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EP0548617B1 - Fuels for spark ignition engines - Google Patents

Fuels for spark ignition engines Download PDF

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Publication number
EP0548617B1
EP0548617B1 EP92120622A EP92120622A EP0548617B1 EP 0548617 B1 EP0548617 B1 EP 0548617B1 EP 92120622 A EP92120622 A EP 92120622A EP 92120622 A EP92120622 A EP 92120622A EP 0548617 B1 EP0548617 B1 EP 0548617B1
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EP
European Patent Office
Prior art keywords
fuel
fuels
weight
detergent component
additives
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
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EP92120622A
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German (de)
French (fr)
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EP0548617A2 (en
EP0548617A3 (en
Inventor
Jürgen Dr. Mohr
Knut Dr. Oppenländer
Jürgen Dr. Thomas
Peter Dr. Schreyer
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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
    • C10L1/146—Macromolecular compounds according to different macromolecular groups, mixtures thereof
    • 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
    • C10L1/143—Organic compounds mixtures of organic macromolecular compounds with organic non-macromolecular compounds
    • C—CHEMISTRY; METALLURGY
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    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/06—Use of additives to fuels or fires for particular purposes for facilitating soot removal
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
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    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
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    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
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    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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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    • 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
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    • 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
    • C10L1/1985—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 polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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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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    • C10L1/00—Liquid carbonaceous fuels
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    • 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
    • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
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    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
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    • C10L1/233—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles
    • C10L1/2335—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring containing nitrogen and oxygen in the ring, e.g. oxazoles morpholino, and derivatives thereof
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    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
    • 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 which contain small amounts of a combination of a nitrogen-containing detergent component and a carrier oil component, the carrier oil component comprising dialkylphenol-started propoxylates.
  • Carburetor and intake system of gasoline engines are increasingly contaminated by contaminants that are caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and the crankcase ventilation gases passed into the carburetor.
  • the first generation of additives could only prevent the formation of deposits in the intake system, but not remove existing deposits, whereas the modern additives of the second generation can do both ("keep-clean” and "clean-up effect") and because of changed thermal properties, in particular also at zones of higher temperatures, namely at the inlet valves.
  • carrier oils in particular play a central role here.
  • the addition of carrier oil can have a positive effect on engine areas which are normally not reached by the conventional additives, which mainly act in the intake system.
  • US Pat. No. 4,877,416 discloses fuel mixtures which, in addition to an amine as detergent component, contain a carrier oil.
  • a carrier oil Poly (oxyalkylene) monools with hydrocarbon end groups are mentioned as carrier oil.
  • a large number of possible radicals are mentioned as hydrocarbon end groups, including in particular C7-C30-alkylphenyl.
  • a carrier oil is described which was obtained by butoxylation of dodecylphenol.
  • the compatibility with one another must also be taken into account when selecting additives.
