EP0188786A1 - Motor fuels - Google Patents

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Publication number
EP0188786A1
EP0188786A1 EP85116331A EP85116331A EP0188786A1 EP 0188786 A1 EP0188786 A1 EP 0188786A1 EP 85116331 A EP85116331 A EP 85116331A EP 85116331 A EP85116331 A EP 85116331A EP 0188786 A1 EP0188786 A1 EP 0188786A1
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Prior art keywords
fuels
fuels according
molar amount
amines
small amounts
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German (de)
French (fr)
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EP0188786B1 (en
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Knut Dr. Oppenlaender
Erich Dr. Schwartz
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BASF SE
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BASF SE
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    • 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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B1/00—Engines characterised by fuel-air mixture compression
    • F02B1/02—Engines characterised by fuel-air mixture compression with positive ignition
    • F02B1/04—Engines characterised by fuel-air mixture compression with positive ignition with fuel-air mixture admission into cylinder

Definitions

  • the invention relates to fuels for gasoline engines containing tetraamides of ethylenediaminetetraacetic acid.
  • first-mentioned imides and amide-imides also have a carburetor-cleaning effect in the dosage range mentioned, they are essentially good valve cleaners, which are expediently to be combined with special carburetor cleaners.
  • the object was therefore to improve the properties of the imides and amide imides of nitrilotriacetic acid and ethylenediaminetetraacetic acid which are highly effective as valve cleaning agents in such a way that they have both a highly effective valve cleaning and carburetor cleaning action.
  • tetraamides of ethylenediaminetetraacetic acid are obtained by methods known per se, for example by reacting ethylenediaminetetraacetic acid with the amines mentioned in succession or the mixtures of the amines at temperatures of 150 to 220 ° C., generally 160 to 200 ° C. Hp / P
  • the procedure is such that the amines or the amine mixture are placed in a stirred vessel under a nitrogen atmosphere and the ethylenediaminetetraacetic acid is introduced at approximately 80 ° C. and the mixture is kept at 160 to 200 ° C. for 4 to 10 hours with stirring. until an acid number ⁇ 10 is reached.
  • the amines or the amine mixtures consist per mole of ethylenediaminetetraacetic acid of about 3 moles of diisotridecylamine or isotridecylamine (as can be obtained, for example, from tetramerpropylene, oxidation and amination) and about 1 mole of one or more of the amines dicyclohexylamine, 3- (2-ethyl-) hexoxypropylamine of the formula
  • the products described, for example, in DE-PS 2 144 199 can be used as gasifier cleaners (b) known per se and suitable in combination with the tetraamides (a) to be used according to the invention.
  • the amides of the C 12 to C 2 o fatty acids with polyamines having 2 to 4 nitrogen atoms and 2 to 8 carbon atoms examples include di-oleic acid diethylenetriamine diamide, di-stearic acid dipropylenetriamine diamide, di-palmitic acid diethylenetriamine diamide, di-lauric acid methyldipropylenetriamine diamide.
  • Further reaction products are those of the acids mentioned with aminoethylpropylenediamine or bis-aminopropylpropylenediamine.
  • the carburetor cleaners (b) are generally used in a weight ratio, based on component (a), of from 1 to 0.05 to 0.3.
  • the new fuel additives have both a clean-keeping effect on the intake elements of the engine and a dirt-removing effect on already contaminated carburettors and valves.
  • the fuels according to the invention can additionally contain known phenol or amine-based antioxidants.
  • Residual oils from oxo alcohol synthesis have proven to be good solvents or solubilizers for the components to be added to the fuel.
  • Oxoalcohol residues from butanol, isobutanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol or dodecanol synthesis are preferably used.
  • the use of oxo alcohol residues from butanol synthesis is particularly advantageous.
  • other solvents or solvent mixtures can also be used which result in a homogeneous mixture of the components in the weight ratios mentioned above.
  • the effect of the gasoline additives according to the invention is not only limited to gasoline. It has been shown that they can also be used in aviation fuels, especially in aviation fuels for piston engines.
  • the compounds according to the invention act not only in carburetor engines, but also in engines with fuel injection systems.
  • the fuels provided with the new addition may contain other, conventional additives, Z .B. octane-improving additives or oxygen-containing components, such as methanol, ethanol or methyl tertiary butyl ether.
  • An excellently effective fuel additive contains e.g. the components in the approximate weight ratios a: b: c as 1: 0.15: 0.15.
  • each individual component in its proportion in the mixture can vary between 0.01 and 10.
  • the phenolic antioxidant c) can also be dispensed with entirely.
  • Table 2 below shows the cleaning and keeping-clean effect of the fuel additives according to the invention.

