EP0385633B1 - Combustible de distillat moyen ayant une stabilité au stockage modifiée - Google Patents

Combustible de distillat moyen ayant une stabilité au stockage modifiée Download PDF

Info

Publication number
EP0385633B1
EP0385633B1 EP90301791A EP90301791A EP0385633B1 EP 0385633 B1 EP0385633 B1 EP 0385633B1 EP 90301791 A EP90301791 A EP 90301791A EP 90301791 A EP90301791 A EP 90301791A EP 0385633 B1 EP0385633 B1 EP 0385633B1
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
butyl
concentrate
phenol
Prior art date
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
Application number
EP90301791A
Other languages
German (de)
English (en)
Other versions
EP0385633A1 (fr
Inventor
John Gray Bostick
Larry John Cunningham
John Vincent Hanlon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Afton Chemical Corp
Original Assignee
Afton Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Afton Chemical Corp filed Critical Afton Chemical Corp
Publication of EP0385633A1 publication Critical patent/EP0385633A1/fr
Application granted granted Critical
Publication of EP0385633B1 publication Critical patent/EP0385633B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
    • 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
    • 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
    • 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
    • C10L1/18—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
    • C10L1/22—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
    • C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
    • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
    • 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
    • C10L1/2493—Organic compounds containing sulfur, selenium and/or tellurium compounds of uncertain formula; reactions of organic compounds (hydrocarbons, acids, esters) with sulfur or sulfur containing compounds

