EP0436864B1 - Fuels for spark ignition engines - Google Patents

Fuels for spark ignition engines Download PDF

Info

Publication number
EP0436864B1
EP0436864B1 EP90124072A EP90124072A EP0436864B1 EP 0436864 B1 EP0436864 B1 EP 0436864B1 EP 90124072 A EP90124072 A EP 90124072A EP 90124072 A EP90124072 A EP 90124072A EP 0436864 B1 EP0436864 B1 EP 0436864B1
Authority
EP
European Patent Office
Prior art keywords
fuel
carbon atoms
straight
amides
fuels
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP90124072A
Other languages
German (de)
French (fr)
Other versions
EP0436864A1 (en
Inventor
Knut Dr. Oppenlaender
Brigitte Dr. Wegner
Juergen Dr. Mohr
Roland Dr. Schwen
Klaus Dr. Barthold
Juergen Dr. Thomas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0436864A1 publication Critical patent/EP0436864A1/en
Application granted granted Critical
Publication of EP0436864B1 publication Critical patent/EP0436864B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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 with small amounts of amides or amidammonium salts from aminoalkylene polycarboxylic acids and secondary long-chain amines.
  • Carburetor and intake system of gasoline engines are increasingly contaminated by contaminants caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and the crankcase ventilation gases that are led into the carburetor.
  • the first generation of additives could only prevent the formation of deposits in the intake system, but not remove existing deposits again, whereas the modern additives of the second generation can do both ("keep-clean” and “clean-up effect") and indeed, due to changed thermal properties, in particular also at zones of higher temperatures, namely at the inlet valves.
  • the molecular construction principle of fuel detergents can be generalized as a link between polar structures and mostly higher molecular weight, non-polar or lipophilic residues.
  • No. 2,901,335 discloses amine salts of aminocarboxylic acids which are used in leaded fuels to stabilize the lead compounds.
  • A is a straight-chain or branched alkylene radical having 2 to 6 carbon atoms or the rest of the formula and R essentially denotes straight-chain aliphatic radicals, in particular alkyl radicals having 10 to 30, preferably 14 to 24, carbon atoms, the amide structures also partly in the form of the ammonium salt structure of the formula can be present, is particularly effective with regard to carburetor and valve cleaning.
  • the amides or amide ammonium salts e.g. Nitrilotriacetic acid, ethylenediaminetetraacetic acid or propylene-1,2-diaminetetraacetic acid are obtained by reacting the acids with 0.5 to 1.5 mol amine, preferably 0.8 to 1.2 mol amine per carboxyl group.
  • reaction temperatures are about 80 to 200 ° C, with the amides being continuously removed from the water of reaction formed. However, the reaction does not have to be completely led to the amide.
  • Dialkylamines are particularly suitable in which R is a straight-chain alkyl radical having 10 to 30 carbon atoms, preferably 14 to 24 carbon atoms.
  • Dioleylamine, dipalmitinamine, dicoconut fatty amine and dibehenylamine and preferably ditallow fatty amine may be mentioned in particular.
  • the amides or ammonium salts of the amino alkylene polycarboxylic acids of the formulas I and II to be used according to the invention are added to the fuels in amounts of 50 to 1500 ppm, preferably 50 to 1000 ppm, in particular 100 to 500 ppm.
  • Leaded and unleaded regular and premium gasoline can be used as fuels for gasoline engines.
  • the gasolines can also contain components other than hydrocarbons, e.g. Alcohols such as methanol, ethanol, tert-butanol and ethers, e.g. Contain methyl tertiary butyl ether.
  • the fuels generally also contain further additives such as corrosion inhibitors, stabilizers, antioxidants and / or detergents.
  • Corrosion inhibitors are mostly ammonium salts org. Carboxylic acids which tend to form films due to the structure of the starting compounds. Amines to lower the pH are also often found in corrosion inhibitors. Heterocyclic aromatics are mostly used as non-ferrous metal corrosion protection.
  • amines such as para-phenylenediamine, dicyclohexylamine, morpholine or derivatives of these amines are antioxidants or stabilizers call.
  • Phenolic antioxidants such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxiphenylpropionic acid and their derivatives are also added to fuels and lubricants.
  • Amides and imides of polyisobutylene succinic anhydride, polybutene polyamines and long-chain carbonamides and imides are also optionally contained in the fuels as further carburetor, injector and valve detergents.