Abstract

1. A motor fuel for gasoline engines, containing (a) small amounts of tetraamides, obtainable by reacting ethylenedi-aminetetraacetic acid with about three times the molar amount of diisotridecylamine or isotridecylamine and about the molar amount of one or more of the amines dicyclohexyl-amine, 3-(2-ethylhexyloxy)propylamine, di-2-ethylhexyl-amine, isotridecylhydroxybutylamine, isotridecylhydroxy-ethylamine or diethanolamine.

Description

Die Erfindung betrifft Kraftstoffe für Ottomotoren mit einem Gehalt an Tetraamiden der Ethylendiamintetraessigsäure.The invention relates to fuels for gasoline engines containing tetraamides of ethylenediaminetetraacetic acid.

Aus der DE-OS 26 24 630 ist bekannt, zur Verhinderung von Ablagerungen an den Einlaßventilen und in den Vergasern von Ottomotoren und von den damit verbundenen Störungen der Kraftstoff-Luftgemisch-Zusammensetzung, den Kraftstoffen geringe Mengen der Imide oder Amidimide aus Nitrilotriessigsäure und/oder Imide oder Amid-Imide aus Ethylendiamintetraessigsäure und Aminen zuzusetzen.From DE-OS 26 24 630 it is known to prevent deposits on the intake valves and in the carburetors of gasoline engines and the associated disturbances in the fuel-air mixture composition, the fuels, small amounts of the imides or amidimides from nitrilotriacetic acid and / or Add imides or amide imides from ethylenediaminetetraacetic acid and amines.

Es ist ferner bekannt, z.B. aus der DE-PS 21 44 199, daß Umsetzungsprodukte aus Polyaminen, z.B. Diethylentriamin und gesättigten bzw. ungesättigten Fettsäuren, z.B. Ölsäure oder Stearinsäure, gute Vergaserreiniger sind. Sie neigen jedoch bei alleiniger Verwendung im Kraftstoff in höheren Konzentrationen, z.B. oberhalb 50 bis 100 ppm zur Bildung von Ventilablagerungen.It is also known, e.g. from DE-PS 21 44 199 that reaction products of polyamines, e.g. Diethylene triamine and saturated or unsaturated fatty acids, e.g. Oleic acid or stearic acid, which are good carburetor cleaners. However, when used alone in fuel they tend to be at higher concentrations, e.g. above 50 to 100 ppm to form valve deposits.

Die zuerst genannten Imide und Amid-Imide wirken im genannten Dosierungsbereich zwar auch vergaserreinigend, sind jedoch im wesentlichen gute Ventilreiniger, die zweckmäßigerweise mit speziellen Vergaserreinigern zu kombinieren sind.Although the first-mentioned imides and amide-imides also have a carburetor-cleaning effect in the dosage range mentioned, they are essentially good valve cleaners, which are expediently to be combined with special carburetor cleaners.

