EP0700985A1 - Fuels, for spark-ignition engines, containing polyether amines - Google Patents

Fuels, for spark-ignition engines, containing polyether amines Download PDF

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Publication number
EP0700985A1
EP0700985A1 EP95113660A EP95113660A EP0700985A1 EP 0700985 A1 EP0700985 A1 EP 0700985A1 EP 95113660 A EP95113660 A EP 95113660A EP 95113660 A EP95113660 A EP 95113660A EP 0700985 A1 EP0700985 A1 EP 0700985A1
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Prior art keywords
fuels
alkyl
polyetheramines
radical
denotes
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German (de)
French (fr)
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EP0700985B1 (en
Inventor
Knut Dr. Oppenländer
Wolfgang Dr. Günther
Andreas Dr. Henne
Volkmar Dr. Menger
Rainer Dr. Becker
Wolfgang Dr. Reif
Jürgen Dr. Thomas
Harald Dr. Schwahn
Erhard Dr. Henkes
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • 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
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
    • 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
    • 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
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1616—Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1625—Hydrocarbons macromolecular compounds
    • C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
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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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • 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
    • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
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    • C10L1/188—Carboxylic acids; metal salts thereof
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
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    • 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
    • C10L1/18—Organic compounds containing oxygen
    • 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
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • 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
    • 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
    • C10L1/223—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
    • 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
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    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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
    • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • 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
    • 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
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    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)

Definitions

  • EP-A 310 875 discloses polyetheramines of the above type with alkylene radicals derived from propylene oxide or butylene oxide as valve-cleaning additives for petrol.
  • the degree of alkorylation is indicated there with 5 to 100, preferably 5 to 30.
  • Example B describes an iso-tridecanol of molecular weight 730 which has been reacted with butylene oxide and then aminated with ammonia, from which a degree of butoxylation of about 7.5 can be calculated.
  • the radical R1 preferably denotes C8 to C20 alkyl, in particular C9 to C15 alkyl, especially C11 to C14 alkyl; C13-alkyl is very particularly preferred.
  • the mostly long-chain radical R 1 can be linear or preferably branched.
  • radicals R2 and R3 or one of the radicals R2 or R3 do not represent the (poly) aminoalkylene radicals II or III, they mean or preferably means C1 to C4 alkyl, e.g. Methyl or ethyl, or especially hydrogen.
  • the bridge member R4 is preferably linear or branched C2 to C4 alkylene, especially 1,2-ethylene or 1,3-propylene.
  • the number m is an integer and preferably denotes a number from 2 to 6, especially from 2 to 4.
  • the radicals R5 and R6 are preferably C1 to C4 alkyl, e.g. Methyl or ethyl, or especially hydrogen.
  • both radicals R2 and R3 are hydrogen or one of the radicals is hydrogen and the other is 2-aminoethyl, 3-aminopropyl or 3- (N, N-dimethylamino) propyl.
  • the latter radicals are derived from the diamines 1,2-ethylenediamine, 1,3-propylenediamine and 3- (N, N-dimethylamino) propylamine.
  • the degree of butoxylation n is preferably 18 to 25, in particular 20 to 23, especially 22.
  • n represents an average value for a statistical distribution of butoxylation products.
  • polyetheramines I are expediently - as described in EP-A 310 875 - by reacting alcohols of the formula R.sup.1 OH with butylene oxide, where 1,2-butylene oxide, 2,3-butylene oxide, isobutylene oxide or mixtures thereof can be used , and subsequent amination with ammonia or amines of the formula NHR2R3.
  • the gasolines can also contain components other than hydrocarbons, e.g. Alcohols such as methanol, ethanol or tert-butanol as well as ethers, e.g. Methyl tert-butyl ether.
  • the fuels generally also contain additives such as corrosion inhibitors, stabilizers, antioxidants or other detergents.
  • Corrosion inhibitors are usually ammonium salts of organic carboxylic acids, which tend to form films due to the structure of the starting compounds. Amines to increase 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-hydroxyphenylpropionic acid and their derivatives are also added to fuels.
  • the gasifiers, injector and valve detergents may also contain amides and imides of polyisobutylene succinic anhydride, poly (iso) butenamines, poly (iso) butenepolyamines and long-chain carboxamides and imides in the fuels.
  • Mineral oils of the viscosity range SN 500-900, but also Brightstock and synthetic oils such as polyalphaolefin, trimellitic acid ester or polyether can be used as carrier oils for concentrates of the polyetheramines I to be used according to the invention.
  • the esters should contain long-chain, branched alcohols with more than 8 carbon atoms, the polyethers preferably long-chain starters and high propylene oxide or butylene oxide contents in the molecule.
  • the fuels generally contain the polyetheramines I in amounts of 10 to 2000 ppm, based on the pure polyetheramine. Usually, however, 20 to 1000 ppm, preferably 40 to 400 ppm, are sufficient.
  • the polyetheramines I to be used according to the invention serve mainly in the fuels as valve-cleaning additives, i.e. as detergents. However, they can also partially function as carrier oils for other detergents.
  • the fuels described can contain a specific polyetheramine I or a mixture of several polyetheramines I.
  • the engine test was carried out on an Opel Kadett 1.2 liter engine using the cyclic test program CEC-F-04-A-87. The total test duration was 40 hours.
  • the petrol used was standard unleaded premium petrol and the motor oil used was the reference oil RL-139.
  • the intake valves were evaluated gravimetrically.
  • the inlet valves on the underside were carefully mechanically cleaned of deposits from the combustion chamber. Thereafter, surface-adhering, easily soluble parts on the valves were removed by immersion in cyclohexane and the valves were dried by swirling in air. This treatment was done twice in total.
  • the intake valves were then weighed. From the weight difference between the valve weight before and after the experiment, the amount of deposits per intake valve was obtained. The results of these tests are shown in the following tables. table Testing the inlet valve load with an Opel Kadett 1.2 l engine on the test bench with 100 mg polyetheramine per kg unleaded super fuel according to DIN EN 228, 150 l, engine oil RL-139, test duration 40 hours