Landscapes

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Description

Die Erfindung betrifft Kraftstoffe für Ottomotoren mit geringen Mengen an Amiden oder Amidammoniumsalzen aus Aminoalkylenpolycarbonsäuren und sekundären langkettigen Aminen.The invention relates to fuels for gasoline engines with small amounts of amides or amidammonium salts from aminoalkylene polycarboxylic acids and secondary long-chain amines.

Vergaser und Einlaßsystem von Ottomotoren, aber auch Einspritzsysteme für die Kraftstoffdosierung in Otto- und Dieselmotoren werden in zunehmendem Maße durch Verunreinigungen belastet, die durch Staubteilchen aus der Luft, unverbrannte Kohlenwasserstoffreste aus dem Brennraum und die in den Vergaser geleiteten Kurbelwellengehäuseentlüftungsgase verursacht werden.Carburetor and intake system of gasoline engines, but also injection systems for fuel metering in gasoline and diesel engines, are increasingly contaminated by contaminants caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and the crankcase ventilation gases that are led into the carburetor.

Diese Rückstände verschieben das Luft-Kraftstoffverhältnis im Leerlauf und im unteren Teillastbereich, so daß das Gemisch fetter, die Verbrennung unvollständiger und wiederum die Anteile unverbrannter oder teilverbrannter Kohlenwasserstoffe im Abgas größer werden und der Benzinverbrauch steigt.These residues shift the air-fuel ratio at idle and in the lower part-load range, so that the mixture richer, the combustion incomplete and in turn the proportions of unburned or partially burned hydrocarbons in the exhaust gas and the gasoline consumption increases.

Es ist bekannt, daß zur Vermeidung dieser Nachteile Kraftstoffadditive zur Reinhaltung von Ventilen und Vergaser bzw. Einspritzsystemen verwendet werden (vgl. z.B. m. Rossenbeck in Katalysatoren, Tenside, Mineralöladditive, Hrsg. J. Falbe, u. Hasserodt, S. 223 f., G. Thieme-Verlag, Stuttgart, 1978).It is known that in order to avoid these disadvantages, fuel additives are used to keep valves and carburetor or injection systems clean (cf. e.g. Rossenbeck in catalysts, surfactants, mineral oil additives, ed. J. Falbe, and Hasserodt, p. 223 f., G. Thieme Verlag, Stuttgart, 1978).

Je nach Wirkungsweise aber auch nach dem bevorzugten Wirkort solcher Detergent-Additive unterscheidet man heute zwei Generationen.Depending on the mode of action, but also on the preferred place of action of such detergent additives, a distinction is made between two generations.

Die erste Additiv-Generation konnte nur die Bildung von Ablagerungen im Ansaugsystem verhindern, nicht aber bereits vorhandene Ablagerungen wieder entfernen, wohingegen die modernen Additive der zweiten Generation beides bewirken können ("keep-clean-" und "clean-up-Effekt") und zwar, aufgrund veränderter thermischer Eigenschaften, insbesondere auch an Zonen höherer Temperaturen, nämlich an den Einlaßventilen.The first generation of additives could only prevent the formation of deposits in the intake system, but not remove existing deposits again, whereas the modern additives of the second generation can do both ("keep-clean" and "clean-up effect") and indeed, due to changed thermal properties, in particular also at zones of higher temperatures, namely at the inlet valves.

Das molekulare Bauprinzip von Kraftstoff-Detergenzien kann verallgemeinernd angegeben werden als Verknüpfung polarer Strukturen mit meist höhermolekularen, unpolaren oder lipophilen Resten.The molecular construction principle of fuel detergents can be generalized as a link between polar structures and mostly higher molecular weight, non-polar or lipophilic residues.

Als Vertreter der zweiten Additiv-Generation haben sich neben Produkten auf der Basis von Polyisobutenen, z.B. Polyisobutylamine gemäß DE-OS 3 611 230, insbesondere Amide, Imide und Imid/Amide verschiedener Carbonsäuren und Polycarbonsäuren bewährt.In addition to products based on polyisobutenes, for example polyisobutylamines according to DE-OS 3 611 230, in particular amides, imides and imides / amides of various carboxylic acids and polycarboxylic acids have proven successful as representatives of the second generation of additives.

