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WO2007107569A1 - Agent de marquage pour hydrocarbures - Google Patents

Agent de marquage pour hydrocarbures Download PDF

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Publication number
WO2007107569A1
WO2007107569A1 PCT/EP2007/052642 EP2007052642W WO2007107569A1 WO 2007107569 A1 WO2007107569 A1 WO 2007107569A1 EP 2007052642 W EP2007052642 W EP 2007052642W WO 2007107569 A1 WO2007107569 A1 WO 2007107569A1
Authority
WO
WIPO (PCT)
Prior art keywords
mixture
formula
compounds
hydrocarbon
weight
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/EP2007/052642
Other languages
German (de)
English (en)
Inventor
Marcus Eh
Dirk MÜLLER
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.)
Symrise AG
Original Assignee
Symrise AG
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 Symrise AG filed Critical Symrise AG
Priority to EP07727119A priority Critical patent/EP1999236A1/fr
Publication of WO2007107569A1 publication Critical patent/WO2007107569A1/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
    • C10L1/003—Marking, e.g. coloration by addition of pigments
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • 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
    • C10L1/16—Hydrocarbons
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids

Definitions

  • the present invention relates to the use of compounds of the formula (I) given below as (pH-dependent) marking agents for hydrocarbons, in particular for petroleum-derived fuels or lubricants (mineral oils).
  • the invention further relates to corresponding mixtures comprising one or more hydrocarbons and the said marking agents.
  • the present invention relates to methods for labeling a hydrocarbon or a hydrocarbon mixture in which one or more compounds of the formula (I) are added as a marking agent to the hydrocarbon or the hydrocarbon mixture.
  • the invention also relates to a process for the detection of compounds of the formula (I) in a mixture according to the invention under the action of an aqueous, acidic fuchsinschwefeligen solution (eg Schiff's reagent), wherein a visible color reaction occurs (identification of a labeled hydrocarbon or a marked hydrocarbon mixture).
  • an aqueous, acidic fuchsinschwefeligen solution eg Schiff's reagent
  • 1-Alkoxyesters have been described variously in the patent literature, they are e.g. used in the fragrance and flavor industry as depot preparations for the release of aldehydes (see US 4,296,137, US 4,386,063 and EP 1 285 906).
  • EP 0 385 441 describes the use of 1, 4-dimethyl-2-nitrobenzene as a marker for mineral oil products, in particular diesel.
  • the lower detection limit is in the range of 20 to 100 ppm.
  • the detection of the presence of the employed as a marker 1, 4-dimethyl-2-nitrobenzene succeeds via thin-layer chromatography and comprises several steps; he is thus consuming and feasible only in the laboratory. Furthermore, a semi-quantitative method using UV light is described, which is feasible only from a concentration of 100 ppm.
  • (C 1 -C 4 ) -alkyl phenyl ketones such as acetophenone as marker substances for mineral oil products and organic solvents is described in EP 0 310 319.
  • the use concentration of the marker substance should therefore be in the range of 100 to 10,000 ppm and in particular 1000 ppm.
  • the presence of the (CrC 4 ) -Alkylphenylketone used as markers is achieved by a multi-step process, wherein Key component 2,4-dinitrophenylhydrazine is added, which leads to a clearly visible color reaction.
  • Aniline derivatives as marking agents for mineral oils are described in DE 42 38 994.
  • the minimum detection concentration is 10 ppm or below.
  • the presence of the aniline derivatives used as markers can be demonstrated by treating the labeled mineral oil with an aqueous acidic diazonium salt solution so that the aniline derivative couples with the diazonium salt to form an azo dye, ultimately resulting in a clearly visible color reaction.
  • diazonium salts are not safe for safety and health reasons.
  • EP 0 736 080 describes azo dyes as pH-dependent marking agents for labeling hydrocarbons.
  • the minimum detection concentration is 10 ppm or below.
  • the presence of the azo dyes used as markers can be demonstrated by treating the labeled hydrocarbon with an acidic aqueous-alcoholic or acidic alcoholic solution which optionally also contains a metal halide. This results in a clearly visible color reaction.