Es bestand daher die Aufgabe die Eigenschaften der als Ventilreinigungsmitteln hochwirksamen Imiden und Amid-Imiden der Nitrilotriessigsäure und der Ethylendiamintetraessigsäure dahingehend zu verbessern, daß sie sowohl eine hochwirksame Ventilreinigungs- als auch Vergaserreinigungswirkung haben.The object was therefore to improve the properties of the imides and amide imides of nitrilotriacetic acid and ethylenediaminetetraacetic acid which are highly effective as valve cleaning agents in such a way that they have both a highly effective valve cleaning and carburetor cleaning action.

Es wurde nun überraschenderweise gefunden, daß diese Aufgabe gelöst wird mit Kraftstoffen für Ottomotoren, enthaltend (a) geringe Mengen von Tetraamiden erhältlich durch Umsetzung von Ethylendiamintetraessigsäure mit der etwa dreimolaren Menge Diisotridecylamin oder Isotridecylamin und etwa der einmolaren Menge eines oder mehrerer der Amine Dicyclohexylamin, 3-t2-Ethyl-)hexoxypropylamin, Di-2-ethylhexylamin, i-Tridecyl-hydroxybutylamin, i-Tridecyl-hydroxyethylamin oder Diethanolamin.It has now surprisingly been found that this object is achieved with fuels for gasoline engines containing (a) small amounts of tetraamides obtainable by reacting ethylenediaminetetraacetic acid with the approximately three-molar amount of diisotridecylamine or isotridecylamine and approximately the one-molar amount of one or more of the amines dicyclohexylamine, 3 -t2-ethyl-) hexoxypropylamine, di-2-ethylhexylamine, i-tridecyl-hydroxybutylamine, i-tridecyl-hydroxyethylamine or diethanolamine.

Die Tetraamide der Ethylendiamintetraessigsäure werden nach an sich bekannten Methoden, z.B. durch Umsetzung von Ethylendiamintetraessigsäure mit den genannten Aminen nacheinander oder den Gemischen der Amine bei Temperaturen von 150 bis 220°C in der Regel 160 bis 200°C erhalten. Hp/PThe tetraamides of ethylenediaminetetraacetic acid are obtained by methods known per se, for example by reacting ethylenediaminetetraacetic acid with the amines mentioned in succession or the mixtures of the amines at temperatures of 150 to 220 ° C., generally 160 to 200 ° C. Hp / P

Im einzelnen geht man so vor, daß man die Amine bzw. das Amingemisch unter Stickstoffatmosphäre in einem Rührgefäß vorlegt und die Ethylendiamintetraessigsäure bei ungefähr 80°C einträgt und die Mischung unter Rühren 4 bis 10 Stunden auf 160 bis 200°C hält. bis eine Säurezahl < 10 erreicht ist.In detail, the procedure is such that the amines or the amine mixture are placed in a stirred vessel under a nitrogen atmosphere and the ethylenediaminetetraacetic acid is introduced at approximately 80 ° C. and the mixture is kept at 160 to 200 ° C. for 4 to 10 hours with stirring. until an acid number <10 is reached.

Die Amine bzw. die Amingemische bestehen pro Mol Ethylendiamintetraessigsäure aus etwa 3 Mol Diisotridecylamin oder Isotridecylamin (wie sie z.B. aus Tetramerpropylen, Oxierung und Aminierung erhältlich sind) und etwa 1 Mol eines oder mehrerer der Amine Dicyclohexylamin, 3-(2-Ethyl-)hexoxypropylamin der FormelThe amines or the amine mixtures consist per mole of ethylenediaminetetraacetic acid of about 3 moles of diisotridecylamine or isotridecylamine (as can be obtained, for example, from tetramerpropylene, oxidation and amination) and about 1 mole of one or more of the amines dicyclohexylamine, 3- (2-ethyl-) hexoxypropylamine of the formula

Figure imgb0001
Di-2-ethylhexylamin, i-Tridecylhydroxyethylamin der Formel
Figure imgb0002
sowie das entsprechende i-Tridecylhydroxybutylamin oder Diethanolamin.
Figure imgb0001
 Di-2-ethylhexylamine, i-tridecylhydroxyethylamine of the formula
Figure imgb0002
 and the corresponding i-tridecylhydroxybutylamine or diethanolamine.