Hervorzuheben sind hier die bekannten Wirkstoffe auf der Basis von Trilonderivaten und höheren verzweigten Aminen wie sie in EP-A2-0 006 527 beschrieben sind.Of particular note here are the known active substances based on trilone derivatives and higher branched amines, as described in EP-A2-0 006 527.

Aus der US 2 901 335 sind Aminsalze von Aminocarbonsäuren bekannt, die in verbleiten Kraftstoffen zur Stabilisierung der Bleiverbindungen eingesetzt werden.No. 2,901,335 discloses amine salts of aminocarboxylic acids which are used in leaded fuels to stabilize the lead compounds.

Es wurde nun überraschenderweise gefunden, daß der Zusatz zu Kraftstoffen für Ottomotoren in Mengen von 100 bis 1500 ppm von Amiden oder Amidammoniumsalzen der Formeln I und II

Figure imgb0001
Figure imgb0002
und deren Gemische, wobeiIt has now surprisingly been found that the addition to fuels for gasoline engines in amounts of 100 to 1500 ppm of amides or amidammonium salts of the formulas I and II
Figure imgb0001
Figure imgb0002
and their mixtures, where

A einen geradkettigen oder verzweigten Alkylenrest mit 2 bis 6 Kohlenstoffatomen oder den Rest der Formel

Figure imgb0003

und
R im wesentlichen gradkettige aliphatische Reste, insbesondere Alkylreste mit 10 bis 30, bevorzugt 14 bis 24 C-Atomen bedeutet, wobei die Amidstrukturen auch zum Teil in Form der Ammoniumsalzstruktur der Formel
Figure imgb0004
vorliegen können, besonders wirksam in Bezug auf Vergaser- und Ventilreinigung ist.A is a straight-chain or branched alkylene radical having 2 to 6 carbon atoms or the rest of the formula
Figure imgb0003
and
R essentially denotes straight-chain aliphatic radicals, in particular alkyl radicals having 10 to 30, preferably 14 to 24, carbon atoms, the amide structures also partly in the form of the ammonium salt structure of the formula
Figure imgb0004
can be present, is particularly effective with regard to carburetor and valve cleaning.

Die Amide bzw. Amid-Ammoniumsalze z.B. der Nitrilotriessigsäure, der Ethylendiamintetraessigsäure oder der Propylen-1,2-diamintetraessigsäure werden durch umsetzung der Säuren mit 0,5 bis 1,5 Mol Amin, bevorzugt 0,8 bis 1,2 mol Amin pro Carboxylgruppe erhalten.The amides or amide ammonium salts e.g. Nitrilotriacetic acid, ethylenediaminetetraacetic acid or propylene-1,2-diaminetetraacetic acid are obtained by reacting the acids with 0.5 to 1.5 mol amine, preferably 0.8 to 1.2 mol amine per carboxyl group.

Die Umsetzungstemperaturen betragen etwa 80 bis 200°C, wobei zur Herstellung der Amide eine kontinuierliche Entfernung des entstandenen Reaktionswassers erfolgt. Die umsetzung muß jedoch nicht vollständig zum Amid geführt werden.The reaction temperatures are about 80 to 200 ° C, with the amides being continuously removed from the water of reaction formed. However, the reaction does not have to be completely led to the amide.

Als Amine der Formel

Figure imgb0005

kommen insbesondere Dialkylamine in Betracht, in denen R einen geradkettigen Alkylrest mit 10 bis 30 Kohlenstoffatomen, vorzugsweise 14 bis 24 Kohlenstoffatomen, bedeutet. Im einzelnen seien Dioleylamin, Dipalmitinamin, Dikokosfettamin und Dibehenylamin und vorzugsweise Ditalgfettamin genannt.As amines of the formula
Figure imgb0005
Dialkylamines are particularly suitable in which R is a straight-chain alkyl radical having 10 to 30 carbon atoms, preferably 14 to 24 carbon atoms. Dioleylamine, dipalmitinamine, dicoconut fatty amine and dibehenylamine and preferably ditallow fatty amine may be mentioned in particular.

