US3396106A - Lubricants and liquid hydrocarbon fuels containing synergistic mixtures of substituted tetrahydropyrimidines and amine salts of succinamic acids - Google Patents

Lubricants and liquid hydrocarbon fuels containing synergistic mixtures of substituted tetrahydropyrimidines and amine salts of succinamic acids Download PDF

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Publication number
US3396106A
US3396106A US519410A US51941066A US3396106A US 3396106 A US3396106 A US 3396106A US 519410 A US519410 A US 519410A US 51941066 A US51941066 A US 51941066A US 3396106 A US3396106 A US 3396106A
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Prior art keywords
base gasoline
plus
component
carbon atoms
lubricants
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US519410A
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English (en)
Inventor
Jr Harry J Andress
Capowski Julius
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ExxonMobil Oil Corp
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Mobil Oil Corp
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Application filed by Mobil Oil Corp filed Critical Mobil Oil Corp
Priority to US519410A priority Critical patent/US3396106A/en
Priority to GB471/67A priority patent/GB1129782A/en
Priority to DE19671645880 priority patent/DE1645880C/de
Priority to NL676700323A priority patent/NL151732B/xx
Priority to FR90565A priority patent/FR1510281A/fr
Priority to BE692417D priority patent/BE692417A/xx
Priority to AT25967A priority patent/AT269323B/de
Application granted granted Critical
Publication of US3396106A publication Critical patent/US3396106A/en
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
    • 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
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
    • C10M2201/103—Clays; Mica; Zeolites
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/105—Silica
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    • 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
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • 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
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    • 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
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    • 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
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/286—Esters of polymerised unsaturated acids
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    • 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
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    • 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
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • R and R are aliphatic hydrocarbon radicals having from about 8 to about 22 carbon atoms, and from about 1 to about 22 carbon atoms, respectively, and
  • R is a monovalent aliphatic hydrocarbon radical containing from about 4 to about 30 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom, with (b) a primary monoalkyl amine, wherein the alkyl group contains from about 4 to about 30 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom.
  • This invention relates to improved organic compositions and, in one of its aspects, relates more particularly to improved organic compositions in the form of liquid and solid hydrocarbons that are normally susceptible to deterioration by corrosion or oxidation. Still more particularly, in this aspect, the invention relates to improved organic compositions in the form of petroleum distillate hydrocarbon fuels, lubricating oils and greases which, in their uninhibited state, tend to react with and corrode metal surfaces with which they may come into contact in performing their intended functions.
  • Another object of the invention is to provide improved organic compositions in the form of liquid and solid hydrocarbons containing an additive which is adapted to prevent corrosion and oxidative deterioration of metallic surfaces.
  • Still another object of the invention is to provide an effective antioxidant and corrosion inhibiting agent for incorporation into the aforementioned organic compositions.
  • R and R are aliphatic hydrocarbon radicals having from about 8 to about 22 carbon atoms, and from about 1 to about 22 carbon atoms, respectively, and
  • R is a monovalent aliphatic hydrocarbon radical containing from about 4 to about 30 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom, with (b) a primary monoalkyl amine, wherein the alkyl group contains from about 4 to about 30 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom.
  • the present invention in its preferred applications, contemplates organic compositions which are normally susceptible to oxidative and corrosive deterioration, containing a small amount of the aforementioned additive mixture, usually from about .001 to about 10 percent, by weight, of the total of such compositions.
  • this additive is incorporated into liquid hydrocarbon compositions, such as jet fuels, turbine fuels, gasolines and the like, or in lubricating oils, it is preferably employed in an amount from about .001 to about .01 percent, by weight, of the total composition.
  • the additive is incorporated into a hydrocarbon grease composition, it is preferably employed in an amount from about 0.1 to about 5 percent, by weight, of the total grease.
  • the organic compounds improved in accordance with the present invention may comprise any materials that are normally susceptible to deterioration by oxidation or corrosion, in the manner previously described.