Als an sich bekannte, in Kombination mit den erfindungsgemäß zu verwendenden Tetraamiden (a) geeignete Vergaserreiniger (b) kommen die z.B. in DE-PS 2 144 199 beschriebenen Produkte in Betracht. Insbesondere sind die Amide der C12- bis C2o-Fettsäuren mit Polyaminen mit 2 bis 4 Stickstoffatomen und 2 bis 8 Kohienstoffatomen. z.B. Di-ölsäurediethylentriamin-diamid, Di-stearinsäuredipropylentriamin-diamid, Di-palmitinsäurediethylentriamindiamid, Di-laurinsäure-methyldipropylentriamin-diamid zu nennen. Weitere Umsetzungsprodukte sind solche der genannten Säuren mit Aminoethylpropylendiamin oder Bis-aminopropyl-propylendiamin.The products described, for example, in DE-PS 2 144 199 can be used as gasifier cleaners (b) known per se and suitable in combination with the tetraamides (a) to be used according to the invention. In particular, the amides of the C 12 to C 2 o fatty acids with polyamines having 2 to 4 nitrogen atoms and 2 to 8 carbon atoms. Examples include di-oleic acid diethylenetriamine diamide, di-stearic acid dipropylenetriamine diamide, di-palmitic acid diethylenetriamine diamide, di-lauric acid methyldipropylenetriamine diamide. Further reaction products are those of the acids mentioned with aminoethylpropylenediamine or bis-aminopropylpropylenediamine.

Die Vergaserreiniger (b) werden in der Regel im Gewichtsverhältnis, bezogen auf die Komponente (a), von 1 zu 0,05 bis 0,3 angewandt.The carburetor cleaners (b) are generally used in a weight ratio, based on component (a), of from 1 to 0.05 to 0.3.

Die neuen Kraftstoffzusätze weisen sowohl eine die Einlaßelemente des Motors sauberhaltende als auch eine schmutzablösende Wirkung bei bereits verschmutzten Vergasern und Ventilen auf.The new fuel additives have both a clean-keeping effect on the intake elements of the engine and a dirt-removing effect on already contaminated carburettors and valves.

Die erfindungsgemäßen Kraftstoffe können neben den Amiden sowie den Vergaserdetergentien zusätzlich noch bekannte Antioxidantien auf Phenol- oder Aminbasis enthalten. Insbesondere ist es vorteilhaft, Kraftstoffzusätze zur Reinigung und Reinhaltung des Einlaßsystems mit phenolischen Antioxidantien zur Erhöhung der Lagerstabilität der Kraftstoffe zu kombinieren.In addition to the amides and the gasifier detergents, the fuels according to the invention can additionally contain known phenol or amine-based antioxidants. In particular, it is advantageous to combine fuel additives for cleaning and keeping the intake system clean with phenolic antioxidants to increase the storage stability of the fuels.

Als gute Lösungsmittel bzw. Lösungsvermittler für die genannten, den Kraftstoff zuzusetzenden Komponenten haben sich Rückstandsöle aus der Oxoalkoholsynthese erwiesen.Residual oils from oxo alcohol synthesis have proven to be good solvents or solubilizers for the components to be added to the fuel.

