EP0391735A1 - Brennölzusammensetzungen - Google Patents

Brennölzusammensetzungen Download PDF

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Publication number
EP0391735A1
EP0391735A1 EP90303731A EP90303731A EP0391735A1 EP 0391735 A1 EP0391735 A1 EP 0391735A1 EP 90303731 A EP90303731 A EP 90303731A EP 90303731 A EP90303731 A EP 90303731A EP 0391735 A1 EP0391735 A1 EP 0391735A1
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EP
European Patent Office
Prior art keywords
acid
composition according
formula
quaternary ammonium
different
Prior art date
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Granted
Application number
EP90303731A
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English (en)
French (fr)
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EP0391735B1 (de
Inventor
Michael David Sexton
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ExxonMobil Chemical Patents Inc
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Exxon Chemical Patents Inc
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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
    • 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
    • C10L1/222—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
    • C10L1/2235—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 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
    • C10L1/232—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
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
    • C10L1/2412—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides sulfur bond to an aromatic radical
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
    • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
    • 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

  • This invention relates to fuel oil compositions and more especially to fuel oil compositions containing cracked components which are stabilized against sediment formation and colour development during storage. Cracked components are frequently included to give higher yields of diesel fuel and heating oil.
  • fuel compositions comprise a base fuel, which may contain cracked components, and a quaternary ammonium salt in which the cation is derivable from, and advantageously derived from, the reaction of a tertiary amine with an olefin oxide in the presence of excess water to yield a solution of a quaternary ammonium hydroxide, and the anion is derived from an organic acid, subject to the proviso that when the acid is an alkane monocarboxylic acid the alkane is a straight chain alkane.
  • the quaternary ammonium salts may be made in two stages: In the first stage a tertiary amine is reacted with an olefin oxide in the presence of excess water to yield a solution of a quaternary ammonium hydroxide, e.g. in which each R′, which may be the same or different, is an organic group; and each R ⁇ , which may be the same or different, is hydrogen or an organic group.
  • the quaternary ammonium hydroxide is neutralized with an organic acid to form a quaternary ammonium salt, i.e.
  • the olefin oxides are preferably of the formula: where R16, R17, R18, and R19 which may be the same or different, are each hydrogen, or substituted or unsub­stituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, or aryl. Specific examples are ethylene oxide, propylene oxide, but-1-ene oxide, but-2-ene oxide, oct-1-ene oxide and styrene oxide.
  • the organic acid which may be used in the second stage of the reaction and hence forms the anion in the quaternary ammonium salt may be, for example, a car­boxylic acid, carboxylic acid anhydride, phenol, sul­phurized phenol, or sulphonic acid, subject to the proviso that in the aspect of the invention which is a fuel oil composition, unlimited as to type, then when the acid is an alkane monocarboxylic acid the alkane is a straight chain alkane and, preferably, the acid is an alkane 1-carboxylic acid.
  • the carboxylic acid may be, for example:
  • the dicarboxylic acids also include acids of the formula: HOOC-(C r H 2r-2 )COOH where r is an integer of 2 or more.
  • Examples include maleic acid, fumaric acid, pent-2-enedioic acid, hex-2-­enedioic acid; hex-3-enedioic acid, 5-methylhex-2-­enedioic acid; 2,3-di-methylpent-2-enedioic acid; 2-methylbut-2-enedioic acid; 2-dodecylbut-2-enedioic acid; and 2-polyisobutylbut-2-enedioic acid.
  • examples of such acids include 3-methyl­benzene-1,2-
  • the carboxylic acid anhydrides include the anhydrides that may be derived from the carboxylic acids described above. Also included are the anhydrides that may be derived from a mixture of any of the carboxylic acids described above. Specific examples include acetic anhydride, propionic anhydride, benzoic anhydride, maleic anhydride, succinic anhydride, dodecylsuccinic anhydride, dodecenylsuccinic anhydride, an optionally substituted polyisobutylenesuccinic anhydride, advantageously one having a molecular weight of between 500 and 2000 daltons, phthalic anhydride and 4-methylphthalic anhydride.