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Output Control And Ontrol Of Special Type Engine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyethers (AREA)

Abstract

A fuel contains small amts. of polyetheramines of formula R1-(OBu)n-NR2R3 (I), R1 = 2-30C alkyl, R2 and R3 = H, 1-8C alkyl, aminoalkylene of formula -R4-NR5 (II) or polyaminoalkylene of formula -(R4-NR5)m-R6 (III). R4 = 2-10C alkylene, R5 and R6 = H or 1-8C alkyl, Bu - butylene residue derived from butylene oxide, and n = 12-28.

Description

Die vorliegende Erfindung betrifft Kraftstoffe für Ottomotoren, welche geringe Mengen von Polyetheraminen der allgemeinen Formel I

        R¹―(OBu)n―NR²R³     (I)

in der

R¹
einen C₂- bis C₃₀-Alkylrest bezeichnet,
R² und R³
unabhängig voneinander Wasserstoff, C₁- bis C₈-Alkyl, einen Aminoalkylenrest der allgemeinen Formel II

        ―R⁴―NR⁵R⁶     (II)

oder einen Polyaminoalkylenrest der allgemeinen Formel III

        (̵R⁴―NR⁵)m―R⁶     (III)

in denen R⁴ für einen C₂- bis C₁₀-Alkylenrest steht, R⁵ und R⁶ unabhängig voneinander Wasserstoff oder C₁- bis C₈-Alkyl bedeuten und m eine Zahl von 2 bis 8 bezeichnet, bedeuten,
Bu
einen aus Butylenoxid stammenden Butylenrest bezeichnet und
n
für eine Zahl von 12 bis 28 steht,
enthalten.The present invention relates to fuels for gasoline engines which contain small amounts of polyetheramines of the general formula I.

R¹― (OBu) n ―NR²R³ (I)

in the
R¹
denotes a C₂ to C₃₀ alkyl radical,
R² and R³
independently of one another hydrogen, C₁- to C₈-alkyl, an aminoalkylene radical of the general formula II

―R⁴ ― NR⁵R⁶ (II)

or a polyaminoalkylene radical of the general formula III

(̵R⁴ ― NR⁵) m ―R⁶ (III)

in which R⁴ represents a C₂ to C₁₀ alkylene radical, R⁵ and R⁶ independently of one another are hydrogen or C₁ to C₈ alkyl and m denotes a number from 2 to 8,
Bu
denotes a butylene radical derived from butylene oxide and
n
represents a number from 12 to 28,
contain.