Definitions

  • This invention relates generally to improving the stability of middle distillate fuels and more particularly to stabilized middle distillate fuel compositions which contain a combination of N,N-dimethylcyclohexyl amine and a Mannich Base.
  • Patent 3,490,882 discloses stabilized petroleum distillate fuel oils containing N,N-dimethylcyclohexylamine antioxidant and a N,N′-di(ortho-hydroxyarylidene)-1,2-alkylenediamine metal deactivator such as N,N′-disalicylidene-1,2-propylenediamine;
  • U.S. Patent 4,166,726 discloses a fuel additive which is a mixture of a polyalkylene amine and a Mannich Base; and U.S.
  • Patents 4,501,595 and 4,533,361 disclose diesel oil which contains a condensate of tetraethylene pentamine, paraformaldehyde, a hindered phenol such as 2,6-di-t-butylphenol and polyisobutenyl succinic anhydride.
  • a fuel additive concentrate comprising a mixture of N,N-dimethylcyclohexylamine and a Mannich Base which is the reaction product of an aldehyde, an amine and an alkyl phenol selected from (a) hindered phenol having the formula: where R1, R2, R3 are independently selected from hydrogen, t-butyl, t-amyl and isopropyl, provided that at least one of R1, R2 and R3 is hydrogen and at least one of R1 and R2 is t-butyl, t-amyl or isopropyl; and (b) p-alkyl phenol having the formula: where R4 is C9 to C30 alkyl.
  • the concentrate can also contain a N,N′-di(ortho-hydroxyarylidene)-1,2-alkylenediamine metal deactivator such as N,N′-disalicylidene-1,2-propylenediamine.
  • a stabilized fuel containing from 1 to 1400 mg/l of N,N-dimethylcyclohexylamine, from 0.5 to 1100 mg/l of Mannich Base and from 0 to 400 mg/l of an N,N′-di(ortho-hydroxyarylidene)-1,2-alkylenediamine.
  • the N,N-dimethylcyclohexylamine component of the compositions of the invention is a commercially available fuel antioxidant.
  • the N,N′-di(ortho-hydroxyarylidene)-1,2-alkylenediamine component in which, typically, the arylidene radical contains 6-7 carbon atoms and the alkylene radical contains 2-3 carbon atoms, is a metal deactivator whose presence in combination with the other components provides fuel compositions of the invention having the most improved stability.
  • the preferred metal deactivator is N,N′-disalicylidene-1,2-propylenediamine which is commercially available.
  • the Mannich Base component of the invention is produced by the Mannich condensation reaction of a hindered or p-alkyl phenol, an aldehyde, such as formaldehyde, ethanal, propanal, and butanal (preferably formaldehyde in its monomeric form or paraformaldehyde) and primary and secondary amines.
  • a hindered or p-alkyl phenol such as formaldehyde, ethanal, propanal, and butanal (preferably formaldehyde in its monomeric form or paraformaldehyde) and primary and secondary amines.
  • the hindered phenols which are useful in preparing the Mannich Base component of the invention are phenols which are characterized by the presence of at least one and preferably two ortho-t-butyl, t-amyl, and/or isopropyl groups.
  • Specific examples of such hindered phenols include: 2,4-di-t-butylphenol, 2,4-diisopropylphenol, 2,6-diisopropylphenol, 2-t-butylphenol, and 2-t-amylphenol with 2,6-di-t-butylphenol being most preferred.
  • the p-alkyl phenols which are useful in preparing the Mannich Base component of the invention are those which contain from 9 to 30 carbons which can be arranged in either a straight or a branched chain.
  • Preferred phenols are C9 to C12 p-alkylphenols such as, for example, p-nonylphenol and p-dodecylphenol.
  • the amines which are useful in preparing the Mannich Base component of the invention are primary and secondary amines which can be selected from one or more of:
  • amines include 1,3-diaminopropane, 1,2 diaminopropane, dimethylamine, diethylamine, dipropylamine, dibutylamine, N,N-dimethyl-1,3-diaminopropane, 1,1-dimethyldodecylamine, mixed C12-C14 t-alkyl amines, 2-methyl-1,5-pentadiamine, ethylenediamine; cyclic amines such as piperazine, aminoethylpiperazine, morpholine and thiomorpholine; and ethylene polyamines such as diethylene triamine and triethylene tetraamine.
  • the Mannich Base can be formed by reacting from 1 to 5 moles of aldehyde, from about 1 to 2 moles of amine and from 1 to 4 moles of phenol at a temperature of from 0°C to 150°C for 0.5 to 10 hours.
  • An inert solvent such as isopropanol can be used which is distilled from the product along with water formed in the reaction.
  • the Mannich Base product is usually a mixture of materials which may contain unreacted ingredients, especially the phenol.
  • the Mannich Bases can be isolated from the product mixture but the product mixture itself can conveniently be used in forming the compositions of the invention. Examples of Mannich reactions and products are illustrated below: or where R1, R2, R4, R5 and R6 are as defined above.
