EP0700985B1 - Combustibles, pour moteurs à allumage par etincelles, contenant des polyetheramines - Google Patents

Combustibles, pour moteurs à allumage par etincelles, contenant des polyetheramines Download PDF

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Publication number
EP0700985B1
EP0700985B1 EP95113660A EP95113660A EP0700985B1 EP 0700985 B1 EP0700985 B1 EP 0700985B1 EP 95113660 A EP95113660 A EP 95113660A EP 95113660 A EP95113660 A EP 95113660A EP 0700985 B1 EP0700985 B1 EP 0700985B1
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Prior art keywords
polyetheramine
fuels
alkyl
fuel
hydrogen
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EP0700985A1 (fr
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
    • C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
    • 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
    • C10L1/182—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
    • 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
    • C10L1/188—Carboxylic acids; metal salts 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
    • C10L1/18—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
    • 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
    • C10L1/19—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
    • 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
    • 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
    • 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
    • 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 includes polyetheramines of the above type alkylene radicals derived from propylene oxide or butylene oxide as valve cleaning additives known for petrol. Of the Degree of alkoxylation there is 5 to 100, preferably 5 to 30 specified.
  • Example B is a reaction with butylene oxide and then iso-tridecanol of the molecular weight aminated with ammonia 730, from which a degree of butoxylation of approx. 7.5 can be calculated.
  • the radical R 1 preferably denotes C 8 -C 20 -alkyl, in particular C 9 -C 15 -alkyl, especially C 11 -C 14 -alkyl; C 13 alkyl is very particularly preferred.
  • the mostly long-chain radical R 1 can be linear or preferably branched.
  • radicals R 2 and R 3 or one of the radicals R 2 or R 3 do not represent the (poly) aminoalkylene radicals II or III, they mean or preferably mean C 1 -C 4 -alkyl, for example methyl or ethyl, or especially hydrogen.
  • the bridge member R 4 preferably represents linear or branched C 2 -C 4 -alkylene, in particular 1,2-ethylene or 1,3-propylene.
  • the number m is an integer and preferably denotes one Number from 2 to 6, especially from 2 to 4.
  • the radicals R 5 and R 6 are preferably C 1 -C 4 -alkyl, for example methyl or ethyl, or in particular hydrogen.
  • both radicals R 2 and R 3 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 represents.
  • polyetheramines I are expediently - as described in EP-A 310 875 - by reacting alcohols of the formula R 1 ⁇ OH with butylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, isobutylene oxide or mixtures thereof being used here can, and subsequent amination with ammonia or amines of the formula NHR 2 R 3 .
  • the fuels are lead and unleaded normal and Super gasoline into consideration.
  • the petrol can do other Components as hydrocarbons, e.g. Alcohols like methanol, Ethanol or tert-butanol as well as ether, e.g. Methyl tert-butyl ether, contain.
  • ether e.g. Methyl tert-butyl ether
  • Additives such as corrosion inhibitors, stabilizers, antioxidants or other detergents.
  • Corrosion inhibitors are mostly organic ammonium salts Carboxylic acids by appropriate structure of the starting compounds tend to form films. Also amines to increase the pH values are often found in corrosion inhibitors. As non-ferrous metal corrosion protection heterocyclic aromatics are mostly used.
  • Amines in particular are antioxidants or stabilizers such as para-phenylenediamine, dicyclohexylamine, morpholine or To name derivatives of these amines. Also phenolic antioxidants such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid and their derivatives are added to fuels.
  • injector and valve detergents are also optionally amides and imides of polyisobutylene succinic anhydride, Poly (iso) butenamines, poly (iso) butenepolyamines and long chain carboxylic acid amides and imides in fuels contain.
  • Polyetheramines I can mineral oils of the viscosity range SN 500-900, but also Brightstock and synthetic oils such as polyalphaolefin, Trimellitic acid esters or polyethers are used.
  • the esters should be long-chain, branched alcohols With more than 8 carbon atoms, the polyethers are preferably long-chain Starter and high propylene oxide or butylene oxide contents in the Contain molecule.
  • the fuels usually contain the polyetheramines I in Amounts from 10 to 2000 ppm, based on the pure polyetheramine. Usually, however, are already 20 to 1000 ppm, preferably 40 to 400 ppm, sufficient.
  • the polyetheramines I to be used according to the invention are used in fuels mainly as valve cleaning additives, i.e. as detergents. But you can also partially Perform the function of carrier oils for other detergents.
  • the fuels described can be a specific polyetheramine I or a mixture of several polyether amines I.
  • the engine test was on an Opel Kadett 1.2-1 engine using the cyclic test program CEC-F-04-A-87 carried out.
  • the total test duration was 40 hours.
  • the used Gasoline was standard unleaded gasoline and the engine oil used is the reference oil RL-139.
  • 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. Testing the intake valve load with an Opel Kadett 1.2-1 engine on the test bench with 100 mg polyetheramine per kg unleaded super fuel in accordance with 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