  • the primary object of the present invention to provide alternative or improved means for marking hydrocarbons (especially hydrocarbon mixtures such as mineral oils, eg diesel).
  • the marking agents should fulfill a number of requirements, in particular: easy accessibility
  • the stated object is achieved by a mixture comprising
  • hydrocarbons one or more hydrocarbons, a marking agent for the hydrocarbon (s), and preferably one or more further additives,
  • the labeling agent comprises one or more compounds of the formula (I) or consists of one or more compounds of the formula (I)
  • R 1 is a branched or unbranched alkyl group having 1 to 6 C atoms, preferably a branched or unbranched alkyl group having 1 to 5 C atoms, particularly preferably an unbranched alkyl group having 1 to 3 C atoms and especially preferably ethyl,
  • R 2 is H or a branched or unbranched alkyl group having 1 to 6 C atoms, preferably H or a branched or unbranched alkyl group having 1 to 5 C atoms, more preferably an unbranched alkyl group having 1 to 3 C atoms, and particularly preferred Methyl, and
  • the proviso is:
  • a mixture according to the invention in the form of a fuel comprising 1-ethoxyethyl acetate or 1-methoxyethyl acetate does not comprise any lead-containing anti-knock agent.
  • fuels comprising a lead-containing anti-knock agent and 1-ethoxyethyl acetate or 1-methoxyethyl acetate to increase the octane number reference is made to US 3,087,801.
  • a mixture according to the invention for which the following applies: The mixture does not consist of 5-35% by weight of acetaldehyde diethyl acetal, 2-8% by weight of dibutyl ether, 10-35% by weight of alcohol and 22-83% by weight. % Kerosene or light oil (with regard to mixtures having the stated composition, see EP 1 149 887 A2).
  • a mixture according to the invention in the form of a fuel comprising a compound of the
  • a mixture according to the invention comprising kerosene or light oil is preferably free from acetaldehyde diethyl acetal.
  • a mixture according to the invention for which the following applies:
  • the mixture does not comprise a lead-containing anti-knock agent.
  • a mixture comprising kerosene or light oil is free from acetaldehyde diethyl acetal.
  • any combination of a preferred meaning of one of the groups R 1 , R 2 or Y with one of the meanings of the other groups given is itself a preferred combination.
  • R 1 group an unbranched alkyl group having 1 to 2 C atoms, irrespective of whether R 2 and / or Y themselves have a preferred meaning or not.
  • the marking agent comprises one or more compounds of the formula (I) or consists of one or more compounds of the formula (I)
  • R 1 is a branched or unbranched alkyl group having 1 to 5 C atoms
  • R 2 is H or a branched or unbranched alkyl group having 1 to 5 C atoms and
  • the marking agent comprises one or more compounds of formula (I) or consists of one or more compounds of formula (I), wherein
  • R 1 is an unbranched alkyl group having 1 to 3 C atoms
  • the marking agents to be used according to the invention which comprise one or more compounds of the formula (I), meet all the requirements indicated above. They are very stable, especially in mineral oils, and the detection reaction with Schiff's reagent is very rapid and reliable. Because of the color reaction occurring in the detection with Schiff's reagent, photometric quantification of the compounds of the formula (I) is also possible. This allows, for example, to detect an undesirable dilution of an originally used hydrocarbon mixture (e.g., a mineral oil such as diesel).
  • an originally used hydrocarbon mixture e.g., a mineral oil such as diesel.
  • the marking agent comprises one or more compounds of the formula (I) or consists of one or more compounds of the formula (I), where in the compound of the formula (I) or in one of the compounds of Formula (I)
  • R 1 is ethyl
  • R 2 is methyl
  • the labeling agents of the formula (I) to be used according to the invention react under hydrolyzing action of an aqueous acid fuchsinschwefeligen acid solution (Schiff's reagent) to form acetaldehyde, which in turn enters into a color reaction with the fuchsinschwefeligen acid, i. it comes to a color change, along with a clearly visible color deepening.
  • an aqueous acid fuchsinschwefeligen acid solution Schotefeligen acid solution
  • Schiff's reagent also: Schiff's reagent, fuchsin / sulfuric acid
  • fuchsin / sulfuric acid is a detection agent for aldehydes introduced by H. Schiff.