  • additive mixtures of the invention are usually prepared and marketed in the form of concentrates for addition to the fuel by the customer although the individual components could be added directly into the fuel.
  • Suitable proportions of additives in the concentrates of the invention include from 25 to 95 wt% N,N-dimethylcyclohexylamine, from 0 to 25 wt% N,N′-di(ortho-hydroxyarylidene)-1,2-alkylenediamine and, from 5 to 75 wt% Mannich Base.
  • the concentrates are added to the fuel in effective amounts to provide improved stability.
  • Suitable amounts of additive concentrate in the fuel are from 1 to 500 pounds per thousand barrels (Ptbs) (3 to 1500 mg/l, preferred 2.5 to 100 Ptbs or 8 to 300 mg/l).
  • Ptbs pounds per thousand barrels
  • This will provide a stabilized fuel containing from 1 to 1400 mg/liter (preferred 2 to 250 mg/l) N,N-dimethylcyclohexylamine, from 0 to 400 mg/l (preferred 0 to 100 mg/l) N,N′-di(ortho-hydroxyarylidene)-1,2-alkylenediamine metal deactivator and from 1 to 1100 mg/l (preferred 1 to 250 mg/l) of Mannich Base.
  • the metal deactivator When used, the metal deactivator is present in amounts of 1.0% to 25 wt% of concentrate or .3 to 400 mg/l of fuel.
  • the concentrates can also contain an inert diluent or solvent which can be, for example, an aliphatic hydrocarbon such as kerosene or an aromatic hydrocarbon such as xylene.
  • the middle distillate fuels whose stability is improved by the invention typically include those boiling within a temperature range of 150°-400°C which may commonly be labeled as kerosene, fuel oil, diesel oil, No. 1-D, or No. 2-D.
  • compositions of the invention are further illustrated by, but are not intended to be limited to, the following examples wherein parts are parts by weight unless otherwise indicated.
  • a Mannich Base reaction product of formaldehyde, 1,3-diaminopropane and 2,6-di-t-butylphenol is prepared by the following process.
  • Additive blends of the reaction product were prepared and tested in different fuels using both the D 4625 43°C (110°F) Storage Stability Test, in which the color change (using ASTM D1500) and the total insolubles in the fuel (reported in mg/100 ml) are determined on 400 ml samples stored for 13 weeks in the dark and the F-21-61 149°C (300°F) Accelerated Stability Test in which the color change and insoluble gums are determined on 50 ml samples heated to 149°C for a selected time, which was 90 minutes, allowed to cool in the dark, tested for color (ASTM D1500), and then filtered (using a 4.25 cm Whatman #1 filter paper) and the filtrate discarded. The filter is washed clean of fuel with isooctane and measured for deposits by comparison with a set of reference papers.
  • the blend compositions and test results in comparison to untreated fuel and blends without the Mannich Base product are reported in Table I below.
  • a significant difference in stability at 149°C is indicated by a color difference of about 1/2 number and/or a deposit difference of 2 numbers and a significant difference in stability at 43°C is indicated by a color difference of about 1/2 number and a deposit difference of 20%.
  • the results in Table I show that the blends of the invention which contain Mannich Base in addition to DMCA or DMCA and MDA gave significantly better overall stability when compared to comparable blends which did not contain the Mannich Base, for example, blend 3 vs blend 2 and blend 5 vs blend 4 of Fuel #1.
  • a Mannich Base reaction product of formaldehyde, dimethylamine, and 2,6-di-t-butylphenol is prepared by the following process.
  • a Mannich Base reaction product of formaldehyde, C12-C14 t-alkyl amine mixture (Primene 81R) and 2,6-di-t-butyl phenol is prepared by the process described in Example 2 using 95.5 grams (0.5 mole) of Primene 81R in place of the dimethylamine.
  • the product yield is 200 grams or 82% of theory which contains N-[3,5-di-t-butyl-4-hydroxybenzyl]-mixed C12-C14 t-alkyl amines.
  • blends 4 and 7 according to the invention which contain the Mannich Base in addition to DMCA and MDA have better stability at the same total additive levels compared to blends 2 and 5 containing only DMCA and MDA.
  • a Mannich Base reaction product of formaldehyde, 1,2-diaminopropane, and 2,6-di-t-butyl phenol is prepared by the following process.
  • blend 4 of the invention containing the Mannich Base has improved stability compound to blend 2 which containing DMCA alone.
  • Blend 5 containing the Mannich Base has improved stability over blend 3 which contained DMCA and MDA alone.
  • a Mannich Base reaction product of formaldehyde, N,N-dimethyl-1,3-diaminopropane, and p-dodecylphenol was prepared by the following procedure.
  • blends 3 and 5 of the invention have over-all improved stability compared to blends at the same total additive level which did not include the Mannich Base.

