US3544463A - Overbased oil-soluble metal salts - Google Patents

Overbased oil-soluble metal salts Download PDF

Info

Publication number
US3544463A
US3544463A US785394A US3544463DA US3544463A US 3544463 A US3544463 A US 3544463A US 785394 A US785394 A US 785394A US 3544463D A US3544463D A US 3544463DA US 3544463 A US3544463 A US 3544463A
Authority
US
United States
Prior art keywords
grams
carbon dioxide
oil
equivalents
mixture
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
Application number
US785394A
Other languages
English (en)
Inventor
Emil Koft Jr
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.)
ExxonMobil Oil Corp
Original Assignee
Mobil Oil Corp
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 Mobil Oil Corp filed Critical Mobil Oil Corp
Application granted granted Critical
Publication of US3544463A publication Critical patent/US3544463A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/24—Epoxidised acids; Ester derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/26—Overbased carboxylic acid salts
    • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/20—Containing nitrogen-to-oxygen bonds
    • C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
    • C10M2227/081—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds with a metal carbon bond belonging to a ring, e.g. ferocene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Definitions

  • Overbased oil-soluble metal salts are prepared by reacting a mixture comprising an oil-soluble organic acid, an alcohol and a diluent with sequential addition, under intermediate refluxing, of a metal oxide and carbon dioxide under anhydrous conditions and in the presence of a halide. Liquid hydrocarbon fuels and lubricants containing the above described salts are also provided.
  • This invention relates to overbased oil-soluble metal salts and their use as neutralizing agents and dispersants in liquid hydrocarbon fuels and lubricants.
  • the invention relates to the preparation of overbased oil-soluble metal salts which possess increased proportions of the oil-dispersible metal. More particularly, in this aspect, the invention relates to the preparation of overbased oil-soluble metal salts possessing increased proportions of the oil-dispersible metal over that of the normal salt, to the extent that such salts are sufficiently basic as to eflect complete neutralization and dispersancy of liquid hydrocarbon fuels and lubricants, such as motor fuels, heating oils, lubricating oils and greases.
  • Oil-soluble metal salts have found utility as additives in liquid hydrocarbon fuels and lubricants for neutralizing the corrosive effects of acidic products encountered in fuels employed in modern internal combustion engines, for example, gasoline and diesel engines, or in lubricating oils and grease compositions in which such oils are employed as lubricating vehicles.
  • the aforementioned salts it has been found, however, that the normal oil-soluble metal salt possesses insufficient basicity to obtain the desired neutralizing effect in the aforementioned liquid hydrocarbon fuels and lubricants, either in the course of consumption or extended use.
  • highly overbased oil-soluble salts are prepared, as more fully hereinafter discussed by reacting a mixture comprising an oilsoluble organic acid, an alcohol and a diluent with sequential addition, under intermediate refluxing, of a metal 3,544,463 Patented Dec. 1, 1970 oxide and carbon dioxide, in which the reaction is conducted under anhydrous conditions and in the presence of a halide.
  • These overbased salts have a metal content ratio of at least 1.5 and, preferably, as high as about 15 to 20 or higher, and a total base number (TBN), as hereinafter defined, from about 50 to about 500.
  • step-wise addition of the metal oxide and carbon dioxide, with intermediate refluxing, to a solution of a mixture of the organic acid and alcohol, in the presence of a diluent is carried out, in which the mixture comprises one equivalent of the acid, at least about 0.1 equivalent of the alcohol, and wherein the metal oxide is present in an amount of at least 1.5 equivalents, and wherein carbon dioxide is present in a ratio from about 0.1:1 to about 1:1 per equivalent of the metal oxide.
  • the overbasing is conducted under anhydrous conditions, as previously indicated, and in the presence of a halide, capable of releasing a halogen ion, which is added prior to carbonation, in any desired amount, in order to permit incorporation of the carbon dioxide.
  • the halide is employed in any desired amount and, preferably, in an amount from about 0.2% to about 5%, by weight of the amount of metal oxide present.
  • an important feature of the present invention in carrying out the overbasing reaction resides in conducting this treatment under intermediate refluxing of the metal oxide and carbon dioxide and in conducting the reaction under anhydrous conditions.
  • the organic acid employed in the preparation of the novel overbased salts of the present invention may comprise any oil-soluble organic acid or mixtures of such acids, and particularly preferred are sulfonic acids such as oil-soluble petroleum sulfonic acids, including mahogany sulfonic acids, alkylated aromatic sulfonic acids, paraffin wax sulfonic acids, mono-wax (eicosane)-substituted naphthalene sulfonic acid, petroleum naphthene sulfonic acids, polyisobutylene sulfonic acids, monoand poly-wax or other alkyl substituted benzene sulfonic acids, monoand poly-wax or other alkyl substituted naphthalene sulfonic acids, monoand poly-wax or other substituted cyclohexyl sulfonic acids, and their mixtures, dodecylbenzene sulfonic acids, didodecylbenzene s