  • phenols from which the anion of the quaternary ammonium compound may be derived are of many different types. Examples of suitable phenols include:
  • examples of such phenols include 2,2′-dihydroxy-5,5′-dimethyldiphenylmethane; 5,5′-­dihydroxy-2,2′-dimethyldiphenylmethane; 4,4′-dihydroxy-­2,2′-dimethyl-dimethyldiphenylmethane ; 2,2′-dihydroxy-­5,5′-dinonyldiphenylmethane; 2,2′-dihydroxy-5,5′-­didodecylphenylmethane 2,2′,4,4′-tetra-t-butyl-3,3′-­dihydroxy-5,5′-didodecylphenylmethane; and 2,2′,4,4′-­tetra-t-
  • sulphurized phenols of the formula: where R20 and R21 which may be the same or different are as defined above, and m and n are integers, for each m and n greater than 1 each R20 and R21 may be the same or different, and x is 1,2,3 or 4.
  • phenols examples include: 2,2′-dihydroxy-5,5′-dimethyldiphenylsulphide; 5,5′-dihydroxy-2,2′-di-t-butyldiphenyldisulphide; 4,4′-dihydroxy-3,3′-di-t-butyldiphenylsulphide; 2,2′-dihydroxy-5,5′-dinonyldiphenyldisulphide; 2,2′-dihydroxy-5,5′-didodecyldiphenyldisulphide; 2,2′-dihydroxy-5,5′-didodecyldiphenyltrisulphide; and 2,2′-dihydroxy-5,5′-didodecyldiphenyltetrasulphide.
  • the hydrocarbon group(s) may be bonded to the benzene ring through a carbonyl group or a thio-keto group. Alternatively the hydrocarbon group(s) may be bonded to the benzene ring through a sulphur, oxygen or nitrogen atom.
  • sulphonic acids examples include: benzene sulphonic acid; o-toluene­sulphonic acid, m-toluenesulphonic acid; p-toluene­sulphonic acid; 2,3-dimethylbenzenesulphonic acid; 2,4-dimethylbenzenesulphonic acid; 2,3,4-trimethylbenzenesulphonic acid; 4-ethyl-2,3-dimethylbenzenesulphonic acid; 4-ethylbenzenesulphonic acid; 4-n-propylbenzenesulphonic acid; 4-n-butylbenzenesulphonic acid; 4-isobutylbenzenesulphonic acid; 4-sec-butylbenzenesulphonic acid; 4-t-butylbenzenesulphonic acid; 4-nonylbenzenesulphonic acid; 2-dodecylbenzenesulphonic acid; 4-dodecylbenzenesulphonic acid; 4-cycl
  • sulphonic acids of the type listed above where R22 is derived from the polymerization of a low molecular weight olefin e.g. polypropylbenzenesulphonic acid and polyisobutylenebenzenesulphonic acid.
  • sulphonic acids of the formula: R23-SO3H where R23 is substituted or unsubstituted alkyl, cycloalkyl, alkenyl or cycloalkenyl examples include methylsulphonic acid; ethylsulphonic acid; n-propylsulphonic acid; n-butylsulphonic acid; isobutylsulphonic acid; sec-butylsulphonic acid; t-butylsulphonic; nonylsulphonic acid; dodecylsulphonic acid; polypropylsulphonic acid; polyisobutylsulphonic acid; cyclohexylsulphonic acid; and 4-methylcyclohexylsulphonic acid.
  • the quaternary ammonium salts may be made in two stages, the first stage of which comprises the reaction of a tertiary amine with an olefin oxide.
  • tertiary amine Generally 1 mole of the tertiary amine is treated with A moles of the olefin oxide (where A is the number of tertiary nitrogens in the amine molecule) in the presence of an excess of water over that required by the stoichiometry of the reaction.
  • pyridine (1 mole) is treated with an olefin oxide (1 mole) in water (>1 mole).
  • Triethylenediamine (1 mole) is treated with an olefin oxide (2 moles) in water (>2 mole).
  • Hexamine (1 mole) is treated with an olefin oxide (4 moles) in water (>4 moles).
  • the olefin oxide may be used in excess if required, or desired, the excess olefin oxide then reacting with the quaternary ammonium hydroxide.
  • One possible mechanism for this further reaction with olefin oxide is illustrated by the equations:
  • any quantity of water may be used as long as it represents an excess over that required by the stoichiometry of the reaction.
  • the reaction may be carried out in the following ways:
  • the amine is mixed with the water in the reactor and the olefin oxide is added to the stirred reaction mixture.
  • the olefin oxide may be added as:
  • the rate of addition of the olefin oxide is not critical for the quality of the final product but a slow addition rate may be used to control an exothermic reaction.
  • the olefin oxide is mixed with the water in the reactor and the amine is added to the reaction mixture.
  • the amine may be added as:
  • slow addition of the amine may be used to control an exothermic reaction.
  • the mixed reactants may be heated together at a given temperature while the third reactant is added at a rate sufficient to maintain a steady reaction.