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

Claims (6)

  1. Combustible pour moteurs à allumage par étincelle, contenant de petites quantités de polyétheramines de formule générale I R1―(OBu)n―NR2R3 dans laquelle
    R1
    représente un reste alkyle en C2-C30,
    R2 et R3
    représentent indépendamment l'un de l'autre, un atome d'hydrogène, un groupement alkyle en C1-C8, un reste aminoalkylène de formule générale II ―R4―NR5R6 ou un reste polyaminoalkylène de formule générale III (R4―NR5)m―R6 dans laquelle R4 est mis pour un reste alkylène en C2-C10, R5 et R6 sont mis indépendamment l'un de l'autre pour un atome d'hydrogène ou un groupement alkyle en C1-C8 et m représente un nombre de 2 à 8,
    Bu
    représente un reste butylène venant d'un oxyde de butylène et
    n
    représente un nombre de 12 à 28.
  2. Carburants selon la revendication 1, contenant des polyétheramines I pour lesquelles R1 représente un reste alkyle en C9-C15 ramifié.
  3. Carburants selon les revendications 1 ou 2, contenant des polyétheramines I pour lesquelles les deux restes R2 et R3 représentent des atomes d'hydrogène ou bien l'un des restes R2 et R3 représente un atome d'hydrogène et l'autre un groupement 2-aminoéthyle, 3-aminopropyle ou 3-(N,N-diméthylamino)propyle.
  4. Carburants selon l'une quelconque des revendications 1 à 3, contenant des polyétheramines I, pour lesquelles le degré de butoxylation n vaut de 20 à 23.
  5. Carburants selon l'une quelconque des revendications 1 à 4, contenant 10-2000 mg de polyétheramines I par kg de carburant.
  6. Utilisation de polyétheramines I selon l'une quelconque des revendications 1 à 5 en tant qu'additif de nettoyage de soupapes dans des carburants pour moteur à allumage par étincelle.
EP95113660A 1994-09-09 1995-08-31 Combustibles, pour moteurs à allumage par etincelles, contenant des polyetheramines Expired - Lifetime EP0700985B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4432038A DE4432038A1 (de) 1994-09-09 1994-09-09 Polyetheramine enthaltende Kraftstoffe für Ottomotoren
DE4432038 1994-09-09

Publications (2)

Publication Number Publication Date
EP0700985A1 EP0700985A1 (fr) 1996-03-13
EP0700985B1 true EP0700985B1 (fr) 1999-03-03

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EP95113660A Expired - Lifetime EP0700985B1 (fr) 1994-09-09 1995-08-31 Combustibles, pour moteurs à allumage par etincelles, contenant des polyetheramines

Country Status (5)

Country Link
US (1) US5660601A (fr)
EP (1) EP0700985B1 (fr)
JP (1) JP3725588B2 (fr)
DE (2) DE4432038A1 (fr)
ES (1) ES2127976T3 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7850744B2 (en) 2004-08-05 2010-12-14 Basf Aktiengesellschaft Heterocyclic compounds containing nitrogen as a fuel additive in order to reduce abrasion
US9862904B2 (en) 2013-12-31 2018-01-09 Shell Oil Company Unleaded fuel compositions