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)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Claims (10)

  1. Concentré d'additifs pour combustible, comprenant un mélange de N,N-diméthylcyclohexylamine et d'une base de Mannich qui est le produit de réaction d'un aldéhyde, d'une amine primaire ou secondaire et d'un alkylphénol choisi entre (a) un phénol à encombrement stérique répondant à la formule :
    Figure imgb0046
        dans laquelle R₁, R₂, R₃ sont choisis, indépendamment, entre l'hydrogène et les radicaux tertio-butyle, tertio-amyle et isopropyle, sous réserve que l'un au moins de R₁, R₂ et R₃ soit l'hydrogène et que l'un au moins de R₁ et R₂ soit un radical tertio-butyle, tertio-amyle ou isopropyle ; et (b) un p-alkylphénol répondant à la formule :
    Figure imgb0047
        dans laquelle R₄ est un groupe alkyle en C₉ à C₃₀ ; ledit concentré contenant, sur la base de son poids total, 25 à 95 % en poids de N,N-diméthylcyclohexylamine et 5 à 75 % en poids de base de Mannich.
  2. Concentré suivant la revendication 1, qui contient aussi 1 à 25 % en poids de N,N′-di(ortho-hydroxy-arylidène)-1,2-alkylènediamine comme désactivateur des métaux.
  3. Concentré suivant la revendication 1 ou 2, dans lequel l'aldéhyde est le formaldéhyde et l'amine consiste en une ou plusieurs des amines suivantes :
    A. des alkylmono-amines de formule :
    Figure imgb0048
        dans laquelle R₅ est choisi entre H et des radicaux alkyle en C₁ à C₅, et R₆ est choisi entre des radicaux alkyle en C₁ à C₁₄ et le groupe -(CH₂)n-OR₇ dans lequel n a une valeur de 1 à 10 et R₇ est un groupe alkyle en C₁ à C₂₀,
    B. des alkyldiamines de formule :
    Figure imgb0049
        dans laquelle R₅ est choisi entre H et un groupe alkyle en C₁ à C₅, R₈ est un groupe alkylène en C₁ à C₆ et A et B sont choisis, indépendamment, entre H, un groupe alkyle en C₁ à C₅, alkyle en C₁ à C₅ portant un substituant hydroxy et le groupe (CH₂)n-OR₇ dans lequel n a une valeur de 1 à 10 et R₇ est un groupe alkyle en C₁ à C₂₀,
    C. des éthylènepolyamines de formule : H₂N(̵(CH₂)₂NH)̵ n H
    Figure imgb0050
        dans laquelle n a une valeur de 2 à 10, et
    D. des amines cycliques de formule :
    Figure imgb0051
        dans laquelle n et m sont, indépendamment, des nombres entiers de 1 à 3, X est choisi entre CH₂, O, S et NR₉, où R₉ représente H, un radical alkyle en C₁ à C₁₀ ou le groupe (CH₂)n-NH₂ dans lequel n a une valeur de 1 à 10.
  4. Concentré suivant l'une quelconque des revendications précédentes, dans lequel le phénol est un phénol à encombrement stérique et la base de Mannich comprend des N-[3,5-di-tertio-butyl-4-hydroxybenzyl]-tertio-alkylamines à groupes tertio-alkyle mixtes en C₁₂ à C₁₄, la N,N-diméthyl-3,5-di-tertio-butyl-4-hydroxybenzylamine, un composé de formule :
    Figure imgb0052
        dans laquelle R₁ et R₂ sont choisis, indépendamment, entre l'hydrogène, les radicaux tertio-butyle, tertio-amyle et isopropyle sous réserve que l'un au moins de R₁ et R₂ soit un radical tertio-butyle, tertio-amyle ou isopropyle, ou un composé de formule :
    Figure imgb0053
        dans laquelle R₁ et R₂ sont choisis, indépendamment, entre l'hydrogène, les radicaux tertio-butyle, tertio-amyle et isopropyle, sous réserve que l'un au moins de R₁ et R₂ soit un radical tertio-butyle, tertio-amyle ou isopropyle.