  • Carboxylic acids may also be employed as the oilsoluble organic acid and may include aliphatic or aromatic acids. Exemplary of such acids are palmitic acid, stearic acid, myristic acid, oleic acid, linoleic acid, behenic acid, hexatriacontanoic acid, tetrapropylene-substituted glutaric acids, polyisobutene-substituted succinic acids, such as polybutenylsuccinic anhydride, polypropylene-substituted succinic acids, octadecyl-substituted adipic acids, chlorostearic acid, 9-methylstearic acid, dichlorostearic acid, stearylbenzoic acid, poly-Wax(eicosane)-substituted naphthoic acids, dilauryl-decahydronaphthylene carboxylic acid, didodecyltetralin
  • the alcohol employed in the preparation of the novel overbased salts of the present invention may comprise any alcohol having as much as 30 carbon atoms per molecule.
  • the lower alkanols are preferred, viz, C to'C alkanols, of which methanol is most preferable.
  • these alcohols may be monohydric or polyhydric. They may also include lower alkoxyethanols, such as Z-methoxyethanol, 2-ethoxyethanol, Z-propoxyethanol, 2-butoxyethanol, and tetrahydro furfuryl alcohol.
  • alcohols that can be employed, include ethanol, isopropanol, cyclohexanol, decanol, d'odecanol, behenyl alcohol, glycols, including ethylene glycol, diethylene glycol and triethylene glycol, the mono-methylether of ethylene glycol, trimethylene glycol, glycerol, pentaerythritol, benzyl alcohol, sorbitol, phenylethyl alcohol, nitropropanol, chloroethanol, aminoethanol, cinnamyl alcohol, and allyl alcohol.
  • glycols including ethylene glycol, diethylene glycol and triethylene glycol, the mono-methylether of ethylene glycol, trimethylene glycol, glycerol, pentaerythritol, benzyl alcohol, sorbitol, phenylethyl alcohol, nitropropanol, chloroethanol, aminoethanol, cinnamyl alcohol, and allyl alcohol.
  • the diluent employed in the preparation of the overbased salts is preferably a volatile hydrocarbon diluent and may include liquid aromatic and saturated aliphatic hydrocarbons, for example, toluene, xylene, and heptane, generally having boiling points between about 170 and 300 F. These diluents may, therefore, also include such materials as benzene, halogenated aromatic hydrocarbons, such as chlorobenzene or other materials which are normally inert to the reactants. In some instances a process oil diluent, viz, a 100" at 100 F. refined pale paraflin oil may be employed in conjunction with the aforementioned volatile hydrocarbon diluent.
  • process oils which may be used as a diluent include a wide variety of mineral oils, such as naphthenic or paraffinic oils; alkylene polymers, such as polypropylene; and ester oils of polycarboxylic acids and phosphorus acids.
  • mineral oils such as naphthenic or paraffinic oils
  • alkylene polymers such as polypropylene
  • ester oils of polycarboxylic acids and phosphorus acids include a wide variety of mineral oils, such as naphthenic or paraffinic oils; alkylene polymers, such as polypropylene; and ester oils of polycarboxylic acids and phosphorus acids.
  • the volatile liquid inert diluent facilitates the interaction of the reactants as well as the filtration of the crude overbased metal salt-oil concentrate.
  • such amount is, of necessity, based upon the composition of the initial reaction mixture. Amounts varying between about and about 40 weight percent have been found satisfactory.
  • the metal oxide employed for producing the overbased metal salts may comprise an alkaline earth metal base and may include the oxide of calcium, magnesium, barium,
  • Calcium oxide is generally preferred.
  • hydroxides of the aforementioned metals as well as bicarbamates, sulfides, hydrides, formates, mercaptides, alcoholates, and phenates of the aforementioned metals.
  • hydroxides alone of the aforementioned metals results in the production of products which are unsatisfactory with respect to clarity and filterability.
  • the metal oxide is employed in its anhydrous form.
  • the preferred form of the oxide is calcium oxide.
  • Calcium oxide having a mesh size of from 30 to 325, and preferably 90 to 325, is most desirable. Most preferred is the use of calcium oxide having minimum mesh size of about 90.
  • the calcium oxide employed in the following examples was of technical grade and contained about 97.5% calcium oxide.
  • this overbasing reaction is conducted in the presence of a halide, as preferably indicated, which is capable of releasing a halide ion.
  • a halide as preferably indicated, which is capable of releasing a halide ion.
  • inorganic and organic compounds may be employed.
  • metal halides e.g., zinc chloride, stannous chloride, cobalt halides, sodium chloride, sodium bromide, sodium iodide, potassium iodide, calcium chloride, barium chloride, and calcium bromide.
  • halides suitable for this purpose include amine hydrocarbon halides, sulfur halides, ammonium halides, chloranil, guanidine hydrochloride, chloral hydrate and sulfonylchlorides. Particularly preferred are the inorganic halides.
  • the overbasing reaction is carried out by first forming a mixture of the oil-soluble organic acid, alcohol, metal oxide, diluent and halide. Through this mixture, maintained at a temperature below the boiling point of the alcohol, e.g., from about 50 C. to about C., and preferably from about 50 C. to about 55 C., is passed carbon dioxide gas to the extent where inlet and outlet rates are equal. At this point the introduction of carbon dioxide gas in discontinued and the reaction mixture is heated to reflux temperature, e.g., from about 60 C. to about 70 C., and is maintained at this temperature until the desired extent of refluxing has taken place.