Families Citing this family (105)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1122295A4 (fr) * 1998-10-06 2002-02-06 Nippon Mitsubishi Oil Corp Additif pour essence destinee a un moteur a essence a injection directe
US6217624B1 (en) * 1999-02-18 2001-04-17 Chevron Chemical Company Llc Fuel compositions containing hydrocarbyl-substituted polyoxyalkylene amines
US6193767B1 (en) * 1999-09-28 2001-02-27 The Lubrizol Corporation Fuel additives and fuel compositions comprising said fuel additives
US6224642B1 (en) 1999-11-23 2001-05-01 The Lubrizol Corporation Additive composition
US6458172B1 (en) 2000-03-03 2002-10-01 The Lubrizol Corporation Fuel additive compositions and fuel compositions containing detergents and fluidizers
US7204863B2 (en) * 2001-12-11 2007-04-17 Exxonmobil Research And Engineering Company Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits
US7226489B2 (en) 2001-12-12 2007-06-05 Exxonmobil Research And Engineering Company Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits
DE10209830A1 (de) 2002-03-06 2003-09-18 Basf Ag Kraftstoffadditivgemische für Ottokraftstoffe mit synergistischer IVD-Performance
DE10239841A1 (de) * 2002-08-29 2004-03-11 Basf Ag Additivgemische für Kraft- und Schmierstoffe
DE10314809A1 (de) 2003-04-01 2004-10-14 Basf Ag Polyalkenamine mit verbesserten Anwendungseigenschaften
DE10316871A1 (de) 2003-04-11 2004-10-21 Basf Ag Kraftstoffzusammensetzung
CA2576014A1 (fr) * 2004-08-06 2006-02-16 Basf Aktiengesellschaft Additifs de polyamines destines aux carburants et lubrifiants
ES2599063T3 (es) 2004-10-19 2017-01-31 The Lubrizol Corporation Composiciones de aditivo y combustible que contienen un detergente, un fluidizador y sus métodos
MX2008009985A (es) 2006-02-27 2008-10-09 Basf Se Uso de compuestos fenolicos policiclicos como estabilizantes.
EP2115101A1 (fr) * 2006-12-28 2009-11-11 The Lubrizol Corporation Additifs pour combustible pour utilisation dans des mélanges alcool-essence à niveau élevé
CN101622329B (zh) 2007-03-02 2013-03-13 巴斯夫欧洲公司 适合无生命有机材料的抗静电改性和导电性改善的添加剂配制剂
BRPI0814692A2 (pt) 2007-07-16 2015-01-20 Basf Se Mistura sinergística, uso da mistura sinergística, material orgânico inanimado, composição de combustível, concentrado de aditivo, e, composição lubrificante
DE102008037662A1 (de) 2007-08-17 2009-04-23 Basf Se Öllösliches Detergens und Verfahren zur Herstellung funktionalisierter Polyalkene
US8486876B2 (en) 2007-10-19 2013-07-16 Shell Oil Company Functional fluids for internal combustion engines
ES2383491T3 (es) 2008-02-01 2012-06-21 Basf Se Poliisobutenaminas y su uso como detergentes en combustibles
DE102010001408A1 (de) 2009-02-06 2010-08-12 Basf Se Verwendung von Ketonen als Kraftstoffzusatz zur Verringerung des Kraftstoffverbrauches von Dieselmotoren
DE102010039039A1 (de) 2009-08-24 2011-03-03 Basf Se Verwendung von organischen Verbindungen als Kraftstoffzusatz zur Verringerung des Kraftstoffverbrauchs von Dieselmotoren
US8790426B2 (en) 2010-04-27 2014-07-29 Basf Se Quaternized terpolymer
EP2563822A1 (fr) 2010-04-27 2013-03-06 Basf Se Terpolymère quaternisé
AU2011260433A1 (en) 2010-06-01 2012-12-13 Basf Se Low-molecular weight polyisobutyl-substituted amines as detergent boosters
PL2585498T3 (pl) 2010-06-25 2018-10-31 Basf Se Kwaternizowany kopolimer
