal salt is less soluble in the alcohol solution than is said metal salt.
  • the preparation of the colbalt alkoxide-carbonate complex includes the additional step of blowing the solution containing cobalt alkoxide with carbon dioxide to form said cobalt alkoxide-carbonate complex.
  • step (i) the anion of said meta-1 salt is selected from the group consisting of halide, nitrate, sulfate, acetate, ammonium phosphate, bromate, carbonate, citrate, cyanide, dithionate, formate, iodate, nitrite, oxy- 1 late, phosphate, silicate, sulfide, sulfite, tartrate, aluminate, antimonate, arsenate, bismuthate, borate, chromate,
  • manganate manganate, molybdate, selenate, tungstate, uranate, and vanadate.
  • step (a) the oil-soluble dispersing agent is selected from the group consisting of sulfonic acids, metal sulfonates, carboxylic acids, metal carboxylates, phosphorus sulfide-treated olefins, metal salts of phosphorus sulfide-treated olefins, phenolic organic compounds, and metal salts of phenolic organic compounds.
  • step (a) the nonvolatile carrier is selected from the group consisting of mineral lubricating oils'and synthetic lubricating oils.
  • metal of said metal compound, and of said metal alkoxide is selected from the group consisting of cadmium, copper, chromium, manganese, nickel and 6.
  • metal alkoxide is derived from .methoxy ethanol.
  • oil-soluble dispersing agent is selected from the group consisting of oil-soluble sulfonic acids and oil-soluble metal sulfonates.
  • an alcohol-soluble metal-containing intermediate selected from the group consisting of cobalt alkoxide-carbonate complexes and metal alkoxides, wherein the metal of said metal alkoxide is selected from the group consisting of silver, arsenic, bismuth, cadmium, chromium, copper, iron, mercury, manganese, molybdenum, nickel, lead, antimony, tin, vanadium, zinc and zirconium, an oil-soluble dispersing agent selected from the group consisting of sulfonic acids and metal sulfonates, a nonvolatile carrier selected from the group consisting of mineral lubricating oils and synthetic lubricating oils, and water, in an amount in excess of the stoichiometric amount required to hydrolyze all of said alcoholsoluble metal-containing intermediate in the admixture;
  • step (a) said process being characterized further in that the cobalt alkoxide-carbonate complex and the metal alkoxide of step (a) are prepared by a process comprising: 7
  • step (i) reacting an alkali metal hydroxide with an alcohol selected from the group consisting of monoethers of ethylene glycol containing not more than 8 carbon atoms and monoethers of diethylene glycol containing not more than 8 carbon atoms to form an alkali metal alkoxide and water in said alcohol, (ii) removing water from the reaction mixture by azeotropic distillation, and (iii) reacting a metal salt, wherein the metal of said metal salt is selected from the group consisting of cobalt and the metals defined in step (a) above and wherein the anion of said metal salt is selected from the group consisting of halide, nitrate, sulfate, acetate, ammonium phosphate, bromate, carbonate, citrate, cyanide, dithionate,-formate, iodate, nitrite, oxylate, phosphate, silicate, sulfide, sulfite, tartrate, aluminate, antimonate, ar
  • step (ii) uranate and vanadate, with the alkali metal alkoxide of step (ii) to form an alkoxide of the metal of said metal salt, said metal salt being characterized 'further in that the corresponding alkali metal salt is less soluble in-the alcohol solution than in said metal salt,
  • preparation of the cobalt alkoxide-carbonate complex includes the additional step of blowing the solution containing cobalt alkoxide with carbon dioxide to form said cobalt alkoxide-carbonate complex.

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NL281035D NL281035A (zh) 1961-07-17
US124315A US3277002A (en) 1961-07-17 1961-07-17 Process for stably dispersing metal compounds
US124389A US3141745A (en) 1961-07-17 1961-07-17 Dehazing polymer-containing hydrocarbon oils
GB22117/62A GB997335A (en) 1961-07-17 1962-06-07 Process for preparing inorganic dispersions
FR903272A FR1337804A (fr) 1961-07-17 1962-07-06 Procédé de fabrication de produits intermédiares d'alcoxydes métalliques solubes dans l'alcool, convenant pour leur conversion ultérieure en dispersions huileuses stables
BE636928A BE636928Q (fr) 1961-07-17 1963-09-03 Procédé de fabrication de produits intermédiaires d'alcoxydes métalliques solubles dans l'alcool, convenant pour leur conversion ultérieurs en dispersions huileuses stables

