EP0201368B1 - Markierungs- und Denaturierungszusammensetzung besonders geeignet um Dieselöl und gleichartige Ölprodukte zu markieren und zu denaturieren - Google Patents

Markierungs- und Denaturierungszusammensetzung besonders geeignet um Dieselöl und gleichartige Ölprodukte zu markieren und zu denaturieren Download PDF

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Publication number
EP0201368B1
EP0201368B1 EP86400642A EP86400642A EP0201368B1 EP 0201368 B1 EP0201368 B1 EP 0201368B1 EP 86400642 A EP86400642 A EP 86400642A EP 86400642 A EP86400642 A EP 86400642A EP 0201368 B1 EP0201368 B1 EP 0201368B1
Authority
EP
European Patent Office
Prior art keywords
diesel oil
marking
oil
marked
denaturing
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
Application number
EP86400642A
Other languages
English (en)
French (fr)
Other versions
EP0201368A1 (de
Inventor
Carlo Prandi
Alberto Osti
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.)
BASF Italia SpA
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BASF Italia SpA
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Filing date
Publication date
Application filed by BASF Italia SpA filed Critical BASF Italia SpA
Publication of EP0201368A1 publication Critical patent/EP0201368A1/de
Application granted granted Critical
Publication of EP0201368B1 publication Critical patent/EP0201368B1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/003—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, 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
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1857—Aldehydes; Ketones

Definitions

  • the invention relates to marked diesel oil and a method for marking diesel oil and similar oil products.
  • U. S. Patent 4 209 302 discloses the use of naphthylamine derivatives. However, these compounds do not completely satisfy the requirements herein-above, especially because they can easily be extracted from the marked product.
  • the present invention relates to marked diesel oil or similar oil products containing from 1 to 300 ppm of 2-ethylanthraquinone, 2-tert-butylanthraquinone, 1-methyl-4-isopropylanthraquinone, 2-hexylanthraquinone, 1,8-dichloroanthraquinone, 1, 3, 5, 7-tetramethylanthraquinone or hexamethylanthraquinone.
  • the diesel oil and/or similar oil products marked according to the present invention have the following advantages :
  • the marking method according to the present invention should be prescribed, in particular, when an anthraquinone dye and/or an azoic dye is present in the diesel oil, etc. ; best results are obtained when the diesel oil or other similar oil product contains furfural and/or other suitable organic solvents, for example xylenes, these xylenes generally acting as a diluent.
  • Oil products similar to diesel oil are, for example, gasoline, kerosene oil and lamp oil.
  • anthraquinone derivative to be used as a marker can vary within wide limits and the minimum value merely depends upon the indentification test. By using the simple and rapid test described hereinafter, concentrations as low as 1 to 3 ppm can be used.
  • a greater amount is added, in order to obtain in any case a positive result and also to foresee the case where the marked product is diluted at the time the fraud occurs. From a practical point of view, from 1 to 300 ppm and preferably 3-50 ppm can be used.
  • Example 1 was repeated, by carrying out the test on the same diesel oil, without any admixture of the marking solution, the final bottom layer was light brown.
  • Example 1 100 cm 3 of diesel oil, marked as in Example 1, were admixed with 900 cm 3 of previously unmarked diesel oil, thus reducing the amount of marker to 3 mg/dm 3 ; the colorimetric test caused formation of a final bottom layer still red, the intensity of which was much lower than that obtained in Example 1.
  • Example 1 100 cm 3 of unmarked diesel oil, 20 cm 3 of acetone and 10 cm 3 of the dithionite solution of Example 1 were added to 100 cm 3 of diesel oil marked as in Example 1 ; after stirring and decanting, the bottom phase was collected in a volumetric flask. The absorption intensity, after filtration, was determined at 500 nm (nanometer). A calibration plot allowed to confirm with precision the original marker concentration.
  • Example 1 1 g of a composition, obtained by mixing 8 g of 2-ethyl-anthraquinone, 8 g of furfural, 64,8 g of an anthraquinone dye (known according to the COLOR INDEX as « solvent green 33 ») and 7.2 g of mixed xylenes, was added to 4 kg of a diesel oil to be used for motorboats, thus obtaining a fuel containing 20 ppm of 2-ethyl-anthraquinone.
  • the colorimetric test of Example 1 was carried out on 200 cm 3 of the thus marked oil and an aqueous bottom layer presenting a deep red color was obtained.
  • Example 6 was repeated while replacing gasoline by lamp oil to be used for the lighting of fishing boats.
  • the final bottom aqueous layer obtained also presented a deep red color.
  • Example 1 was repeated while modifying the chemical nature of the marker and its concentration ; data and results are in Table 1.