US8911516B2 (en) 2010-06-25 2014-12-16 Basf Se Quaternized copolymer
EP2808350B1 (fr) 2010-07-06 2017-10-25 Basf Se Composés azotés quaternisés exempts d'acide et leur utilisation comme additifs pour carburants et lubrifiants
AR084033A1 (es) 2010-11-30 2013-04-17 Basf Se Preparacion de derivados de homo- o copolimeros de isobuteno
US9296841B2 (en) 2010-11-30 2016-03-29 Basf Se Preparation of isobutene homo- or copolymer derivatives
SG10201509787PA (en) 2010-12-02 2015-12-30 Basf Se Use of the reaction product of a hydrocarbyl-substituted dicarboxylic acid and a nitrogen compound for reducing fuel consumption
US9006158B2 (en) 2010-12-09 2015-04-14 Basf Se Polytetrahydrobenzoxazines and bistetrahydrobenzoxazines and use thereof as a fuel additive or lubricant additive
CN103261175B (zh) 2010-12-09 2016-05-25 巴斯夫欧洲公司 聚四氢苯并噁嗪和双四氢苯并噁嗪及其作为燃料添加剂或润滑剂添加剂的用途
US20120304531A1 (en) 2011-05-30 2012-12-06 Shell Oil Company Liquid fuel compositions
EP2540808A1 (fr) 2011-06-28 2013-01-02 Basf Se Composés d'azote quaternisés et leur utilisation en tant qu'additifs dans des carburants et des lubrifiants
US20130133243A1 (en) 2011-06-28 2013-05-30 Basf Se Quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
EP2589647A1 (fr) 2011-11-04 2013-05-08 Basf Se Polyétheramines quaternisées et leur utilisation en tant qu'additifs dans des carburants et des lubrifiants
EP2604674A1 (fr) 2011-12-12 2013-06-19 Basf Se Utilisation d'alkylamine quaternisé comme additif dans des carburants et des lubrifiants
TR201901211T4 (tr) 2012-02-10 2019-02-21 Basf Se Yakitlar ve yakacak maddeler i̇çi̇n katki olarak i̇mi̇dazolyum tuzlari
US9062266B2 (en) 2012-02-10 2015-06-23 Basf Se Imidazolium salts as additives for fuels
EP2855642B1 (fr) 2012-05-25 2018-03-28 Basf Se Amines tertiaires pour réduire l'encrassement des buses d'injecteurs dans les moteurs à allumage commandé et injection directe.
WO2014019911A1 (fr) 2012-08-01 2014-02-06 Basf Se Procédé d'amélioration de la thermostabilité d'huiles lubrifiantes dans des moteurs à combustion interne
AU2013336727A1 (en) 2012-10-23 2015-05-14 Basf Se Quaternized ammonium salts of hydrocarbyl epoxides and use thereof as additives in fuels and lubricants
US9388354B2 (en) 2012-11-06 2016-07-12 Basf Se Tertiary amines for reducing injector nozzle fouling and modifying friction in direct injection spark ignition engines
WO2014023853A2 (fr) 2012-11-06 2014-02-13 Basf Se Amines tertiaires permettant de réduire l'encrassement des buses d'injecteur et de modifier le frottement dans les moteurs à allumage par étincelle avec injection directe
WO2014096250A1 (fr) 2012-12-21 2014-06-26 Shell Internationale Research Maatschappij B.V. Compositions de carburant liquide comprenant des composés d'écran solaire organiques
WO2014184066A1 (fr) 2013-05-14 2014-11-20 Basf Se Polyalcénylsuccinimides pour réduire l'encrassement d'injecteurs dans des moteurs à allumage commandé et injection directe
HUE051178T2 (hu) 2013-06-07 2021-03-01 Basf Se Alkilén-oxiddal és szénhidrogén-szubsztituált polikarbonsavval kvaternerezett nitrogénvegyületek és alkalmazásuk adalékként üzemanyagokban és kenõanyagokban
EP2811007A1 (fr) 2013-06-07 2014-12-10 Basf Se Utilisation avec de l'oxyde d'alkylène et de l'acide polycarbonique à substitution hydrocarbyle d'alkylamines quaternisés comme additifs dans les carburants et lubrifiants