  • the detergents and carrier oils if present in a concentrate, must not lead to deposition or phase separation. This is according to US 4,877,416 for the alkylphenol-started carrier oils e.g. achieved in that butylene oxide is used as the alkylene oxide, which, however, is relatively expensive to produce and its use is cost-intensive.
  • the alkoxylates according to the invention although no butylene oxide is used for their preparation, have good compatibility with the nitrogen-containing detergent component and also prevent the deposits mentioned in the inlet system and in the combustion chamber.
  • the alkoxylates of the formula I according to the invention also provide compatibility with the detergent when a monoalkyl-substituted propoxylate is present as an additional component of the carrier oil component, although this propoxylate is not readily compatible with the Nitrogen-containing detergent component is compatible.
  • the carrier oil component can therefore also comprise 10 to 5000 ppm (based on the fuel) of a monoalkylphenol-started propoxylate, the structure given in formula I applying to this propoxylate, with the proviso that R 1 is omitted, and in particular, the amount of the monoalkylphenol started propoxylate is not greater than the amount of the dialkylphenol started propoxylate according to formula I.
  • the fuels preferably contain 20 to 2,000 ppm, in particular 50 to 1,000 ppm (all ppm data are in each case based on the weight) of the detergent component a) or of the alkoxylate b).
  • nitrogen-containing detergent component in the mixture with the carrier oils according to the invention it is possible in principle to use any known of the products suitable for this purpose, such as those e.g. with J. Falbe, U. Hasserodt, catalysts, surfactants and mineral oil additives, G. Thieme Verlag Stuttgart 1978, p. 221 f. or in K. Owen, Gasoline and Diesel Fuel Additives, John Wiley & Sons 1989, pp. 23 ff.
  • Amides or imides of polyisobutylene succinic anhydride, polybutene polyamines and long-chain carbonamides and imides are suitable as further detergents or additional dispersants.
  • dialkylphenols used as starters are prepared in a customary manner by Friedel-Crafts alkylation of phenols with the corresponding olefins or olefin mixtures.
  • the propoxylates according to the invention have excellent compatibility, particularly with the polyisobutylamines already mentioned in the respective formulations.
  • Leaded and especially unleaded regular and premium gasoline are considered as fuels for gasoline engines.
  • the gasolines can also contain components other than hydrocarbons, e.g. Alcohols for 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 further detergents.
  • Corrosion inhibitors are mostly ammonium salts org. Carboxylic acids which tend to form films due to the corresponding 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.
  • Antioxidants or stabilizers include, in particular, amines such as para-phenylenediamine, dicyclohexylamine, morpholine or derivatives of these amines.
  • 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.
  • thermogravimetric analyzes as a measure of the effectiveness with regard to combustion chamber deposits, since a general engine test for this does not yet exist.
  • thermogravimetric analyzes provide information about the thermal load capacity of a sample, eg a thermo-oxidative condition.
  • thermo-oxidative condition e.g. a thermo-oxidative condition.
  • they allow conclusions to be drawn about the formation of deposits or residual amounts after such a thermo-oxidative treatment.
  • the high thermal load-bearing capacity combined with the least possible to vanishing residue formation is favorable for use as carrier oil in the sense of this invention.
  • alkoxylates of longer-chain dialkylphenols according to the invention meet all of these requirements (synergism with detergents, demonstrated in the engine test; excellent thermooxidative properties, verified by thermogravimetric analysis) to a high degree.
  • the additive combination of nitrogen-containing detergent component and alkoxylate as carrier oil component is preferably provided as a concentrate which contains 10 to 80% by weight, in particular 30 to 60% by weight, of the detergent component and 5 to 70% by weight .-%, in particular 20 to 60 wt .-% of the carrier oil component, ie of the propoxylate.
  • the concentrate contains a suitable solvent, e.g. aromatic and / or aliphatic hydrocarbons, especially heavy naphtha (Solvesso®).
  • thermogravimetry curve shown in the figure shows the relative mass decrease m / m o as a function of the temperature at a heating rate of 2 ° C. per minute and in the presence of air.
  • the half-life temperature of 260 to 270 ° C indicates sufficient thermo-oxidative stability; at higher temperatures the product disintegrates almost without residue (m is the mass measured in each case, m o the initial mass).