  5. Concentré suivant l'une quelconque des revendications 1 à 3, dans lequel le phénol est un p-alkylphénol et la base de Mannich comprend le N,N-diméthyl-N′-[2-hydroxy-5-dodécylbenzyl]-1,3-diaminopropane.
  6. Concentré suivant la revendication 2, dans lequel le désactivateur de métaux est la N,N′-disalicylidène-1,2-propylènediamine et la base de Mannich est le produit de réaction du formaldéhyde, du 2,6-di-tertio-butylphénol et d'une amine choisie entre le 1,3-diaminopropane, le 1,2-diaminopropane, des tertio-alkylamines à groupes alkyle mixtes en C₁₂ à C₁₄ et la diméthylamine.
  7. Concentré suivant la revendication 2, dans lequel le désactivateur de métaux est la N,N′-disalicylidène1,2-propylènediamine et la base de Mannich est le produit de réaction du formaldéhyde, du p-dodécylphénol et du N,N-diméthyl-1,3-diaminopropane.
  8. Composition de combustible, comprenant un combustible à base de distillat moyen contenant 3 à 1500 mg/l du concentré suivant l'une quelconque des revendications 1 à 7.
  9. Composition de combustible, comprenant un combustible à base de distillat moyen et 1 à 1400 mg/l de N,N-diméthylcyclohexylamine, 0 à 400 mg/l de N,N-di(ortho-hydroxy-arylidène)-1,2-alkylènediamine et 1 à 1100 mg/l d'une base de Mannich qui est le produit de réaction d'un aldéhyde, d'une amine et d'un alkylphénol choisi entre (a) un phénol à encombrement stérique répondant à la formule :
    Figure imgb0054
        dans laquelle R₁, R₂, R₃ sont choisis, indépendamment, entre l'hydrogène, les radicaux tertio-butyle, tertio-amyle et isopropyle, sous réserve que l'un au moins de R₁, R₂ et R₃ soit l'hydrogène et que l'un au moins de R₁ et R₂ soit un radical tertio-butyle, tertio-amyle ou isopropyle ; et (b) un p-alkylphénol répondant à la formule :
    Figure imgb0055
        dans laquelle R₄ est un radical alkyle en C₉ à C₃₀.
  10. Composition de combustible suivant la revendication 9, dans laquelle l'aldéhyde est le formaldéhyde et l'amine est une ou plusieurs des amines suivantes :
    A. des alkylmono-amines de formule :
    Figure imgb0056
        où R₅ est choisi entre H et un radical alkyle en C₁ à C₅, et R₆ est choisi entre un radical alkyle en C₁ à C₁₄ et le groupe -(CH₂)n-OR₇ dans lequel n a une valeur de 1 à 10 et R₇ est un radical alkyle en C₁ à C₂₀,
    B. des alkyldiamines de formule :
    Figure imgb0057
        dans laquelle R₅ est choisi entre H et un radical alkyle en C₁ à C₅, R₈ est un radical alkylène en C₁ à C₆ et A et B sont choisis, indépendamment, entre H, un radical alkyle en C₁ à C₅, alkyle en C₁ à C₅ portant un substituant hydroxy et le groupe (CH₂)n-OR₇ dans lequel n a une valeur de 1 à 10 et R₇ est un radical alkyle en C₁ à C₂₀,
    C. des éthylènepolyamines de formule : H₂N(̵(CH₂)₂NH)̵ n H
    Figure imgb0058
        dans laquelle n a une valeur de 2 à 10, et
    D. des amines cycliques de formule :
    Figure imgb0059
        dans laquelle n et m représentent, indépendamment, des nombres entiers de 1 à 3, X est choisi entre CH₂, O, S et un groupe NR₉ dans lequel R₉ représente H, un radical alkyle en C₁ à C₁₀ ou le groupe (CH₂)n-NH₂ dans lequel n a une valeur de 1 à 10.
EP90301791A 1989-03-02 1990-02-20 Combustible de distillat moyen ayant une stabilité au stockage modifiée Expired - Lifetime EP0385633B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US31874889A 1989-03-02 1989-03-02
US318748 1989-03-02