ES2728510T3 (es) 2013-07-12 2019-10-25 Basf Se Uso de un ácido dicarboxílico sustituido con hidrocarbilo para mejorar o aumentar la separación del agua de los combustibles de gasolina
JP6407274B2 (ja) 2013-07-17 2018-10-17 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 側鎖中にビニリデン二重結合を多く含有する高反応性ポリイソブチレン
US10370610B2 (en) 2013-09-20 2019-08-06 Basf Se Use of specific derivatives of quaternized nitrogen compounds as additives in fuels and lubricants
US20150113867A1 (en) 2013-10-24 2015-04-30 Basf Se Use of an alkoxylated polytetrahydrofuran to reduce fuel consumption
US20150113859A1 (en) 2013-10-24 2015-04-30 Basf Se Use of polyalkylene glycol to reduce fuel consumption
US20150113864A1 (en) 2013-10-24 2015-04-30 Basf Se Use of a complex ester to reduce fuel consumption
EP2883944A1 (fr) 2013-12-13 2015-06-17 Shell Internationale Research Maatschappij B.V. Nouvelles utilisations
US9587195B2 (en) 2013-12-16 2017-03-07 Shell Oil Company Liquid composition
AU2015212878B2 (en) 2014-01-29 2018-03-29 Basf Se Corrosion inhibitors for fuels and lubricants
WO2015113681A1 (fr) 2014-01-29 2015-08-06 Basf Se Additifs à base d'acide polycarbonique, destinés à des carburants et à des lubrifiants
EP3122850A1 (fr) * 2014-03-27 2017-02-01 The Procter & Gamble Company Compositions de nettoyage contenant une polyétheramine
EP2949733A1 (fr) 2014-05-28 2015-12-02 Shell Internationale Research Maatschappij B.V. Compositions d'essence contenant d'absorbants uv de type oxanilide
MY188310A (en) 2014-11-12 2021-11-27 Shell Int Research Use of a fuel composition
DE212015000271U1 (de) 2014-11-25 2017-09-06 Basf Se Korrosionsinhibitoren für Kraft- und Schmierstoffe
JP6807850B2 (ja) 2015-02-27 2021-01-06 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイＳｈｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌｅ Ｒｅｓｅａｒｃｈ Ｍａａｔｓｃｈａｐｐｉｊ Ｂｅｓｌｏｔｅｎ Ｖｅｎｎｏｏｔｓｈａｐ 潤滑組成物の使用
CN107849471B (zh) 2015-07-16 2021-07-16 巴斯夫欧洲公司 作为用于燃料和润滑剂的添加剂的共聚物
DE212016000150U1 (de) 2015-07-24 2018-03-16 Basf Se Korrosionsinhibitoren für Kraft- und Schmierstoffe
BR112018005468B1 (pt) 2015-09-22 2024-01-02 Shell Internationale Research Maatschappij B.V. Composição de combustível de gasolina adequada para uso em um motor de combustão interna, e, uso de nafta derivada de fischer-tropsch
US11959033B2 (en) 2015-11-30 2024-04-16 Shell Usa, Inc. Fuel composition
US10968313B2 (en) 2015-12-03 2021-04-06 China Petroleum & Chemical Corporation Amine polymer and preparation method and use thereof
WO2017144378A1 (fr) 2016-02-23 2017-08-31 Basf Se Acides polycarboxyliques hydrophobes utilisés comme additifs réducteurs d'usure par frottement dans des carburants
WO2018007192A1 (fr) 2016-07-05 2018-01-11 Basf Se Inhibiteurs de corrosion pour carburants et lubrifiants
US11078418B2 (en) 2016-07-05 2021-08-03 Basf Se Corrosion inhibitors for fuels and lubricants
WO2018007445A1 (fr) 2016-07-07 2018-01-11 Basf Se Inhibiteurs de corrosion pour carburants et lubrifiants
WO2018007486A1 (fr) 2016-07-07 2018-01-11 Basf Se Polymères utilisés en tant qu'additifs pour carburants et lubrifiants
WO2018007375A1 (fr) 2016-07-07 2018-01-11 Basf Se Copolymères utilisés en tant qu'additifs pour carburants et lubrifiants
