EP0464489B1 - Carburants contenant un ester, pour moteurs diesel et à allumage par étincelle - Google Patents

Carburants contenant un ester, pour moteurs diesel et à allumage par étincelle Download PDF

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Publication number
EP0464489B1
EP0464489B1 EP91110146A EP91110146A EP0464489B1 EP 0464489 B1 EP0464489 B1 EP 0464489B1 EP 91110146 A EP91110146 A EP 91110146A EP 91110146 A EP91110146 A EP 91110146A EP 0464489 B1 EP0464489 B1 EP 0464489B1
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EP
European Patent Office
Prior art keywords
esters
acid
fuel
acids
diesel engines
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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EP91110146A
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German (de)
English (en)
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EP0464489A1 (fr
Inventor
Jürgen Dr. Mohr
Knut Dr. Oppenlaender
Roland Dr. Schwen
Hans Peter Dr. Rath
Jürgen Dr. Thomas
Hans-Henning Dr. Vogel
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • 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
    • C10L1/2222—(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
    • 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)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B1/00—Engines characterised by fuel-air mixture compression
    • F02B1/02—Engines characterised by fuel-air mixture compression with positive ignition
    • F02B1/04—Engines characterised by fuel-air mixture compression with positive ignition with fuel-air mixture admission into cylinder
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00—Engines characterised by air compression and subsequent fuel addition
    • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition