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Abstract

Fuels for gasoline engines contain a combination of a nitrogen-containing detergent component and an alkoxylate as a carrier oil component, the alkoxylate being a dialkylphenol-initiated propoxylate.

Description

Die Erfindung betrifft Kraftstoffe für Ottomotoren, die geringe Mengen einer Kombination einer Stickstoff-haltigen Detergens-Komponente und einer Trägeröl-Komponente enthalten, wobei die Trägeröl-Komponente Dialkylphenol-gestartete Propoxylate umfaßt.The invention relates to fuels for gasoline engines which contain small amounts of a combination of a nitrogen-containing detergent component and a carrier oil component, the carrier oil component comprising dialkylphenol-started propoxylates.

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 that are caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and the crankcase ventilation gases passed 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 increase 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 (see, for example: M. Rossenbeck in catalysts, surfactants, mineral oil additives, ed. J. Falbe, U. Hasserodt, p. 223 f ., G. Thieme Verlag, Stuttgart 1978).

Je nach Wirkungsweise, aber auch nach dem bevorzugten Wirkort solcher Detergens-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, whereas the modern additives of the second generation can do both ("keep-clean" and "clean-up effect") and because of changed thermal properties, in particular also at zones of higher temperatures, namely at the inlet valves.

Auch die Frage nach der Zunahme des Oktanzahlbedarfs eines Ottomotors, bedingt durch Ablagerungen im Brennraum über eine gewisse Laufzeit, und die Möglichkeit, hier durch gezielte Additivierung des Kraftstoffes positiv einzugreifen, geraten immer mehr in den Blickpunkt des Interesses bei der Entwicklung neuer Additive.The question of the increase in the octane number requirement of a gasoline engine, due to deposits in the combustion chamber over a certain period of time, and the possibility of intervening positively through targeted fuel additives are increasingly becoming the focus of interest in the development of new additives.

Durch geschickte Kombination solcher das Einlaßsystem reinhaltender Detergentien mit weiteren Komponenten kann ein breiteres Wirkungsspektrum solcher Formulierungen erzielt werden.By cleverly combining such detergents that keep the inlet system clean with other components, a broader spectrum of activity of such formulations can be achieved.

Insbesondere den sogenannten Trägerölen kommt hierbei eine zentrale Aufgabe zu.The so-called carrier oils in particular play a central role here.

So gelingt es zum einen, mit speziellen, meist synthetischen Trägerölkomponenten aufgrund synergistischer Effekte den Wirkungsgrad der Detergentien im Vergaser oder Einlaßsystem zu erhöhen. Bestimmte Additive entfalten diese Wirkung überhaupt erst in Kombination mit einem Öl.On the one hand, it is possible to increase the efficiency of the detergents in the gasifier or intake system with special, mostly synthetic carrier oil components due to synergistic effects. Certain additives only develop this effect in combination with an oil.

Zum anderen können durch Trägerölzugaben Motorbereiche positiv beeinflußt werden, die von den herkömmlichen, vorwiegend im Einlaßsystem wirkenden Additiven normalerweise nicht erreicht werden.On the other hand, the addition of carrier oil can have a positive effect on engine areas which are normally not reached by the conventional additives, which mainly act in the intake system.

Hierzu sind vor allem die bereits angesprochenen Brennraumablagerungen (ORI-Problem) zu nennen.Above all, the already mentioned combustion chamber deposits (ORI problem) should be mentioned.

Aus der US 4,877,416 sind Kraftstoffgemische bekannt, die neben einem Amin als Detergens-Komponente ein Trägeröl enthalten. Als Trägeröl werden Poly(oxyalkylen)monoole mit Kohlenwasserstoff-Endgruppen genannt. Als Kohlenwasserstoff-Endgruppen sind eine große Zahl von möglichen Resten erwähnt, darunter insbesondere C₇-C₃₀-Alkylphenyl. Beispielhaft wird ein Trägeröl beschrieben, das durch Butoxilierung von Dodecylphenol erhalten wurde.US Pat. No. 4,877,416 discloses fuel mixtures which, in addition to an amine as detergent component, contain a carrier oil. Poly (oxyalkylene) monools with hydrocarbon end groups are mentioned as carrier oil. A large number of possible radicals are mentioned as hydrocarbon end groups, including in particular C₇-C₃₀-alkylphenyl. As an example, a carrier oil is described which was obtained by butoxylation of dodecylphenol.

Neben den Effekten bezüglich der Reinhaltung von Ventilen und Einlaßsystem und der Verhinderung von Brennraumablagerungen ist bei der Auswahl der Additive jedoch auch noch die Verträglichkeit untereinander zu berücksichtigen. So dürfen die Detergentien und Trägeröle, wenn sie in einem Konzentrat vorliegen, nicht zu Abscheidungen oder Phasentrennung führen. Dies wird gemäß der US 4,877,416 bei den Alkylphenol-gestarteten Trägerölen z.B. dadurch erreicht, daß als Alkylenoxid Butylenoxid verwendet wird, das jedoch verhältnisgemäß aufwendig herzustellen und dessen Einsatz kostenintensiv ist.In addition to the effects of keeping valves and intake systems clean and preventing combustion chamber deposits, the compatibility with one another must also be taken into account when selecting additives. For example, the detergents and carrier oils, if present in a concentrate, must not lead to deposition or phase separation. This is according to US 4,877,416 for the alkylphenol-started carrier oils e.g. achieved in that butylene oxide is used as the alkylene oxide, which, however, is relatively expensive to produce and its use is cost-intensive.

