US3658707A - Fuel oil and lubricating oil compositions - Google Patents

Fuel oil and lubricating oil compositions Download PDF

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Publication number
US3658707A
US3658707A US858505A US3658707DA US3658707A US 3658707 A US3658707 A US 3658707A US 858505 A US858505 A US 858505A US 3658707D A US3658707D A US 3658707DA US 3658707 A US3658707 A US 3658707A
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additive
carbon atoms
acid
groups
composition
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US858505A
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David James Delafield
Alan H Edwards
Keith Owen
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
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    • 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
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    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
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    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • 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
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    • 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
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation

Definitions

  • This invention relates to fuel or lubricating oil compositions and in particular gasoline compositions.
  • additives have been proposed for use in gasoline and other fuels which reduce corrosion and in the case of .gasoline act as anti-icing agents and carburettor detergents. Such additives have not however been completely successful when moisture is present in the fuel, since haze and emulsion problems can arise together with an unacceptable loss of the additive either into the aqueous phase or by adsorption onto tank or pipe line surfaces particularly when rust is present. Additives have also been proposed for use in lubricating oil compositions to reduce corrosion but frequently the pressure of such additives can further aggravate problems of emulsion formation When moisture is present particularly for example in steam turbine oils.
  • improved fuel or oil compositions comprise a major proportion by weight of a fuel or lubricating oil and a minor proportion by weight of (A) (i) a mono or poly-carboxylic acid which contains 10 to 60 carbon atoms per molecule, or an anhydride or an ester of such an acid; or (ii) the reaction product of said acid, anhydride or ester with a hydroxy or an amino compound, and a minor proportion by weight of (B) an ester of an alkoxylated phenolaldehyde resin, (A) and (B) preferably being dissolved in a diluent or solvent.
  • A a mono or poly-carboxylic acid which contains 10 to 60 carbon atoms per molecule, or an anhydride or an ester of such an acid; or (ii) the reaction product of said acid, anhydride or ester with a hydroxy or an amino compound, and a minor proportion by weight of (B) an ester of an alkoxylated phenolaldehyde resin
  • composition can contain any fuel, e.g. a kerosine, a gas oil, a distillate fuel such as a diesel fuel, an aviation jet fuel, the preferred fuel is a gasoline.
  • a fuel e.g. a kerosine, a gas oil, a distillate fuel such as a diesel fuel, an aviation jet fuel
  • the preferred fuel is a gasoline.
  • the gasoline can be a conventional gasoline for internal combustion engines, and these are supplied in a number of grades.
  • lSuch gasolines may consist of mixtures of hydrocarbons of various types, including aromatics, olefins, paraifins, isoparafiins naphthenes and sometimes diolefins.
  • the gasolines are derived from petroleum by refinnig processes such as fractional distillation, thermal cracking, steam cracking, catalytic cracking, catalytic reforming, polymerisation, hydroforming, alkylation and isomerization.
  • Motor gasolines usually boil between 25 and 225 C. when tested by ASTM Method D86.
  • Aviation gasolines are prepared by blending constituents similar to those found in motor gasolines but usually have narrower boiling ranges from about 37.5 C. to 165 C.
  • Suitable lubricating oils include animal, vegetable, or mineral oils, for example, petroleum oil fractions ranging from spindle oil to SAE 30, 40 or 50 lubricating oil grades; castor oil, fish oils, oxidised mineral oil or bright stocks.
  • Synthetic esters may also be used, e.g. diesters such as those prepared by esterifying carboxylic acids such as adipic or sebacic acid with monohydride alcohols; or complex esters obtained by the esterification of a polyhydric alcohol (e.g. a polyglycol) with a dibasic acid (e.g. sebasic acid or adipic acid) and a monohydride alcohol (e.g. 2-ethyl-hexanol or a C oxo alcohol).
  • a polyhydric alcohol e.g. a polyglycol
  • dibasic acid e.g. sebasic acid or adipic acid
  • monohydride alcohol e.g. 2-ethyl-hexan
  • additive (A) (i) is a monoor poly-carboxylic acid or an anhydride theerof it is preferably a compound represented by one of the following formulae wherein one of R and is a hydrocarbyl group containing 10 to 50 carbon atoms, and the other is either a hydrocarbyl group containing 10 to 50 carbon atoms, or hydrogen; X and Y are hydrogen atoms or hydrocarbyl groups and m is zero or an integer and n is zero or an integer. Of course R and must not be such that the total number of carbon atoms per molecule exceeds 60.