Aus der EP-A 310 875 sind Polyetheramine des obigen Typs mit aus Propylenoxid oder Butylenoxid stammenden Alkylenresten als ventilreinigende Additive für Ottokraftstoffe bekannt. Der Alkorylierungsgrad ist dort mit 5 bis 100, vorzugsweise 5 bis 30 angegeben. Als Beispiel B wird ein mit Butylenoxid umgesetztes und anschließend mit Ammoniak aminiertes iso-Tridecanol des Molgewichtes 730 beschrieben, woraus ein Butoxylierungsgrad von ca. 7,5 errechnet werden kann.EP-A 310 875 discloses polyetheramines of the above type with alkylene radicals derived from propylene oxide or butylene oxide as valve-cleaning additives for petrol. The degree of alkorylation is indicated there with 5 to 100, preferably 5 to 30. Example B describes an iso-tridecanol of molecular weight 730 which has been reacted with butylene oxide and then aminated with ammonia, from which a degree of butoxylation of about 7.5 can be calculated.

Derartige Polyetheramine haben zwar schon im Prinzip eine gute ventilreinigende Wirkung, jedoch ist eine weitere Verbesserung noch wünschenswert. Aufgabe der vorliegenden Erfindung war es daher, Kraftstoffadditive bereitzustellen, die eine solche weitere Verbesserung bewirken.In principle, such polyetheramines already have a good valve-cleaning effect, but a further improvement is still desirable. The object of the present invention was therefore, to provide fuel additives that bring about such further improvement.

Demgemäß wurden die oben definierten Polyetheramine I enthaltenden Kraftstoffe gefunden.Accordingly, the fuels containing polyetheramines I defined above were found.

Der Rest R¹ bezeichnet vorzugsweise C₈- bis C₂₀-Alkyl, insbesondere C₉- bis C₁₅-Alkyl, vor allem C₁₁- bis C₁₄-Alkyl; ganz besonders bevorzugt wird C₁₃-Alkyl. Der meist langkettige Rest R¹ kann linear oder vorzugsweise verzweigt sein.The radical R¹ preferably denotes C₈ to C₂₀ alkyl, in particular C₉ to C₁₅ alkyl, especially C₁₁ to C₁₄ alkyl; C₁₃-alkyl is very particularly preferred. The mostly long-chain radical R 1 can be linear or preferably branched.

Stehen die Reste R² und R³ oder einer der Reste R² oder R³ nicht für die (Poly)Aminoalkylenreste II bzw. III, bedeuten sie bzw. bedeutet er vorzugsweise C₁- bis C₄-Alkyl, z.B. Methyl oder Ethyl, oder insbesondere Wasserstoff.If the radicals R² and R³ or one of the radicals R² or R³ do not represent the (poly) aminoalkylene radicals II or III, they mean or preferably means C₁ to C₄ alkyl, e.g. Methyl or ethyl, or especially hydrogen.

Das Brückenglied R⁴ steht vorzugsweise für lineares oder verzweigtes C₂- bis C₄-Alkylen, insbesondere für 1,2-Ethylen oder 1,3-Propylen.The bridge member R⁴ is preferably linear or branched C₂ to C₄ alkylene, especially 1,2-ethylene or 1,3-propylene.

Die Zahl m ist eine ganze Zahl und bezeichnet vorzugsweise eine Zahl von 2 bis 6, vor allem von 2 bis 4.The number m is an integer and preferably denotes a number from 2 to 6, especially from 2 to 4.

Die Reste R⁵ und R⁶ bedeuten vorzugsweise C₁- bis C₄-Alkyl, z.B. Methyl oder Ethyl, oder insbesondere Wasserstoff.The radicals R⁵ and R⁶ are preferably C₁ to C₄ alkyl, e.g. Methyl or ethyl, or especially hydrogen.

In einer bevorzugten Ausführungsform der Erfindung bedeuten beide Reste R² und R³ Wasserstoff oder einer der Reste bedeutet Wasserstoff und der andere 2-Aminoethyl, 3-Aminopropyl oder 3-(N,N-Dimethylamino)propyl. Die letztgenannten Reste leiten sich von den Diaminen 1,2-Ethylendiamin, 1,3-Propylendiamin bzw. 3-(N,N-Dimethylamino)propylamin ab.In a preferred embodiment of the invention both radicals R² and R³ are hydrogen or one of the radicals is hydrogen and the other is 2-aminoethyl, 3-aminopropyl or 3- (N, N-dimethylamino) propyl. The latter radicals are derived from the diamines 1,2-ethylenediamine, 1,3-propylenediamine and 3- (N, N-dimethylamino) propylamine.

Der Butoxylierungsgrad n beträgt vorzugsweise 18 bis 25, insbesondere 20 bis 23, vor allem 22. Dabei stellt n einen Durchschnittswert für eine statistische Verteilung von Butoxylierungsprodukten dar.The degree of butoxylation n is preferably 18 to 25, in particular 20 to 23, especially 22. Here, n represents an average value for a statistical distribution of butoxylation products.