Es bestand daher die Aufgabe, Kombinationen von Additiven für Kraftstoffe zu finden, die zum einen synergistische Wirkung im Hinblick auf Einlaßsystemreinhaltung in Ottomotoren entfalten, andererseits den Anstieg des Oktanzahlbedarfs eines Motors möglichst gering halten bzw. sogar verhindern und die in konzentrierter Lösung gut miteinander verträglich sind, d.h. sich nicht entmischen. Die Additive sollen sich zudem aus möglichst leicht zugänglichen Stoffen herstellen lassen und thermostabil sein.It was therefore the task of finding combinations of additives for fuels which, on the one hand, have a synergistic effect with regard to keeping the intake system clean in gasoline engines, on the other hand keep the increase in the octane requirement of an engine as small as possible or even prevent it, and which are well compatible with one another in concentrated solution , ie don't segregate. The additives should also be able to be made from easily accessible substances and should be thermostable.

Diese Aufgabe wird gelöst durch Kraftstoffe für Ottomotoren, die enthalten eine Kombination aus

  • a) 10 bis 5 000 ppm einer Stickstoff-haltigen Detergens-Komponente und
  • b) 10 bis 5 000 ppm eines Alkoxylats der folgenden Formel I
    Figure imgb0001
     in der bedeuten
    R¹ und R
    unabhängig voneinander einen verzweigten oder unverzweigten C₆-C₃₀-Alkylrest,
    einer der beiden Reste R³ Methyl und der andere Wasserstoff
    und
    n=
    1 bis 100.
This task is solved by fuels for gasoline engines that contain a combination of
  • a) 10 to 5,000 ppm of a nitrogen-containing detergent component and
  • b) 10 to 5000 ppm of an alkoxylate of the following formula I
    Figure imgb0001
     in the mean
    R¹ and R
    independently of one another are a branched or unbranched C₆-C₃₀ alkyl radical,
    one of the two residues R³ is methyl and the other is hydrogen
    and
    n =
    1 to 100.

Überraschenderweise hat sich gezeigt, daß die erfindungsgemäßen Alkoxylate, obwohl zu ihrer Herstellung kein Butylenoxid verwendet wird, eine gute Verträglichkeit mit der Stickstoff-haltigen Detergens-Komponente aufweisen und außerdem die genannten Ablagerungen im Einlaßsystem und im Brennraum verhindern.Surprisingly, it has been found that the alkoxylates according to the invention, although no butylene oxide is used for their preparation, have good compatibility with the nitrogen-containing detergent component and also prevent the deposits mentioned in the inlet system and in the combustion chamber.

Als besonders vorteilhaft hat sich herausgestellt, daß durch die erfindungsgemäßen Alkoxylate der Formel I eine Verträglichkeit mit dem Detergens auch dann noch gegeben ist, wenn als zusätzlicher Bestandteil der Trägeröl-Komponente ein monoalkylsubstituiertes Propoxylat vorhanden ist, obwohl dieses Propoxylat für sich nicht ohne weiteres mit der Stickstoff-haltigen Detergens-Komponente verträglich ist.It has been found to be particularly advantageous that the alkoxylates of the formula I according to the invention also provide compatibility with the detergent when a monoalkyl-substituted propoxylate is present as an additional component of the carrier oil component, although this propoxylate is not readily compatible with the Nitrogen-containing detergent component is compatible.

Die Trägeröl-Komponente kann daher neben dem Bestandteil b) noch 10 bis 5 000 ppm (bez. auf den Kraftstoff) eines Monoalkylphenol-gestarteten Propoxylats umfassen, wobei für dieses Propoxylats die in Formel I angegebene Struktur mit der Maßgabe gilt, daß R¹ wegfällt, und insbesondere gilt, daß die Menge des Monoalkylphenol-gestarteten Propoxylats nicht größer ist als die Menge des Dialkylphenol-gestarteten Propoxylats nach Formel I.In addition to component b), the carrier oil component can therefore also comprise 10 to 5000 ppm (based on the fuel) of a monoalkylphenol-started propoxylate, the structure given in formula I applying to this propoxylate, with the proviso that R 1 is omitted, and in particular, the amount of the monoalkylphenol started propoxylate is not greater than the amount of the dialkylphenol started propoxylate according to formula I.