  • a field of specific applicability is the improvement of liquid hydrocarbons in accordance with the present invention, boiling from about F. to about 750 F.
  • distillate fuel oils having an initial boiling point from about 75 F. to about 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.
  • 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 are 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 MIL-F-5-624B.
  • 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 the aforementioned additives, an antioxidation and anticorrosion agents.
  • the aforementioned additives may also be incorporated, as anti-corrosion agents, in grease compositions.
  • Such greases may comprise a combination of a 'wide variety of lubricating vehicles and thickening or gelling agents.
  • greases in which the aforementioned additives 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.
  • oils may have viscosity indexes varying from below 0 to about 100 or higher. Viscosity indexes from about 70 to about 95 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 sufficient 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 included 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 100 F., and particularly those fallingwithin 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, chain-type 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 additive mixtures 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 non-soap 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 a particular environment; however, in all other respects, any material which is normally employed for thickening or gelling hydrocarbon fluids for forming grease, can be used in preparing the aforementioned improved grease in accordance with the present invention.
  • the di-substituted tetrahydropyrimidine component of the novel additive mixtures of the present invention is prepared, in general, by condensing one mole of a straightchain carboxylic acid (either substituted or unsubstituted) having an aliphatic hydrocarbon radical, containing from about 1 to about 22 carbon atoms, with one mole of a straight-chain diamine, having an aliphatic hydrocarbon radical containing from about 8 to about 22 carbon atoms.
  • the reaction may be represented by the following general equation:
  • R is an aliphatic hydrocarbon radical having from about 8 to about 22 carbon atoms
  • R is an aliphatic hydrocarbon radicaLhaving from about 1 to about 22 carbon atoms.
  • the afore-mentioned condensation reaction is, in general, carried out at an elevated temperature, and, preferably, at a temperature from about 250 C. to about 310 C.
  • Example 1 A mixture of 128 grams (0.5 mol) palmitic acid, 200 grams 0.5 mol) of a mixture of tallow N-alkyl tIimethylene diamines, containing aliphatic hydrocarbon radicals having from 16 to 18 carbon atoms (commercially available under the trade name Diam 26 and manufactured by General Mills) and grams of xylene, was refluxed at a temperature from about C. to about 250 C. for a period of about six hours. The temperature was maintained at 250" C. until the evolution of water had ceased. The resulting product comprised a mixture of tallow (C to C pentadecyl substituted tetrahydropyrimidines.
  • Example 2 A mixture of 200 grams (0.5 mol) of hydroxyphenyl stearic acid, 200 grams (0.5 mol) of the aforementioned Diam 26 of Example 1, and 100 grams of xylene, was refiuxed at a temperature from about 140 C. to about 280 C. for a period of about six hours. The temperature was maintained at 280 C. until the evolution of waterhad ceased. The resulting product comprised a mixture of tallow (C to C hydroxyphenylheptadecyl substituted tetrahydropyrimidines.
  • Example 3 A mixture of 130 grams (0.5 mol) palmitic acid, 200 grams (0.5 mol) of oleyl diamine (commercially available under the trade name Formonyte 808 and manufactured by Foremost Food and Chemical Co.), and 100 grams of xylene, was refluxed at a temperature from about 140 C. to about 260 C. for a period of about six hours. The temperature was maintained at 260 C. until the evolution of water had ceased. The resulting product was an oleyl pentadecyl substituted tetrahydropyrimidine.
  • oleyl diamine commercially available under the trade name Formonyte 808 and manufactured by Foremost Food and Chemical Co.
  • Example 4 A mixture of 151 grams (0.53 mol) of oleic acid, 207 grams (0.53 mol) of the aforementioned Formonyte 808 of Example 3, and 100 grams of xylene, was refluxed at a temperature from about 140 C. to about 260 C. for a period of about six hours. The temperature was maintained at 260 C. until the evolution of water had ceased. The resulting product was an oleylheptadecenyl substituted tetrahydropynimidine.
  • Example 5 A mixture of 128 grams (0.5 mol) palmitic acid, 200 grams (0.5 mol) of N aminopropyl oleyl amine, and 100 grams of xylene was refluxed at a temperature from about 140 -C. to-about 290 C. for a period of about eight hours. The temperature was maintained at 290 C. until the evolution of water had ceased. The resulting product was a pentadecyl substituted tetrahydropyrirnidine.
  • the other'component of the novel additive mixtures of the present invention is, in general, prepared by reacting, at elevated temperature, succinic acid anhydride with a primary monoalk-yl amine having a tertiary carbon atom attached to the nitrogen atom, and containing from about 4 to about 30, and preferably from about 12 to about 15, carbon atoms per molecule, to form the corresponding succinamic acid.