Vorzugsweise verwendet man Oxoalkoholrückstände aus der Butanol-, Isobutanol-, Pentanol-, Hexanol-, Heptanol-, Oktanol-, Nonanol-, Dekanol-, Undekanol- oder Dodekanolsynthese. Besonders vorteilhaft ist die Verwendung von Oxoalkoholrückständen aus der Butanolsynthese. Daneben sind auch andere Lösungsmittel bzw. Lösungsmittelgemische verwendbar, die eine homogene Mischung der Komponenten in den weiter oben genannten Gewichtsverhältnissen ergeben. Die Wirkung der erfindungsgemäßen Benzinzusätze ist nicht nur auf Fahrbenzine beschränkt. Es hat sich gezeigt, daß man sie auch in Flugbenzinen verwenden kann, insbesondere in Flugbenzinen für Kolbenmotoren. Desgleichen wirken die erfindungsgemäßen Verbindungen nicht nur in Vergasermotoren, sondern auch bei Motoren mit Einspritzanlagen für den Kraftstoff.Oxoalcohol residues from butanol, isobutanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol or dodecanol synthesis are preferably used. The use of oxo alcohol residues from butanol synthesis is particularly advantageous. In addition, other solvents or solvent mixtures can also be used which result in a homogeneous mixture of the components in the weight ratios mentioned above. The effect of the gasoline additives according to the invention is not only limited to gasoline. It has been shown that they can also be used in aviation fuels, especially in aviation fuels for piston engines. Likewise, the compounds according to the invention act not only in carburetor engines, but also in engines with fuel injection systems.

Die mit dem neuen Zusatz versehenen Kraftstoffe können noch weitere, übliche Zusätze, Z.B. oktanzahlverbessernde Zusätze oder auch sauerstoffhaltige Komponenten, z.B. Methanol, Ethanol oder Methyltertiärbutylether enthalten.The fuels provided with the new addition may contain other, conventional additives, Z .B. octane-improving additives or oxygen-containing components, such as methanol, ethanol or methyl tertiary butyl ether.

Die Kraftstoffzusätze werden den Kraftstoffen für Ottomotoren in der Regel in Mengen von 10 bis 2000 Vol.-ppm, vorzugsweise von 50 bis 1000 Vol.-ppm, zudosiert. Die Gewichtsverhältnisse der einzelnen Komponenten in den Kraftstoffzusätzen können in relativ weiten Grenzen schwanken. Besonders wirksame Kombinationen enthalten z.B.

  • a) 1 bis 10 Gew.-Teile der ventil- und vergaserreinigenden Amide aus Ethylendiamintetraessigsäure,
  • b) 0,15 bis 1,5 Gew.-Teile von Vergaserdetergentien, z.B. der Kondensationsprodukte aus gesättigten oder ungesättigten C12-C20-Fettsäuren und Polyaminen mit 2 bis 8 Kohlenstoffatomen und 2 bis 4 Stickstoffatomen und gegebenenfalls ferner
  • c) 0,15 bis 1,5 Gew.-Teile eines phenolischen Antioxidants, z.B. alkylsubstituierter sterisch gehinderter Phenole und außerdem
The fuel additives are generally added to the fuels for gasoline engines in amounts of 10 to 2000 ppm by volume, preferably 50 to 1000 ppm by volume. The weight ratios of the individual components in the fuel additives can fluctuate within relatively wide limits. Particularly effective combinations include, for example
  • a) 1 to 10 parts by weight of the valve and gasifier cleaning amides from ethylenediaminetetraacetic acid,
  • b) 0.15 to 1.5 parts by weight of gasifier detergents, for example the condensation products of saturated or unsaturated C 12 -C 20 fatty acids and polyamines having 2 to 8 carbon atoms and 2 to 4 nitrogen atoms and optionally further
  • c) 0.15 to 1.5 parts by weight of a phenolic antioxidant, for example alkyl-substituted sterically hindered phenols and also

Ein hervorragend wirksamer Kraftstoffzusatz enthält z.B. die Komponenten in den ungefähren Gewichtsverhältnissen a:b:c wie 1:0,15:0,15.An excellently effective fuel additive contains e.g. the components in the approximate weight ratios a: b: c as 1: 0.15: 0.15.