  • a temperature below the boiling point of the alcohol e.g., from about 50 C. to about C., and preferably from about 50 C. to about 55 C.
  • the temperature of the reaction mixture is then lowered, e.g., to about 50 C., and additional metal oxide is added.
  • the addition of the metal oxide is then followed by further carbonation employing additional carbon dioxide gas.
  • More diluent is added, if necessary, and the temperature of the reaction mixture is raised sufficiently high to effect removal of the volatile components by distillation, e.g., 150 C. Vacuum is then applied and the reaction mixture is held under reduced pressure at this temperature for a desired period of time.
  • Example 1 A mixture of 150 grams (0.196 equivalents of crackedwax benzene sulfonic acid, 40 grams (0.102 equivalents) of dodecyl phenol sulfide (prepared by the reaction of dodecyl phenol with sulfur dichloride in a mole ratio of 6:5) as a solution in chlorobenzene (75% active), 150 cc. methanol (3.71 equivalents), 550 cc. chlorobenzene (5.4 equivalents), 70 grams calcium oxide (2.4 equivalents), 4 grams calcium formate (.061 equivalents) and 2 grams of anhydrous ammonium chloride (.037 equivalents) was carbonated at the rate of 400 cc. per minute and at a temperature from about 50 C. to about 55 C.
  • Example 2 The same mixture, as described in Example 1, was carbonated, under the previously described conditions, to result in a carbon dioxide increase of 52 grams in the first treatment step.
  • the introduction of carbon dioxide gas was then discontinued and the reaction mixture was then heated to reflux temperature (60-68 C.) and held at this temperature for a period of 30 minutes.
  • the temperature was then lowered to 50 C. and a second charge of calcium oxide (70 grams) was added.
  • This addition was followed by carbonation with a further quantity of carbon dioxide gas and resulted in a carbon dioxide gain of 45 grams, making a total gain of 97 grams.
  • 135 grams of the aforementioned diluent oil of Example 1 was added and the mixture was heated to a temperature of 150 C. to remove volatile components by distillation.
  • the reference to the total base number of the salt (TBN) in the foregoing and subsequent examples indicates the amount of calcium available for neutralizing acids. This value is found by titrating the product with perchloric acid, the base number being reported in terms of milligrams of KOH per gram of sample.
  • Example 3 A mixture of 145 grams (0.19 equivalents) of a cracked-wax benzene sulfonic acid, 40 grams (0.102 equivalent) of dodecyl phenol sulfide (prepared by the reaction of dodecyl phenol with sulfur dichloride in a mole ratio of 6:5) as a solution in chlorobenzene (75% active), 125 cc. methanol (3.09 equivalents), 500 cc. chlorobenzene (4.9 equivalents), 85 grams calcium oxide (2.91 equivalents), 2.5 grams calcium formate (.038 equivalent) and 1.3 grams of anhydrous zinc chloride (.019 equivalent), was carbonated at a temperature from about 50 C. to about 55 C. until no further absorption was observed.
  • Clay filter aid material was then added and the chlorobenzene solution was filtered.
  • the solvent was removed from the filtrate by distillation at a temperature of 150 C. Vacuum was applied (28" of Hg) and the reaction mixture was held under reduction pressure for a period of 30 minutes at 15 C. After release of the vacuum to the atmosphere, the resulting product was obtained in an amount of 431 grams of a bright material, having the following analysis:
  • Example 4 The same procedure utilizing the same reactants employed in Example 3 was repeated except that 2.2 grams of stannous chloride instead of 1.3 grams of zinc chloride was employed. The total uptake of carbon dioxide was 102 grams (4.64 equivalents). The resulting product,
  • Example 5 A mixture of 230 grams (0.301 equivalent) of a crackedwax benzene sulfonic acid, 125 cc. methanol (3.09 equivalents), 500 cc. chlorobenzene (4.9 equivalents), 75 grams calcium oxide (2.67 equivalents), and 4 grams of stannous chloride was carbonated at a temperature from about 50 C. until no further carbon dioxide gas was absorbed. The introduction of carbon dioxide gas was then discontinued and the reaction mixture was then heated to reflux temperature (60-70 C.) and held at this temperature for a period of 30 minutes. The temperature was then lowered to 50 C. and a second charge of 70 grams (2.5 equivalents) of calcium oxide was added.
  • Example 6 A mixture of 230 grams (0.301 equivalent) of cracked-wax benzene sulfonic acid, 40 grams (0.049 equivalent) of an oil solution of nonylphenol sulfide (present in an amount of 35%, by weight, in a SUS at 100 F., pale paraflin oil diluent), 200 cc. chlorobenzene (1.96 equivalents), 100 cc. methanol (2.5 equivalents), 75 grams calcium oxide (2.67 equivalents), 4 grams calcium formate (.06, equivalent), and 4 grams of guanidine hydrochloride was carbonated in accordance with the procedure of Example 2 and the reaction mixture was then heated to reflux temperature (60-70 C.) and held at this temperature for a period of 30 minutes.
  • an oil solution of nonylphenol sulfide present in an amount of 35%, by weight, in a SUS at 100 F., pale paraflin oil diluent
  • 200 cc. chlorobenzene (1.96 equivalents)