Die erfindungsgemäß zu verwendenden Amide bzw. Ammoniumsalze der Amino-Alkylenpolycarbonsäuren der Formeln I und II werden den Kraftstoffen in Mengen von 50 bis 1500 ppm, bevorzugt 50 bis 1000 ppm, insbesondere 100 bis 500 ppm, zugesetzt.The amides or ammonium salts of the amino alkylene polycarboxylic acids of the formulas I and II to be used according to the invention are added to the fuels in amounts of 50 to 1500 ppm, preferably 50 to 1000 ppm, in particular 100 to 500 ppm.

Als Kraftstoffe für Ottomotoren kommen verbleites und unverbleites Normal- und Superbenzin in Betracht. Die Benzine können auch andere Komponenten als Kohlenwasserstoffe, z.B. Alkohole wie Methanol, Ethanol, tert.-Butanol sowie Ether, z.B. Methyltertiärbutylether enthalten. Neben den erfindungsgemäß zu verwendenden Amiden der Aminoalkylenpolycarbonsäuren enthalten die Kraftstoffe in der Regel noch weitere Zusätze wie Korrosionsinhibitoren, Stabilisatoren, Antioxidantien und/oder Detergents.Leaded and unleaded regular and premium gasoline can be used as fuels for gasoline engines. The gasolines can also contain components other than hydrocarbons, e.g. Alcohols such as methanol, ethanol, tert-butanol and ethers, e.g. Contain methyl tertiary butyl ether. In addition to the amines of aminoalkylene polycarboxylic acids to be used according to the invention, the fuels generally also contain further additives such as corrosion inhibitors, stabilizers, antioxidants and / or detergents.

Korrosionsinhibitoren sind meist Ammoniumsalze org. Carbonsäuren, die durch entsprechende Struktur der Ausgangsverbindungen zur Filmbildung neigen. Auch Amine zur Absenkung des pH-Wertes finden sich häufig in Korrosionsinhibitoren. Als Buntmetallkorrosionsschutz werden meist heterocyclische Aromaten eingesetzt.Corrosion inhibitors are mostly ammonium salts org. Carboxylic acids which tend to form films due to the structure of the starting compounds. Amines to lower the pH are also often found in corrosion inhibitors. Heterocyclic aromatics are mostly used as non-ferrous metal corrosion protection.

Als Antioxidantien oder Stabilisatoren sind insbesondere Amine wie para-Phenylendiamin, Dicyclohexylamin, Morpholin oder Derivate dieser Amine zu nennen. Auch phenolische Antioxidantien wie 2,4-di-tert.-Butylphenol oder 3,5-Di-tert.-butyl-4-hydroxiphenylpropionsäure und deren Derivate werden Kraft- und Schmierstoffen zugesetzt.In particular, amines such as para-phenylenediamine, dicyclohexylamine, morpholine or derivatives of these amines are antioxidants or stabilizers call. Phenolic antioxidants such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxiphenylpropionic acid and their derivatives are also added to fuels and lubricants.

Als weitere Vergaser-, Injector- und Ventildetergents sind ferner gegebenenfalls Amide und Imide des Polyisobutylenbernsteinsäureanhydrids, Polybutenpolyamine sowie langkettige Carbonamide und -imide in den Kraftstoffe enthalten.Amides and imides of polyisobutylene succinic anhydride, polybutene polyamines and long-chain carbonamides and imides are also optionally contained in the fuels as further carburetor, injector and valve detergents.

