WO1999029811A1 - Method for defoaming fuels - Google Patents
Method for defoaming fuels Download PDFInfo
- 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
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
- C10L1/222—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
- C10L1/04—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, 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
- 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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Degasification And Air Bubble Elimination (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP98964442A EP1036141A1 (en) | 1997-12-04 | 1998-11-25 | Method for defoaming fuels |
CA002312064A CA2312064A1 (en) | 1997-12-04 | 1998-11-25 | Method for defoaming fuels |
AU19642/99A AU735528B2 (en) | 1997-12-04 | 1998-11-25 | Method for defoaming fuels |
JP2000524388A JP2001526300A (en) | 1997-12-04 | 1998-11-25 | Method for degassing fuel |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1997153792 DE19753792A1 (en) | 1997-12-04 | 1997-12-04 | Process for defoaming fuels |
DE19753792.8 | 1997-12-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999029811A1 true WO1999029811A1 (en) | 1999-06-17 |
Family
ID=7850721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/007613 WO1999029811A1 (en) | 1997-12-04 | 1998-11-25 | Method for defoaming fuels |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1036141A1 (en) |
JP (1) | JP2001526300A (en) |
AU (1) | AU735528B2 (en) |
CA (1) | CA2312064A1 (en) |
DE (1) | DE19753792A1 (en) |
WO (1) | WO1999029811A1 (en) |
Citations (4)
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 (en) * | 1989-07-17 | 1991-02-07 | Henkel Kommanditgesellschaft Auf Aktien | Process for preparing quaternary ammonium compounds |
EP0464489A1 (en) * | 1990-06-29 | 1992-01-08 | BASF Aktiengesellschaft | Ester containing fuels, for spark ignition- and diesel engines |
DE4334365A1 (en) * | 1993-10-08 | 1995-04-13 | Henkel Kgaa | Quaternized fatty acid triethanolamine ester salts with improved water solubility |
-
1997
- 1997-12-04 DE DE1997153792 patent/DE19753792A1/en not_active Withdrawn
-
1998
- 1998-11-25 EP EP98964442A patent/EP1036141A1/en not_active Withdrawn
- 1998-11-25 WO PCT/EP1998/007613 patent/WO1999029811A1/en not_active Application Discontinuation
- 1998-11-25 JP JP2000524388A patent/JP2001526300A/en active Pending
- 1998-11-25 CA CA002312064A patent/CA2312064A1/en not_active Abandoned
- 1998-11-25 AU AU19642/99A patent/AU735528B2/en not_active Ceased
Patent Citations (4)
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 (en) * | 1989-07-17 | 1991-02-07 | Henkel Kommanditgesellschaft Auf Aktien | Process for preparing quaternary ammonium compounds |
EP0464489A1 (en) * | 1990-06-29 | 1992-01-08 | BASF Aktiengesellschaft | Ester containing fuels, for spark ignition- and diesel engines |
DE4334365A1 (en) * | 1993-10-08 | 1995-04-13 | Henkel Kgaa | Quaternized fatty acid triethanolamine ester salts with improved water solubility |
Also Published As
Publication number | Publication date |
---|---|
AU1964299A (en) | 1999-06-28 |
AU735528B2 (en) | 2001-07-12 |
CA2312064A1 (en) | 1999-07-19 |
JP2001526300A (en) | 2001-12-18 |
EP1036141A1 (en) | 2000-09-20 |
DE19753792A1 (en) | 1999-06-10 |
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