  • Example 7 The same procedure utilizing the same reactants employed in Example 6 was repeated, except that 80 grams of calcium oxide (2.85 equivalents) was employed, in place of the 75 grams of calcium oxide of Example 6, and 2 grams of chloranil was employed, instead of the 4 grams of guanidine hydrochloride of Example 6. After carbonation and refluxing had taken place, there were added 80 grams (2.85 equivalents) of additional calcium oxide, and an additional 1 gram of chloranil. This addition was followed by carbonation with a further quantity of carbon dioxide gas and resulted in a total carbon dioxide gain of 109 grams. 160 grams of the diluent oil of Example 1 was added and the mixture was heated to a temperature of 150 C. to remove volatile components by distillation.
  • Example 8 The same procedure utilizing the same reactants employed in Example 7 was repeated, except that no calcium formate was employed and 10 grams of chloral hydrate was employed to replace the quanidine hydrochloride. The final product was obtained in an amount of 454 grams of a bright material, having the following analysis:
  • Example 9 A mixture of 81 grams (0.094 equivalent) of polypropylene (800 molecular weight), phosphonic acid (2.7% P), 150 cc. chlorobenzene (1.45 equivalents), 60 cc. (1.47 equivalents) methanol and 6 grams (0.15 equivalent) calcium hydroxide was refluxed for a period of 30 minutes. The reaction mixture temperature was then lowered to 50 C; and 11 grams (0.38 equivalent) calcium oxide and 0.5 gram ammonium chloride were added to the mixture. The mixture was then carbonated at a temperature from about 50 C. to about 55 C. until the inlet and outlet rate were equal.
  • Example 10 A mixture of 88.5 grams (0.306 equivalents) of a tall oil, and 500 ml. (4.9 equivalents) of chlorobenzene was stirred in a flask and then, with stirring, 125 ml. (3.09 equivalents) of methanol was added. An amount of 20.5 grams (0.89 equivalents) of calcium oxideand 1.0 gram 0.0187 equivalents) of ammonium chloride were added to the stirred flask contents. The resulting mixture was heated to 50-55 C. and carbon dioxide addition was started. The carbon dioxide addition required 45 minutes. The carbon dioxide uptake was determined as 11 grams (0.5 equiva lents) and then the mixture was refluxed at 65 C. for a period of 30 minutes.
  • Hy-flo filter aid Ten grams was added to the stripped product and the resulting mass was filtered hot through a 0.5 bed of Hyflo filter aid under house vacuum.
  • the final product was a clear, amber fluid having the following analysis:
  • Example I A mixture of 145 grams (0.19' equivalents) crackedwax (C -C benzene sulfonic acid, 30 grams (0.10 equivalents) nonyl phenol sulfide, cc. methanol, 500 cc. chlorobenzene,, 80 grams (2.78 equivalents) calcium oxide, 4 grams (0.06 equivalents) calcium for-mate and 2 grams (0.037 equivalents) ammonium chloride was carbonated with gaseous carbon dioxide at 50-55 C. until no further absorption was observed. Carbonation was discontinued and the clear reaction mixture was heated to reflux and held at this temperature (62-69 C.) for a half hour. The reaction was then cooled to 50 C.
  • the carbon dioxide are added in a sequential or step-wise manner, under intermediate reflux and under anhydrous conditions until .the desired amount of overbasing is achieved.
  • the significance of observing these criteria is apparent when it is noted, as in Example 1, where the reaction is conducted without intermediate reflux, an unfilterable, semi-solid, product is obtained.
  • This refluxing is essential in order to decompose the product produced by the reaction of the metal oxide and carbon dioxide. Omission of such refluxing causes a gelling or thickening of the resulting product, impairing its use as a neutralizaing agent in the aforementioned fuels and lubricants.
  • Another critical feature in the preparation of the overbased salts of the present invention resides in conducting the reaction under substantially anhydrous conditions.
  • the Overbased metal salts of the present invention contemplates the use of these salts as neutralizing agents in liquid hydrocarbon fuels and lubricants.
  • these salts may' be employed in any minor proportion, and particularly in concentrations ranging from about .001 to about 50%, by weight, of the total fuel or lubricant composition. More specifically, when incorporated into liquid hydrocarbon fuels, e.g., jet fuels, diesel fuels, turbine fuels, gasolines or the like, these salts are preferably employed in amounts from about .001 to about 0.1% by weight, of the total fuel composition. When incorporated in hydrocarbon grease compositions, they are preferably employed in an amount from about 0.1 to about by weight, of the total grease composition.
  • distillate fuel oils having an initial boiling point from about 75 F. to about 135 F. and an end boiling point from about 250 F. to about 750 F.
  • distillate fuel oils is not intended to be restricted to straight-run distillate fractions.
  • These distillate fuel oils can be straight-run distillate fuel oils, catalytically or thermally cracked (including hydrocracked) distillate fuel oils, or mixtures of straight-run distillate fuel oils, naphthas and the like, with cracked distillate stocks.
  • such fuel oils can be treated in accordance with well-known commercial methods, such as acid or caustic treatment, hydrogenation, solvent-refining, clay treatment, and the like.
  • distillate fuel oils are characterized by their relatively low viscosity, pour point and the like.