Die Polyetheramine I werden zweckmäßigerweise - wie in der EP-A 310 875 beschrieben - durch Umsetzung von Alkoholen der Formel R¹―OH mit Butylenoxid, wobei hier 1,2-Butylenoxid, 2,3-Butylenoxid, Isobutylenoxid oder Gemische hieraus zum Einsatz kommen können, und anschließende Aminierung mit Ammoniak oder Aminen der Formel NHR²R³ hergestellt.The polyetheramines I are expediently - as described in EP-A 310 875 - by reacting alcohols of the formula R.sup.1 OH with butylene oxide, where 1,2-butylene oxide, 2,3-butylene oxide, isobutylene oxide or mixtures thereof can be used , and subsequent amination with ammonia or amines of the formula NHR²R³.

Als Kraftstoffe kommen verbleite und unverbleite Normal- und Superbenzine in Betracht. Die Benzine können auch andere Komponenten als Kohlenwasserstoffe, z.B. Alkohole wie Methanol, Ethanol oder tert.-Butanol sowie Ether, z.B. Methyl-tert.-butylether, enthalten. Neben den erfindungsgemäß zu verwendenden Polyetheraminen I enthalten die Kraftstoffe in der Regel noch weiter Zusätze wie Korrosionsinhibitoren, Stabilisatoren, Antioxidantien oder weitere Detergentien.Leaded and unleaded regular and premium petrol are considered as fuels. The gasolines can also contain components other than hydrocarbons, e.g. Alcohols such as methanol, ethanol or tert-butanol as well as ethers, e.g. Methyl tert-butyl ether. In addition to the polyetheramines I to be used according to the invention, the fuels generally also contain additives such as corrosion inhibitors, stabilizers, antioxidants or other detergents.

Korrosionsinhibitoren sind meist Ammoniumsalze organischer Carbonsäuren, die durch entsprechende Struktur der Ausgangsverbindungen zur Filmbildung neigen. Auch Amine zur Erhöhung des pH-Wertes finden sich häufig in Korrosionsinhibitoren. Als Buntmetallkorrosionsschutz werden meist heterocyclische Aromaten eingesetzt.Corrosion inhibitors are usually ammonium salts of organic carboxylic acids, which tend to form films due to the structure of the starting compounds. Amines to increase 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-hydroxyphenylpropionsäure und deren Derivate werden Kraftstoffe 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-hydroxyphenylpropionic acid and their derivatives are also added to fuels.

Als Vergaser-, Injektor- und Ventildetergentien sind ferner gegebenenfalls Amide und Imide des Polyisobutylenbernsteinsäureanhydrids, Poly(iso)butenamine, Poly(iso)butenpolyamine sowie langkettige Carbonsäureamide und -imide in den Kraftstoffen enthalten.The gasifiers, injector and valve detergents may also contain amides and imides of polyisobutylene succinic anhydride, poly (iso) butenamines, poly (iso) butenepolyamines and long-chain carboxamides and imides in the fuels.

Als Trägeröle für Konzentrate der erfindungsgemäß zu verwendenden Polyetheramine I können Mineralöle des Viskositätsbereiches SN 500-900, aber auch Brightstock und Syntheseöle wie Polyalphaolefin, Trimellithsäureester oder Polyether eingesetzt werden. Die Ester sollten möglichst langkettige, verzweigte Alkohole mit mehr als 8 C-Atomen, die Polyether vorzugsweise langkettige Starter und hohe Propylenoxid- oder Butylenoxid-Gehalte im Molekül enthalten.Mineral oils of the viscosity range SN 500-900, but also Brightstock and synthetic oils such as polyalphaolefin, trimellitic acid ester or polyether can be used as carrier oils for concentrates of the polyetheramines I to be used according to the invention. The esters should contain long-chain, branched alcohols with more than 8 carbon atoms, the polyethers preferably long-chain starters and high propylene oxide or butylene oxide contents in the molecule.

Die Kraftstoffe enthalten die Polyetheramine I in der Regel in Mengen von 10 bis 2000 ppm, bezogen auf das reine Polyetheramin. Meist sind aber bereits 20 bis 1000 ppm, vorzugsweise 40 bis 400 ppm, ausreichend.The fuels generally contain the polyetheramines I in amounts of 10 to 2000 ppm, based on the pure polyetheramine. Usually, however, 20 to 1000 ppm, preferably 40 to 400 ppm, are sufficient.

