EP0310875A1 - Fuels containing a polyether amine for spark ignition engines - Google Patents

Fuels containing a polyether amine for spark ignition engines Download PDF

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EP0310875A1
EP0310875A1 EP19880115566 EP88115566A EP0310875A1 EP 0310875 A1 EP0310875 A1 EP 0310875A1 EP 19880115566 EP19880115566 EP 19880115566 EP 88115566 A EP88115566 A EP 88115566A EP 0310875 A1 EP0310875 A1 EP 0310875A1
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polyether
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French (fr)
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Dieter Dr. Franz
Charalampos Dr. Gousetis
Claus Peter Jakob
Helmut Dr. Mach
Hans-Peter Dr. Rath
Klaus Starke
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BASF SE
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BASF SE
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic 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
    • C10L1/2225(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing

Abstract

Fuels for spark-ignition engines, containing small quantities of a polyether-amine of the formula I <IMAGE> in which R<1> is the radical of a monohydric or polyhydric alcohol or of an amine, each having 2 to 30 carbon atoms, X is an oxygen atom or an <IMAGE> group, in which R<4> is a second radical R<1> or a second radical <IMAGE> R<2> is the alkylene radical derived from propylene oxide or butylene oxide, m is one of the numbers 5 to 100 and R<3> is hydrogen or an alkyl radical having 1 to 20 carbon atoms, R<5> is hydrogen, and R<5> and R<3> can also each be the radical <IMAGE> the molecular weight Mn is 500 to 5000, the polyether-amines having been prepared by amination of polyethers of the formula II <IMAGE> in which R<1>, X, R<2> and m are as defined above, with ammonia or primary aliphatic amines, are novel ether-amine additives having an improved valve-cleaning action.

Description

  • Die Erfindung betrifft Kraftstoffe für Ottomotoren, die geringe Mengen eines Polyetheramins enthalten, wobei das Polyetheramin durch Aminierung von Polyethern hergestellt ist. The invention relates to fuels for gasoline engines, containing small amounts of a polyetheramine wherein the polyetheramine is prepared by amination of polyethers.
  • Polyetheramine sind als Kraftstoffadditive zur Reinhaltung und Reinigung von Vergasern, Einspritzdüsen und Ventilen bekannt und zB Gegenstand der PCT-Anmeldung WO 85/01956 oder der EP-B1 0 100 665. Polyetheramines are known as fuel additives for keeping and cleaning of carburetors, fuel injectors and valves, and for example, the subject of the PCT application WO 85/01956 or EP-B1 0100665.
  • Dort sind Verbindungen beschrieben, die ausgehend von Ethylenchlorhydrin, Alkoxylierung, Verätherung der Endhydroxylgruppe und Ersatz des Chloratoms durch eine Aminogruppe hergestellt werden. There are compounds described which are prepared from ethylene chlorohydrin, alkoxylation, etherification of the Endhydroxylgruppe and replacement of the chlorine atom by an amino group.
  • Obgleich diese Polyetheramine ausgezeichnete Ventilreiniger mit ausgeprägtem Reinigungseffekt im Einlaßsystem des Motors sind, haben Sie den Nachteil eines von der Herstellung verbleibenden Chlorgehalts. Although these polyetheramines are excellent cleaners valve with a pronounced cleaning effect in the intake system of the engine, they have the disadvantage of a remaining from the production of chlorine content. Kraftstoff- oder Ölzusätze, die Chlor enthalten, sind jedoch aus Gründen der Korrosion und des Umweltschutzes unerwünscht. Fuel or oil additives which contain chlorine, but are undesirable for reasons of corrosion and environmental protection.
  • Es bestand daher die Aufgabe chlorfreie, als Kraftstoffadditive geeignete Polyetheramine bereitzustellen. It was therefore the task chlorine-free, provide as fuel additives suitable polyether amines. Es bestand weiterhin die Aufgabe, die bekannten Polyetheramine in ihrer Wirkung zu verbessern, bzw. mit geringer Aufwandmenge die gleiche Wirkung zu erzielen. It was furthermore to improve the known polyether amines in effect the task, or to achieve the same effect with low application rate.