  • the principal property which characterizes these contemplated hydrocarbons, however, is their distillation range. As hereinbefore indicated, this range will lie between about 75 F. and about 750 F. Obviously, the distillation range of each individual fuel oil will cover a narrower boiling range, falling, nevertheless, within the above-specified limits. Likewise, each fuel oil will boil substantially, continuously, throughout its distillation range.
  • fuel oils Nos, 1, 2 and 3 fuel oils, used in heating and as Diesel fuel oils, gasoline and the jet combustion fuels, as previously indicated.
  • the domestic fuel oils generally conform to the specifications set forth as ASTM Specification D396-48T.
  • Specifications for Diesel fuels are defined in ASTM Specification D975-48T.
  • Typical jet fuels are defined in Military Specification Ml1.F5624'B.
  • hydrocarbon lubricating oils of varying viscosity and pour points, falling both within and outside the indicated ranges for the aforementioned fuel oils may also be effectively treated through the use of these salts.
  • the aforementioned greases may comprise a combination of a Wide variety of lubricating vehicles and thickening or gelling agents.
  • greases in which the aforementioned salts are particularly effective may comprise any of the conventional hydrocarbon oils of lubricating viscosity, as the oil vehicle, and may include mineral or synthetic lubricating oils, aliphatic phosphates, esters and diesters, silicates, siloxanes and oxalkyl ethers and esters.
  • Mineral lubricating oils, employed as the lubricating vehicle may be of any suitable lubricating viscosity range from about 45 SSU at 100 F. to about 6,000 SSU at 100 F., and preferably, from about 50 to about 250 SSU at 210 F.
  • oils may have viscosity indexes varying from below 0 to about 100 or higher. Viscosity indexes from about 70 to about are preferred. The average molecular weights of these oils may range from about 250 to about 800,
  • the lubricating oil is employed in the grease composition in an amount suflicient to constitute the balance of the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be inclined in the grease formulation.
  • the oil vehicles employed in the novel grease formulations of the present invention may comprise mineral or synthetic oils of lubricating viscosity.
  • mineral oils having a viscosity of at least 40 SSU at F, and particularly those falling within the range from about 60 SSU to about 6,000 SSU at 100 F. may be employed.
  • synthetic vehicles are employed rather than mineral oils, or in combination therewith, as the lubricating vehicle, various compounds of this type may be successfully utilized.
  • Typical synthetic vehicles include: polypropylene, propylene, glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(2-ethyl hexyl) sebacate, di- (Z-ethyl hexyl) adipate, di-butyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chaintype polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis (p-phenoxy phenyl) ether, phenoxy phenyl ethers, etc.
  • the lubricating vehicles of the aforementioned improved greases of the present invention containing the above-described salts are combined with a grease-forming quantity of a thickening agent.
  • a thickening agent for this purpose, a wide variety of materials may be employed.
  • These thickening or gelling agents may include any of the conventional metal salts or soaps, which are dispersed in the lubricating vehicle in grease-forming quantities, in such degree as to impart to the resulting grease composition, the desired consistency.
  • Other thickening agents that may be employed in the grease formation may comprise the nonsoap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials.
  • grease thickeners may be employed which do not melt and dissolve when used at the required temperature within the particular environment; however, in all other respects, any material which is normally employed for thickening or gelling hydrocarbon fluids for forming greases, can be used in preparing the aforementioned improved grease in accordance with the present invention.
  • An overbased oil-soluble metal salt prepared by the process which comprises the steps of:
  • step (2) reacting carbon dioxide under substantially anhydrous conditions with the mixture of step (1) at a temperature not higher than about the boiling point of said alcohol until the inlet and outlet rates are equal, wherein the carbon dioxide-alkaline earth metal oxide ratio is from about 0.121 to about 1:1,
  • step (6) reacting carbon dioxide under substantially anhydrous conditions with the mixture of step (5) at a temperature not higher than the boiling point of said alcohol until the inlet and outlet rates are equal,
  • step (6) heating the mixture of step (6) to a temperature at least as high as the boiling point of said diluent to remove volatile ingredients
  • An overbased oil-soluble salt as defined in claim 1, wherein said diluent comprises a halogenated aromatic hydrocarbon.
  • An overbased oil-soluble salt as defined in claim 1, wherein said halide is selected from the group consisting of ammonium and metal halides.
  • mixture of step (1) contains as additional components, eflective amounts of at least one member selected from the group consisting of dodecyl phenol sulfide, calcium formate, nonyl phenol sulfide, and polybutenyl succinic anhydride.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
US785394A 1968-12-19 1968-12-19 Overbased oil-soluble metal salts Expired - Lifetime US3544463A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US78539468A 1968-12-19 1968-12-19