  • R is preferably an alkyl or an alkenyl group containing 12 to 20 carbon atoms and X and Y are preferably hydrogen atoms, and m and n are each preferably integers of between 1 and 5.
  • the groups R X and Y can be straight or branched chain, cyclic or acyclic, and although they may be aromatic they are preferably aliphatic.
  • Suitable examples of acid (1) are oleic acid, stearic acid, palmitic acid, and lauric acid.
  • acid (2) one may use polypropenyl, or polyisob-utenyl succinic acids, e.g. tetrapropenyl succinic acid.
  • anhydrides (3) and (4) include lauric anhydride and a polypropenyl succinic anhydride such as tetrapro penylsuccinic anhydride.
  • additive (A) (i) can be an ester of a monoor poly-carboxylic acid, and such esters include the esters of acids (1) and (2) described above. These esters are preferably derived from a low boiling alcohol e.g. one containing 1 to 5 car- HO (CXYh?
  • X, Y and Z are hydrocarbyl groups or hydrogen atoms and m is zero or an integer and n is zero or an integer, and R is a hydrocarbyl group containing 1 to 50 carbon'atoms, or a hydrocarbyl group containing 1 to 50 carbon and also one or more ether linkages, or may be hydrogen if both m and n are integers. Preferably neither m nor n exceeds 5.
  • Particularly suitable alcohols are monohydric alcohols, e.g. those containing less than 20 carbon atoms per molecule, especially monohydric alcohols containing from 4 to 12. carbon atoms per molecule.
  • suitable alcohols from which additive (A) is derived include butanol-l, pentanol-l, isooctanol, isodecanol or dodecanol-l.
  • the additive can be derived from a glycol, e.g., one containing 2 to 60 carbon atoms, for example ethylene glycol, butylene glycols, pinacone, tetramethylene glycol etc. in which case one mole of glycol reacts with two moles of acid or anhydride.
  • Aromatic alcohols e.g. benzyl alcohol, toluyl alcohol, may also be used; as may phenolic compounds, such as phenol itself, the cresols, xylols or catechol.
  • ether-alcohols which are for example obtained by reacting aliphatic alcohols with an alkylene oxide.
  • Suitable ether alcohols contain for example 2 to 40 carbon atoms per molecule, and include methoXy-methanol, ethoxy butanol, or ethoxyethanol.
  • Suitable amino compounds include p-, sor t-monoamines, diamines, polyamines, or hydroxyamino compounds.
  • Suitable amino compounds from which additive (A) (ii) may be derived include amines of the formulae where R R and R are alkyl, alkaryl or alkenyl groups containing 1 to 200 carbon atoms, or hydroxy or amino substituted alkyl or alkaryl groups containing 1 to 200 carbon atoms, or hydrogen atoms.
  • amides or salts of the following formulae are formed where R is as defined previously. At least one of the groups R R R and R should contain at least carbon, atoms, particularly between 12 and 20 carbon atoms.
  • Suitable nonamines are those of the formula R NH R3R4NH 0r R3R4R5N
  • R3, R4 and R5 BIC hydrocarbyl or substituted hydrocarbyl e.g. alkyl, cyclo alkyl, aryl, alkenyl, substituted aryl or heterocyclic radicals.
  • the groups R R or R can be for example octyl, nonyl, decyl, undecyl, pentadecyl, hexadecyl, octadecyl, eicosyl, octadecenyl, or octadecadienyl.
  • the groups R R and R can vary widely, and may for example contain from 1 to 30 carbon atoms, preferably 8-22 carbon atoms.
  • Aromatic monoamines include aniline, substituted anilines, benzylamine and naphthylamine.
  • Suitable heterocyclic amines include furyl amine, piperidine and N-vinyl pyrrolidone.
  • Suitable polyamines which can be used include aliphatic polyamines, and heterocyclic polyamines.
  • the preferred polyamines are alkylene polyamines, and hydroxy alkylene polyamines.