  • Es wurde nun überraschenderweise gefunden, daß Kraftstoffe für Ottomotoren, die geringe Mengen Polyetheramine enthalten, eine sehr gute Ventil- und Vergaserreinigungswirkung haben und kein Chlor aufweisen, wenn die Polyetheramine solche der Formel I It has now surprisingly been found that fuels for gasoline engines, containing small quantities of polyether amines contain, have a very good valve and carburetor detergency and have no chlorine when the polyetheramines of the formula I
    Figure imgb0001
    sind, in der R 1 den Rest eines ein- oder mehrwertigen Alkohols, oder eines Amins jeweils mit 2 bis 30 Kohlenstoffatomen, X ein Sauerstoffatom oder eine are in the R 1 is the radical of a mono- or polyhydric alcohol, or an amine each having 2 to 30 carbon atoms, X is an oxygen atom or a
    Figure imgb0002
    in der R4- für einen zweiten Rest R 1 oder einen zweiten Rest in the R4 for a second rest R 1 or a second residual
    Figure imgb0003
    steht, R 2 den aus Propylen- oder Butylenoxid stammenden Alkylenrest, m die Zahlen 5 bis 100 und R 3 Wasserstoff oder einen Alkylrest mit 1 bis 20 Kohlenstoffatomen, R 5 Wasserstoff und R 5 und R 3 jeweils ferner den Rest , R 2 originating from propylene or butylene alkylene group, m the numbers 5 to 100 and R 3 is hydrogen or an alkyl radical having 1 to 20 carbon atoms, R 5 is hydrogen and R 5 and R 3 each further comprise the remainder
    Figure imgb0004
    bedeuten können, das Molekulargewicht M N 500 bis 5000 beträgt und wobei die Polyetheramine durch Aminierung von Polyethern der Formel II may mean the molecular weight M N is 500 to 5,000 and wherein the polyetheramine by amination of polyethers of the formula II
    Figure imgb0005
    in der R 1 , X, R 2 und m die genannten Bedeutungen haben, mit Ammoniak oder primären aliphatischen Aminen hergestellt sind. have R 1, X, R 2 and m have the meanings given above, are prepared with ammonia or primary aliphatic amines.
  • Die erfindungsgemäß zu verwendenden Polyetheramine werden im allgemeinen in zwei Stufen synthetisiert. The present invention to be used polyether amines are generally synthesized in two stages. In einem ersten Schritt stellt man durch Propoxylierung und/oder Butoxylierung von Alkoholen oder Aminen in an sich bekannter Weise Verbindungen der Formel II her. In a first step is prepared by propoxylation and / or butoxylation of alcohols or amines in the manner known per se compounds of the formula II forth.
  • Als Alkanol kommen dabei ein- oder mehrwertige Alkohole in Betracht, wobei jedoch bei mehrwertigen Alkoholen das Verhältnis von OH- zu CH= 2 -Gruppen nicht größer als 1:3 sein soll. Alkanol thereby alcohols, mono- or polyhydric into consideration, however, in polyhydric alcohols, the ratio of OH to CH 2 groups = not greater than 1: should be. 3 Die bevorzugten Monoalkohole sind insbesondere verzweigte Alkanole mit 3 bis 30 Kohlenstoffatomen, vorzugsweise 4 bis 15 Kohlenstoffatomen. The preferred monoalcohols are particularly branched alkanols having 3 to 30 carbon atoms, preferably 4 to 15 carbon atoms. Im einzelnen kommen als Starter neben Ethanol, den n- und Isoalkoholen des Propanols, Butanols, Pentanols, Hexanols, Oktanols wie 2-Ethyl-hexanol, Nonanol und Dekanol, Stearylalkohol, Cetylalkohol sowie Alfole der allgemeinen Formel In detail, the n and Isoalkoholen of propanol, butanol, pentanol, hexanol, octanol, such as 2-ethyl-hexanol, nonanol and decanol, stearyl alcohol, cetyl alcohol and Alfols of the general formula as an initiator in addition to ethanol,
    Figure imgb0006
    in der n 1 bis 11 bedeuten in Betracht. wherein n represents 1 to 11 into consideration. Schließlich sind Oxoalkohole auf Basis von a-Olefinen mit 5 bis 30 C-Atomen insbesondere Diisobuten-Codimer, Tri- bis Dekamer-propylen und Di- bis Octamerbuten zu nennen. Finally, oxo alcohols are, in particular diisobutene codimer based on alpha-olefins having 5 to 30 carbon atoms, may be mentioned tri- to decamer of propylene and di- to Octamerbuten. Als Diole kommen zB Hexandiol und Dodekandiol in Betracht, doch müssen hier bei der Alkoxilierung größere Butylenoxid-Mengen verwendet werden, so daß Diole weniger bevorzugt sind. As diols such as hexanediol and dodecanediol into account, but must be used in the alkoxylation larger butylene oxide amounts here so that diols are less preferred.