Definitions

  • the invention relates to fuels for gasoline engines or diesel engines which contain small amounts of esters of alkylalkanolamines or alkylaminopolyalkylene glycols with polycarboxylic acids as additives.
  • Carburetors and lapping systems of gasoline engines are increasingly contaminated by contaminants caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and the crankcase ventilation gases that are led into the carburetor.
  • the first additive generation could only prevent the formation of deposits in the intake system, but not remove existing deposits, whereas the modern additives of the second generation can do both ("keep-clean” and "clean-up effect"), in particular due to their improved thermostability in zones of higher temperatures, namely in the in-valve.
  • Esters of such, in particular higher, carboxylic acids with aliphatic alcohols are used less frequently because of their often difficult preparative accessibility.
  • EP-A-117 108 discloses esters of monocarboxylic acids which are suitable as a "cold flow improver".
  • No. 3,426,062 describes esters of special halogen-containing polycyclic dicarboxylic acids which are already unfavorable as fuel additives due to their halogen content.
  • US 3 183 070 and US 3 088 815 disclose esters of monoalkyl dihydroxyalkyl amines.
  • the formulations must contain higher-boiling, thermostable solvent components (e.g. mineral oils or synthetic oils) that facilitate the drainage of the products from the inlet valves.
  • thermostable solvent components e.g. mineral oils or synthetic oils
  • R1 and R2 are a C6 to C30 alkyl radical
  • R3 is the hydroxylalkyl radical of the general formula II in which R4 is hydrogen or a C1- to C6-alkyl radical and m is the number from 0 to 100
  • fuels with reaction products of polyhalopolyhydropolycyclodicarboxylic acids, anhydrides or esters with N, N-dicycloalkylalkanolamines are excluded, contain.
  • the amount of the ester according to the invention contained in the fuels is generally 10 to 5000 mg, preferably 50 to 2000 mg, in particular 100 to 1000 mg, of the ester per kg of fuel.
  • the ester additives to be used according to the invention are generally synthesized in several stages.
  • the mixture is expediently prepared by alkoxylation with alkylene oxides having 2 to 8 carbon atoms, preferably 2 to 6 carbon atoms, in particular 2 to 4 carbon atoms, or mixtures of these alkylene oxides of secondary amines of the general formula III in which R1 is a C6 to C30 alkyl radical, preferably a C6 to C24 alkyl radical, in particular a C6 to C20 alkyl radical, and R5 is a C6 to C30 alkyl radical, preferably a C6 to C24 alkyl radical, in particular one C6- to C20-alkyl radical, where R1 and R5 as alkyl radicals can be the same or different, the alkylalkanolamines or alkylaminopolyalkylene glycols of the general formula I in a manner known per se.
  • the alkoxylation is optionally carried out in the presence of alkali such as potassium hydroxide solution, sodium hydroxide solution, sodium methylate, expediently at elevated temperatures, for example at temperatures from 80 to 160 ° C., preferably 100 to 160 ° C.
  • alkali such as potassium hydroxide solution, sodium hydroxide solution, sodium methylate
  • Suitable alkylene oxides are, for example, ethylene oxide, propylene oxide, 1,2-butylene oxide, isobutylene oxide, 1,2-pentene oxide, ethylene oxide being preferred.
  • amines III which may be mentioned are dihexylamine, dicyclohexylamine, dioctylamine, didecylamine, diisotridecylamine, dicetylamine, distearylamine, dicerylamine.
  • the amine is reacted in a manner known per se, for example in the presence of water, with 1 mol of alkylene oxide or a mixture of alkylene oxides per 1 mol of secondary amine III (see, for example, SP McManus et al. Synth. Commun. 1973, 177).
  • the alkylalkanolamines obtained in this way are expediently reacted with an amount of alkylene oxides such that m in the hydroxyalkyl radicals of the alkylaminopolyalkylene glycols obtained means the numbers 1 to 100, preferably 1 to 50, in particular 1 to 30.
  • the compounds of formula I obtained are then in a further step to the esters of polycarboxylic acids according to known methods of ester formation, e.g. implemented by esterification processes or transesterification processes.
  • the methods of ester formation are e.g. in Houben-Weyl, Methods of Organic Chemistry, Volume VIII, Oxygen Compounds III (1952), pages 516 to 555.
  • the ester formation is generally carried out at temperatures from 40 to 220 ° C., preferably 50 to 200 ° C., in particular 60 to 180 ° C.
  • the esterification can be carried out with and without a catalyst.
  • the esterification is preferably carried out in the presence of acidic catalysts, e.g. Mineral acids such as sulfuric acid, phosphoric acid, p-toluenesulfonic acid, and Lewis acids such as BF3, dibutyltin dilaurate.
  • a volatile, water-insoluble diluent such as benzene, toluene, xylene or else chloroform and carbon tetrachloride.
  • esters are conveniently prepared via transesterification, starting from the esters of polycarboxylic acids with lower alcohols such as methanol, ethanol, propanol, by reacting them with the compounds of the general formula I in the presence of basic or acidic catalysts, preferably Lewis acidic catalysts, with expedient removal by distillation of the lower alcohol released.
  • lower alcohols such as methanol, ethanol, propanol
  • Suitable carboxylic acids on which the esters are based are, for example, aliphatic, cycloaliphatic and aromatic polycarboxylic acids, which can also be substituted, for example as hydroxypolycarboxylic acids or amino, imino and nitrilopolycarboxylic acids.
  • the carboxylic acids have 4 to 26, preferably 5 to 20, carbon atoms.
  • the polycarboxylic acids which are preferably used are generally those having 2 to 6, preferably 2 to 4, carboxyl groups.
  • Suitable aliphatic polycarboxylic acids are e.g. Dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid and citric acid.
  • Aromatic polycarboxylic acids include e.g. Phthalic acid, terephthalic acid, isophthalic acid, trimellitic acid, hemimellitic acid, trimesic acid, pyromellitic acid, mellitic acid into consideration.
  • polycarboxylic acids are nitrilotriacetic acid and ethylenediaminetetraacetic acid.
  • esters according to the invention are generally obtained as colorless to light yellow, in some cases. viscous, oily products, which are often similar to lubricants in their physical properties.
  • esters according to the invention are their excellent thermal stability, which results from the results of thermogravimetric or differential thermal analysis.
  • esters according to the invention can be prepared in a simple manner in good yield from the higher carboxylic acids and the aminoalkanol compounds I, since it was known that esters of such carboxylic acids with aliphatic alcohols, i.e. Alcohols that do not contain amino groups are often difficult to obtain from a preparative perspective.
  • the carrier oils have an additional washing function, often also a synergistic effect in combination with the detergents.
  • the carrier oils are usually high-boiling, viscous, thermostable liquids. They coat the hot metal surface (e.g. the inlet valves) with a thin film of liquid and thereby prevent or delay the formation or deposition of decomposition products on the metal surfaces.
  • high-boiling, refined mineral oil fractions mostly vacuum distillates
  • a particularly good carrier oil is Brightstock in combination with low-boiling, highly refined lubricating oil fractions.
  • Synthetic components have also been used as carrier oils.
  • Esters in particular have been described as suitable carrier oils (e.g. DE 10 62 484, DE 21 29 461 and DE 23 04 086).
  • the carrier oils are generally added to the fuels in an amount of 50 to 5000 mg, preferably 100 to 2000 mg, of carrier oil per kg of fuel.
  • the ester is tested as an additive, particularly for its suitability as a valve and carburetor cleaner, by means of a motor test according to CEC-F-02-T 79 in an Opel Kadett 1.2-1 engine.
  • the following table shows the results of the application tests.
  • the effect of known detergents and the carboxylic acid alkanolamine esters used according to the invention are also compared here, also in combination with synthetic carrier oils in gasoline for internal combustion engines.
  • the amounts of detergents and carrier oils specified in the table were added to premium petrol (unleaded, RON 95) according to DIN 51607, which was used in test bench tests with a 1.2-1 Opel Kadett engine according to CEC-F-02-T-79 were.
  • the reference oil RL 51 was used as engine oil.
  • the amounts of detergents refer to pure active substances without solvents.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (3)