  • the succinamic acid, thus produced is then reacted, at elevated temperature, with an additional quantity of the aforementioned amine to form the corresponding amine salt.
  • novel additives of the present invention comprise mixtures of the aforementioned (l) the'disubstituted tetrahydropyrimidine, and (2) the amine salt of the aforementioned succinamic acid and primary monoalkyl amine.
  • the novel additives of the present invention comprise mixtures of the aforementioned (l) the'disubstituted tetrahydropyrimidine, and (2) the amine salt of the aforementioned succinamic acid and primary monoalkyl amine.
  • a particularly effective additive agent comprises a mixture in which components (1) and (2) are individually present in an amount from about 10 to about percent, by weight, of the additive mixture.
  • Component (2) in the examples comprised a mixture of amine salts produced by reacting a mixture of the aforementioned succinamic acids (a), wherein R was a monovalent aliphatic hydrocarbon radical containing from about 12 to about 15 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom, with a mixture of :primary monoalkyl amines (b), wherein the alkyl group contained from about 12 to about 15 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom.
  • a succinamic acids
  • R was a monovalent aliphatic hydrocarbon radical containing from about 12 to about 15 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom
  • b primary monoalkyl amines
  • the deposit-forming tendencies of a fuel are determined in an 8-hour engine test. This accelerated test, when run on fuels that contain no detergents, produces an amount of deposit equivalent to the amount observed in 4,000 miles of operation in field tests on taxicab fleets.
  • a sixcylinder Chevrolet engine is equipped with notched rings to increase the amount of blowby. Engine is operated for 8 hours, using the fuel under test, at alternate idle and running cycles. In the idle cycle, the engine is run at idling speed of 400 r.p.m. with no load, for five minutes. Then, for one minute, the engine is run at a speed of 2500 r.p.m. under a load of 30 B.H.P. and at 9.4 in mercury manifold pressure.
  • the blowby and part of the exhaust are released into the carburetor air intake during the idling cycle.
  • Base gasoline 0 Base gasoline plus Ex. 1. 4 Base gasoline plus 6 Component (2). Base gasoline plus Ex. 1 [2 lbs. each of Ex. 1
  • Base gasoline 0 Base gasoline plus Ex. 3... 4.
  • Base gasoline 0 Severe rust. Base gasoline plus Ex 4.-. 6 0. Base gasoline plus Com- 6 Light rust.
  • Base gasoline 0..- Severe rust. Base gasoline plus Ex. 10. 0. Base gasoline plus Com- 6--.- Light rust.
  • synergistic mixture of the addition agents of the present invention are effective in inhibiting gasoline fuels against rusting.
  • Organic compositions selected from the group consisting of lubricants and liquid hydrocarbon fuels containing a small amount, sufiicient to inhibit corrosion, of a synergistic mixture consisting essentially of from about to about 90% by weight of each of:
  • R is a monovalent aliphatic hydrocarbon radical containing from about 4 to about 30'carbon atoms and having a tertiary carbon atom directly attached. to the nitrogen atom, with (b) a'primary monoalkyl amine, wherein the alkyl group contains from-about 4 to about 30 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom.
  • composition in accordance with claim 1 wherein said composition comprises a lubricant comprises a lubricant.
  • composition in accordance with claim 1 wherein said composition is a liquid hydrocarbon comprising a petroleum distillate fuel oil having an initial boiling point from'about 75 F. to about t35 F. and an endboiling point from about 250 F. to about 750 F.
  • R and R are aliphatic hydrocarbon-radicals having from about 8 to about 22 carbon atoms, and from about 1 to about 22 carbon atoms, respectively,
  • R is a monovalent aliphatic hydrocarbon-radical containing from about 4 to about 30 carbon atoms-and having a tertiary carbon atom directly attached to.
  • alkyl group contains from about 4 to about 30 carbon atoms and having a tertiary carbon atom directly attached to the nitrogen atom.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)
US519410A 1966-01-10 1966-01-10 Lubricants and liquid hydrocarbon fuels containing synergistic mixtures of substituted tetrahydropyrimidines and amine salts of succinamic acids Expired - Lifetime US3396106A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US519410A US3396106A (en) 1966-01-10 1966-01-10 Lubricants and liquid hydrocarbon fuels containing synergistic mixtures of substituted tetrahydropyrimidines and amine salts of succinamic acids
GB471/67A GB1129782A (en) 1966-01-10 1967-01-04 Stabilised lubricant and fuel compositions
DE19671645880 DE1645880C (de) 1966-01-10 1967-01-09 KohlenwasseTStoffgemisch auf Eidol basis zur Verwendung als Brennol, Heizöl, Kraftstoff, Schmieröl oder Schmierfett
NL676700323A NL151732B (nl) 1966-01-10 1967-01-09 Werkwijze ter bereiding van organische samenstellingen onder toepassing van een toevoegsel voor het tegengaan van de oxyderende en/of corroderende werking.
FR90565A FR1510281A (fr) 1966-01-10 1967-01-10 Compositions organiques perfectionnées
BE692417D BE692417A (fr) 1966-01-10 1967-01-10
AT25967A AT269323B (de) 1966-01-10 1967-01-10 Brennstoff-, Schmier- und Fettzusammensetzungen