  • Es ist aber auch möglich, das Hydroformylierungsprodukt eines niedrigmolekularen Polyisobutens di ein Polyisobutylenalkohol mit 33 bis 61 Kohlenstoffatomen zu alkoxylieren. However, it is also possible to alkoxylate the hydroformylation of a low molecular polyisobutene di a Polyisobutylenalkohol with 33-61 carbon atoms.
  • Die als Starter zu verwendenden Amine sind in der Regel primäre und sekundäre Monoamine insbesondere verzweigte Alkylamine mit 3 bis 30, vorzugsweise 4 bis 15, C-Atomen. To be used as a starter amines are generally primary and secondary monoamines, particularly branched alkylamines with 3 to 30, preferably 4 to 15, carbon atoms. Im einzelnen kommen zB die den oben genannten Alkoholen entsprechende Amine in Betracht. In detail, for example, there are the alcohols mentioned above corresponding amines.
  • Aus Kostengründen und weil weniger einheitliche Produkte entstehen, sind Amine jedoch weniger als Starter geeignet als die Alkohole. For cost reasons and because less uniform products arise amines are less suitable as a starter as the alcohols.
  • Die Alkoxylierung mit Propylenoxid und/oder Butylenoxid erfolgt in an sich bekannter Weise. The alkoxylation with propylene oxide and / or butylene oxide in a known per se. Eine allgemeine Herstellvorschrift wird weiter unten angegeben. A general method of preparation is given below. Die Menge an Propylenoxid bzw. Butylenoxid kann in weiteren Bereichen schwanken. The amount of propylene oxide or butylene oxide can vary in other areas. In der Regel verwendet man 3 bis 100, vorzugsweise 5 bis 30 Mol Alkylenoxid pro Mol Starter. As a rule 3 used to 100, preferably 5 to 30 moles of alkylene oxide per mole of initiator. Die angewandte Menge und die Wahl von Propylenoxid oder Butylenoxid hängt jedoch davon ab, welches Startermolekül verwendet wurde. However, the amount used and the choice of propylene or butylene depends on which primer was used. Enthält das Startermolekül einen langkettigen hydrophoben Rest wie Polyisobutylenalkohol, können größere Mengen Propylenoxid zur Anwendung kommen, ja, es können sogar geringe Mengen Ethylenoxid toleriert werden, obgleich Ethylenoxid normalerweise nicht verwendet wird. Contains the initiator molecule is a long chain hydrophobic moiety as Polyisobutylenalkohol, larger amounts of propylene oxide may be used, yes, it can be tolerated, although ethylene oxide is not normally used even small amounts of ethylene oxide.
  • Insgesamt gilt, daß die Polyalkoxide und deren Menge so gewählt werden, daß eine Mindestlöslichkeit von 50 Gew.% in einem Kohlenwasserstoff zB Toluol oder Mineralöl SN 200 zur Herstellung eines Masterbatch gewährleistet ist. Overall, it holds that the polyalkoxides and the amount thereof are selected such that a minimum solubility of 50 wt.% In a hydrocarbon such as toluene or mineral oil SN 200 is ensured for the preparation of a masterbatch.