  • suitable polyalkylene polyamines are those compounds having the formula H N(RNH H where R is an alkylene radical or a hydrocarbyl substituted alkylene radical and y is an integer.
  • suitable polyamines are diethylene triamine, triethylene tetramine, or tetra-ethylene pentarnine.
  • hydroxyamino compounds which may be used include monohydroxyamines of the formula R4 R3'I IR6OH dihydroxyamines of the formula R OH R1011 or trihydroxyamines of the formula HO-RuN where R and R are hydrogen or hydrocarbyl groups and R R and R are divalent hydrocarbon, e.g. alkylene groups.
  • the groups R and R may be alkenyl, alkyl, cycloalkyl, or phenyl groups and the groups R R and R may be alkylene groups of the formula z). where x is preferably a whole number from 1 to 8.
  • hydroxyamino compounds should preferably contain from 1 to 40 carbon atoms.
  • monoalkanolamines especially where the nitrogen atom is substituted by alkyl groups, e.g. monoalkanolamines of the formula N n 0H where R and R are alkyl groups, e.g. C to C alkyl groups and R is an alkylene group, e.g. a C to C alkylene group.
  • R and R are alkyl groups, e.g. C to C alkyl groups and R is an alkylene group, e.g. a C to C alkylene group.
  • N,N diethyl ethanolamine or N,N dibutyl hexanolarnine may be used.
  • monoalkanolamines in which one or more of the alkyl groups also contains an amino substituent, i.e. amino alkyl monoalkanolamines, e.g. amino ethyl ethanolamine, amino propyl ethanolamine, amino propyl butanolamine, etc.
  • amino alkyl monoalkanolamines e.g. amino ethyl ethanolamine, amino propyl ethanolamine, amino propyl butanolamine, etc.
  • analogous amino alkyl dialkanolamines e.g. N-amino ethyl diethanolamine.
  • the additive (A) (ii) is preferably the reaction product of a hydroxy or an amino compound with a succinic acid, anhydride or ester which has been substituted by one or more hydrocarbyl groups.
  • Particularly suitable hydrocarbyl groups are alkenyl or alkyl groups, e.g. those containing from 3 to 55 carbon atoms, especially 10 to 40 carbon atoms.
  • the substituted succinic acid can be represented by the general formula where one of R and R is hydrogen, and the other is an alkenyl group.
  • the alkenyl group can be straight-chain or branched chain and is preferably derived from a polyolefin, e.g. polypropenyl, polyisobutenyl or polypentenyl, and preferably of MW 50 to 600.
  • this substituent group can be a hydrocarbyl group which itself is substituted by a small proportion (e.g. less than 10%) of other atoms or groups, e. g. halogen atoms or nitro groups.
  • anhydride or ester
  • an ester it is preferably derived from a low boiling alcohol, e.g. one containing 1 to carbon atoms per molecule.
  • a low boiling alcohol e.g. one containing 1 to carbon atoms per molecule.
  • the methyl, ethyl, propyl, butyl or pentyl esters should preferably be used.
  • esters represented by the formula 0 ca c 1 a ⁇ m where either one of the groups R and R is an alkenyl group containing from 8 to 40 carbon atoms and the other of the groups R and R is a hydrogen atom, and R is C to C alkyl group, or the group wherein R and R are C; to C alkyl groups and R is a C to C alkylene group, the total number of carbon atoms in the groups R R and R being from 4 to 12.
  • the mono-ester may conveniently be prepared by reaction of equimolar proportions of the substituted succinic acid or its anhydride with a mono-hydroxy compound. Usually simple admixture is suflicient, but when reacting a hydroxyamine with the substituted anhydride heating may be necessary.
  • additive (A) (ii) can be a mono-, di-, or polyester, or an amide, or an amidine.
  • additive (A) (ii) can be an ammonium or amine salt of the reaction product between an amino or hydroxy compound and a monoor poly-carboxylic acid, the anhydride thereof, of the ester thereof (e.g. a substituted succinic acid, anhydride or ester).
  • a monoor poly-carboxylic acid e.g. a monoor poly-carboxylic acid, the anhydride thereof, of the ester thereof (e.g. a substituted succinic acid, anhydride or ester).