  • the reactants may be heated in a pressure vessel but, when heating the reactants to promote the reaction, a temperature greater than 100°C should be avoided to prevent decomposition of the quaternary ammonium hydroxide.
  • the second stage of the reaction comprises neutralization of the quaternary ammonium hydroxide formed in the first stage with the organic acid.
  • the neutralization reaction may be carried out at ambient temperature but generally an elevated temperature is used. When the reaction is completed the water and any solvents used may be removed by heating under vacuum.
  • the product is generally diluted with mineral oil, diesel fuel, kerosene, or an inert hydrocarbon solvent to prevent the product being too viscous.
  • the fuel composition advantageously comprises a minor proportion by weight of the quaternary ammonium compound, preferably less than 1% by weight, more preferively from 0.000001 to 0.1%, especially 2 to 200 ppm.
  • the cracked component in the fuel oil which leads to the undesirable colour formation and sediment is generally obtained by cracking of heavy oil and may be fuel oil in which the main constituent is a fraction otained from a residual oil.
  • Typical methods available for the thermal cracking are visbreaking and delayed coking.
  • the fuels may be obtained by catalytic cracking, the prin­cipal methods being moving-bed cracking and fluidized-­bed cracking.
  • the distillate oil is extracted by normal or vacuum distillation, the boiling point of the distillate oil obtained usually being 60-­500°C, and is a fraction called light-cycle oil, preferably corresponding to the boiling point range of light oil of 150-400°C.
  • Compositions composed entirely of this fuel or fuels which are mixtures of the cracked fraction and normal distillates may be used in the present invention.
  • the proportion by weight of direct-distillation fraction and cracked fraction in a fuel oil composition which is a mixture can vary considerably, but is usually 1:0.03 - 1:2 and preferably 1:0.05 - 1:1.
  • the content of cracked fraction is usually 5-97%, and preferably 10-50%, based on the weight of the composi­tion.
  • the present invention accordingly also provides a fuel oil composition
  • a fuel oil composition comprising a distillate fraction and a cracked fraction and a quaternary ammonium compound the cation of which is the reaction product of a tertiary amine, an olefin oxide, and water, the anion being derived from an organic acid.
  • the invention also provides the use of such a compound in inhibiting sediment and colour formation in a fuel oil composition, especially one containing a component obtained by the cracking of heavy oil.
  • the fuel oil compositions of the present invention may contain other additives such as antioxidants, anticorrosion agents, fluidity improvers, agents absorbing ultraviolet radiation, detergents, dispersants and cetane improvers in small amounts (for example, usually less than 2% based on the weight of the composition).
  • additives such as antioxidants, anticorrosion agents, fluidity improvers, agents absorbing ultraviolet radiation, detergents, dispersants and cetane improvers in small amounts (for example, usually less than 2% based on the weight of the composition).
  • Table 1 shows the effect on sediment and colour in the AMS 77.061 test of blending different amounts of the straight distillate fuel with the unhydrofined catalyti­cally cracked gas oil.
  • Table 2 shows the nitrogen and sulphur contents of various fuels.
  • Table 3 shows the effect on colour and sediment of doping the stable fuel (A) with compounds containing nitrogen and sulphur.
  • Table 4 shows the effect on sediment and colour in the AMS 77.061 test of adding 100 ppm of quaternary ammonium compounds to a fuel containing 20% of cracked components. Comparison of the results for the fuels treated with quaternary ammonium compounds with the results for the untreated fuel show that the compounds of this invention control sediment and colour.
  • Table 5 shows the long term storage characteristics of fuel to which has been added 100 ppm of quaternary ammonium compound. It can be seen that the sediment and colour of the treated fuel are much better in the long term than that of the untreated fuel.
  • Table 1 The Effect of Fuel Composition on Sediment and Colour in the AMS 77.061 Accelerated Stability Test Fuel A wt.% Fuel B wt.% Sediment mg/100 ml Colour (a) 100 0 0.14 ⁇ 0.09 ⁇ 0.5, ⁇ 0.5, ⁇ 0.5 80 20 0.61 ⁇ 0.13 ⁇ 1.0, 1.0, 1.0 60 40 1.12 ⁇ 0.10 ⁇ 1.0, ⁇ 1.0, ⁇ 1.0, ⁇ 1.0 40 60 1.80 ⁇ 0.04 ⁇ 2.0, ⁇ 2.0 20 80 2.10 ⁇ 0.10 ⁇ 2.0, ⁇ 2.0 0 100 2.90 6.0 (a) Colour change (ASTM D1500 test) Table 2 The Nitrogen and Sulphur Contents of Various Fuels Type of Fuel Nitrogen (ppm) Sulphur (%) Unhydrofine