  • In einer zweiten Stufe werden dann die Polyether im allgemeinen ohne weitere Vorbehandlung einer Aminierung nach an sich bekannten Methoden unterworfen. In a second step, the polyether generally, without further pretreatment amination then be subjected to methods known per se. Unter Aminierung wird dabei die Einführung einer -NHR 3 -Gruppe in den Polyether mit endständiger OH-Gruppe unter Wasserabspaltung verstanden. Amination under the introduction of an -NHR 3 group is understood in the polyether having a terminal OH group with elimination of water. Die Methodik ist im einzelnen in Houben-Weyl 11/1, Kapitel llb, Seiten 108 - 134 beschrieben, worauf hiermit Bezug genommen wird. The methodology is IIb in detail in Houben-Weyl 11/1, chapters, pages 108 - 134 described, which is incorporated herein by reference.
  • Wie bei allen aminierenden Hydrierungen können die noch freien Wasserstoffatome am Stickstoff durch weitere Reste As with all aminating hydrogenation the remaining free hydrogen atoms on the nitrogen can further radicals
    Figure imgb0007
    ersetzt werden und es entsteht ein Gemisch von primären, sekundären und tertiären Aminen. be replaced and there is a mixture of primary, secondary and tertiary amines.
  • Die Aminierungsreaktion wird zweckmäßig bei Temperaturen zwischen 160 und 250 ° C und Drücken bis zu 600 bar, vorzugsweise 80 - 300 bar durchgeführt. The amination reaction is advantageously carried out at temperatures of between 160 and 250 ° C and pressures up to 600 bar, preferably 80 - 300 bar performed. Als Katalysatoren kommen vorzugsweise kobalt- und nickelhaltige Katalysatoren auf Trägern wie Si0 2 oder A1 2 0 3 , aber auch Raney Nickel oder Raney Kobalt kommen in Frage. As catalysts, preferably catalysts are cobalt and nickel containing on carriers such as Si0 2 or A1 2 0 3, but also Raney nickel or Raney cobalt are suitable. Ein quantitativer Umsatz der OH Gruppen ist für den Anwendungszweck nicht erforderlich, besonders dann, wenn der als Ausgangsverbindung der Formel benutzte Polyether auch als Trägeröl für die Benzinadditivformulierung verwendet wird. A quantitative conversion of the OH groups is not required for the intended use, especially if that is the starting compound of formula used polyether as a carrier oil for the gasoline additive formulation. Der Teilumsatz kann sogar vorteilhaft sein, da man höhere Raum-Zeit-Ausbeuten erhält. The partial conversion may even be beneficial as you get higher space-time yields. Im allgemeinen wendet man bei der Aminierung das Ammoniak bzw. das Amin im Überschuß zB im 10- bis 60fachen, vorzugsweise 15- bis 40fachen molaren Überschuß an. In general, it applies in the amination the ammonia or the amine in excess, for example in the 10- to 60-fold, preferably 15- to 40-fold molar excess of. Dabei ist die Verwendung von Ammoniak bevorzugt. The use of ammonia is preferred. Als primäre Amine für die Aminierung sind vor allem Methyl-, Ethyl- oder Butylamin zu nennen. Suitable primary amines for the amination especially methyl, ethyl or butyl may be mentioned.
  • Als Kraftstoff kommen verbleites und unverbleites Normal- und Superbenzin in Betracht. leaded and unleaded regular and premium grade gasoline as fuel. Die Benzine können auch andere Komponenten als Kohlenwasserstoffe, zB Alkohole wie Methanol, Ethanol, tert. The gasolines may also contain components other than hydrocarbons, for example alcohols such as methanol, ethanol, tert. Butanol sowie Ether, zB Methyltertiärbutylether enthalten. Butanol, and ethers, for example, contain methyl tertiary butyl ether. Neben den erfindungsgemäß zu verwendenden Polyetheraminen enthalten die Kraftstoffe in der Regel noch weiter Zusätze wie Korrosionsinhibitoren, Stabilisatoren, Antioxydantien, Detergents etc. In addition to the invention to be used polyetheramines the fuels even further usually contain additives such as corrosion inhibitors, stabilizers, antioxidants, detergents etc.