Es ist auch möglich, zu der erfindungsgemäßen Additiv-Kombination noch andere Trägeröl-Komponenten zuzugeben, z.B. Ester aus Monocarbonsäuren oder Polycarbonsäuren und Alkanolen oder Polyolen, wie sie in der DE 38 38 918 A1 beschrieben sind.It is also possible to add other carrier oil components to the additive combination according to the invention, e.g. Esters from monocarboxylic acids or polycarboxylic acids and alkanols or polyols, as described in DE 38 38 918 A1.

Als bevorzugte Alkoxylate werden Verbindungen eingesetzt, in denen R¹ und/oder R einen verzweigten oder unverzweigten C₇-C₁₈-Alkylrest bedeuten und n = 5 bis 50, insbesondere n = 7 bis 30, ist.Compounds in which R¹ and / or R are a branched or unbranched C₇-C₁₈ alkyl radical and n = 5 to 50, in particular n = 7 to 30, are used as preferred alkoxylates.

Bevorzugt enthalten die Kraftstoffe 20 bis 2 000 ppm, insbesondere 50 bis 1 000 ppm (alle ppm-Angaben sind jeweils bezogen auf das Gewicht) der Detergens-Komponente a) bzw. des Alkoxylats b).The fuels preferably contain 20 to 2,000 ppm, in particular 50 to 1,000 ppm (all ppm data are in each case based on the weight) of the detergent component a) or of the alkoxylate b).

Als Stickstoff-haltige Detergens-Komponente in der Mischung mit den erfindungsgemäßen Trägerölen kann prinzipiell jedes bekannte der hierfür geeigneten Produkte eingesetzt werden, wie sie z.B. bei J. Falbe, U. Hasserodt, Katalysatoren, Tenside und Mineralöladditive, G. Thieme Verlag Stuttgart 1978, S. 221 f. oder bei K. Owen, Gasoline und Diesel Fuel Additives, John Wiley & Sons 1989, S. 23 ff. beschrieben sind.As a nitrogen-containing detergent component in the mixture with the carrier oils according to the invention it is possible in principle to use any known of the products suitable for this purpose, such as those e.g. with J. Falbe, U. Hasserodt, catalysts, surfactants and mineral oil additives, G. Thieme Verlag Stuttgart 1978, p. 221 f. or in K. Owen, Gasoline and Diesel Fuel Additives, John Wiley & Sons 1989, pp. 23 ff.

Vorzugsweise verwendet man Verbindungen mit einer Amin-, Amid- oder Imid-Gruppe, insbesondere Polyisobutylamine gemäß EP 0 244 616, Ethylendiamintetraessigsäureamide und/oder -imide gemäß EP 0 188 786 oder Polyetheramine gemäß EP 0 356 725, wobei auf die Definitionen in diesen Literaturstellen hiermit Bezug genommen wird.Compounds with an amine, amide or imide group, in particular polyisobutylamines according to EP 0 244 616, ethylenediaminetetraacetic acid amides and / or imides according to EP 0 188 786 or polyether amines according to EP 0 356 725 are preferably used, referring to the definitions in these references reference is hereby made.

Auch Mischungen derartiger Detergentien können eingesetzt werden.Mixtures of such detergents can also be used.

Als weitere Detergentien bzw. zusätzliche Dispergatoren sind Amide oder Imide des Polyisobutylenbernsteinsäureanhydrids, Polybutenpolyamine sowie langkettige Carbonamide und -imide geeignet.Amides or imides of polyisobutylene succinic anhydride, polybutene polyamines and long-chain carbonamides and imides are suitable as further detergents or additional dispersants.

Die Herstellung der Alkoxylate ist allgemein bekannt und z.B. in der EP 376 236 Al beschrieben.The preparation of the alkoxylates is well known and e.g. described in EP 376 236 A1.

Die als Starter eingesetzten Dialkylphenole werden in üblicher Weise durch Friedel-Crafts-Alkylierung von Phenolen mit den entsprechenden Olefinen oder Olefingemischen hergestellt.The dialkylphenols used as starters are prepared in a customary manner by Friedel-Crafts alkylation of phenols with the corresponding olefins or olefin mixtures.

Die erfindungsgemäßen Propoxylate weisen ausgezeichnete Verträglichkeit besonders mit den bereits genannten Polyisobutylaminen in den jeweiligen Formulierungen auf.The propoxylates according to the invention have excellent compatibility, particularly with the polyisobutylamines already mentioned in the respective formulations.