Die erfindungsgemäß zu verwendenden Polyetheramine I dienen in den Kraftstoffen hauptsächlich als ventilreinigende Additive, d.h. als Detergentien. Sie können aber auch teilweise die Funktion von Trägerölen für weitere Detergentien ausüben.The polyetheramines I to be used according to the invention serve mainly in the fuels as valve-cleaning additives, i.e. as detergents. However, they can also partially function as carrier oils for other detergents.

Die beschriebenen Kraftstoffe können ein bestimmtes Polyetheramin I oder eine Mischung aus mehreren Polyetheraminen I enthalten.The fuels described can contain a specific polyetheramine I or a mixture of several polyetheramines I.

Im folgenden wird die Wirkung der Polyetheramine I im Motor erläutert.The effect of polyetheramines I in the engine is explained below.

HerstellungsbeispieleManufacturing examples

Gemäß den allgemeinen Herstellungsvorschriften der EP-A 310 875 für Polyether durch alkalikatalysierte Oxalkylierung und für Polyetheramine durch Umsetzung dieser Polyether mit Ammoniak unter reduzierenden Bedingungen wurden durch Umsetzung von 1 mol iso-Tridecanol (aus Tetramerpropylen) mit

Beispiel A:
8 mol 1,2-Butylenoxid (zum Vergleich)
Beispiel B:
22 mol 1,2-Butylenoxid (erfindungsgemäß)
Beispiel C:
35 mol 1,2-Butylenoxid (zum Vergleich)
und durch anschließende Aminierung mit NH₃/H₂/Raney-Nickel die drei Polyetheramine A, B und C erhalten.According to the general preparation instructions of EP-A 310 875 for polyethers by alkali-catalyzed oxalkylation and for polyetheramines by reacting these polyethers with ammonia under reducing conditions, by reacting 1 mol of iso-tridecanol (from tetramer propylene) with
Example A:
8 mol 1,2-butylene oxide (for comparison)
Example B
22 mol 1,2-butylene oxide (according to the invention)
Example C
35 mol 1,2-butylene oxide (for comparison)
and by subsequent amination with NH₃ / H₂ / Raney nickel the three polyetheramines A, B and C are obtained.

Motorische PrüfungMotor test

Die motorische Prüfung wurde auf einem Opel Kadett 1,2-l-Motor unter Verwendung des cyclischen Testprogramms CEC-F-04-A-87 durchgeführt. Die Gesamttestdauer betrug 40 Stunden. Das verwendete Benzin war marktübliches unverbleites Superbenzin und das verwendete Motorenöl das Referenzöl RL-139.The engine test was carried out on an Opel Kadett 1.2 liter engine using the cyclic test program CEC-F-04-A-87. The total test duration was 40 hours. The petrol used was standard unleaded premium petrol and the motor oil used was the reference oil RL-139.

Die Auswertung der Einlaßventile erfolgte gravimetrisch. Dazu wurden die Einlaßventile nach dem Ausbau an ihrer Unterseite sorgfältig mechanisch von Ablagerungen aus dem Verbrennungsraum befreit. Danach wurden oberflächlich haftende, leicht-lösliche Anteile auf den Ventilen durch Eintauchen in Cyclohexan entfernt und die Ventile durch Schwenken an der Luft getrocknet. Diese Behandlung wurde insgesamt zweimal vorgenommen. Anschließend wurden die Einlaßventile gewogen. Aus der Gewichtsdifferenz zwischen dem Ventilgewicht vor und nach dem Versuch ergab sich die Menge an Ablagerungen pro Einlaßventil. Die Ergebnisse dieser Versuche sind in der folgenden Tabellen wiedergegeben. Tabelle Prüfung der Einlaßventilbelastung mit einem Opel Kadett 1,2-l-Motor auf dem Prüfstand mit jeweils 100 mg Polyetheramin pro kg unverbleitem Superkraftstoff gemäß DIN EN 228, 150 l, Motorenöl RL-139, Testdauer 40 Stunden Beispiel Nr. Polyetheramin Ventilablagerung mg/Einlaßventil 1 ohne (Grundwert) 491 2 A 294 3 B 19 4 C 283 The intake valves were evaluated gravimetrically. For this purpose, the inlet valves on the underside were carefully mechanically cleaned of deposits from the combustion chamber. Thereafter, surface-adhering, easily soluble parts on the valves were removed by immersion in cyclohexane and the valves were dried by swirling in air. This treatment was done twice in total. The intake valves were then weighed. From the weight difference between the valve weight before and after the experiment, the amount of deposits per intake valve was obtained. The results of these tests are shown in the following tables. table Testing the inlet valve load with an Opel Kadett 1.2 l engine on the test bench with 100 mg polyetheramine per kg unleaded super fuel according to DIN EN 228, 150 l, engine oil RL-139, test duration 40 hours Example No. Polyetheramine Valve deposit mg / inlet valve 1 without (basic value) 491 2nd A 294 3rd B 19th 4th C. 283