Publications (1)

Publication Number Publication Date
US3544463A true US3544463A (en) 1970-12-01

Family

ID=25135378

Family Applications (1)

Application Number Title Priority Date Filing Date
US785394A Expired - Lifetime US3544463A (en) 1968-12-19 1968-12-19 Overbased oil-soluble metal salts

Country Status (6)

Country Link
US (1) US3544463A (nl)
BE (1) BE743368A (nl)
DE (1) DE1963803A1 (nl)
FR (1) FR2026567A1 (nl)
GB (1) GB1233327A (nl)
NL (1) NL6918972A (nl)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4066561A (en) * 1974-01-04 1978-01-03 Mobil Oil Corporation Organometallic compounds and compositions thereof with lubricants
US4083792A (en) * 1976-01-02 1978-04-11 Mobil Oil Corporation Overbased metal complexes and compositions thereof with lubricants
US4328111A (en) * 1978-11-20 1982-05-04 Standard Oil Company (Indiana) Modified overbased sulfonates and phenates
US4698170A (en) * 1983-07-11 1987-10-06 Rhone-Poulenc Recherches Process for the preparation of very highly alkaline, calcium-based detergent-dispersant additives and products produced therefrom
US4775490A (en) * 1987-07-30 1988-10-04 The Lubrizol Corporation Magnesium overbasing process
US4847457A (en) * 1984-02-24 1989-07-11 Ciba-Geigy Corporation Methylphosphonic acid amine salt lubricant additives
US4957642A (en) * 1987-12-29 1990-09-18 Exxon Chemical Patents Inc. Magnesium phenate detergents
US5032299A (en) * 1987-07-30 1991-07-16 The Lubrizol Corporation Magnesium overbasing process
US5037565A (en) * 1973-10-05 1991-08-06 The Lubrizol Corporation Basic alkali metal sulfonate dispersions, process for their preparation, and lubricants containing same
US5259966A (en) * 1992-11-10 1993-11-09 The Lubrizol Corporation Low chlorine overbased calcium salts
US5281345A (en) * 1989-07-26 1994-01-25 Bp Chemicals (Additives) Limited Process for the preparation of a lubricating oil additive concentrate with an organic halide catalyst
US5330665A (en) * 1982-05-22 1994-07-19 Bp Chemicals (Additives) Limited Production of either an alkaline earth metal alkyl phenate or a sulphurised alkaline earth metal alkyl phenate
US5384053A (en) * 1988-06-04 1995-01-24 Bp Chemicals (Additives) Limited Production of a lubricating oil additive concentrate
US5401424A (en) * 1993-10-04 1995-03-28 The Lubrizol Corporation Mixed carboxylate overbased gels
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
US5519076A (en) * 1994-02-24 1996-05-21 Nissan Ferro Organic Chemical Co, Ltd. Halogen-containing resin composition
US5714443A (en) * 1986-11-29 1998-02-03 Bp Chemicals (Additives) Limited Sulphurised alkaline earth metal hydrocarbyl phenates, their production and use thereof
US6090759A (en) * 1986-11-29 2000-07-18 Lubrizol Adibis Holdings (Uk) Ltd. Alkaline earth metal hydrocarbyl phenates, their sulphurized derivatives, their production and use thereof
US6153565A (en) * 1996-05-31 2000-11-28 Exxon Chemical Patents Inc Overbased metal-containing detergents
US6281179B1 (en) * 1996-05-31 2001-08-28 Infineum Usa L.P. Process for preparing an overbased metal-containing detergents
CN1074453C (zh) * 1996-05-31 2001-11-07 埃克森美孚化学专利公司 高碱性含金属清净剂
US6429178B1 (en) * 1996-05-31 2002-08-06 Infineum Usa L.P. Calcium overbased metal-containing detergents
US6429179B1 (en) * 1996-05-31 2002-08-06 Infineum U.S.A. L.P. Calcium overbased metal-containing detergents