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US3907906A (en) * 1972-03-29 1975-09-23 Continental Oil Co Process of recovering alcohols and oil from waste mixtures
US3915727A (en) * 1973-03-05 1975-10-28 Continental Oil Co Method for selectively modifying the permeability of subterranean formation
US4104180A (en) * 1975-05-23 1978-08-01 Exxon Research & Engineering Co. Production of overbased metal phenates
US4295981A (en) * 1979-07-27 1981-10-20 Burnop Victor C Production of overbased magnesium detergent additives
US4837190A (en) * 1986-05-09 1989-06-06 Akzo America Inc. Organic solvent soluble polyvalent metal alkoxy alkoxides
US4847239A (en) * 1987-12-07 1989-07-11 Texas Alkyls, Inc. Hydrocarbon soluble copper alkoxide compositions
EP0382376A1 (en) * 1989-02-03 1990-08-16 General Atomics Method for the preparation of high purity copper alkoxides
US5059703A (en) * 1987-12-07 1991-10-22 Texas Alkyls, Inc. Hydrocarbon soluble copper alkoxide compositions
US5104997A (en) * 1988-09-30 1992-04-14 Fmc Corporation Mass treatment of cellulosic materials
US5143633A (en) * 1989-06-19 1992-09-01 Societe Nationale Elf Aquitaine Overbased additives for lubricant oils containing a molybdenum complex, process for preparing them and compositions containing the said additives
EP0560087A1 (de) * 1992-03-12 1993-09-15 Hoechst Aktiengesellschaft Verfahren zur Stabilisierung ethanolischer Ethylmagnesiumcarbonat-Lösungen
EP0597210A1 (de) * 1992-11-07 1994-05-18 Hüls Aktiengesellschaft Lagerstabile Lösungen von carbonisiertem Magnesiumethylat in Ethanol sowie deren Herstellung und Verwendung
US7615519B2 (en) 2004-07-19 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US7615520B2 (en) 2005-03-14 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antioxidant properties
US7682526B2 (en) 2005-12-22 2010-03-23 Afton Chemical Corporation Stable imidazoline solutions
US7709423B2 (en) 2005-11-16 2010-05-04 Afton Chemical Corporation Additives and lubricant formulations for providing friction modification
US7767632B2 (en) 2005-12-22 2010-08-03 Afton Chemical Corporation Additives and lubricant formulations having improved antiwear properties
US7776800B2 (en) 2005-12-09 2010-08-17 Afton Chemical Corporation Titanium-containing lubricating oil composition

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US3907691A (en) * 1974-07-15 1975-09-23 Chevron Res Extreme-pressure mixed metal borate lubricant
USRE32235E (en) * 1976-04-29 1986-08-26 The Lubrizol Corporation Magnesium-containing complexes, method for their preparation, and compositions containing the same
US4200544A (en) * 1976-04-29 1980-04-29 The Lubrizol Corporation Magnesium-containing greases and method for their preparation
US4260500A (en) * 1979-02-21 1981-04-07 The Lubrizol Corporation Magnesium-containing complexes, method for their preparation, and compositions containing the same
US4253976A (en) * 1979-02-21 1981-03-03 The Lubrizol Corporation Magnesium oxide-carboxylate complexes, method for their preparation, and compositions containing the same
CA1290314C (en) * 1986-01-21 1991-10-08 David E. Ripple Lubricant composition containing transition metals for viscosity control
FR2716891B1 (fr) * 1994-03-03 1996-06-14 Inst Francais Du Petrole Produits colloïdaux contenant du calcium, du baryum et/ou du magnésium ainsi que du bismuth, modifiés par action d'acides carboxyliques contenant du soufre et éventuellement de l'azote.
FR2810341B1 (fr) * 2000-06-19 2003-03-28 Ge Energy Products France Snc Utilisation de composes du nickel comme inhibiteurs de la corrosion vanadique et procede de combustion mettant en oeuvre de tels composes du nickel
US20080168709A1 (en) * 2007-01-16 2008-07-17 Aradi Allen A Safe combustion additives and methods of formulation
CN114369482A (zh) * 2021-12-29 2022-04-19 烟台大学 一种纳米级超滑粉体减摩添加剂制备和使用方法