BeispieleExamples A) Herstellung der NitriloessigsäureamideA) Preparation of the nitriloacetic acid amides

  • 1) 240 g (0.48 Mol) Ditalgfettamin und 35 g (0.12 Mol) Ethylendiaminotetraessigsäure wurden aufgeschmolzen und auf 190°C erhitzt, wobei das entstandene Reaktionswasser kontinuierlich abdestillierte. Die Umsetzung wurde nach ca. 25 Stunden bei einer Säurezahl < 5 und einer Aminzahl < 1.1 abgebrochen. Durch Anlegen von Wasserstrahlvakuum (2 Stunden, 120°C) wurde das Reaktionswasser vollständig entfernt. Man erhielt 265 g eines braunen, wachsartigen Feststoffes der zur leichteren Handhabung z.B. mit Xylol verdünnt werden kann.1) 240 g (0.48 mol) of ditallow fatty amine and 35 g (0.12 mol) of ethylenediaminotetraacetic acid were melted and heated to 190 ° C., during which the water of reaction formed distilled off continuously. The reaction was stopped after about 25 hours with an acid number <5 and an amine number <1.1. The water of reaction was completely removed by applying a water jet vacuum (2 hours, 120 ° C.). This gave 265 g of a brown, waxy solid which, for easier handling, e.g. can be diluted with xylene.
  • 2) 100 g (0.2 Mol) Ditalgfettamin und 14.6 g (0.05 Mol) Ethylendiaminotetraessigsäure wurden 8 Stunden auf 180°C erwärmt. Nach dieser Zeit waren ca. 50 % des Amins zum Amid abreagiert (Säurezahl 45.8, Theorie 49.7). Man erhielt 97.6 g des Amid/Ammoniumsalzes als hellbraunen, wachsartigen Feststoff.2) 100 g (0.2 mol) of ditallow fatty amine and 14.6 g (0.05 mol) of ethylenediaminotetraacetic acid were heated at 180 ° C. for 8 hours. After this time, about 50% of the amine had reacted to the amide (acid number 45.8, theory 49.7). 97.6 g of the amide / ammonium salt were obtained as a light brown, waxy solid.
  • 3) In eine Schmelze von 229.5 (0.45 Mol Ditalgfettamin wurden bei 80°C 28.65 g (0.15 Mol) Nitrilotriessigsäure (Trilon A) eingetragen. Anschließend wurde die Reaktionsmischung 10 Stunden auf 180 bis 190°C erhitzt. Zur vollständigen Entfernung des Reaktionswassers wurde das Produkt noch 2 Stunden bei 120°C am Wasserstrahlvakuum getrocknet. Man erhielt 249 g (Theorie 250 g) hellbraunen, wachsartigen Feststoff.3) 28.65 g (0.15 mol) of nitrilotriacetic acid (Trilon A) were introduced into a melt of 229.5 (0.45 mol of ditallow fatty amine at 80 ° C.) The reaction mixture was then heated at 180 to 190 ° C. for 10 hours The product was dried for 2 hours under a water jet vacuum at 120 ° C. 249 g (theory 250 g) of light brown, waxy solid were obtained.
B) Prüfung als VentilreinigerB) Testing as a valve cleaner

Figure imgb0006
Figure imgb0006

Claims (6)

  1. A fuel for gasoline engines, containing an amount, effective as a detergent, of amides or amide ammonium salts of the formulae I and II
    Figure imgb0013
    Figure imgb0014
     or a mixture thereof, where A is straight-chain or branched alkylene of 2 to 6 carbon atoms or the radical of the formula
    Figure imgb0015
     and the radicals R, independently of one another, are essentially straight-chain aliphatic radicals of 10 to 30 carbon atoms, it being possible for some of the amido groups furthermore to be present as alkylammonium carboxylate groups having the stated radicals R.
  2. A fuel as claimed in claim 1, containing amides or amide ammonium salts or a mixture thereof, wherein R is straight-chain alkyl of 14 to 24 carbon atoms.
  3. A fuel as claimed in claim 1, containing compounds of the formula
    Figure imgb0016
     where R is straight-chain alkyl of 10 to 30 carbon atoms, it being possible for some of the amido groups to be present as dialkylammonium carboxylate groups of the amines
    Figure imgb0017
  4. A fuel as claimed in claim 1, containing the compounds of the formulae I and II in amounts of from 50 to 1,500 ppm, based on the fuel.
  5. A fuel as claimed in any of claims 1 to 4, containing compounds of the formulae I and II, where
    Figure imgb0018
     is the radical of di-tallow fatty amine.
  6. A fuel as claimed in claim 1, which contains further fuel detergents, anti-icing agents, corrosion inhibitors and/or antioxidants.
EP90124072A 1990-01-10 1990-12-13 Fuels for spark ignition engines Expired - Lifetime EP0436864B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4000539A DE4000539A1 (en) 1990-01-10 1990-01-10 FUELS FOR OTTO ENGINES
DE4000539 1990-01-10

