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WO1999029811A1 - Procede pour empecher des carburants de mousser - Google Patents

Procede pour empecher des carburants de mousser Download PDF

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Publication number
WO1999029811A1
WO1999029811A1 PCT/EP1998/007613 EP9807613W WO9929811A1 WO 1999029811 A1 WO1999029811 A1 WO 1999029811A1 EP 9807613 W EP9807613 W EP 9807613W WO 9929811 A1 WO9929811 A1 WO 9929811A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
radical
compounds
fuel
fuels
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.)
Ceased
Application number
PCT/EP1998/007613
Other languages
German (de)
English (en)
Inventor
Thorsten LÖHL
Günter Uphues
Bernd Boutty
Peter Neumann
Frank Bongardt
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.)
Henkel AG and Co KGaA
BASF Personal Care and Nutrition GmbH
Original Assignee
Henkel AG and Co KGaA
Cognis Deutschland GmbH and Co KG
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 Henkel AG and Co KGaA, Cognis Deutschland GmbH and Co KG filed Critical Henkel AG and Co KGaA
Priority to CA002312064A priority Critical patent/CA2312064A1/fr
Priority to JP2000524388A priority patent/JP2001526300A/ja
Priority to EP98964442A priority patent/EP1036141A1/fr
Priority to AU19642/99A priority patent/AU735528B2/en
Publication of WO1999029811A1 publication Critical patent/WO1999029811A1/fr
Anticipated expiration legal-status Critical
Ceased 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/08—Liquid carbonaceous fuels essentially based on blends of hydrocarbons for compression ignition
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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

Definitions

  • the present application relates to a method for defoaming fuels, in particular diesel fuels, the use of certain quaternary ammonium compounds as defoamers for fuels and a diesel fuel which contains these quaternary ammonium compounds.
  • Fuels in particular the hydrocarbon mixtures used as diesel fuels, have the unpleasant property of developing foam in connection with air when they are filled into storage tanks, such as storage tanks and fuel tanks of motor vehicles. This leads to a delay in the discharge process and inadequate filling of the container. It is therefore common to add defoamers to the fuels. These defoamers should be effective in the lowest possible concentration and must not hinder the combustion process of the fuel, e.g. through the formation of residues that negatively affect the engine's operation.
  • the object of the present application was therefore to find silicone-free additives for defoaming fuels. Surprisingly, it was found that certain quaternary ammonium salts have excellent properties as defoamers for fuels.
  • the invention therefore relates to a process for defoaming fuels, an effective amount of at least one compound of the formula (I) being added to the fuel
  • radicals R 1 , R 2 and R 3 independently of one another are an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms, an aryl or alkylaryl radical or a radical of the formula (II),
  • the compounds of the formula (I) are known and are mainly used as textile-softening components or for the antistatic finishing of fabrics. Examples of compounds of the formula (I) can be found in documents WO 94/06899 and DE 42 03 489 AI of the applicant. which reveal quaternary diesteramine compounds in soft care agents for textiles. EP 239 910 A2 also describes textile care agents which contain readily biodegradable quaternary mono- and diesteramine compounds.
  • fuels are understood to mean all energy-supplying supplies whose free combustion energy is converted into mechanical work. This includes all types of engine and aviation fuels that are liquid at room temperature and normal pressure.
  • Motor fuels e.g. for car or truck engines, usually contain hydrocarbons, e.g. petrol or higher-boiling petroleum fractions.
  • the process according to the invention is particularly suitable for defoaming diesel fuels.
  • Diesel fuels are flame-retardant mixtures of liquid hydrocarbons that are used as fuels for constant pressure or burner motors. The composition is inconsistent and depends on the manufacturing method. Diesel fuels are obtained from gas oil by cracking or from tars obtained from the smoldering of lignite or hard coal. Conventional products have a density between 0.83 and 0.88 g / cm 3 , a boiling point between 170 and 360 ° C and flash points between 70 and 100 ° C.
  • the compounds of the formula (I) are added to the fuel in effective amounts. Effective concentrations are preferably in the range between 5 and 1000 ppm and in particular between 10 and 50 ppm, based on all the fuel.
  • the compounds of the formula (I) are effective defoamers for fuels and additionally have a corrosion-inhibiting action.
  • the substances of the formula (I) represent technically quaternized mono-, di- or trifatty acid amine ester compounds which can be obtained by known synthetic methods.
  • the quaternary compounds can be obtained, for example, by reacting tertiary mono-, di- or trialkanolamines, preferably triethanol or triisopropanolamine or methyldiethanolamine or dimethylethanolamine, with saturated or unsaturated linear or branched C g . 22 fatty acids or their derivatives, such as esters or chlorides, are formed.
  • esters formed in the reaction with the alkanolamines are then quaternized, for example with methyl chloride, benzyl chloride or dimethyl sulfate.
  • Suitable fatty acids are, for example, the saturated representatives, such as caprylic, capric, lauric, myristic, palmitic, stearic or arachic acid or mixtures thereof.
  • unsaturated fatty acids are linoleic, linolaidic or linolenic acid.
  • Suitable derivatives are in particular the alkyl esters, preferably the methyl esters of the above-mentioned fatty acids.
  • Naturally occurring fatty acid mixtures of both animal and vegetable origin are also suitable. Coconut or palm kernel fatty acids are particularly preferred.
  • the present application also relates to the use of compounds of the formula (I) as defoamers for fuels, in particular for diesel fuels.
  • the compounds of the formula (I) can be added to the fuels either directly or in the form of solutions or dispersions in suitable solvents.
  • suitable solvents are short-chain alcohols with 1 to 6 carbon atoms, in particular ethanol, propanol and isopropanol, or aliphatic or aromatic hydrocarbons, such as hexane, heptane or toluene.
  • the solutions or dispersions preferably contain the compounds of the formula (I) in amounts between 10 and 80% by weight.
  • a diesel fuel which contains compounds of the formula (I) in amounts of between 5 and 1000 ppm. It is preferably low-sulfur diesel fuel with a sulfur content of at most 0.2% by weight, and the sulfur content is preferably at most 0.005% by weight.
  • the diesel fuel can also contain other common additives, for example friction modifiers, flow improvers, anti-wax-setting additives or other, conventional corrosion inhibitors. However, the diesel fuel is preferably free of additional corrosion inhibitors.
  • a corrosion test was carried out in accordance with ASTM D 665-92.
  • steel test specimens were immersed in 330 ml of a diesel oil / water mixture (10 parts by volume of oil to 1 part by volume of water) over a period of 24 hours at a temperature of 60 ° C.
  • the test specimen was then cleaned with water and optically examined for corrosion with reference to a reference test specimen.
  • the test specimens were evaluated according to the NACE scheme.
  • To the surface of the test specimen, which shows rust is measured and evaluated according to the following scheme:
  • defoamers according to the invention also show good results in corrosion inhibition. Of particular note are the good results of the mixtures of defoamers El and E2.