  • Korrosionsinhibitoren sind meist Ammoniumsalze org. Corrosion inhibitors are generally organic ammonium salts. Carbonsäuren, die durch entsprechende Struktur der Ausgangsverbindungen zur Filmbildung neigen. Carboxylic acids, which tend to have an appropriate structure of the starting compounds for the film formation. Auch Amine zur Erhöhung des pH-Wertes finden sich häufig in Korrosionsinhibitoren. Amines for increasing the pH are also frequently present in corrosion inhibitors. Als Buntmetallkorrosionsschutz werden meist heterocyclische Aromaten eingesetzt. As nonferrous metal corrosion protection heterocyclic aromatics are generally used.
  • Als Antioxidantien oder Stabilisatoren sind insbesondere Amine wie paraPhenylendiamin, Dicyclohexylamin, Morpholin oder Derivate dieser Amine zu nennen. Antioxidants or stabilizers are in particular amines, such as para-phenylenediamine, dicyclohexylamine, morpholine or derivatives of these amines. 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. Phenolic antioxidants such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxiphenylpropionsäure and derivatives thereof are added to fuels and lubricants.
  • Als Vergaser-, Injector- und Ventildetergents sind ferner gegebenenfalls Amide und Imide des Polyisobutylenbernsteinsäureanhydrids, Polybutenamine, Polybutenpolyamine sowie langkettige Carbonamide und -imide in den Kraftstoffen enthalten. As a carburetor, and Injector- valve Detergents are further optionally amides and imides of polyisobutylene succinic anhydride, polybutene, polybutenepolyamines and long-chain carboxylic amides and imides in the fuels contain.
  • Als Trägeröle für Konzentrate der erfindungsgemäß zu verwendenden Polyetheramine können Mineralöle des Viskositätsbereiches SN 500-900, aber auch Brightstock und Syntheseöle wie Polyalphaolefin, Trimellithsäureester oder Polyether eingesetzt werden. The carrier oils for concentrates according to the invention to be used polyether mineral oils of the viscosity range SN 500-900, as well as bright stock and synthetic oils such as polyalphaolefin, trimellitic or polyether can be used. Die Ester sollten möglichst langkettige, verzweigte Alkohole größer Ca, die Polyether vorzugsweise langkettige Starter und hohe PO- oder BuO-Gehalte, bezogen auf die Alkylenoxidmenge, im Molekühl enthalten. The ester should be long-chain branched alcohols preferably greater Ca, the polyether preferably long chain starter and high PO or BuO contents based on the alkylene oxide contained in the Molekühl.
  • Die Kraftstoffe enthalten die Polyetheramine der Formel I in der Regel in Mengen von 10 bis 2000 ppm bezogen auf das reine Polyetheramin. The fuels contain the polyetheramines of the formula I usually in amounts of 10 to 2000 ppm based on the pure polyetheramine. Meist sind aber bereits 20 bis 1000 ppm, vorzugsweise 40 bis 400 ppm, ausreichend. But usually are 20 to 1000 ppm, preferably 40 to 400 ppm is sufficient.
  • Im folgenden wird die Herstellung der Polyetheramine und ihre Wirkung im Motor im einzelnen erläutert. In the following the production of polyether amines and their effect in the engine will be explained in detail.
  • Herstellungsbeispiel Preparation example
  • 1. Die Herstellung der Polyether erfolgt nach bekannten Verfahren der Oxalkylierung mit Alkali. 1. The preparation of the polyethers are prepared by known methods of oxyalkylation with alkali.