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  • 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)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP90303731A 1989-04-06 1990-04-06 Brennölzusammensetzungen Expired - Lifetime EP0391735B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898907801A GB8907801D0 (en) 1989-04-06 1989-04-06 Improved fuel oil compositions
GB8907801 1989-04-06

Publications (2)

Publication Number Publication Date
EP0391735A1 true EP0391735A1 (de) 1990-10-10
EP0391735B1 EP0391735B1 (de) 1995-08-16

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EP90303731A Expired - Lifetime EP0391735B1 (de) 1989-04-06 1990-04-06 Brennölzusammensetzungen

Country Status (6)

Country Link
EP (1) EP0391735B1 (de)
JP (1) JP2851908B2 (de)
AT (1) ATE126528T1 (de)
CA (1) CA2013825A1 (de)
DE (1) DE69021611T2 (de)
GB (1) GB8907801D0 (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2682684A1 (fr) * 1991-10-22 1993-04-23 Rouet Jean Procede de traitement des hydrocarbures paraffiniques.
WO2001088066A1 (fr) * 2000-05-19 2001-11-22 Nippon Mitsubishi Oil Corporation Additif pour carburant diesel et composition de carburant diesel
CN100335598C (zh) * 2005-09-12 2007-09-05 李宇翔 高清洁柴油稳定剂
EP0956328B2 (de) † 1996-10-11 2010-07-07 Infineum USA L.P. Kraftstoffe mit schmieradditiven
US9255236B2 (en) 2010-07-06 2016-02-09 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US9574149B2 (en) 2011-11-11 2017-02-21 Afton Chemical Corporation Fuel additive for improved performance of direct fuel injected engines
EP3004294B1 (de) 2013-06-07 2017-04-19 Basf Se Mit alkylenoxid und hydrocarbyl-substituierter polycarbonsäure quaternisierter stickstoffverbindungen als additive in kraft- und schmierstoffen
EP2430131B1 (de) 2009-05-15 2017-09-06 The Lubrizol Corporation Quaternäre ammoniumamidsalze
EP3174847B1 (de) 2014-07-28 2019-11-13 Innospec Limited Quaternäre ammoniumverbindungen und deren verwendung als kraftstoff- oder schmiermitteladditive
US11999920B2 (en) 2021-09-10 2024-06-04 Ecolab Usa Inc. Cold flow additives for plastic-derived synthetic feedstock

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Publication number Priority date Publication date Assignee Title
FR1301479A (fr) * 1961-07-26 1962-08-17 Standard Oil Co Huile lourde stabilisée
US3419366A (en) * 1965-08-02 1968-12-31 Gulf Research Development Co Alkoxylated quaternary ammonium salts of esters of salicylic acid as microbicides
US3527804A (en) * 1967-04-20 1970-09-08 Universal Oil Prod Co Hydroxyalkyl polysubstituted alkylene polyamines
FR2249948A1 (de) * 1973-11-07 1975-05-30 Lubrizol Corp
US3962104A (en) * 1973-06-27 1976-06-08 Exxon Research And Engineering Company Lubricating oil compositions
US4056531A (en) * 1973-09-07 1977-11-01 Ethyl Corporation Polymonoolefin quaternary ammonium salts of triethylenediamine
EP0220892A2 (de) * 1985-10-21 1987-05-06 Mobil Oil Corporation Zusatzverbindung zur Verbesserung von Fliesseigenschaften von Heizöl und diese enthaltendes Heizöl
EP0293192A1 (de) * 1987-05-27 1988-11-30 Exxon Chemical Patents Inc. Dieselbrennstoffzusammensetzung

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JPS543487A (en) * 1977-06-09 1979-01-11 Citizen Watch Co Ltd Thin-type crystal oscillator

