EP0310319B1 - Use of alkyl (c1-c4)-phenyl-ketone for marking oil products and organic solvents - Google Patents

Use of alkyl (c1-c4)-phenyl-ketone for marking oil products and organic solvents Download PDF

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Publication number
EP0310319B1
EP0310319B1 EP88308912A EP88308912A EP0310319B1 EP 0310319 B1 EP0310319 B1 EP 0310319B1 EP 88308912 A EP88308912 A EP 88308912A EP 88308912 A EP88308912 A EP 88308912A EP 0310319 B1 EP0310319 B1 EP 0310319B1
Authority
EP
European Patent Office
Prior art keywords
ketone
phenyl
alkyl
marked
organic solvents
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
EP88308912A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0310319A3 (en
EP0310319A2 (en
Inventor
Sisto Sergio Papa
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.)
ACNA Chimica Organica SpA
Original Assignee
ACNA Chimica Organica SpA
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 ACNA Chimica Organica SpA filed Critical ACNA Chimica Organica SpA
Priority to AT88308912T priority Critical patent/ATE74949T1/de
Publication of EP0310319A2 publication Critical patent/EP0310319A2/en
Publication of EP0310319A3 publication Critical patent/EP0310319A3/en
Application granted granted Critical
Publication of EP0310319B1 publication Critical patent/EP0310319B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1857—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/007—Coloured or dyes-containing lubricant compositions

Definitions

  • the present invention relates to the use of alkyl (C1-C4)-phenyl ketone for marking oil products and organic solvents.
  • oil products such as fuel oils, petroleum fractions for motor traction and the like, e.g. gasoline, kerosene and so on, or organic solvents such as turpentine, alcohols and so on, is associated the different selling price which the same oil product or solvent may have, because of the taxation to which it is subjected according to the final use.
  • Diesel oil for agricultural or fishing purposes is taxed less than Diesel oil for motor traction.
  • the marking substances which can be used to this purpose should be stable under the application conditions, not present in the natural products; they should be of such a type as not to affect the physico-chemical properties of the organic solvent or of the oil product, they should be sufficiently soluble and preferably their use should be allowed also in the form of concentrated solutions; they should further be eliminatable with difficulty or not quite eliminatable by physical or physico-chemical methods, usable in small amounts and moreover they should be detectable by simple, quick and sensitive analytical methods.
  • alkyl (C1-C4)-phenyl-ketone defined according to the present invention, allows working under conditions of higher stability and sensitivity in comparison with some recent tracers which have been the subject of particular interest, such as nitro-derivatives of benzene and homologues thereof.
  • the alkyl (C1-C4)-phenyl-ketone has the advantages of being a highly soluble liquid (possibility of preparing a liquid masterbatch), not toxic and not requiring particular expedients for handling.
  • aceto-phenone because of the absence of nitrogen in its structure, is more resistant to reducing agents and is more easily detectable and measurable, also in amounts in the order of 100 ppm, by a simpler chromatic detection text.
  • alkyl (C1-C4)-phenyl-ketone is used in an amount from 100 to 10,000 ppm for marking oil products or organic solvents.
  • methyl-phenyl-ketone acetophenone
  • any organic solvent can be marked, such as turpentine, acetone, alcohols, glycols, esters, aliphatic amines or any product or oil product cut, such as Diesel oil, gasoline, kerosene, benzene, toluene, xylene, aliphatic hydrocarbons and cyclohexane.
  • alkyl-phenyl-ketone which can be used as marking agent can vary within wide limits, the minimum amount being only dependent on the sensitivity of the detection text. Acceptable working results are obtained by weight amounts comprised from 100 to 10,000 ppm, on the marked product.
  • alkyl (C1-C4)-phenyl-ketones as marking substances, many advantages are obtained.
  • acetophenone is a known product widely used.
  • the marking products used in the present invention can be added either as a highly concentrated solution (liquid master-batch), or as such, because they are liquids and because of their easy and complete solubility in aromatic hydrocarbons as well as in the main industrial solvents.
  • Suitable solvents are for instance the aromatic and/or aliphatic hydrocarbons.
  • the simple identification method referred to herein does not require a complicated apparatus and can be quickly performed also by a non-specialized worker.
  • Said method comprises bringing into contact a small volume, generally about 20 cm3, of marked oil product or of marked solvent with a certain amount of methanol, of reagent and of an aqueous-methanolic solution of potassium hydroxide, as illustrated in the examples.
  • Example 1 1,000 cm3 were obtained of a mixture containing 100 ppm of tracer. On 20 cm3 of the marked Diesel oil the test was carried out as described in Example 1. Two layers were obtained, the lower of which was coloured purple with a much lower intensity than that of the Example 1, but nevertheless still apparent.
  • acetophenone 1 g was dissolved in 1,000 cm3 of gasoline. A concentration of 1,000 ppm was obtained without any particular colouration of the gasoline. 100 cm3 of marked gasoline were added to 900 cm3 of un-marked gasoline. 1,000 cm3 were obtained of gasoline containing 100 ppm of tracer. 20 cm3 of this mixture were handled as described in example 1 and, also in this case, after 5 minutes a purple colouration was obtained. By carrying out the test on 20 cm3 of un-marked gasoline no colouration was obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Color Printing (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Paints Or Removers (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
EP88308912A 1987-09-28 1988-09-26 Use of alkyl (c1-c4)-phenyl-ketone for marking oil products and organic solvents Expired - Lifetime EP0310319B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88308912T ATE74949T1 (de) 1987-09-28 1988-09-26 Verwendung von alkyl (c1-c4)-phenyl-keton zum markieren von oelprodukten und von organischen loesungsmitteln.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2205087 1987-09-28
IT22050/87A IT1222752B (it) 1987-09-28 1987-09-28 Metodo di marcatura di prodotti petroliferi e di solventi organici