  • a) Starter Alkohol a) starting alcohol
  • Im einen Autoklaven mit Rührer werden bezogen auf den gesamten Ansatz 0,1 Gew.% KOH fein pulverisiert im Alkohol unter Rühren verteilt und bei 200 mbar auf 130°C erhitzt. In an autoclave equipped with a stirrer% KOH, based on the total batch 0.1 wt. Finely pulverized dispersed with stirring and heated to 130 ° C at 200 mbar in the alcohol. Dabei werden restliche Wasserspuren abgezogen. While remaining traces of water are withdrawn. Dann wird der Autoklav geschlossen und Alkylenoxid so zudosiert, daß ein Druck von 6 bar nicht überschritten wird. The autoclave is then closed and alkylene oxide metered in such that a pressure of 6 bar is not exceeded. Die Dosierung verschiedener Alkylenoxide kann gleichzeitig oder nacheinander erfolgen, so daß statistische Polyether oder Blöcke entstehen .mit mehr oder minder scharfen Übergängen. The dosage of different alkylene oxides can be simultaneously or sequentially, so that random polyether or blocks are formed .with more or less sharp transitions. Nach Zulaufende der Alkylenoxide fällt der Druck im Verlauf von 3 bis 10 h auf 2 bis 3 bar. After the end of the alkylene oxides, the pressure drops in the course of 3 to 10 hours to 2 to 3 bar. Ist dieser Druck erreicht, kühlt man auf 80 °C und entspannt über ein Membranventil und evakuiert bis auf 20 bis 30 mbar. If this pressure is reached, the mixture is cooled to 80 ° C and depressurized via a diaphragm valve and evacuated to 20 to 30 mbar. Nach Aufrechterhalten des verminderten Drucks für ca. 1 h, setzt man dann äquivalente Mengen sauren lonenaustauschers zur Entfernung von Kalium zu und filtiert. After maintaining the reduced pressure for about 1 h, is then reacted, equivalent amounts of acidic ion exchanger to and filtered to remove potassium.
  • b) Starter Amine b) Starter amines
  • Für die Umsetzung mit Aminen ist eine Vorreaktion notwendig. For the reaction with amines preliminary reaction is necessary. Dazu werden im Autoklaven unter Rühren die Amine mit 1 bis 4 moläquivalenten Alkylenoxid, je nach Zahl der NH Bindungen des Amins (NH 2 = 2 NH) und 5 Gew.% Wasser versetzt und man rührt bei 130°C ca. 10 h. For this purpose the amines with 1 to 4 molar equivalents of alkylene oxide, depending on the number of NH bonds of the amine (NH 2 = NH 2) and 5% water in an autoclave under stirring wt. And the mixture is stirred at 130 ° C for about 10 hours. Danach wird auf 80 C abgekühlt, entspannt und bis auf 30 bis 40 mbar evakuiert. It is then cooled to 80 C, laid up to 30 to 40 mbar and evacuated. Dabei wird Wasser quantitativ entfernt. Water is removed quantitatively. Danach setzt man wie unter a) beschrieben mit Zugabe von pulverisierter KOH die Alkoxylierung fort. Thereafter, as described under a) is described with the addition of powdered KOH, the alkoxylation proceeds.
  • 2. Die gemäß a) und b) hergestellten Polyether werden im allgemeinen ohne weitere Vorbehandlung der nachfolgenden Aminierung unterworfen. 2. The polyethers a) and b) produced in accordance are generally subjected, without further pretreatment of the subsequent amination. Bei höheren Polyetherviskositäten empfiehlt sich jedoch eine Verdünnung mit Lösemittel, vorzugsweise verzweigte Aliphaten wie Isododekan, so daß man eine Viskosität von 50 - 200 mm 2 /s bei 20 . At higher Polyetherviskositäten however recommended dilution with solvent, preferably branched aliphatic compounds such as isododecane, so that a viscosity 50-200 mm 2 / s at 20th C erhält. C is obtained. 800 g Polyether oder Polyetherlösung werden mit 1 I Ammoniak und 100 g Raney-Nickel in einem 5 I-Rollautoklaven mit 200 bar Wasserstoff bei 180°C 5 Stunden lang behandelt. 800 g of polyether or polyether solution are treated for 5 hours with 1 l of ammonia and 100 g of Raney nickel in a 5 I-Rollautoklaven with 200 bar hydrogen at 180 ° C. Nach dem Abkühlen trennt man den Katalysator durch Filtrieren ab, verdampft überschüssiges Ammoniak und destilliert das Reaktionswasser azeotrop oder unter leichtem Stickstoffstrom ab. After cooling, the catalyst is separated by filtering off excess ammonia evaporated and azeotroped the reaction water or from under a slight stream of nitrogen.