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1301479A (fr) * 1961-07-26 1962-08-17 Standard Oil Co Huile lourde stabilisée
US3419366A (en) * 1965-08-02 1968-12-31 Gulf Research Development Co Alkoxylated quaternary ammonium salts of esters of salicylic acid as microbicides
US3527804A (en) * 1967-04-20 1970-09-08 Universal Oil Prod Co Hydroxyalkyl polysubstituted alkylene polyamines
US3962104A (en) * 1973-06-27 1976-06-08 Exxon Research And Engineering Company Lubricating oil compositions
US4056531A (en) * 1973-09-07 1977-11-01 Ethyl Corporation Polymonoolefin quaternary ammonium salts of triethylenediamine
FR2249948A1 (de) * 1973-11-07 1975-05-30 Lubrizol Corp
EP0220892A2 (de) * 1985-10-21 1987-05-06 Mobil Oil Corporation Zusatzverbindung zur Verbesserung von Fliesseigenschaften von Heizöl und diese enthaltendes Heizöl
EP0293192A1 (de) * 1987-05-27 1988-11-30 Exxon Chemical Patents Inc. Dieselbrennstoffzusammensetzung

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2682684A1 (fr) * 1991-10-22 1993-04-23 Rouet Jean Procede de traitement des hydrocarbures paraffiniques.
EP0956328B2 (de) † 1996-10-11 2010-07-07 Infineum USA L.P. Kraftstoffe mit schmieradditiven
WO2001088066A1 (fr) * 2000-05-19 2001-11-22 Nippon Mitsubishi Oil Corporation Additif pour carburant diesel et composition de carburant diesel
JP4537642B2 (ja) * 2000-05-19 2010-09-01 新日本石油株式会社 燃料油添加剤及び燃料油組成物
CN100335598C (zh) * 2005-09-12 2007-09-05 李宇翔 高清洁柴油稳定剂
EP2514807B1 (de) 2009-05-15 2018-07-11 The Lubrizol Corporation Quartäre Ammoniumamidsalze
US10913910B2 (en) 2009-05-15 2021-02-09 The Lubrizol Corporation Quaternary ammonium amide and/or ester salts
EP2430131B1 (de) 2009-05-15 2017-09-06 The Lubrizol Corporation Quaternäre ammoniumamidsalze
US10479950B2 (en) 2009-05-15 2019-11-19 The Lubrizol Corporation Quaternary ammonium amide and/or ester salts
US10023819B2 (en) 2009-05-15 2018-07-17 The Lubrizol Corporation Quaternary ammonium amide and/or ester salts
US9255236B2 (en) 2010-07-06 2016-02-09 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US9587194B2 (en) 2010-07-06 2017-03-07 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US9988589B2 (en) 2010-07-06 2018-06-05 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US10336957B2 (en) 2010-07-06 2019-07-02 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US10344241B2 (en) 2010-07-06 2019-07-09 Basf Se Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants
US9574149B2 (en) 2011-11-11 2017-02-21 Afton Chemical Corporation Fuel additive for improved performance of direct fuel injected engines
US10407634B2 (en) 2013-06-07 2019-09-10 Basf Se Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants
US10676685B2 (en) 2013-06-07 2020-06-09 Basf Se Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants
EP3205705B1 (de) 2013-06-07 2020-08-12 Basf Se Mit alkylenoxid und hydrocarbyl-substituierter polycarbonsäure quaternisierte stickstoffverbindungen und ihre verwendung als additiv in kraft- und schmierstoffen
EP3004294B1 (de) 2013-06-07 2017-04-19 Basf Se Mit alkylenoxid und hydrocarbyl-substituierter polycarbonsäure quaternisierter stickstoffverbindungen als additive in kraft- und schmierstoffen
US11111449B2 (en) 2013-06-07 2021-09-07 Basf Se Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants
US11912950B2 (en) 2013-06-07 2024-02-27 Basf Se Use of nitrogen compounds quaternised with alkylene oxide and hydrocarbyl-substituted polycarboxylic acid as additives in fuels and lubricants
EP3174847B1 (de) 2014-07-28 2019-11-13 Innospec Limited Quaternäre ammoniumverbindungen und deren verwendung als kraftstoff- oder schmiermitteladditive
US11999920B2 (en) 2021-09-10 2024-06-04 Ecolab Usa Inc. Cold flow additives for plastic-derived synthetic feedstock

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DE69021611T2 (de) 1996-02-22
JPH0362889A (ja) 1991-03-18
CA2013825A1 (en) 1990-10-06
EP0391735B1 (de) 1995-08-16
DE69021611D1 (de) 1995-09-21
GB8907801D0 (en) 1989-05-17
ATE126528T1 (de) 1995-09-15
JP2851908B2 (ja) 1999-01-27

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