  1. Carburants ou combustibles pour moteurs à combustion interne et moteurs diesel, contenant de faibles quantités d'esters d'acides polycarboxyliques et d'alkylalcanolamines ou d'alkylaminopolyalkylènegycols répondant à la formule générale I
    Figure imgb0009
     dans laquelle
    R₁ et R₂ sont chacun un radical alkyle en C₆-C₃₀, et
    R₃ est le résidu hydroxyalkyle répondant à la formule générale II
    Figure imgb0010
     dans laquelle R₄ est un hydrogène ou un radical alkyle en C₁-C₆, et m vaut de 0 à 100,
    à l'exclusion des carburants et combustibles contenant des produits de la réaction, avec des N,N-dicycloalkylalcanolamines, d'acides polyhalogénopolyhydropolycyclodicarboxyliques, de leurs anhydrides ou de leurs esters.
  2. Carburants ou combustibles selon la revendication 1, contenant des esters dérivant d'acides polycarboxyliques ayant de 2 à 4 groupes carboxyles.
  3. Carburants ou combustibles selon les revendications 1 ou 2, contenant de 10 à 5000 mg de l'ester par kg de carburant ou combustible.
EP91110146A 1990-06-29 1991-06-20 Carburants contenant un ester, pour moteurs diesel et à allumage par étincelle Expired - Lifetime EP0464489B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4020664 1990-06-29
DE4020664A DE4020664A1 (de) 1990-06-29 1990-06-29 Ester enthaltende kraftstoffe fuer ottomotoren und dieselmotoren

Publications (2)

Publication Number Publication Date
EP0464489A1 EP0464489A1 (fr) 1992-01-08
EP0464489B1 true EP0464489B1 (fr) 1994-01-19

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ID=6409288

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EP91110146A Expired - Lifetime EP0464489B1 (fr) 1990-06-29 1991-06-20 Carburants contenant un ester, pour moteurs diesel et à allumage par étincelle

Country Status (4)

Country Link
US (1) US5194068A (fr)
EP (1) EP0464489B1 (fr)
CA (1) CA2046004C (fr)
DE (2) DE4020664A1 (fr)