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1299253A (en) * 1970-05-12 1972-12-13 Exxon Research Engineering Co Detergent compositions
GB1469289A (en) * 1974-07-05 1977-04-06 Exxon Research Engineering Co Detergent additives
FR2529226B1 (fr) * 1982-06-24 1987-01-16 Orogil Procede de preparation d'alkylphenates sulfurises de metaux alcalino-terreux utilisables comme additifs pour huiles lubrifiantes
DE3406447C2 (de) * 1984-02-22 1995-03-16 Christian Bartenbach Abschirmung für eine Leuchte mit stabförmiger Lampe
US4882662A (en) * 1987-02-17 1989-11-21 Siemens Aktiengesellschaft Grid of lamellae for a lamp

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2881206A (en) * 1957-04-08 1959-04-07 Sinclair Refining Co Process for preparing stable high detergency barium sulfonates
US3014866A (en) * 1958-12-29 1961-12-26 California Research Corp Lubricating oil compositions
US3256186A (en) * 1963-02-12 1966-06-14 Lubrizol Corp Process for producing carbonated basic metal compositions
US3347790A (en) * 1965-07-01 1967-10-17 Lubrizol Corp Lubricating compositions containing metal salts of acids of phosphorus

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2881206A (en) * 1957-04-08 1959-04-07 Sinclair Refining Co Process for preparing stable high detergency barium sulfonates
US3014866A (en) * 1958-12-29 1961-12-26 California Research Corp Lubricating oil compositions
US3256186A (en) * 1963-02-12 1966-06-14 Lubrizol Corp Process for producing carbonated basic metal compositions
US3282835A (en) * 1963-02-12 1966-11-01 Lubrizol Corp Carbonated bright stock sulfonates and lubricants containing them
US3347790A (en) * 1965-07-01 1967-10-17 Lubrizol Corp Lubricating compositions containing metal salts of acids of phosphorus