ES2948483T3 (es) 2016-12-15 2023-09-13 Basf Se Polímeros como aditivos de combustible diésel para motores diésel de inyección directa
WO2018114348A1 (fr) 2016-12-19 2018-06-28 Basf Se Additifs pour améliorer la stabilité thermique des carburants
RU2019122807A (ru) 2016-12-20 2021-01-22 Басф Се Применение смеси комплексного сложного эфира с монокарбоновой кислотой для уменьшения трения
RU2019135830A (ru) 2017-04-11 2021-05-11 Басф Се Алкоксилированные амины в качестве присадок к топливу
WO2018188986A1 (fr) 2017-04-13 2018-10-18 Basf Se Polymères utilisés en tant qu'additifs pour carburants et lubrifiants
JP7357016B2 (ja) 2018-07-02 2023-10-05 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ 液体燃料組成物
US20220306960A1 (en) 2019-06-26 2022-09-29 Basf Se New Additive Packages for Gasoline Fuels
WO2021063733A1 (fr) 2019-09-30 2021-04-08 Basf Se Utilisation de composés azotés quaternisés avec de l'oxyde d'alkylène et de l'acide polycarboxylique à substitution hydrocarbyle en tant qu'additifs dans des carburants et des lubrifiants
EP4048760A1 (fr) 2019-10-22 2022-08-31 Shell Internationale Research Maatschappij B.V. Procédé de réduction de dépôts de soupape d'admission
EP3933014A1 (fr) 2020-06-30 2022-01-05 Basf Se Additivation de carburants permettant de réduire les allumages non contrôlés dans des moteurs à combustion interne
PL3940043T3 (pl) 2020-07-14 2024-02-19 Basf Se Inhibitory korozji do paliw silnikowych i smarów
EP4182420A1 (fr) 2020-07-20 2023-05-24 Shell Internationale Research Maatschappij B.V. Composition de carburant
EP3945126B1 (fr) 2020-07-31 2024-03-13 Basf Se Compositions de débrumage pour carburants
WO2022106301A1 (fr) 2020-11-20 2022-05-27 Basf Se Mélanges pour améliorer ou renforcer la séparation de l'eau de carburants
CN116568782A (zh) 2020-12-16 2023-08-08 巴斯夫欧洲公司 用于改进添加剂包的稳定性的新的混合物
CN116829684A (zh) 2021-01-27 2023-09-29 巴斯夫欧洲公司 支化烷基伯胺作为添加剂用于汽油燃料
CN117178047A (zh) 2021-04-26 2023-12-05 国际壳牌研究有限公司 燃料组合物
MX2023012347A (es) 2021-04-26 2023-10-30 Shell Int Research Composiciones de combustible.
EP4105301A1 (fr) 2021-06-15 2022-12-21 Basf Se Nouveaux paquets d'additifs pour l'essence
WO2022263244A1 (fr) 2021-06-16 2022-12-22 Basf Se Bétaïnes quaternisées servant d'additifs dans des carburants
CN118043435A (zh) 2021-09-29 2024-05-14 国际壳牌研究有限公司 燃料组合物
EP4163353A1 (fr) 2021-10-06 2023-04-12 Basf Se Procédé de réduction de dépôts sur les soupapes d'admission
GB202118100D0 (en) 2021-12-14 2022-01-26 Innospec Ltd Methods and uses relating to fuel compositions
EP4269541A1 (fr) 2022-04-29 2023-11-01 Basf Se Nouveaux mélanges pour améliorer ou renforcer la séparation de l'eau à partir de carburants
WO2024017743A1 (fr) 2022-07-20 2024-01-25 Shell Internationale Research Maatschappij B.V. Compositions de carburant
WO2024083782A1 (fr) 2022-10-21 2024-04-25 Shell Internationale Research Maatschappij B.V. Compositions de carburant
DE102022131356A1 (de) 2022-11-28 2023-01-12 Basf Se Formamidine als Kraftstoffadditive
DE102022131890A1 (de) 2022-12-01 2023-01-26 Basf Se Guanidinderivate als Kraftstoffadditive
EP4382588A1 (fr) 2022-12-06 2024-06-12 Basf Se Additifs pour améliorer la stabilité thermique de carburants
DE102022132342A1 (de) 2022-12-06 2023-01-26 Basf Se Guanidiniumsalze als Kraftstoffadditive