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US2125961A (en) * 1937-08-16 1938-08-09 Standard Oil Co Color stable viscous hydrocarbon oil
US2229528A (en) * 1938-03-23 1941-01-21 Standard Oil Co Stabilized hydrocarbon oil
US2252664A (en) * 1938-07-16 1941-08-12 Socony Vacuum Oil Co Inc Alkyl substituted metal aryl hydroxylate-metal carboxylate salts and a method of making them
US2585520A (en) * 1948-12-03 1952-02-12 Shell Dev Lubricating compositions containing highly basic metal sulfonates
US2671758A (en) * 1949-09-27 1954-03-09 Shell Dev Colloidal compositions and derivatives thereof
US2676925A (en) * 1950-12-30 1954-04-27 California Research Corp Method of dispersing metal oxides and hydroxides in lubricating oils
GB774683A (en) * 1952-11-03 1957-05-15 Anglamol Ltd Improvements in or relating to lubricating compositions
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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3907906A (en) * 1972-03-29 1975-09-23 Continental Oil Co Process of recovering alcohols and oil from waste mixtures
US3915727A (en) * 1973-03-05 1975-10-28 Continental Oil Co Method for selectively modifying the permeability of subterranean formation
US4104180A (en) * 1975-05-23 1978-08-01 Exxon Research & Engineering Co. Production of overbased metal phenates
US4295981A (en) * 1979-07-27 1981-10-20 Burnop Victor C Production of overbased magnesium detergent additives
US4837190A (en) * 1986-05-09 1989-06-06 Akzo America Inc. Organic solvent soluble polyvalent metal alkoxy alkoxides
US4847239A (en) * 1987-12-07 1989-07-11 Texas Alkyls, Inc. Hydrocarbon soluble copper alkoxide compositions
US5059703A (en) * 1987-12-07 1991-10-22 Texas Alkyls, Inc. Hydrocarbon soluble copper alkoxide compositions
US5104997A (en) * 1988-09-30 1992-04-14 Fmc Corporation Mass treatment of cellulosic materials
EP0382376A1 (en) * 1989-02-03 1990-08-16 General Atomics Method for the preparation of high purity copper alkoxides
US5143633A (en) * 1989-06-19 1992-09-01 Societe Nationale Elf Aquitaine Overbased additives for lubricant oils containing a molybdenum complex, process for preparing them and compositions containing the said additives
EP0560087A1 (de) * 1992-03-12 1993-09-15 Hoechst Aktiengesellschaft Verfahren zur Stabilisierung ethanolischer Ethylmagnesiumcarbonat-Lösungen
US5326897A (en) * 1992-03-12 1994-07-05 Hoechst Aktiengesellschaft Process for the stabilization of ethanolic ethylmagnesium carbonate solutions
EP0597210A1 (de) * 1992-11-07 1994-05-18 Hüls Aktiengesellschaft Lagerstabile Lösungen von carbonisiertem Magnesiumethylat in Ethanol sowie deren Herstellung und Verwendung
US5456801A (en) * 1992-11-07 1995-10-10 Huels Aktiengesellschaft Storage-stable solutions of carbonated magnesium ethylate in ethanol and their preparation and use
US7615519B2 (en) 2004-07-19 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antiwear properties
US7615520B2 (en) 2005-03-14 2009-11-10 Afton Chemical Corporation Additives and lubricant formulations for improved antioxidant properties
US7709423B2 (en) 2005-11-16 2010-05-04 Afton Chemical Corporation Additives and lubricant formulations for providing friction modification
US7776800B2 (en) 2005-12-09 2010-08-17 Afton Chemical Corporation Titanium-containing lubricating oil composition
US7682526B2 (en) 2005-12-22 2010-03-23 Afton Chemical Corporation Stable imidazoline solutions
US7767632B2 (en) 2005-12-22 2010-08-03 Afton Chemical Corporation Additives and lubricant formulations having improved antiwear properties

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GB997335A (en) 1965-07-07
FR1337804A (fr) 1963-08-12

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