  • ester e.g. a substituted succinic acid, anhydride or ester
  • additives (A)(ii) are the reaction products of a fatty acid (e.g. oleic acid, linoleic and stearic acid) and an amino alkyl monoalkanolamine, (e.g. amino ethyl ethanolamine, or amino propyl propanolamine).
  • a fatty acid e.g. oleic acid, linoleic and stearic acid
  • amino alkyl monoalkanolamine e.g. amino ethyl ethanolamine, or amino propyl propanolamine
  • the fuel or oil compositions of this invention may include mixtures of two or more of the above described additives (A) (i) and/or (A) (ii).
  • the phenol from which the ester of an alkoxylated phenolaldehyde resin (B) is derived may contain a substituent such as a hydrocarbyl or a substituted hydrocarbyl group or an acyl group.
  • This substituent may be in the para position with respect to the phenolic group, but can however be in the metaor ortho positions.
  • Substituted hydrocarbyl groups may be hydrocarbyl groups substituted with, for example, halogen atoms.
  • the hydrocarbyl group is unsubstituted.
  • This hydrocarbyl group can be an alkyl group, e.g. a branched chain alkyl group, but can also be, for example, an alkenyl group.
  • Particularly suitable substituted or unsubstituted hydrocarbon groups are those containing between 1 and 30 carbon atoms, e.g. methyl, t-butyl, hexyl, decyl, tetradecyl, octadecyl or stearyl, eicosyl, tetracosyl, hexacosyl or mixtures of these groups.
  • the phenol is condensed with an aldehyde.
  • the aldehyde is preferably formaldehyde, or para formaldehyde but other aldehydes, especially those containing not more than 25, e.g. less than 8 carbon atoms per molecule could be used instead, e.g. acetaldehyde, butyraldehyde, benzaldehyde, or propionaldehyde.
  • Furfuraldehyde may also be employed.
  • the phenol-aldehyde resin from which the ester is prepared may be prepared by methods well known in the art.
  • phenol-aldehyde resin is derived from phenol itself
  • a particularly suitable method of preparation is that given in Preparative Methods of Polymer Chemistry, Interscience Publishers Inc., New York by Sorenson and Campbell, p. 295 (1961 ed.) i.e. heating together phenol and aldehyde in the presence of an acid catalyst.
  • O.6O.95 moles of aldehyde be employed to every mole of phenol.
  • the alkylene oxide contains not more than 4 carbon atoms per molecule, e.g. ethylene oxide, propylene oxide or butylene oxide.
  • the resin may be reacted with the alkylene oxide in the presence of a catalyst, e.g. an alkaline catalyst such as sodium acetate, sodium hydroxide or sodium 'methvl ate.
  • a catalyst e.g. an alkaline catalyst such as sodium acetate, sodium hydroxide or sodium 'methvl ate.
  • the amount of alkaline catalyst may be small, e.g. between 0.1% and 2% by weight.
  • the reaction may take place under pressure, e.g. up to pressures of 20 atmospheres, and the reaction temperature may be as high as 200 C.
  • the alkoxylation is conveniently carried out in the presence of an inert solvent, e.g. xylene, Decalin, or diethyl ether.
  • an inert solvent e.g. xylene, Decalin, or diethyl ether.
  • the quantity of alkylene oxide reacted is from 1 to 2 moles per hydroxyl radical in the resin.
  • the alkoxylated phenolaldehyde resin is reacted with a carboxylic acid, or a derivative thereof, preferably a mono-carboxylic acid.
  • a carboxylic acid or a derivative thereof, preferably a mono-carboxylic acid.
  • mono-carboxylic acids containing between 8 and 32 carbon atoms per molecule, e.g. the higher fatty acids.
  • saturated fatty acids include lauuric acid, myristic acid, palmitic acid and stearic acid; whilst unsaturated fatty acids include oleic acid, linoleic acid and linolenic acid.
  • Additive (B) may if desired also incorporate a homopolymer of an alkylene oxide (e.g. ethylene oxide, propylene oxide) or a copolymer of a mixture of alkylene oxides (e.g. ethylene oxide and propylene oxide), formed by reaction with an alkanolamine such as methanolarnine, a dialkanolamine such as dipropanolamine.
