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WO1996000271A1 - Utilisation de composes carbonyle pour marquer des hydrocarbures - Google Patents

Utilisation de composes carbonyle pour marquer des hydrocarbures Download PDF

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Publication number
WO1996000271A1
WO1996000271A1 PCT/EP1995/002330 EP9502330W WO9600271A1 WO 1996000271 A1 WO1996000271 A1 WO 1996000271A1 EP 9502330 W EP9502330 W EP 9502330W WO 9600271 A1 WO9600271 A1 WO 9600271A1
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WO
WIPO (PCT)
Prior art keywords
hydrocarbons
carbonyl compounds
alkyl
formula
hydrogen
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/EP1995/002330
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German (de)
English (en)
Inventor
Silvana Rabacchi
Virginio Sarto
Francesco Piscitelli
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
Original Assignee
BASF Italia 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 BASF Italia SpA filed Critical BASF Italia SpA
Priority to PL95317941A priority Critical patent/PL317941A1/xx
Priority to JP8502759A priority patent/JPH10502111A/ja
Priority to MX9700119A priority patent/MX9700119A/es
Priority to BR9508104A priority patent/BR9508104A/pt
Priority to EP95923333A priority patent/EP0766724A1/fr
Priority to AU27928/95A priority patent/AU2792895A/en
Publication of WO1996000271A1 publication Critical patent/WO1996000271A1/fr
Priority to NO965554A priority patent/NO965554L/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • G01—MEASURING; TESTING
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    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
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    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
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    • 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
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Definitions