Sie unterstützen deren Wirkung als Einlaßsystemreiniger unter anderem auch im Sinne einer Detergens-Einsparung.They support their effect as an inlet system cleaner, among other things in terms of saving detergents.

Als Kraftstoffe für Ottomotoren kommen verbleites und insbesondere unverbleites Normal- und Superbenzin in Betracht. Die Benzine können auch andere Komponenten als Kohlenwasserstoffe, z.B. Alkohole für Methanol, Ethanol, tert.-Butanol sowie Ether, z.B. Methyltertiärbutylether enthalten. Neben den erfindungsgemäß zu verwendenden alkoxylierten Polyetheraminen enthalten die Kraftstoffe in der Regel noch weitere Zusätze wie Korrosionsinhibitoren, Stabilisatoren, Antioxidantien und/oder weitere Detergentien.Leaded and especially unleaded regular and premium gasoline are considered as fuels for gasoline engines. The gasolines can also contain components other than hydrocarbons, e.g. Alcohols for methanol, ethanol, tert-butanol and ethers, e.g. Contain methyl tertiary butyl ether. In addition to the alkoxylated polyetheramines to be used according to the invention, the fuels generally also contain further additives such as corrosion inhibitors, stabilizers, antioxidants and / or further 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 corresponding 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.Antioxidants or stabilizers include, in particular, amines such as para-phenylenediamine, dicyclohexylamine, morpholine or derivatives of these amines. 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 Maß für die Wirksamkeit im Hinblick auf Brennraumablagerungen werden von verschiedenen Autoren (s. z.B. US 4,877,416) die Ergebnisse thermogravimetrischer Analysen herangezogen, da ein genereller Motortest hierfür noch nicht existiert.Various authors (see e.g. US 4,877,416) use the results of thermogravimetric analyzes as a measure of the effectiveness with regard to combustion chamber deposits, since a general engine test for this does not yet exist.

Thermogravimetrische Analysen liefern zum einen Aussagen über die thermische Belastbarkeit einer Probe, z.B. einer thermooxidativen Bedingungen. Andererseits lassen sie Rückschlüsse auf die Bildung von Ablagerungen bzw. Restmengen nach einer solchen thermooxodativen Behandlung zu. Erfahrungsgemäß günstig für den Einsatz als Trägeröl im Sinne dieser Erfindung ist die hohe thermische Belastbarkeit verbunden mit möglichst geringer bis verschwindender Rückstandbildung.On the one hand, thermogravimetric analyzes provide information about the thermal load capacity of a sample, eg a thermo-oxidative condition. On the other hand, they allow conclusions to be drawn about the formation of deposits or residual amounts after such a thermo-oxidative treatment. Experience has shown that the high thermal load-bearing capacity combined with the least possible to vanishing residue formation is favorable for use as carrier oil in the sense of this invention.

Die erfindungsgemäßen Alkoxylate längerkettiger Dialkylphenole erfüllen alle diese Forderungen (Synergismus mit Detergentien, belegt im Motortest; ausgezeichnete thermooxidative Eigenschaften, belegt durch thermogravimetrische Analyse) in hohem Maße.The alkoxylates of longer-chain dialkylphenols according to the invention meet all of these requirements (synergism with detergents, demonstrated in the engine test; excellent thermooxidative properties, verified by thermogravimetric analysis) to a high degree.

Die Additiv-Kombination aus Stickstoff-haltiger Detergens-Komponente und Alkoxylat als Trägerölkomponente wird bevorzugt als Konzentrat zur Verfügung gestellt, das 10 bis 80 Gew.-%, insbesondere 30 bis 60 Gew.-%, der Detergens-Komponente und 5 bis 70 Gew.-%, insbesondere 20 bis 60 Gew.-% der Trägerölkomponente, d.h. des Propoxylats, enthält. Zur Vervollständigung auf 100 Gew.-% enthält das Konzentrat ein geeignetes Lösungsmittel, z.B. aromatische und/oder aliphatische Kohlenwasserstoffe, insbesondere Schwernaphtha (Solvesso®).The additive combination of nitrogen-containing detergent component and alkoxylate as carrier oil component is preferably provided as a concentrate which contains 10 to 80% by weight, in particular 30 to 60% by weight, of the detergent component and 5 to 70% by weight .-%, in particular 20 to 60 wt .-% of the carrier oil component, ie of the propoxylate. To complete to 100% by weight, the concentrate contains a suitable solvent, e.g. aromatic and / or aliphatic hydrocarbons, especially heavy naphtha (Solvesso®).