  • General Preparation Procedure for Schiff's Reagent dissolve fuchsin in distilled water and decolorize after addition of hydrochloric acid with sodium sulfite (formation of sulfur dioxide). This colorless solution turns red with aldehyde addition; for the mechanism of reaction, see literature (e.g., Anal Chem 32, 1307-1311 (1960)).
  • Fuchsin (empirical formula: C 2 OH 19 N 3 , M R 301, 39) has the following structural formula [(methyl fuchsin, 3-methyl parafuchsin, 4 - [(4-aminophenyl) - (4-imino-2,5-cyclohexadiene-1 -ylidene) -methyl] -2-methylaniline, Basic Violet 14, CI 42510]
  • aqueous acid fuchsinschwefeliger acid solution is a well-known in the art commercially available fuchsinschwefelige acid (Schiff's reagent) for the detection of aldehydes to understand. (e.g., Merck KGaA, 64271 Darmstadt, article number: 109034).
  • the mixtures according to the invention are present under normal conditions (1013 mbar, 25 ° C.) in the liquid state. They comprise one or more hydrocarbons, which are preferably straight-chain or branched-chain aliphatic or aromatic hydrocarbons, in particular hydrocarbons derived from petroleum. Usually, several different hydrocarbons are present in a mixture according to the invention, i. there is a hydrocarbon mixture.
  • Preferred hydrocarbon mixtures present in a mixture according to the invention are mineral oils, i. energy sources (fuels, fuels) or lubricants (oils and fats) produced from petroleum (crude oil).
  • Hydrocarbon mixtures comprising a plurality of hydrocarbons which can be marked particularly preferably by the marking agents to be used according to the invention are, in particular, mineral oils (see above), in the context of the present invention mineral oils being fuels, in particular gasoline (in particular gasoline according to DIN EN 228), Kerosene (eg Aviation gasoline in accordance with ASTM D910 grade 100 LL or jet fuel, jet fuel such as Jet A-1 or Jet B) or diesel (in particular according to DIN EN 590) and oils, in particular fuel oil (in particular according to DIN 51603) or engine oil. Particular preference is again given to the so-called middle distillates, which have a boiling range of from 180 to 360 ° C. under atmospheric pressure (1013 mbar); diesel fuel according to DIN EN 590 is particularly preferred.
  • mineral oils being fuels, in particular gasoline (in particular gasoline according to DIN EN 228), Kerosene (eg Aviation gasoline in accordance with ASTM D910 grade 100 LL or jet fuel, jet fuel such as Jet A-1 or Jet B) or diesel (in particular according
  • a mixture according to the invention therefore comprises (in particular if it comprises petroleum-derived fuels or lubricants which contain a plurality of hydrocarbons), preferably in a total concentration in the range from 0.0001 to 2% by volume, based on the total volume of the mixture, of one or more Additives selected from the group consisting of: flow improvers (flow improvers, anti-settling, eg diesel fuel wax anti-settling additives, WASA), oxidation inhibitors (antioxidants), metal deactivators, corrosion inhibitors, anti-foams, ignition accelerators, detergents, particle-reducing Substances, anti-knock agents, anti-carburetor additives, anti-repellency agents, anti-smoke agents, biocides, conductivity improvers, burn-off aids, fragrances, anti-wear agents and viscosity improvers.
  • a petroleum-derived fuels or lubricants which contain a plurality of hydrocarbons
  • Additives selected from the group consisting of: flow improvers (
  • the marking agent one or more hydrocarbons (eg, a mineral oil such as a middle distillate (eg diesel)) in the form of a mixture with one or more solution or Add diluents.
  • the solvent or diluents must be compatible with the marking agent (s) and the hydrocarbons to be marked.
  • Preferred solvents or diluents are substances from one of the following groups L1 and L2 or a mixture of substances from both groups L1 and L2, consisting of:
  • the invention also relates to a corresponding mixture comprising marking agents and a solvent or diluent compatible therewith (and preferably with the hydrocarbons to be marked).
  • a mixture according to the invention preferably comprises
  • (L1) isopropyl myristate, benzyl benzoate, diethyl phthalate and mixtures thereof,
  • Diluent the abovementioned provisos, which apply to a" mixture comprising one or more hydrocarbons and a marking agent "according to the invention, according to.
  • Solvents of the group L2 are e.g. under the name Shellsol D60 or Shellsol D100 (mixtures of n- and iso-paraffins) or Shellsol T (mixture of iso-paraffins) commercially available.