  • Beispiele Examples
  • Nach den unter 1 a) b) und 2 angegebenen Methoden wurden folgende Produkte hergestellt: According to under 1 a) b) and 2 above methods the following products were prepared:
    • A: Starter: iso-Tridekanol (aus Tetramerpropylen) A: Starter: iso-tridecanol (from tetramer)
      • Alkylenoxid: PO/BuO Gewichtsverhältnis 1:1 Alkylene: PO / BuO weight ratio 1: 1
      • Molgewicht M N : 1950 Molecular weight M N: 1950
      • Aminzahl: 31 Amine number: 31
    • B: Starter: iso-Tridekanol (aus Trimerbuten) B: Starter: iso-tridecanol (from trimeric butene)
      • Alkylenoxid: BuO Alkylene: BuO
      • Molgewicht M N des Polyethers: 730 Molecular weight M N of the polyether: 730
      • Aminzahl: 92 Amine number: 92
    • C: Starter: Polyisobutylalkohol M N 455 C: Starter: polyisobutyl M N 455
      • Alkylenoxid: PO Alkylene: PO
      • Molgewicht M N des Polyethers: 890 Molecular weight M N of the polyether: 890
      • Aminzahl: 73 Amine number: 73
    • D: Starter: Diisotridecylamin D: Starter: diisotridecylamine
      • Alkylenoxid: PO/BuO Gewichtsverhältnis 70/30 Alkylene: PO / BuO weight ratio 70/30
      • Molgewicht M N des Polyethers: 1650 Molecular weight M N of the polyether: 1650
      • Aminzahl: 41 Amine number: 41
    • E: Wie A, jedoch mit dem Ausgangsprodukt der Aminierung und Mineralöl SN 800 im Gewichtsverhältnis 1:2:1 (Aminoether:Polyether:Mineralöl) verdünnt E: As A, but with the output product of the amination and mineral oil SN 800 in a weight ratio diluted 1: 2: 1 (mineral oil aminoether: polyether)
    • F: Mischung des Ausgangs-Polyethers gemäß B, Polyetheramin gemäß B und Schmieröldispersant aus Polyisobutenylbernsteinsäureanhydrid und Triethylentetramin (MV 2:1) im Gewichtsverhältnis 6:2:1, wobei das eingesetzte Polyisobutenderivat nur 60 % Wirksubstanz enthält F: A mixture of the starting polyether according to B, B and polyetheramine according Schmieröldispersant from polyisobutenyl succinic anhydride and triethylene tetramine (MV 2: 1) in a weight ratio of 6: 2: 1, wherein the polyisobutene used contains only 60% of active substance
    Durchführung der motorischen Prüfungen Implementation of engine testing
  • Die motorischen Prüfungen mit den Additiven bzw. Additivpaketen wurden auf einem Daimler Benz M 102.980 Motor mit nachfolgendem Wechsellastprogramm durchgeführt. The engine testing with the additives or additive packages were carried out on a Daimler Benz M 102 980 engine with subsequent alternating load program.
    Figure imgb0008
  • Die Laufzeit betrug 60 Stunden, die Zahl der Zyklen 800. Als Kraftstoff wurde unverbleites, alkoholhaltiges Superbenzin (3 % Methanol, 2 % tert. Butanol), als Motorenöl, das Referenzöl des Opel Kadett Tests CEC-F-0 2 -C-79, RL 51 verwendet. The run time was 60 hours, the number of cycles 800. As fuel was unleaded, alcoholic premium gasoline (3% methanol, 2% tert. Butanol), as an engine oil, the reference oil of the Opel Kadett test CEC-F-0 2 -C-79 , RL 51 used.