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NL (1) NL151732B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4273664A (en) * 1978-06-02 1981-06-16 Snamprogetti S.P.A. Rust-preventing agent for aqueous systems and rust-inhibiting lubricating compositions
US4495076A (en) * 1984-05-03 1985-01-22 Mobil Oil Corporation Lubricating oil composition containing reaction product of tetrahydropyrimidines
US4498908A (en) * 1984-05-03 1985-02-12 Mobil Oil Corporation Liquid fuel composition containing reaction product of tetrahydropyrimidines

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2699427A (en) * 1952-10-02 1955-01-11 Gulf Oil Corp Mineral oil compositions containing amidic acids or salts thereof
US2844446A (en) * 1956-02-02 1958-07-22 Universal Oil Prod Co Stabilization of hydrocarbon distillates
US2987522A (en) * 1958-03-17 1961-06-06 Petrolite Corp Amidine products
US3024236A (en) * 1958-06-04 1962-03-06 Petrolite Corp Derivatives of pyrimidine and imidazoline
US3031282A (en) * 1958-01-07 1962-04-24 Socony Mobil Oil Co Inc Stabilized distillate fuel oil
US3089761A (en) * 1958-05-16 1963-05-14 Socony Mobil Oil Co Inc Fuel oil composition
US3251854A (en) * 1963-05-29 1966-05-17 Rohm & Haas Cyclic amidines
US3251853A (en) * 1962-02-02 1966-05-17 Lubrizol Corp Oil-soluble acylated amine

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2699427A (en) * 1952-10-02 1955-01-11 Gulf Oil Corp Mineral oil compositions containing amidic acids or salts thereof
US2844446A (en) * 1956-02-02 1958-07-22 Universal Oil Prod Co Stabilization of hydrocarbon distillates
US3031282A (en) * 1958-01-07 1962-04-24 Socony Mobil Oil Co Inc Stabilized distillate fuel oil
US2987522A (en) * 1958-03-17 1961-06-06 Petrolite Corp Amidine products
US3089761A (en) * 1958-05-16 1963-05-14 Socony Mobil Oil Co Inc Fuel oil composition
US3024236A (en) * 1958-06-04 1962-03-06 Petrolite Corp Derivatives of pyrimidine and imidazoline
US3251853A (en) * 1962-02-02 1966-05-17 Lubrizol Corp Oil-soluble acylated amine
US3251854A (en) * 1963-05-29 1966-05-17 Rohm & Haas Cyclic amidines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4273664A (en) * 1978-06-02 1981-06-16 Snamprogetti S.P.A. Rust-preventing agent for aqueous systems and rust-inhibiting lubricating compositions
US4388199A (en) * 1978-06-02 1983-06-14 Snamprogetti S.P.A. Aqueous rust-inhibiting and lubricating compositions
US4495076A (en) * 1984-05-03 1985-01-22 Mobil Oil Corporation Lubricating oil composition containing reaction product of tetrahydropyrimidines
US4498908A (en) * 1984-05-03 1985-02-12 Mobil Oil Corporation Liquid fuel composition containing reaction product of tetrahydropyrimidines

Also Published As

Publication number Publication date
BE692417A (fr) 1967-07-10
FR1510281A (fr) 1968-01-19
NL6700323A (fr) 1967-07-11
NL151732B (nl) 1976-12-15
GB1129782A (en) 1968-10-09
DE1645880A1 (de) 1970-05-27
AT269323B (de) 1969-03-10

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