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5037565A (en) * 1973-10-05 1991-08-06 The Lubrizol Corporation Basic alkali metal sulfonate dispersions, process for their preparation, and lubricants containing same
US4066561A (en) * 1974-01-04 1978-01-03 Mobil Oil Corporation Organometallic compounds and compositions thereof with lubricants
US4083792A (en) * 1976-01-02 1978-04-11 Mobil Oil Corporation Overbased metal complexes and compositions thereof with lubricants
US4328111A (en) * 1978-11-20 1982-05-04 Standard Oil Company (Indiana) Modified overbased sulfonates and phenates
US5330665A (en) * 1982-05-22 1994-07-19 Bp Chemicals (Additives) Limited Production of either an alkaline earth metal alkyl phenate or a sulphurised alkaline earth metal alkyl phenate
US4698170A (en) * 1983-07-11 1987-10-06 Rhone-Poulenc Recherches Process for the preparation of very highly alkaline, calcium-based detergent-dispersant additives and products produced therefrom
US4847457A (en) * 1984-02-24 1989-07-11 Ciba-Geigy Corporation Methylphosphonic acid amine salt lubricant additives
US5714443A (en) * 1986-11-29 1998-02-03 Bp Chemicals (Additives) Limited Sulphurised alkaline earth metal hydrocarbyl phenates, their production and use thereof
US6090759A (en) * 1986-11-29 2000-07-18 Lubrizol Adibis Holdings (Uk) Ltd. Alkaline earth metal hydrocarbyl phenates, their sulphurized derivatives, their production and use thereof
US6090760A (en) * 1986-11-29 2000-07-18 Lubrizol Adibis Holdings (Uk) Ltd. Sulphurized alkaline earth metal hydrocarbyl phenates, their production and use thereof
US4775490A (en) * 1987-07-30 1988-10-04 The Lubrizol Corporation Magnesium overbasing process
US5032299A (en) * 1987-07-30 1991-07-16 The Lubrizol Corporation Magnesium overbasing process
US4957642A (en) * 1987-12-29 1990-09-18 Exxon Chemical Patents Inc. Magnesium phenate detergents
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
US5281345A (en) * 1989-07-26 1994-01-25 Bp Chemicals (Additives) Limited Process for the preparation of a lubricating oil additive concentrate with an organic halide catalyst
US5259966A (en) * 1992-11-10 1993-11-09 The Lubrizol Corporation Low chlorine overbased calcium salts
US5401424A (en) * 1993-10-04 1995-03-28 The Lubrizol Corporation Mixed carboxylate overbased gels
US5519076A (en) * 1994-02-24 1996-05-21 Nissan Ferro Organic Chemical Co, Ltd. Halogen-containing resin composition
US6153565A (en) * 1996-05-31 2000-11-28 Exxon Chemical Patents Inc Overbased metal-containing detergents
US6281179B1 (en) * 1996-05-31 2001-08-28 Infineum Usa L.P. Process for preparing an overbased metal-containing detergents
CN1074453C (zh) * 1996-05-31 2001-11-07 埃克森美孚化学专利公司 高碱性含金属清净剂
US6417148B1 (en) * 1996-05-31 2002-07-09 Infineum Usa L.P. Overbased metal-containing detergents
US6429178B1 (en) * 1996-05-31 2002-08-06 Infineum Usa L.P. Calcium overbased metal-containing detergents
US6429179B1 (en) * 1996-05-31 2002-08-06 Infineum U.S.A. L.P. Calcium overbased metal-containing detergents

Also Published As

Publication number Publication date
GB1233327A (nl) 1971-05-26
FR2026567A1 (nl) 1970-09-18
NL6918972A (nl) 1970-06-23
BE743368A (nl) 1970-06-18
DE1963803A1 (de) 1970-07-09

Similar Documents

Publication Publication Date Title
US3544463A (en) Overbased oil-soluble metal salts
US3216936A (en) Process of preparing lubricant additives
US5338470A (en) Alkylated citric acid adducts as antiwear and friction modifying additives
USRE29661E (en) Sulfurized metal phenates
US3256186A (en) Process for producing carbonated basic metal compositions
JP4768734B2 (ja) アルキルヒドロキシカルボン酸ホウ酸エステルを含む燃料及び潤滑添加剤
US3697499A (en) Polysulfurized olefins
JPH03501628A (ja) 改良された解乳化性を示す潤滑剤および機能流体組成物
US4057504A (en) Method of preparing overbased lubricating oil additives
EP0535149B1 (en) A process for preparing improved sulfurized olefin extreme pressure/anti-wear additives and compositions thereof
JPH0696610B2 (ja) 置換カルボン酸およびその誘導体の製造方法
US3474035A (en) Lubricating oil containing overbased sulfurized calcium alkylphenolate
US3557171A (en) Metal salts of reaction product of an alkyl phenol and an ethyleneamine
US3810837A (en) Overbased sulfurized calcium alkylphenolate manufacture
US2785128A (en) Metal salts of organic acids of phosphorus
US5039310A (en) Polyether substituted mannich bases as fuel and lubricant ashless dispersants
US2766291A (en) Metal salts of alkyl phenol sulfides
JPH0832904B2 (ja) 組成物、コンセントレ−ト、潤滑剤組成物、燃料組成物、および内燃機関の燃料消費量を低減する方法
US3655560A (en) Fuels and lubricants containing aminoguanidine antioxidants
US2856361A (en) Superbasic alkaline earth metal sulfonates
US3210275A (en) Lubricating composition containing metal salts of hindered phosphorodithioates
US3117089A (en) Compositions of matter having anti-rust properties
US4985157A (en) Mixed alkoxylated alcohol-hydroquinone/resorcinol borates-antioxidants
US3350310A (en) Preparation of overbased calcium alkylphenate sulfides
US3864435A (en) Oligomeric phosphorodiamidate