Publications (3)

Publication Number Publication Date
EP0310319A2 EP0310319A2 (en) 1989-04-05
EP0310319A3 EP0310319A3 (en) 1989-08-23
EP0310319B1 true EP0310319B1 (en) 1992-04-15

Family

ID=11190735

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88308912A Expired - Lifetime EP0310319B1 (en) 1987-09-28 1988-09-26 Use of alkyl (c1-c4)-phenyl-ketone for marking oil products and organic solvents

Country Status (7)

Country Link
EP (1) EP0310319B1 (enExample)
AT (1) ATE74949T1 (enExample)
DE (1) DE3870129D1 (enExample)
ES (1) ES2032973T3 (enExample)
GR (1) GR3005039T3 (enExample)
IT (1) IT1222752B (enExample)
PT (1) PT88601B (enExample)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1269947B (it) * 1994-06-24 1997-04-16 Basf Italia Composizione marcante-denaturante particolarmente adatta per marcare e denaturare combustibili
EP1837389A1 (de) 2006-03-21 2007-09-26 Symrise GmbH & Co. KG Markierungsmittel für Kohlenwasserstoffe
NL2007874C2 (en) * 2011-11-25 2013-05-28 Progression Industry B V The application of chemical compounds presents a styrene production process in a fuel.
EP2738154A1 (en) * 2012-11-30 2014-06-04 Inter-Euro Technology Limited Improved fuel markers

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB287192A (en) * 1926-10-25 1928-03-22 British Dyestuffs Corp Ltd Improvements in and relating to fuels for internal combustion engines
US2165261A (en) * 1936-11-28 1939-07-11 Standard Oil Dev Co Stabilized kerosene
DE2345190B2 (de) * 1973-09-07 1976-07-08 Lemke, Ralf, Dr., 4620 Castrop-Rauxel Kennzeichnung von gasoelen durch solvatochrome indikatoren

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Dictionary of Organic Compounds, Volume 1, Eyre and Spottiswood Ltd. *

Also Published As

Publication number Publication date
GR3005039T3 (enExample) 1993-05-24
EP0310319A3 (en) 1989-08-23
IT1222752B (it) 1990-09-12
EP0310319A2 (en) 1989-04-05
ATE74949T1 (de) 1992-05-15
PT88601B (pt) 1992-11-30
ES2032973T3 (es) 1993-03-01
DE3870129D1 (de) 1992-05-21
IT8722050A0 (it) 1987-09-28
PT88601A (pt) 1988-10-01

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