  • an alkanolamine such as methanolarnine
  • a dialkanolamine such as dipropanolamine
  • the additives (A) and (B) may if desired be dissolved in a diluent, e.g. toluene, kerosine or xylene.
  • concentration may be, for example, around 25 to 75 wt. percent, e.g. 50 Wt. percent.
  • Suitable quantities of additives (A) and (B) are 0.00005 wt. percent to 0.025 wt. percent e.g. about 0.0025 wt. percent of (A) and 0.000005 to 0.025 wt. percent e.g. about 0.0005 wt. percent of (B) based on the total weight of the fuel composition.
  • suitable quantities are for example 0.005 wt. percent to 0.5 wt. percent, particularly 0.015 to 0.03 wt. percent of (A) and 0.005 to 0.5 wt. percent, particularly 0.025 to 0.25 wt. percent of (B), based on the total weight of the oil composition.
  • gasoline may also incorporate other additives.
  • gasoline may also contain anti-knock agents, e.g. tetra ethyl lead, halohydrocarbon scavengers, e.g. ethylene dibromide or ethylene dichloride, or deposit modifiers, e.g.
  • organic esters of oxy acids of phosphorus, or antioxidants e.g. 2,4-dimethyl-6-t-butyl phenol and N,N di sec butyl para phenylene diamine.
  • the ester was then mixed with about /3 its weight of copolymer of ethylene oxide and propylene oxide with diethanolamine having a MW of about 4000 to 5000. This mixture was then diluted about 50% with a heavy aromatic naphtha solvent to give additive (B).
  • a gasoline composition was prepared by adding to gasoline 0.0001 wt. percent of additive (A') and 0.0001 wt. percent of additive (B').
  • the advantages of this composition over gasoline compositions containing only (A') (B) are indicated by the following test procedure.
  • compositions were prepared having the following compositions Percent area rusted Number of days exposed. 1 2 3 4 Gasoline itself 50 Composition (1) Nil Trace Trace Composition (2) Nil Trace Trace 10 Composition (3) 5 5 10 10 Thus, it can be seen that minimum rusting takes place when gasoline compositions of the invention (compositions 1 and 2) are used.
  • An oil composition comprising a major proportion by weight of an oil selected from the group consisting of a fuel oil and a lubricating oil and a minor proportion by Weight in an amount suflicient to inhibit corrosion of a mixture comprising:
  • Additive A which is selected from the group consisting of monoand poly-carboxylic acids which contain 10 to 60 carbon atoms per molecule, anhydrides of such acids and monoor polyesters of such acids; monoor polyamides and amino salts of such acids and mixtures thereof; said esters being derived from a hydroxy compound of the formula where X, Y and Z are hydrocarbyl groups or hydrogen atoms and m is zero or an integer, and n is zero or an integer, and R is a hydrocarbyl group containing 1 to 50 carbon atoms, or a hydrocarbyl group containing 1 to 50 carbon atoms and one or more ether linkages, or hydrogen when both m and n are integers, or hydroxyamine of the formula where R and R are hydrogen or hydrocarbyl groups, and R R and R are divalent hydrocarbon groups; said amides being derived from an amine chosen from the group consisting of (i) monoamines (ii) aromatic monoamines (iii) aliphatic polyamines
  • composition as claimed in claim 1 wherein the fuel is a gasoline.
  • additive (B) is derived from a phenol substituted with a hydrocarbyl group.
  • composition as claimed in claim 1 wherein the aldehyde is formaldehyde or para formaldehyde.
  • additive (B) is derived from an alkylene oxide containing not more than 4 carbon atoms per molecule.
  • additive ('B) is derived from a mono-carboxylic acid having between 8 and 32 carbon atoms per molecule.
  • Additive (B) also incorporates a homopolymer of an alkylene oxide or a copolymer of alkylene oxides, said homoor copolymer containing the residue of an alkanolor dial kanolamine.
  • Additive A is selected from the group consisting of:
  • R and R is a hydrocarbyl group containing 10 to 50 carbon atoms, and the other is either a hydrocarbyl group containing 10 to 50 carbon atoms, or hydrogen.
  • composition as claimed in claim 9 wherein m and n are each integers of between 1 and 5.