Die Prüfung der Produkte auf ihre Eignung als Kraftstoffadditive erfolgt mittels Motorentest:The products are tested for suitability as fuel additives using an engine test:

Nach CEC-F-02-T-79 wird die Wirkung als Ventilreiniger getestet.According to CEC-F-02-T-79, the effect as a valve cleaner is tested.

BeispieleExamples Herstellung eines erfindungsgemäßen AlkoxylatsPreparation of an alkoxylate according to the invention

300 Gew.-Teile eines Gemisches aus 55 Gew.-% Dinonylphenol und 45 Gew.-% Nonylphenol werden mit 0,8 Gew.-Teilen K-tert.-butylat in Autoklaven vorgelegt und mit 620 Gew.-Teilen Propylenoxid bei 120 bis 125°C umgesetzt. Nach beendeter Reaktion wird das so erhaltene Propoxylat mit Magnesiumsilikat solange behandelt, bis der Kalium-Gehalt unter 1 ppm liegt.300 parts by weight of a mixture of 55% by weight of dinonylphenol and 45% by weight of nonylphenol are placed in autoclaves with 0.8 parts by weight of K-tert-butoxide and with 620 parts by weight of propylene oxide at 120 to 125 ° C implemented. After the reaction has ended, the propoxylate obtained in this way is treated with magnesium silicate until the potassium content is below 1 ppm.

Ergebnisse der MotortestsResults of the engine tests

Prüfungen als Einlaßsystem- und Ventilreiniger

Figure imgb0002
Tests as an intake system and valve cleaner
Figure imgb0002

Ergebnis der thermogravimetrischen AnalyseResult of the thermogravimetric analysis

Die in der Figur abgebildete Thermogravimetrie-Kurve zeigt die relative Massenabnahme m/mo in Abhängigkeit von der Temperatur bei einer Aufheizrate von 2°C pro Minute und in Anwesenheit von Luft. Die Halbwertstemperatur von 260 bis 270°C zeigt eine ausreichende thermooxidative Stabilität an; bei höheren Temperaturen zerfällt das Produkt nahezu rückstandsfrei (m ist dabei die jeweils gemessene Masse, mo die Anfangsmasse).The thermogravimetry curve shown in the figure shows the relative mass decrease m / m o as a function of the temperature at a heating rate of 2 ° C. per minute and in the presence of air. The half-life temperature of 260 to 270 ° C indicates sufficient thermo-oxidative stability; at higher temperatures the product disintegrates almost without residue (m is the mass measured in each case, m o the initial mass).

Claims (6)

  1. A fuel for gasoline engines, containing a combination of
    a) from 10 to 5,000 ppm of a nitrogen-containing detergent component and
    b) from 10 to 5,000 ppm of an alkoxylate of the following formula I
    Figure imgb0004
     where R¹ and R independently of one another are each branched or straight-chain C₆-C₃₀-alkyl, one of the two radicals R³ is methyl and the other is hydrogen and n is from 1 to 100.
  2. A fuel as claimed in claim 1, wherein the detergent component a) is at least one compound having an amino, amido or imido group.
  3. A fuel as claimed in claim 2, wherein the detergent component a) is or contains a polyisobutylamine.
  4. A fuel as claimed in claim 1, wherein R¹ or R is branched or straight-chain C₇-C₁₈-alkyl.
  5. A fuel as claimed in claim 1, wherein n is from 5 to 50, in particular from 7 to 30.
  6. A concentrate of components a) and b) as claimed in claim 1 in a solvent, containing from 10 to 80% by weight of the nitrogen-containing detergent component a) and from 5 to 70% by weight of the alkoxylate b) of the formula I and an amount of solvent required as the remainder to 100% by weight.
EP92120622A 1991-12-20 1992-12-03 Fuels for spark ignition engines Expired - Lifetime EP0548617B1 (en)

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DE4142241A DE4142241A1 (en) 1991-12-20 1991-12-20 FUELS FOR OTTO ENGINES
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ATE135394T1 (en) 1996-03-15
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EP0548617A3 (en) 1993-07-21
US5298039A (en) 1994-03-29

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