Landscapes

  • 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)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Degasification And Air Bubble Elimination (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)

Abstract

L'invention concerne un procédé permettant d'empêcher des carburants de mousser, selon lequel une quantité efficace d'au moins un des composés de la formule (I) est ajouté au carburant concerné. Dans la formule (I), les restes R<1>, R<2> et R<3> désignent indépendamment les uns des autres un reste alkyle ou un reste hydroxyalkyle ayant entre 1 et 4 atomes de C, un reste aryle ou un reste alkylaryle ou un reste de la formule (II), A<-> est un anion, n vaut un nombre compris entre 2 et 3, p vaut un nombre compris entre 1 et 3 et R<4> désigne un reste alkyle ou un reste alkényle ayant entre 7 et 21 atomes de C et 0, 1, 2 ou 3 liaisons doubles.
PCT/EP1998/007613 1997-12-04 1998-11-25 Procede pour empecher des carburants de mousser Ceased WO1999029811A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002312064A CA2312064A1 (fr) 1997-12-04 1998-11-25 Procede pour empecher des carburants de mousser
JP2000524388A JP2001526300A (ja) 1997-12-04 1998-11-25 燃料を脱泡するための方法
EP98964442A EP1036141A1 (fr) 1997-12-04 1998-11-25 Procede pour empecher des carburants de mousser
AU19642/99A AU735528B2 (en) 1997-12-04 1998-11-25 Method for defoaming fuels

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19753792.8 1997-12-04
DE1997153792 DE19753792A1 (de) 1997-12-04 1997-12-04 Verfahren zum Entschäumen von Treibstoffen

Publications (1)

Publication Number Publication Date
WO1999029811A1 true WO1999029811A1 (fr) 1999-06-17

Family

ID=7850721

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/007613 Ceased WO1999029811A1 (fr) 1997-12-04 1998-11-25 Procede pour empecher des carburants de mousser

Country Status (6)

Country Link
EP (1) EP1036141A1 (fr)
JP (1) JP2001526300A (fr)
AU (1) AU735528B2 (fr)
CA (1) CA2312064A1 (fr)
DE (1) DE19753792A1 (fr)
WO (1) WO1999029811A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3801475A (en) * 1969-12-19 1974-04-02 Petro Tex Chem Corp Anti-foaming process by the addition of a quaternary ammonium salt
WO1991001295A1 (fr) * 1989-07-17 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de composes quaternaires de l'ammonium
EP0464489A1 (fr) * 1990-06-29 1992-01-08 BASF Aktiengesellschaft Carburants contenant un ester, pour moteurs diesel et à allumage par étincelle
DE4334365A1 (de) * 1993-10-08 1995-04-13 Henkel Kgaa Quaternierte Fettsäuretriethanolaminester-Salze mit verbesserter Wasserlöslichkeit

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3801475A (en) * 1969-12-19 1974-04-02 Petro Tex Chem Corp Anti-foaming process by the addition of a quaternary ammonium salt
WO1991001295A1 (fr) * 1989-07-17 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de composes quaternaires de l'ammonium
EP0464489A1 (fr) * 1990-06-29 1992-01-08 BASF Aktiengesellschaft Carburants contenant un ester, pour moteurs diesel et à allumage par étincelle
DE4334365A1 (de) * 1993-10-08 1995-04-13 Henkel Kgaa Quaternierte Fettsäuretriethanolaminester-Salze mit verbesserter Wasserlöslichkeit

Also Published As

Publication number Publication date
JP2001526300A (ja) 2001-12-18
AU1964299A (en) 1999-06-28
AU735528B2 (en) 2001-07-12
DE19753792A1 (de) 1999-06-10
EP1036141A1 (fr) 2000-09-20
CA2312064A1 (fr) 1999-07-19

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