  • composition as claimed in claim 10 wherein the acid or anhydride is selected from the group consisting of polypropenyl and polyisobutenyl succinic acids and a polypropenyl succinic anhydride.
  • additive (A) is derived from a monohydric alcohol containing from 4 to 12 carbon atoms per molecule.
  • additive (A) is derived from said monoamine selected from the group consisting of amines of the formulae R NH R R NH and R R R N where R R and R are hydrocarbyl or substituted hydrocarbyl.
  • Additive (A) is derived from said hydroxyamine.
  • additive (A) is derived from a monoalkanolamine where R and R are C to C alkyl groups and R is a C to C alkylene group.
  • Additive (A) is derived from said monoamine of the formula where R R and R are alkyl, alkaryl or alkenyl groups containing 1 to 200 carbon atoms, or hydroxy or amino substituted alkyl or alkaryl groups containing 1 to 200 carbon atoms, or hydrogen atoms.
  • additive (A) is derived from a monoalkanolamine in which one or more of the alkyl groups also contains an amino substituent.
  • a composition as claimed in claim 20 wherein the amino alkyl monoalkanolamine is selected from the group consisting of aminoethyl ethanolamine, amino propyl ethanolamine, and amino propyl butanolamine.
  • Additive (A) contains an acid portion derived from a succinic acid, anhydride or ester which has been substituted by one or more hydrocarbyl groups.
  • composition as claimed in claim 22 wherein the hydrocarbyl group is selected from the groups consisting of alkenyl and alkyl groups containing from 10 to 40 carbon atoms.
  • additive (A) is an ester represented by the formula Il -CH iii-ca where either one of the groups R and is an alkenyl group containing from 8 to 40 carbon atoms, and the other of the groups R, and
  • R is a C to C alkyl group, or the group wherein R and R are C to C alkyl groups and R is a C to C alkylene group, the total number of carbon carbon atoms in the groups R R and R being from 4 to 12.
  • composition as claimed in claim 26 wherein the fatty acid is selected from acids consisting of oleic acid, linoleic acid and stearic acid.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
US858505A 1968-09-19 1969-09-16 Fuel oil and lubricating oil compositions Expired - Lifetime US3658707A (en)

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DK (1) DK128688B (enrdf_load_stackoverflow)
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US4100083A (en) * 1974-05-30 1978-07-11 Mobil Oil Corporation Lubricant compositions containing an amine salt of a half ester of succinic acid
DE2939227A1 (de) * 1978-09-27 1980-04-17 Lubrizol Corp Stickstoffhaltiges carbonsaeurederivat
US4364743A (en) * 1979-09-05 1982-12-21 Erner William E Synthetic liquid fuel and fuel mixtures for oil-burning devices
US4368133A (en) * 1979-04-02 1983-01-11 The Lubrizol Corporation Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives
US4435297A (en) 1978-09-27 1984-03-06 The Lubrizol Corporation Carboxylic acid derivatives of alkanol tertiary monoamines
US4448703A (en) * 1981-02-25 1984-05-15 The Lubrizol Corporation Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same
US4471091A (en) * 1982-08-09 1984-09-11 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4486573A (en) * 1982-08-09 1984-12-04 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4489194A (en) * 1982-08-09 1984-12-18 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4564460A (en) 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526A (en) * 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4596663A (en) * 1982-08-09 1986-06-24 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4613342A (en) * 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4623684A (en) 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4666620A (en) * 1978-09-27 1987-05-19 The Lubrizol Corporation Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same
US4708753A (en) * 1985-12-06 1987-11-24 The Lubrizol Corporation Water-in-oil emulsions
US4725373A (en) * 1986-02-24 1988-02-16 The Dow Chemical Company Novel compositions prepared from alkyl substituted nitrogen-containing aromatic heterocyclic compounds and dicarboxylic acid monoanhydrides