  • Particularly preferred mixtures according to the invention which comprise one or more hydrocarbons preferably comprise (a) a total amount of the hydrocarbon or hydrocarbons (eg in the form of a mineral oil, in particular a diesel fuel) of at least 80% by weight, preferably at least 90% by weight. , preferably at least 95% by weight, more preferably at least 98% by weight, and preferably, (b) a total amount of marking agent or formula (I) in the range from 10 ppm to 1000 ppm, preferably in the range of 25 ppm to 250 ppm, and more preferably in the range 30 ppm to 100 ppm, each based on the total weight of the mixture.
  • a total amount of the hydrocarbon or hydrocarbons eg in the form of a mineral oil, in particular a diesel fuel
  • marking agent or formula (I) in the range from 10 ppm to 1000 ppm, preferably in the range of 25 ppm to 250 ppm, and more preferably in the range 30 ppm to 100 pp
  • the invention also relates to the use of one or more compounds of the formula (I)
  • R 1 , R 2 and Y have the abovementioned meaning, preferably one of the meanings given above as preferred, as a marking agent for hydrocarbons, in particular for petroleum-derived fuels or lubricants.
  • a marking agent for hydrocarbons in particular for petroleum-derived fuels or lubricants.
  • the invention further relates to a method for labeling a hydrocarbon or a hydrocarbon mixture (and optionally identifying the labeled hydrocarbon or the marked mixture), in particular for marking a petroleum-derived fuel or lubricant, comprising the following step:
  • R 1 , R 2 and Y are as defined above, to the hydrocarbon or the hydrocarbon mixture, wherein the total added amount of the compound or compounds of formula (I) is sufficient to the compound or compounds of formula (I) in the mixture by Schiff's reagent.
  • a mixture according to the invention in the form of a fuel comprising 1-ethoxyethyl acetate or 1-methoxyethyl acetate does not comprise a lead-containing anti-knock agent.
  • a process according to the invention for which the following applies: The mixture does not consist of 5-35% by weight of acetaldehyde diethyl acetal, 2-8% by weight of dibutyl ether, 10-35% by weight of alcohol and 22-83% by weight. -% kerosene or light oil.
  • a mixture according to the invention comprising kerosene or light oil is preferably free of acetaldehyde diethyl acetal.
  • the mixture does not comprise a lead-containing anti-knock agent.
  • the following applies preferably: A mixture comprising kerosene or light oil is free from acetaldehyde diethyl acetal.
  • the amount of the one or more compounds of the formula (I) is preferably in the form of a mixture according to the invention which, in addition to the marking agent, also comprises one of the preferred solvents or diluents Hydrocarbon or the hydrocarbon mixture.
  • a hydrocarbon marked according to the invention or a hydrocarbon mixture marked according to the invention is preferably identified by reaction with Schiff's reagent.
  • a preferred method according to the invention for labeling a hydrocarbon or a hydrocarbon mixture and identifying the labeled hydrocarbon or the marked hydrocarbon mixture comprises the following identification steps:
  • a corresponding method comprises the following additional step (after reaction with Schiff's reagent):
  • the compounds of the formula (I) to be used according to the invention can be prepared in a simple manner and thus provide inexpensive and readily available In contrast to the resulting from hydrolysis aldehydes they behave in mixtures with hydrocarbons to be marked (especially in the above-mentioned hydrocarbon mixtures such as mineral oils such as diesel or the like) extremely compatible, stable and unobtrusive.
  • Example 1 Detection reaction of 1-ethoxyethyl acetate in diesel fuel
  • diesel fuel namely commercial, ready-to-use diesel fuel, which contained a total of about 500 ppm of conventional additives: flow improvers (flow improvers, anti-settling, here: WASA), oxidation inhibitors, metal deactivators, corrosion inhibitors, foam inhibitors (anti-foam ), Ignition accelerators, detergents, biocides.
  • WASA flow improvers
  • oxidation inhibitors metal deactivators
  • corrosion inhibitors corrosion inhibitors
  • foam inhibitors anti-foam
  • Ignition accelerators Ignition accelerators
  • detergents biocides
  • the aqueous phase was photometrically measured against a solution of known concentration of product dye and quantified here by the amount of 1-ethoxyethyl acetate.
  • Diesel fuel (see Example 1) was admixed with 0.1% by weight or 1.0% by weight of 1-ethoxyethyl acetate of the formula (Ia) and then added