Auch andere Gewichtsverhältnisse sind möglich, wobei je nach gewünschter Wirkung am Einlaßventil und/oder Vergaser jede Einzelkomponente in ihrem Anteil am Gemisch zwischen 0,01 und 10 variieren kann. Auch kann je nach gewünschter Wirkung des Kraftstoffzusatzes auf das Vergaserdetergent b) und gegebenenfalls das phenolische Antioxidant c) ganz verzichtet werden.Other weight ratios are also possible, depending on the desired effect on the inlet valve and / or carburetor, each individual component in its proportion in the mixture can vary between 0.01 and 10. Depending on the desired effect of the fuel additive on the carburetor detergent b) and optionally the phenolic antioxidant c) can also be dispensed with entirely.

Die nachfolgende Tabelle 2 zeigt die Reinigungs- und Reinhaltewirkung der erfindungsgemäßen Kraftstoffzusätze.

Figure imgb0003
Figure imgb0004
 Table 2 below shows the cleaning and keeping-clean effect of the fuel additives according to the invention.
Figure imgb0003
Figure imgb0004

Claims (6)

1. Kraftstoffe für Ottomotoren, enthaltend (a) geringe Mengen von Tetraamiden, erhältlich durch Umsetzung von Ethylendiamintetraessigsäure mit der etwa dreimolaren Menge Diisotridecylamin oder Isotridecylamin und etwa der einmolaren Menge eines oder mehrerer der Amine Dicyclohexylamin, 3-(2-Ethyl-)hexoxypropylamin, Di-2-ethylhexylamin, i-Tridecyl-hydroxybutylamin, i-Tridecyl-hydroxyethylamin oder Diethanolamin.1. Fuels for gasoline engines, containing (a) small amounts of tetraamides, obtainable by reacting ethylenediaminetetraacetic acid with the approximately three-molar amount of diisotridecylamine or isotridecylamine and approximately the one-molar amount of one or more of the amines dicyclohexylamine, 3- (2-ethyl-) hexoxypropylamine, Di-2-ethylhexylamine, i-tridecyl-hydroxybutylamine, i-tridecyl-hydroxyethylamine or diethanolamine. 2. Kraftstoffe nach Anspruch 1, enthaltend zusätzlich (b) geringe Mengen gesättigter und/oder ungesättigter Fettsäureamide, erhalten aus C12- bis C20-Fettsäuren und Polyaminen mit 2 bis 8 Kohlenstoffatomen und 2 bis 4 Stickstoffatomen.2. Fuels according to claim 1, additionally containing (b) small amounts of saturated and / or unsaturated fatty acid amides obtained from C 12 - to C 20 fatty acids and polyamines having 2 to 8 carbon atoms and 2 to 4 nitrogen atoms. 3. Kraftstoffe nach Ansprüchen 1 und 2, gekennzeichnet durch ein Gewichtsverhältnis der Summe von (a) zu (b) wie 1 zu 0,05 bis 0,3.3. Fuels according to claims 1 and 2, characterized by a weight ratio of the sum of (a) to (b) such as 1 to 0.05 to 0.3. 4. Kraftstoffe gemäß Ansprüchen 1 und 2, enthaltend ferner (c) alkylsubstituierte sterisch gehinderte Phenole als Antioxidantien.4. Fuels according to claims 1 and 2, further comprising (c) alkyl-substituted sterically hindered phenols as antioxidants. 5. Kraftstoffe gemäß Ansprüchen 1 bis 4, gekennzeichnet durch einen Gehalt von a und b von zusammen 10 bis 2000 ppm.5. Fuels according to claims 1 to 4, characterized by a content of a and b of together 10 to 2000 ppm. 6. Kraftstoffe gemäß Ansprüchen 1 bis 5, gekennzeichnet durch einen Gehalt von a bis c von 50 bis 1000 ppm.6. Fuels according to claims 1 to 5, characterized by a content of a to c of 50 to 1000 ppm.
EP85116331A 1985-01-11 1985-12-20 Motor fuels Expired EP0188786B1 (en)

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DE19853500709 DE3500709A1 (en) 1985-01-11 1985-01-11 FUELS FOR OTTO ENGINES
DE3500709 1985-01-11