US4770803A (en) * 1986-07-03 1988-09-13 The Lubrizol Corporation Aqueous compositions containing carboxylic salts
US4781730A (en) * 1987-06-05 1988-11-01 The Lubrizol Corporation Fuel additive comprising a hydrocarbon soluble alkali or alkaline earth metal compound and a demulsifier
US4828633A (en) * 1987-12-23 1989-05-09 The Lubrizol Corporation Salt compositions for explosives
US4840687A (en) * 1986-11-14 1989-06-20 The Lubrizol Corporation Explosive compositions
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US4863534A (en) * 1987-12-23 1989-09-05 The Lubrizol Corporation Explosive compositions using a combination of emulsifying salts
US5041622A (en) * 1988-04-22 1991-08-20 The Lubrizol Corporation Three-step process for making substituted carboxylic acids and derivatives thereof
US5047175A (en) * 1987-12-23 1991-09-10 The Lubrizol Corporation Salt composition and explosives using same
US5064546A (en) * 1987-04-11 1991-11-12 Idemitsu Kosan Co., Ltd. Lubricating oil composition
US5129972A (en) * 1987-12-23 1992-07-14 The Lubrizol Corporation Emulsifiers and explosive emulsions containing same
US5273672A (en) * 1987-03-02 1993-12-28 Idemitsu Kosan Company Limited Lubricating oil composition containing a partial ester of a polyhydric alcohol and a substituted succinic acid ester
US5527491A (en) * 1986-11-14 1996-06-18 The Lubrizol Corporation Emulsifiers and explosive emulsions containing same
US5964907A (en) * 1996-08-14 1999-10-12 Akzo Nobel N.V. Fuel compositions containing esteramines
USRE36479E (en) * 1986-07-03 2000-01-04 The Lubrizol Corporation Aqueous compositions containing nitrogen-containing salts
WO2001038463A1 (de) * 1999-11-19 2001-05-31 Basf Aktiengesellschaft Verwendung von fettsäuresalzen von alkoxylierten oligoaminen als schmierfähigkeitsverbesserer für mineralölprodukte
US20040010966A1 (en) * 2002-04-24 2004-01-22 Aradi Allen A. Additives for fuel compositions to reduce formation of combustion chamber deposits
US20040010967A1 (en) * 2002-04-24 2004-01-22 Aradi Allen A. Friction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof
US20070094921A1 (en) * 2002-04-24 2007-05-03 William Colucci Methods to improve the low temperature compatibility of amide friction modifiers in fuels and amide friction modifiers
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FR2364266A1 (fr) * 1976-09-13 1978-04-07 Mobil Oil Compositions lubrifiantes perfectionnees contenant des sels d'esters partiels d'acides alkyl- ou alcenylsucciniques
FR2510598A1 (fr) * 1981-07-30 1983-02-04 Inst Francais Du Petrole Utilisation d'additifs azotes comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs
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FR2699550B1 (fr) * 1992-12-17 1995-01-27 Inst Francais Du Petrole Composition de distillat moyen de pétrole contenant des additifs azotés utilisables comme agents limitant la vitesse de sédimentation des paraffines.

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US3920414A (en) * 1972-10-27 1975-11-18 Exxon Research Engineering Co Crude oils containing nitrogen dispersants and alkoxylated ashless surfactants usable as diesel fuels
US4100083A (en) * 1974-05-30 1978-07-11 Mobil Oil Corporation Lubricant compositions containing an amine salt of a half ester of succinic acid
DE2939227A1 (de) * 1978-09-27 1980-04-17 Lubrizol Corp Stickstoffhaltiges carbonsaeurederivat
US4329249A (en) * 1978-09-27 1982-05-11 The Lubrizol Corporation Carboxylic acid derivatives of alkanol tertiary monoamines and lubricants or functional fluids containing the same
US4435297A (en) 1978-09-27 1984-03-06 The Lubrizol Corporation Carboxylic acid derivatives of alkanol tertiary monoamines
US4666620A (en) * 1978-09-27 1987-05-19 The Lubrizol Corporation Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same
US4368133A (en) * 1979-04-02 1983-01-11 The Lubrizol Corporation Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives
US4364743A (en) * 1979-09-05 1982-12-21 Erner William E Synthetic liquid fuel and fuel mixtures for oil-burning devices
US4448703A (en) * 1981-02-25 1984-05-15 The Lubrizol Corporation Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same