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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Lubricants (AREA)

Claims (8)

1. Markiertes Dieselöl bzw. ähnliche Ölprodukte enthaltend 1 bis 300 ppm 2-Ethylanthrachinon, 2-tert-Butylanthrachinon, 1-Methyl-4-isopropylanthrachinon, 2-Hexylanthrachinon, 1,8-Dichloranthrachinon, 1, 3, 5, 7-Tetramethylanthrachinon oder Hexamethylanthrachinon.
2. Markiertes Dieselöl gemäß Anspruch 1, enthaltend 3 bis 50 ppm der besagten Anthrachinonverbindungen.
3. Markiertes Dieselöl gemäß Anspruch 1 oder 2, außerdem enthaltend Furfural und/oder ein Anthrachinonfarbstoff.
4. Markiertes Dieselöl gemäß Anspruch 1, 2 oder 3, enthaltend 2-Ethylanthrachinon.
5. Verfahren zur Markierung und/oder Denaturierung von Dieselöl oder anderen ähnlichen Ölprodukten, dadurch gekennzeichnet, daß dem zu markierenden und/oder denaturierenden Produkt 2-Ethylanthrachinon, 2-tert-Butylanthrachinon, 1-Methyl-4-isopropylanthrachinon, 2-Hexylanthrachinon, 1,8-Dichioranthrachinon, 1, 3, 5, 7-Tetramethylanthrachinon oder Hexamethylanthrachinon zusammen mit einem entsprechenden Lösungsmittel zugesetzt wird.
6. Verfahren gemäß Anspruch 5, dadurch gekennzeichnet, daß zusätzlich Furfural und/oder Anthrachinonfarbstoff zugesetzt werden.
7. Verfahren gemäß Anspruch 5 oder 6, dadurch gekennzeichnet, daß die Menge des besagten Anthrachinonderivats bezüglich des zu markierenden und/oder denaturierenden Ölprodukts 1 bis 300 ppm, bevorzugt 3 bis 50 ppm beträgt.
8. Verfahren gemäß Anspruch 5, 6 oder 7, dadurch gekennzeichnet, daß die Anthrachinonverbindung 2-Ethylanthrachinon ist.
EP86400642A 1985-04-12 1986-03-26 Markierungs- und Denaturierungszusammensetzung besonders geeignet um Dieselöl und gleichartige Ölprodukte zu markieren und zu denaturieren Expired EP0201368B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2031685 1985-04-12
IT20316/85A IT1200452B (it) 1985-04-12 1985-04-12 Composizione denaturante e marcante,particolarmente adatta per gasolio

Publications (2)

Publication Number Publication Date
EP0201368A1 EP0201368A1 (de) 1986-11-12
EP0201368B1 true EP0201368B1 (de) 1989-07-19

Family

ID=11165673

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86400642A Expired EP0201368B1 (de) 1985-04-12 1986-03-26 Markierungs- und Denaturierungszusammensetzung besonders geeignet um Dieselöl und gleichartige Ölprodukte zu markieren und zu denaturieren

Country Status (3)

Country Link
EP (1) EP0201368B1 (de)
DE (1) DE3664476D1 (de)
IT (1) IT1200452B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6274381B1 (en) 1998-11-09 2001-08-14 Rohm And Haas Company Method for invisibly tagging petroleum products using visible dyes
US6811575B2 (en) 2001-12-20 2004-11-02 Rohm And Haas Company Method for marking hydrocarbons with anthraquinones
US7157611B2 (en) 2002-07-11 2007-01-02 Rohm And Haas Company Pyrazinoporphyrazines as markers for liquid hydrocarbons
JP3806118B2 (ja) 2003-06-13 2006-08-09 ローム アンド ハース カンパニー 置換アントラキノンでの炭化水素のマーキング方法。
DE10361504A1 (de) * 2003-12-23 2005-07-28 Basf Ag Kraft- und Schmierstoffadditiv-Konzentrate, enthaltend mindestens ein Anthrachinon-derivat als Markierungsstoff
US6977177B1 (en) 2004-05-26 2005-12-20 Rohm And Haas Company Method for marking hydrocarbons with substituted anthraquinones
US7635596B2 (en) 2004-12-15 2009-12-22 Rohm And Haas Company Method for monitoring degradation of lubricating oils
CN1321965C (zh) * 2005-07-22 2007-06-20 清华大学 蒽醌衍生物的合成方法
US12031098B2 (en) 2019-12-03 2024-07-09 Sicpa Holding Sa Method of marking a petroleum hydrocarbon

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE524604A (de) *
GB361310A (en) * 1930-06-18 1931-11-18 Howard Ferguson Improvements in and relating to motor fuels or like combustible liquids
GB851639A (en) * 1958-09-26 1960-10-19 Exxon Research Engineering Co Improved hydrocarbon oils
US3164449A (en) * 1961-03-01 1965-01-05 Du Pont Anthraquinone dyes for gasoline
DE2702985C2 (de) * 1977-01-26 1979-02-15 Basf Ag, 6700 Ludwigshafen Verfahren zur Herstellung von deckenden Pyranthronpigmenten

Also Published As

Publication number Publication date
IT1200452B (it) 1989-01-18
IT8520316A0 (it) 1985-04-12
DE3664476D1 (en) 1989-08-24
EP0201368A1 (de) 1986-11-12

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