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP90116830A Division-Into EP0408087A1 (fr) 1989-03-02 1990-02-20 Bases de mannich utiles dans un combustible de distillat moyen ayant une stabilité au stockage améliorée
EP90116830A Division EP0408087A1 (fr) 1989-03-02 1990-02-20 Bases de mannich utiles dans un combustible de distillat moyen ayant une stabilité au stockage améliorée

Publications (2)

Publication Number Publication Date
EP0385633A1 EP0385633A1 (fr) 1990-09-05
EP0385633B1 true EP0385633B1 (fr) 1993-04-07

Family

ID=23239444

Family Applications (2)

Application Number Title Priority Date Filing Date
EP90116830A Ceased EP0408087A1 (fr) 1989-03-02 1990-02-20 Bases de mannich utiles dans un combustible de distillat moyen ayant une stabilité au stockage améliorée
EP90301791A Expired - Lifetime EP0385633B1 (fr) 1989-03-02 1990-02-20 Combustible de distillat moyen ayant une stabilité au stockage modifiée

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP90116830A Ceased EP0408087A1 (fr) 1989-03-02 1990-02-20 Bases de mannich utiles dans un combustible de distillat moyen ayant une stabilité au stockage améliorée

Country Status (5)

Country Link
EP (2) EP0408087A1 (fr)
JP (1) JPH02292392A (fr)
AU (1) AU619957B2 (fr)
CA (1) CA2010183A1 (fr)
DE (1) DE69001269T2 (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2010183A1 (fr) 1989-03-02 1990-09-02 John G. Bostick Distillat moyen a stabilite au stockage amelioree
GB2239258A (en) * 1989-12-22 1991-06-26 Ethyl Petroleum Additives Ltd Diesel fuel compositions containing a manganese tricarbonyl
US5944858A (en) * 1990-09-20 1999-08-31 Ethyl Petroleum Additives, Ltd. Hydrocarbonaceous fuel compositions and additives therefor
EP0482253A1 (fr) * 1990-10-23 1992-04-29 Ethyl Petroleum Additives Limited Compositions de combustible bonnes pour l'environnement, et additifs pour
US5169410A (en) * 1991-09-24 1992-12-08 Betz Laboratories, Inc. Methods for stabilizing gasoline mixtures
JPH0940759A (ja) * 1995-07-28 1997-02-10 Asahi Denka Kogyo Kk エポキシ樹脂硬化性組成物
GB9621263D0 (en) † 1996-10-11 1996-11-27 Exxon Chemical Patents Inc Lubricity additives for fuel oil compositions
AU2002241114A1 (en) * 2001-03-26 2002-10-08 Octel America Inc Composition
JP2009542889A (ja) * 2006-07-11 2009-12-03 インノスペック フューエル スペシャルティーズ エルエルシー 石油および再生可能燃料のブレンド用の安定剤組成物
DE102007031461A1 (de) * 2007-07-05 2009-01-08 Sappok, Manfred, Dipl.-Phys. Dr. Verfahren zum Stabilisieren von Heizöl oder Dieselöl, insbesondere aus der Depolimerisation von kohlenwasserstoffhaltigen Rückständen
CA2696885C (fr) 2007-08-24 2015-10-13 Albemarle Corporation Melanges antioxydants aptes a etre utilises dans des biodiesels
WO2009040582A1 (fr) * 2007-09-27 2009-04-02 Innospec Limited Compositions de combustible
AU2008303345B2 (en) * 2007-09-27 2013-05-30 Innospec Limited Fuel compositions
WO2009040585A1 (fr) * 2007-09-27 2009-04-02 Innospec Limited Compositions de combustible
JP2012503040A (ja) * 2008-09-17 2012-02-02 エクソンモービル リサーチ アンド エンジニアリング カンパニー ランシマ−ト試験によって測定されるバイオディーゼルの酸化安定性の向上方法
PL2855642T3 (pl) * 2012-05-25 2018-10-31 Basf Se Trzeciorzędowe aminy do zmniejszania zarastania dyszy wtryskiwacza w silnikach z zapłonem iskrowym z bezpośrednim wtryskiem
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
CN113527163B (zh) * 2021-08-10 2023-06-13 新乡市瑞丰新材料股份有限公司 一种烷基酚类清净剂的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442791A (en) * 1966-11-17 1969-05-06 Betz Laboratories Anti-foulant agents for petroleum hydrocarbons

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2984550A (en) 1956-09-06 1961-05-16 Nalco Chemical Co Color stabilization of petroleum oils and compositions therefor
US2928790A (en) * 1956-10-03 1960-03-15 Ethyl Corp Petroleum hydrocarbon oil stabilized against oxidative deterioration
US3502671A (en) * 1964-03-02 1970-03-24 Commercial Solvents Corp Selected n-substituted diazoles and diazines and processes for preparing same
US3446808A (en) * 1964-05-25 1969-05-27 Universal Oil Prod Co Borates of n-hydroxyalkyl-nitrogen-heterocyclic saturated compounds
US3490882A (en) 1966-08-11 1970-01-20 Du Pont Stabilized distillate fuel oils and additive compositions therefor
US3634575A (en) * 1968-10-02 1972-01-11 Celanese Corp Melt extrusion of acrylonitrile polymers
US3725480A (en) * 1968-11-08 1973-04-03 Standard Oil Co Ashless oil additives
US3634515A (en) * 1968-11-08 1972-01-11 Standard Oil Co Alkylene polyamide formaldehyde
US3701641A (en) * 1969-08-29 1972-10-31 Cities Service Oil Co Stabilized distillate hydrocarbon fuel oil compositions and additives therefor
US4025316A (en) * 1974-11-06 1977-05-24 Exxon Research And Engineering Company Mannich base reaction products useful as liquid hydrocarbon additives
US4172707A (en) * 1975-09-12 1979-10-30 E. I. Du Pont De Nemours & Company Mannich bases containing tertiary amines
US4166726A (en) 1977-12-16 1979-09-04 Chevron Research Company Diesel fuel containing polyalkylene amine and Mannich base
US4501595A (en) 1984-05-25 1985-02-26 Texaco Inc. Middle distillate fuel oil of improved storage stability containing condensate of Mannich base and alkenyl succinic acid anhydride
US4533361A (en) 1984-10-09 1985-08-06 Texaco Inc. Middle distillate containing storage stability additive
DE3481911D1 (de) * 1984-11-13 1990-05-17 Mobil Oil Corp Mannich-basen als oelzusaetze.
US4668412A (en) * 1985-06-27 1987-05-26 Texaco Inc. Lubricating oil containing dispersant VII and pour depressant
US4749468A (en) * 1986-09-05 1988-06-07 Betz Laboratories, Inc. Methods for deactivating copper in hydrocarbon fluids
US4915857A (en) * 1987-05-11 1990-04-10 Exxon Chemical Patents Inc. Amine compatibility aids in lubricating oil compositions
CA2010183A1 (fr) 1989-03-02 1990-09-02 John G. Bostick Distillat moyen a stabilite au stockage amelioree
US9442791B2 (en) * 2014-11-07 2016-09-13 International Business Machines Corporation Building an intelligent, scalable system dump facility