US4489194A (en) * 1982-08-09 1984-12-18 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4486573A (en) * 1982-08-09 1984-12-04 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4564460A (en) 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526A (en) * 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4596663A (en) * 1982-08-09 1986-06-24 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4613342A (en) * 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4623684A (en) 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4471091A (en) * 1982-08-09 1984-09-11 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4708753A (en) * 1985-12-06 1987-11-24 The Lubrizol Corporation Water-in-oil emulsions
US4844756A (en) * 1985-12-06 1989-07-04 The Lubrizol Corporation Water-in-oil emulsions
US4725373A (en) * 1986-02-24 1988-02-16 The Dow Chemical Company Novel compositions prepared from alkyl substituted nitrogen-containing aromatic heterocyclic compounds and dicarboxylic acid monoanhydrides
US4770803A (en) * 1986-07-03 1988-09-13 The Lubrizol Corporation Aqueous compositions containing carboxylic salts
USRE36479E (en) * 1986-07-03 2000-01-04 The Lubrizol Corporation Aqueous compositions containing nitrogen-containing salts
US4840687A (en) * 1986-11-14 1989-06-20 The Lubrizol Corporation Explosive compositions
US5527491A (en) * 1986-11-14 1996-06-18 The Lubrizol Corporation Emulsifiers and explosive emulsions containing same
US5273672A (en) * 1987-03-02 1993-12-28 Idemitsu Kosan Company Limited Lubricating oil composition containing a partial ester of a polyhydric alcohol and a substituted succinic acid ester
US5064546A (en) * 1987-04-11 1991-11-12 Idemitsu Kosan Co., Ltd. Lubricating oil composition
US4781730A (en) * 1987-06-05 1988-11-01 The Lubrizol Corporation Fuel additive comprising a hydrocarbon soluble alkali or alkaline earth metal compound and a demulsifier
US4863534A (en) * 1987-12-23 1989-09-05 The Lubrizol Corporation Explosive compositions using a combination of emulsifying salts
US5047175A (en) * 1987-12-23 1991-09-10 The Lubrizol Corporation Salt composition and explosives using same
US5129972A (en) * 1987-12-23 1992-07-14 The Lubrizol Corporation Emulsifiers and explosive emulsions containing same
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US5041622A (en) * 1988-04-22 1991-08-20 The Lubrizol Corporation Three-step process for making substituted carboxylic acids and derivatives thereof
US6013115A (en) * 1996-08-14 2000-01-11 Akzo N.V. Fuel additive compositions for simultaneously reducing intake valve and combustion chamber deposits
US5964907A (en) * 1996-08-14 1999-10-12 Akzo Nobel N.V. Fuel compositions containing esteramines
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JP2003514979A (ja) * 1999-11-19 2003-04-22 ビーエーエスエフ アクチェンゲゼルシャフト 石油製品のための潤滑性改良剤としてのアルコキシル化オリゴアミンの脂肪酸塩の使用
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US20040010966A1 (en) * 2002-04-24 2004-01-22 Aradi Allen A. Additives for fuel compositions to reduce formation of combustion chamber deposits
US20040010967A1 (en) * 2002-04-24 2004-01-22 Aradi Allen A. Friction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof
US20070094921A1 (en) * 2002-04-24 2007-05-03 William Colucci Methods to improve the low temperature compatibility of amide friction modifiers in fuels and amide friction modifiers
US7402185B2 (en) * 2002-04-24 2008-07-22 Afton Chemical Intangibles, Llc Additives for fuel compositions to reduce formation of combustion chamber deposits
US7435272B2 (en) 2002-04-24 2008-10-14 Afton Chemical Intangibles Friction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof
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US9873847B2 (en) * 2013-03-07 2018-01-23 The Lubrizol Corporation Ion tolerant corrosion inhibitors and inhibitor combinations for fuels

Also Published As

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DE1946239A1 (de) 1970-03-26
BE739045A (enrdf_load_stackoverflow) 1970-03-18
FR2018439A1 (enrdf_load_stackoverflow) 1970-05-29
GB1241327A (en) 1971-08-04
DK128688B (da) 1974-06-17
SE365815B (enrdf_load_stackoverflow) 1974-04-01
JPS4945771B1 (enrdf_load_stackoverflow) 1974-12-06
DE1946239B2 (de) 1976-10-14
NL6914044A (enrdf_load_stackoverflow) 1970-03-23

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