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0398101A1 (en) * 1989-05-19 1990-11-22 BASF Aktiengesellschaft Reaction products of aminoalkylene-polycarboxylic acids with secondary amines and crude oil middle distillates containing them
US5090967A (en) * 1985-05-14 1992-02-25 Lindstroem Arne Method and composition for providing an improved combustion in processes of combustion containing hydrocarbon compounds
EP0484736A1 (en) * 1990-11-09 1992-05-13 BASF Aktiengesellschaft Fuels for spark ignition engines
WO1995003378A1 (en) * 1993-07-21 1995-02-02 Basf Aktiengesellschaft Reaction products of amino alkylene carboxylic acids and petroleum middle distillates containing them
CN103420843A (en) * 2013-07-30 2013-12-04 苏州环科新材料有限公司 Synthetic method for diiso-tridecylamine
WO2015175778A1 (en) * 2014-05-15 2015-11-19 Croda, Inc. Lubricating oils
US11781086B2 (en) 2014-05-15 2023-10-10 Equus Uk Topco Ltd Lubricating oils and greases

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US3407051A (en) * 1960-10-31 1968-10-22 Eastman Kodak Co Thermally stabilized, liquid hydrocarbon fuels
US3455665A (en) * 1968-03-05 1969-07-15 Mobil Oil Corp Liquid hydrocarbon compositions containing amides of ethylene diamine tetra acetic acid as anti-static agents
DE2144199A1 (en) * 1971-09-03 1973-03-08 Basf Ag Fuels for petrol engines - contg fatty acid amides and esters to reduce carburettor deposits
US4478604A (en) * 1982-04-01 1984-10-23 Phillips Petroleum Company Gasoline compositions containing branched chain amines or derivatives thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3407051A (en) * 1960-10-31 1968-10-22 Eastman Kodak Co Thermally stabilized, liquid hydrocarbon fuels
US3224957A (en) * 1962-01-12 1965-12-21 Nalco Chemical Co Process of reducing deposition of deposits on heat exchange surfaces in petroleum refinery operations
US3455665A (en) * 1968-03-05 1969-07-15 Mobil Oil Corp Liquid hydrocarbon compositions containing amides of ethylene diamine tetra acetic acid as anti-static agents
DE2144199A1 (en) * 1971-09-03 1973-03-08 Basf Ag Fuels for petrol engines - contg fatty acid amides and esters to reduce carburettor deposits
US4478604A (en) * 1982-04-01 1984-10-23 Phillips Petroleum Company Gasoline compositions containing branched chain amines or derivatives thereof

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5090967A (en) * 1985-05-14 1992-02-25 Lindstroem Arne Method and composition for providing an improved combustion in processes of combustion containing hydrocarbon compounds
EP0398101A1 (en) * 1989-05-19 1990-11-22 BASF Aktiengesellschaft Reaction products of aminoalkylene-polycarboxylic acids with secondary amines and crude oil middle distillates containing them
EP0484736A1 (en) * 1990-11-09 1992-05-13 BASF Aktiengesellschaft Fuels for spark ignition engines
WO1995003378A1 (en) * 1993-07-21 1995-02-02 Basf Aktiengesellschaft Reaction products of amino alkylene carboxylic acids and petroleum middle distillates containing them
CN103420843A (en) * 2013-07-30 2013-12-04 苏州环科新材料有限公司 Synthetic method for diiso-tridecylamine
WO2015175778A1 (en) * 2014-05-15 2015-11-19 Croda, Inc. Lubricating oils
US11104860B2 (en) 2014-05-15 2021-08-31 Croda, Inc. Lubricating oils
US11781086B2 (en) 2014-05-15 2023-10-10 Equus Uk Topco Ltd Lubricating oils and greases

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DE3561889D1 (en) 1988-04-21
DE3500709A1 (en) 1986-07-17

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