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

L'invention concerne un mélange comprenant un ou plusieurs hydrocarbures, un agent de marquage pour ledit ou lesdits hydrocarbures, ainsi que de préférence un ou plusieurs additifs supplémentaires, l'agent de marquage comprenant ou étant constitué d'un ou de plusieurs composés de formule (I), R<SUP>1</SUP> étant un groupement alkyle linéaire ou ramifié ayant de 1 à 6 atomes de carbone, de préférence un groupement alkyle linéaire ou ramifié ayant de 1 à 5 atomes de carbone, plus préférablement un groupement alkyle linéaire ayant de 1 à 3 atomes de carbone et notamment un groupement éthyle, R<SUP>2</SUP> est H ou un groupement alkyle linéaire ou ramifié ayant de 1 à 6 atomes de carbone, de préférence H ou un groupement alkyle linéaire ou ramifié ayant de 1 à 5 atomes de carbone, plus préférablement un groupement alkyle linéaire ayant de 1 à 3 atomes de carbone et notamment un groupement méthyle, et Y représente CH<SUB>2</SUB>, CH-CH<SUB>3</SUB> ou C=O, de préférence CH<SUB>2</SUB> ou C=O, plus préférablement C=O.
PCT/EP2007/052642 2006-03-21 2007-03-20 Agent de marquage pour hydrocarbures Ceased WO2007107569A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07727119A EP1999236A1 (fr) 2006-03-21 2007-03-20 Agent de marquage pour hydrocarbures

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06111515.0 2006-03-21
EP06111515A EP1837389A1 (fr) 2006-03-21 2006-03-21 Marqueurs pour hydrocarbures

Publications (1)

Publication Number Publication Date
WO2007107569A1 true WO2007107569A1 (fr) 2007-09-27

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ID=36830725

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/052642 Ceased WO2007107569A1 (fr) 2006-03-21 2007-03-20 Agent de marquage pour hydrocarbures

Country Status (2)

Country Link
EP (2) EP1837389A1 (fr)
WO (1) WO2007107569A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3087801A (en) * 1959-01-27 1963-04-30 Texaco Inc Motor fuel containing octane appreciator
US5984983A (en) * 1998-12-04 1999-11-16 Morton International, Inc. Use of carbonyl compounds as markers
EP1149887A2 (fr) * 2000-04-26 2001-10-31 Yoshiro Hamada Combustible peu polluant

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4296137A (en) 1980-08-07 1981-10-20 International Flavors & Fragrances Inc. Flavoring with 1-ethoxy-1-ethanol acetate
US4386063A (en) 1980-12-18 1983-05-31 International Flavors & Fragrances Inc. Flavor use of mixtures containing 1-n-butoxy-1-ethanol acetate
US4387036A (en) 1981-07-29 1983-06-07 International Flavors & Fragrances Inc. 1-Ethoxy-1-ethanol acetate-acetaldehyde mixtures for augmenting or enhancing the aroma of detergents
IT1222752B (it) 1987-09-28 1990-09-12 Acna Chimica Organica Metodo di marcatura di prodotti petroliferi e di solventi organici
IT1229123B (it) 1989-03-01 1991-07-22 Acna Chimica Organica Tracciante per prodotti petroliferi
DE4238994A1 (de) 1992-11-19 1994-05-26 Basf Ag Aniline als Markierungsmittel für Mineralöle
DE4343823A1 (de) 1993-12-22 1995-06-29 Basf Ag Verwendung von Azofarbstoffen zum Markieren von Kohlenwasserstoffen sowie neue Azofarbstoffe
DE10140787A1 (de) 2001-08-20 2003-03-06 Haarmann & Reimer Gmbh Depotpräparate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3087801A (en) * 1959-01-27 1963-04-30 Texaco Inc Motor fuel containing octane appreciator
US5984983A (en) * 1998-12-04 1999-11-16 Morton International, Inc. Use of carbonyl compounds as markers
EP1149887A2 (fr) * 2000-04-26 2001-10-31 Yoshiro Hamada Combustible peu polluant

Also Published As

Publication number Publication date
EP1837389A1 (fr) 2007-09-26
EP1999236A1 (fr) 2008-12-10

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