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EP0561947A1 (fr) * 1990-12-03 1993-09-29 Mobil Oil Corporation Additifs multifonctionnels ameliorant les proprietes a basse temperature de combustibles distilles et compositions les contenant
DE59308532D1 (de) * 1992-08-22 1998-06-18 Clariant Gmbh Polyfunktionelle Demulgatoren für Rohöle
US5284495A (en) * 1992-09-17 1994-02-08 Mobil Oil Corporation Oligomeric/polymeric multifunctional additives to improve the low-temperature properties of distillate fuels
DE4324394A1 (de) * 1993-07-21 1995-01-26 Basf Ag Umsetzungsprodukte von Aminoalkylencarbonsäuren sowie Erdölmitteldestillate, die diese enthalten
DE4344222A1 (de) * 1993-12-23 1995-06-29 Veba Oel Ag Otto-Kraftstoffe
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US5628804A (en) * 1995-12-21 1997-05-13 Ethyl Corporation Polyether esteramide containing additives and methods of making and using same
US5964907A (en) * 1996-08-14 1999-10-12 Akzo Nobel N.V. Fuel compositions containing esteramines
EP0829527A1 (fr) 1996-09-12 1998-03-18 Exxon Research And Engineering Company Concentré additif pour des compositions de combustibles
US6001141A (en) * 1996-11-12 1999-12-14 Ethyl Petroleum Additives, Ltd. Fuel additive
DE19753792A1 (de) * 1997-12-04 1999-06-10 Henkel Kgaa Verfahren zum Entschäumen von Treibstoffen
US5891203A (en) * 1998-01-20 1999-04-06 Ethyl Corporation Fuel lubricity from blends of a diethanolamine derivative and biodiesel
DE29805178U1 (de) 1998-03-21 1998-11-05 Mts Maschinenbau Gmbh Stapelsäulen
CA2403573A1 (fr) 2000-03-31 2001-10-04 James R. Ketcham Composition d'additif de carburant destinee a ameliorer la distribution de charge modifiant le coefficient de frottement
US6835217B1 (en) 2000-09-20 2004-12-28 Texaco, Inc. Fuel composition containing friction modifier
US7182795B2 (en) * 2002-03-13 2007-02-27 Atton Chemical Intangibles Llc Fuel lubricity additives derived from hydrocarbyl succinic anhydrides and hydroxy amines, and middle distillate fuels containing same
KR101143114B1 (ko) * 2003-11-13 2012-05-08 인피늄 인터내셔날 리미티드 고온에서 제트연료에서의 침적물 형성을 억제하는 방법
US7696136B2 (en) 2004-03-11 2010-04-13 Crompton Corporation Lubricant compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters
EP1705234A1 (fr) * 2005-03-24 2006-09-27 Basf Aktiengesellschaft Utilisation d'additifs détergents afin d'empêcher ou de réduire la formation des dépôts dans les systèmes d'injection pour moteurs diesel à injection directe
WO2008013844A2 (fr) * 2006-07-25 2008-01-31 General Vortex Energy, Inc. Système, appareil et procédé de combustion d'un métal et autres combustibles
CN102373109B (zh) * 2010-08-12 2013-09-04 中国石油化工股份有限公司 一种生物柴油的脱氮方法
US9476005B1 (en) 2013-05-24 2016-10-25 Greyrock Energy, Inc. High-performance diesel fuel lubricity additive
US11493274B2 (en) 2019-12-04 2022-11-08 Greyrock Technology, Llc Process for the commercial production of high-quality catalyst materials
CA3102382A1 (fr) * 2018-06-08 2019-12-12 Huntsman Petrochemical Llc Polyesters d'amine d'alkyle alcoxyles utilises comme abaisseurs de point d'ecoulement destines a des carburants

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Also Published As

Publication number Publication date
CA2046004C (fr) 1996-07-16
DE59100880D1 (de) 1994-03-03
US5194068A (en) 1993-03-16
EP0464489A1 (fr) 1992-01-08
DE4020664A1 (de) 1992-01-02
CA2046004A1 (fr) 1991-12-30

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