Claims (6)

Kraftstoffe für Ottomotoren, enthaltend geringe Mengen von Polyetheraminen der allgemeinen Formel I

        R¹―(OBu)n―NR²R³     (I)

in der R¹   einen C₂- bis C₃₀-Alkylrest bezeichnet, R²   und R³ unabhängig voneinander Wasserstoff, C₁- bis C₈-Alkyl, einen Aminoalkylenrest der allgemeinen Formel II

        ―R⁴―NR⁵R⁶     (II)

oder einen Polyaminoalkylenrest der allgemeinen Formel III

        (̵R⁴―NR⁵)m―R⁶     (III)

in denen R⁴ für einen C₂- bis C₁₀-Alkylenrest steht, R⁵ und R⁶ unabhängig voneinander Wasserstoff oder C₁- bis C₈-Alkyl bedeuten und m eine Zahl von 2 bis 8 bezeichnet, bedeuten, Bu   einen aus Butylenoxid stammenden Butylenrest bezeichnet und n   für eine Zahl von 12 bis 28 steht. Fuels for gasoline engines containing small amounts of polyetheramines of the general formula I.

R¹― (OBu) n ―NR²R³ (I)

in the R¹ denotes a C₂ to C₃₀ alkyl radical, R² and R³ independently of one another hydrogen, C₁- to C₈-alkyl, an aminoalkylene radical of the general formula II

―R⁴ ― NR⁵R⁶ (II)

or a polyaminoalkylene radical of the general formula III

(̵R⁴ ― NR⁵) m ―R⁶ (III)

in which R⁴ represents a C₂ to C₁₀ alkylene radical, R⁵ and R⁶ independently of one another are hydrogen or C₁ to C₈ alkyl and m denotes a number from 2 to 8, Bu denotes a butylene oxide originating from butylene oxide and n stands for a number from 12 to 28. Kraftstoffe nach Anspruch 1, enthaltend Polyetheramine I, bei denen R¹ einen verzweigten C₉- bis C₁₅-Alkylrest bezeichnet.Fuels according to Claim 1, containing polyetheramines I, in which R¹ denotes a branched C₉ to C₁₅ alkyl radical. Kraftstoffe nach Anspruch 1 oder 2, enthaltend Polyetheramine I, bei denen beide Reste R² und R³ Wasserstoff bedeuten oder einer der Reste R² und R³ Wasserstoff und der andere 2-Aminoethyl, 3-Aminopropyl oder 3-(N,N-Dimethylamino)propyl bedeutet.Fuels according to claim 1 or 2, containing polyetheramines I, in which both radicals R² and R³ are hydrogen or one of the radicals R² and R³ is hydrogen and the other is 2-aminoethyl, 3-aminopropyl or 3- (N, N-dimethylamino) propyl . Kraftstoffe nach den Ansprüchen 1 bis 3, enthaltend Polyetheramine I, bei denen der Butoxylierungsgrad n 20 bis 23 beträgt.Fuels according to Claims 1 to 3, containing polyetheramines I, in which the degree of butoxylation n is 20 to 23. Kraftstoffe nach den Ansprüchen 1 bis 4, enthaltend 10 bis 2000 mg pro kg Kraftstoff der Polyetheramine I.Fuels according to claims 1 to 4, containing 10 to 2000 mg per kg of fuel of the polyether amines I. Verwendung von Polyetheraminen I gemäß den Ansprüchen 1 bis 5 als ventilreinigende Additive in Kraftstoffen für Ottomotoren.Use of polyether amines I according to claims 1 to 5 as valve-cleaning additives in fuels for gasoline engines.
EP95113660A 1994-09-09 1995-08-31 Fuels, for spark-ignition engines, containing polyether amines Expired - Lifetime EP0700985B1 (en)

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ES2127976T3 (en) 1999-05-01
JP3725588B2 (en) 2005-12-14
EP0700985B1 (en) 1999-03-03

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