  • Die Auswertung der Einlaßventile erfolgt gravimetrisch. The evaluation of the intake valves gravimetric. Dazu werden die Einlaßventile nach dem Ausbau an ihrer Unterseite sorgfältig mechanisch von Ablagerungen aus dem Verbrennungsraum befreit. For this, the intake valves are carefully freed after the expansion on its bottom mechanically from deposits from the combustion chamber. Danach werden oberflächlich haftende, leicht lösliche Anteile auf den Ventilen durch Eintauchen in Cyclohexan entfernt und die Ventile durch Schwenken an der Luft getrocknet. Thereafter, superficially adhering, easily soluble components are removed on the valves by immersion in cyclohexane and the valves dried by pivoting in the air. Diese Behandlung wird insgesamt zweimal vorgenommen. This treatment is carried out twice in total. Anschließend werden die Einlaßventile gewogen. Then, the intake valves are weighed. Aus der Gewichtsdifferenz zwischen dem Ventilgewicht vor und nach dem Versuch ergibt sich die Menge an Ablagerungen pro Einlaßventil. From the weight difference between the valve weight before and after the experiment, the amount is of deposits per intake valve. Die Ergebnisse dieser Versuche sind in Tabelle 1 wiedergegeben. The results of these tests are shown in Table 1 below.
    Figure imgb0009

Claims (4)

  1. 1. Kraftstoffe für Ottomotoren, enthaltend geringe Mengen eines Polyetheramins, dadurch gekennzeichnet, daß das Polyetheramin ein solches der Formel I 1. fuels for gasoline engines, containing small amounts of a polyetheramine, characterized in that the polyetheramine one of the formula I
    Figure imgb0010
    ist, in der R 1 den Rest eines ein- oder mehrwertigen Alkohols, oder eines Amins jeweils mit 2 bis 30 Kohlenstoffatomen, X ein Sauerstoffatom oder eine is in which R 1 is the radical of a mono- or polyhydric alcohol, or an amine each having 2 to 30 carbon atoms, X is an oxygen atom or a
    Figure imgb0011
    in der R 4 für einen zweiten Rest R 1 oder einen zweiten Rest in which R 4 is a second radical R 1 or a second rest
    Figure imgb0012
    steht, R 2 den aus Propylen- oder Butylenoxid stammenden Alkylenrest, m die Zahlen 5 bis 100 und R 3 Wasserstoff oder einen Alkylrest mit 1 bis 20 Kohlenstoffatomen, R 5 Wasserstoff und R 5 und R 3 jeweils ferner den Rest , R 2 originating from propylene or butylene alkylene group, m the numbers 5 to 100 and R 3 is hydrogen or an alkyl radical having 1 to 20 carbon atoms, R 5 is hydrogen and R 5 and R 3 each further comprise the remainder
    Figure imgb0013
    bedeuten können, das Molekulargewicht M N 500 bis 5000 beträgt und wobei die Polyetheramine durch Aminierung von Polyethern der Formel II may mean the molecular weight M N is 500 to 5,000 and wherein the polyetheramine by amination of polyethers of the formula II
    Figure imgb0014
    in der R 1 , X, R 2 und m die genannten Bedeutungen haben, mit Ammoniak oder primären aliphatischen Aminen hergestellt sind. have R 1, X, R 2 and m have the meanings given above, are prepared with ammonia or primary aliphatic amines.
  2. 2. Kraftstoffe gemäß Anspruch 1, enthaltend ein Polyetheramin der Formel I, in der R 3 und R S Wasserstoff bedeuten. 2. A fuel as claimed in claim 1, containing a polyetheramine of the formula I where R 3 and R S are hydrogen.
  3. 3. Kraftstoffe gemäß Anspruch 1 und 2, enthaltend ein Polyetheramin der Formel I, in der R 1 einen Alkylrest mit 5 bis 15 Kohlenstoffatomen und X Sauerstoff bedeutet. 3. A fuel as claimed in claim 1 and 2, containing a polyetheramine of the formula I in which R 1 represents an alkyl group having 5 to 15 carbon atoms and X is oxygen.
  4. 4. Kraftstoffe für Ottomotoren gemäß Ansprüchen 1 bis 3, enthaltend 10 bis 2000 mg eines Polyetheramins der Formel I pro kg Kraftstoff. 4. fuels for gasoline engines according to claims 1 to 3, containing 10 to 2000 mg of a polyetheramine of the formula I per kg of fuel.
EP19880115566 1987-09-30 1988-09-22 Fuels containing a polyether amine for spark ignition engines Withdrawn EP0310875A1 (en)

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DE19873732908 DE3732908A1 (en) 1987-09-30 1987-09-30 Polyether-containing fuels for gasoline engines
DE3732908 1987-09-30

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