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3440029A (en) * 1964-05-20 1969-04-22 Dow Chemical Co Gasoline containing anti-icing additive
GB1403248A (en) * 1972-10-27 1975-08-28 British Petroleum Co Amino ethers
US4247301A (en) * 1978-06-19 1981-01-27 Chevron Research Company Deposit control and dispersant additives
US4332595A (en) * 1980-12-05 1982-06-01 Texaco Inc. Ether amine detergent and motor fuel composition containing same
US4392866A (en) * 1981-11-05 1983-07-12 Texaco Inc. Etheramine corrosion inhibitor for alcohols
US4604103A (en) * 1982-07-30 1986-08-05 Chevron Research Company Deposit control additives--polyether polyamine ethanes
EP0100665B1 (fr) * 1982-07-30 1987-04-08 Chevron Research Company Additifs contrôlant des dépôts de carburants hydrocarbones et de lubrifiants utilisés dans des moteurs à combustion interne
DE3371966D1 (de) * 1982-11-27 1987-07-16 Peak Pattern Co Comminuting apparatus
US4526587A (en) * 1983-05-31 1985-07-02 Chevron Research Company Deposit control additives-methylol polyether amino ethanes
US4527996A (en) * 1983-10-31 1985-07-09 Chevron Research Company Deposit control additives - hydroxy polyether polyamines
DE3611230A1 (de) * 1986-04-04 1987-10-08 Basf Ag Polybutyl- und polyisobutylamine, verfahren zu deren herstellung und diese enthaltende kraft- und schmierstoffzusammensetzungen
DE3700363A1 (de) * 1987-01-08 1988-07-21 Basf Ag Kraft- oder schmierstoffzusammensetzung und verwendung von polybutyl- oder polyisobutylderivaten in denselben
DE3732908A1 (de) 1987-09-30 1989-04-13 Basf Ag Polyetheramine enthaltende kraftstoffe fuer ottomotoren
DE3826608A1 (de) * 1988-08-05 1990-02-08 Basf Ag Polyetheramine oder polyetheraminderivate enthaltende kraftstoffe fuer ottomotoren
US4964879A (en) * 1989-03-27 1990-10-23 Texaco Inc. Middle distillate fuel containing deposit inhibitor
JPH0662965B2 (ja) * 1990-02-02 1994-08-17 花王株式会社 燃料油添加剤及び燃料油添加剤組成物
US5094667A (en) * 1990-03-20 1992-03-10 Exxon Research And Engineering Company Guerbet alkyl ether mono amines
DE4309074A1 (de) * 1993-03-20 1994-09-22 Basf Ag Als Kraftstoffadditiv geeignete Mischungen

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7850744B2 (en) 2004-08-05 2010-12-14 Basf Aktiengesellschaft Heterocyclic compounds containing nitrogen as a fuel additive in order to reduce abrasion
US8814957B2 (en) 2004-08-05 2014-08-26 Basf Aktiengesellschaft Heterocyclic compounds containing nitrogen as a fuel additive in order to reduce abrasion
US9862904B2 (en) 2013-12-31 2018-01-09 Shell Oil Company Unleaded fuel compositions

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US5660601A (en) 1997-08-26
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