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442791A (en) * 1966-11-17 1969-05-06 Betz Laboratories Anti-foulant agents for petroleum hydrocarbons

Also Published As

Publication number Publication date
CA2010183A1 (fr) 1990-09-02
AU5060390A (en) 1990-09-06
DE69001269T2 (de) 1993-07-22
AU619957B2 (en) 1992-02-06
EP0385633A1 (fr) 1990-09-05
EP0408087A1 (fr) 1991-01-16
JPH02292392A (ja) 1990-12-03
DE69001269D1 (de) 1993-05-13

Similar Documents

Publication Publication Date Title
EP0385633B1 (fr) Combustible de distillat moyen ayant une stabilité au stockage modifiée
US3649229A (en) Liquid hydrocarbon fuels containing high molecular weight mannich bases
EP1226188B1 (fr) Procede de preparation de produits d'addition de mannich contenant du polyisobutenphenol
US2945749A (en) Stabilized fuel oil containing tertiary alkyl primary amines
DE2209579C2 (de) Verwendung von Alkylphenol-Aldehyd-Amin-Kondensationsproduktenals Reinhaltungszusätze für Ottokraftstoffe
US4536189A (en) Corrosion inhibitor and motor fuel composition containing the same
DE2452722C2 (fr)
CA1122800A (fr) Polyetheramines/anhydride maleique introduits dans l'essence
US3497334A (en) Liquid hydrocarbon combustion fuels
US5162049A (en) Middle distillate fuels and additives therefor
US2701187A (en) Color stabilization in fuel oils
US4197091A (en) Metal chelate/anti-oxidant combinations with dimer-trimer acids, pipeline corrosion inhibitors
US4144036A (en) Detergent fuel composition
US4290778A (en) Hydrocarbyl alkoxy amino alkylene-substituted asparagine and a motor fuel composition containing same
US2348638A (en) Fuel composition
US4978366A (en) Distillate fuels stabilized with diaminomethane and method thereof
US2867515A (en) Fuel oil compositions containing formaldimine salts
US4867754A (en) Process and composition for stabilized distillate fuel oils
US4353711A (en) Multifunctional gasoline additives
US2163640A (en) Inhibitor and motor fuel stabilized therewith
GB2245588A (en) Reduction of colour and sediment formation in fuel oils
US5215547A (en) Middle distillate fuels and additives therefor
US3190835A (en) Metal deactivators
US4322304A (en) Bis(disubstituted aminomethyl)phenols as ashless hydrocarbon additives
US4871374A (en) Fuel oils stabilized with imine-enamine condensates and method thereof

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE DE ES FR GB IT NL

17P Request for examination filed

Effective date: 19901004

17Q First examination report despatched

Effective date: 19910716

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

XX Miscellaneous (additional remarks)

Free format text: VERBUNDEN MIT 89420398.3/0367687 (EUROPAEISCHE ANMELDENUMMER/VEROEFFENTLICHUNGSNUMMER) DURCH ENTSCHEIDUNG VOM 12.02.93.

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE ES FR GB IT NL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRE;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.SCRIBED TIME-LIMIT

Effective date: 19930407

Ref country code: NL

Effective date: 19930407

Ref country code: BE

Effective date: 19930407

Ref country code: FR

Effective date: 19930407

Ref country code: ES

Free format text: THE PATENT HAS BEEN ANNULLED BY A DECISION OF A NATIONAL AUTHORITY

Effective date: 19930407

REF Corresponds to:

Ref document number: 69001269

Country of ref document: DE

Date of ref document: 19930513

EN Fr: translation not filed
NLV1 Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19940220

26N No opposition filed
GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19940220

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19941101