Publications (2)

Publication Number Publication Date
EP0436864A1 EP0436864A1 (en) 1991-07-17
EP0436864B1 true EP0436864B1 (en) 1993-09-22

Family

ID=6397836

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90124072A Expired - Lifetime EP0436864B1 (en) 1990-01-10 1990-12-13 Fuels for spark ignition engines

Country Status (3)

Country Link
EP (1) EP0436864B1 (en)
CA (1) CA2033829A1 (en)
DE (2) DE4000539A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2022360759A1 (en) * 2021-10-04 2024-02-29 Innospec Fuel Specialties Llc Improvements in fuels

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2901335A (en) * 1954-10-05 1959-08-25 Standard Oil Co Additive for leaded gasoline
US3893825A (en) * 1970-12-30 1975-07-08 Universal Oil Prod Co Inhibition of corrosion
DE2531469C3 (en) * 1975-07-15 1980-10-23 Basf Ag, 6700 Ludwigshafen Use of w -N.N.N'.N'tetrasubstituted aminoalkanoic acid amides, w -N, N, N ', N'tetrasubstituted aminobutyric acid amides and processes for their preparation
DE2828038A1 (en) * 1978-06-26 1980-01-10 Basf Ag FUELS FOR OTTO ENGINES

Also Published As

Publication number Publication date
DE59002846D1 (en) 1993-10-28
CA2033829A1 (en) 1991-07-11
DE4000539A1 (en) 1991-07-11
EP0436864A1 (en) 1991-07-17

Similar Documents

Publication Publication Date Title
EP0617056B1 (en) Process for manufacturing fuel additives
EP0689576B1 (en) Mixtures suitable for use as fuel additives
EP0548617B1 (en) Fuels for spark ignition engines
EP0772664B1 (en) Hydrogenated reaction products of polyolefins and nitrogen oxides or mixtures of nitrogen oxides and oxygen and their use as additives for fuels or lubricants
EP0464489B1 (en) Ester containing fuels, for spark ignition- and diesel engines
EP0613938A1 (en) Hydrocarbon fuel compositions incorporating nitrogen-containing dispersants
EP0568873B1 (en) Beta-aminonitriles and N-alkyl-1,3-propylenediamines as well as their use as fuel and lubricant additives
US4863487A (en) Hydrocarbon fuel detergent
US5213585A (en) Alkoxylated polyetherdiamines preparation thereof, and gasolines containing same
US3873278A (en) Gasoline
JPH02196889A (en) Nitrogenous additive composition for engine fuel,and engine fuel containing said composition
US5348560A (en) Carbamates, their preparation and fuels and lubricants containing the carbamates
EP0436864B1 (en) Fuels for spark ignition engines
US4895578A (en) Hydrocarbon fuel detergent
US5282872A (en) Fuel for Otto-cycle engines
DE3942860A1 (en) Fuel for otto engine - contg. alkoxylated poly:isobutyl:amine as oil sludge dispersant
EP0567810A1 (en) Fuels and lubricants, containing N-alkyl carboxylic acid amide
US3923474A (en) Alkyldiaminoamids of fatty acids as gasoline additives
EP0484736B1 (en) Fuels for spark ignition engines
EP0081744B1 (en) Fuel additives for internal-combustion engines
DE4433271A1 (en) Use of carboxylic acid esters
DE4444912A1 (en) Use of carboxylic acid esters

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19901213

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE DE FR GB IT NL

17Q First examination report despatched

Effective date: 19920205

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR GB IT NL

REF Corresponds to:

Ref document number: 59002846

Country of ref document: DE

Date of ref document: 19931028

ITF It: translation for a ep patent filed

Owner name: ING. C. GREGORJ S.P.A.

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 19931012

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19931115

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19931215

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19931224

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19931231

Year of fee payment: 4

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19941213

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19941231

BERE Be: lapsed

Owner name: BASF A.G.

Effective date: 19941231

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19950701

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19941213

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19950831

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19950701

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19950901

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20051213