  • the present invention relates to the use of carbonyl compounds for labeling hydrocarbons, hydrocarbons containing carbonyl compounds as labeling agents, and to a method for detecting carbonyl compounds in hydrocarbons.
  • hydrocarbons e.g. Products from the refining of petroleum
  • heating oil is usually marked, since it is taxed much less than that which is identical in composition to diesel oil.
  • Suitable marking agents for hydrocarbons should in particular
  • the object of the present invention was to provide new marking agents for liquid or liquefiable by compression hydrocarbons. Such markers should be readily available and have the property profile mentioned above. 2
  • R 1 is hydrogen, -C 4 alkyl, -C 4 alkoxy or a radical of the formula
  • X is a direct bond
  • oxygen or imino and Z 1 and Z 2 are each independently hydrogen, C ⁇ -C 4 -alkyl, C ⁇ -C 4 -alkoxy or halogen,
  • R 2 is hydrogen, -CC 4 alkyl or a radical of the formula
  • R 3 is hydrogen, hydroxy, -CC 4 alkyl or -CC 4 alkoxy and
  • L 1 and L 2 each independently represent hydrogen, hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen and
  • the ring A can be benzo-fused, advantageously for labeling hydrocarbons.
  • R 1 , R 2 , R 3 , L 1 , L 2 , Z 1 and Z 2 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
  • R 1 , R 3 , L 1 , L 2 , Z 1 and Z 2 are, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy or tert-butoxy.
  • L 1 , L 2 , Z 1 and Z 2 are, for example, fluorine, chlorine or bromine.
  • Labeling in the sense of the invention means an addition of the carbonyl compounds of the formula I and / or II to hydrocarbons, the hydrocarbons thereby not being visible to the human eye, but the carbonyl compounds of the formula I and / or II being changed by the here Detection methods described in more detail are easily and clearly visible.
  • Hydrocarbons in the sense of the invention are generally understood to mean products such as are obtained in the refining of petroleum. These are e.g. Propane, butane, pentane, hexane, heptane, octane, isooctane, benzene, toluene, xylene, ethylbenzene, tetralin, decalin or dimethylnaphthalene.
  • these are mineral oils, for example fuels, such as gasoline, kerosene or diesel oil, or oils, such as heating oil or motor oil.
  • this also includes products such as those used for processing certain types of plants, e.g. Rape or sunflowers. Such products are also known under the term "bio-diesel”.
  • the hydrocarbons are generally in the liquid state under normal conditions or are in the gaseous state and are e.g. by compression, liquefiable, e.g. Liquefied petroleum gas, such as propane or butane.
  • Carbonyl compounds of the formula I are preferably used, in which R 1 is C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or a radical of the formula
  • Z 1 and Z 2 each have the meaning given above, and R 2 is C ⁇ -C-alkyl, as a marking agent.
  • the carbonyl compounds of the formula I and / or II are used either in bulk or in the form of solutions.
  • Organic solvents are suitable as solvents.
  • Aromatic hydrocarbons such as toluene, xylene, dodecylbenzene, diisopropylnaphthalene or a mixture of higher aromatics, which is commercially available under the name Shellsol AB (Shell), are preferably used.
  • Shellsol AB Shellsol
  • alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol
  • glycols such as butylethylene glycol or methylpropylene glycol
  • amines such as triethylamine, diisooctylamine, dicyclohexylamine, aniline, N-methylaniline, N, N-dimethylaniline, toluidine or xylidine
  • alkanolamines such as 3- (2-methoxyethoxy) propylamine, o-cresol, m-cresol, p-cresol, ketones , such as diethyl ketone or cyclohexanone, lactones such as ⁇ -buty
  • the hydrocarbons preferably have a content of 5 to 1000 ppm, in particular 10 to 1000 ppm, of marking agent. Particularly noteworthy is a content of 10 to 500 ppm, in particular 50 to 100 ppm.
  • the hydrocarbons can also contain other labeling or denaturing agents known per se, such as furfural or C.I. Solvent Red 198 included.
  • carbonyl compounds of the above formulas I and / or II can advantageously be detected in hydrocarbons if the hydrocarbons are treated with an aqueous-alcoholic or aqueous-acetone solution of an iron (III) salt.
  • Suitable iron (III) salts are e.g. Iron (I ⁇ I) halides, such as iron (III) chloride or iron (III) bromide, iron (III) sulfate, iron (III) nitrate or iron (III) acetate.
  • Iron (I ⁇ I) halides such as iron (III) chloride or iron (III) bromide, iron (III) sulfate, iron (III) nitrate or iron (III) acetate.
  • ferric chloride is preferred.
  • the iron (III) salts are used in an aqueous-alcoholic or aqueous-acetone solution.
  • the use of an aqueous-alcoholic solution is preferred.
  • Suitable alcohols for the preparation of the aqueous-alcoholic solution are e.g. Methanol, ethanol, propanol or isopropanol.
  • Methanol e.g. Methanol, ethanol, propanol or isopropanol.
  • methanol or ethanol is preferred, the use of methanol being particularly noteworthy.
  • suitable reagent solutions generally have a content of 0.05 to 0.5% by weight, preferably 0.1 to 0.3% by weight, iron (III) salts, 10 up to 90% by weight, preferably 40 to 70% by weight, of an alcohol or acetone and 10 to 90% by weight, preferably 30 to 60% by weight, Water, the total of the components of course giving 100 wt .-%.
  • the detection is usually carried out by vigorously shaking about 20 ml of labeled hydrocarbon with about 2 ml of reagent solution for about 15 to 20 seconds.
  • the phase is allowed to separate.
  • the lower aqueous phase has a red or violet-brown color. The color depends on the type of marking agent.
  • the content of the marking agent can be determined by methods known per se, e.g. by means of spectroscopic methods.
  • the detection is usually carried out in such a way that in a suitable container, e.g. a test tube, 1 to 2 ml of reagent solution and then drains the liquefied hydrocarbon from a gas bottle containing the liquefied hydrocarbon for about 15 to 30 seconds and collects it in the container.
  • a suitable container e.g. a test tube
  • the hydrocarbon escape from the lying bottle, since in this case it will generally still emerge in the liquid state.
  • the liquefied hydrocarbon is allowed to evaporate.
  • the reagent solution In the presence of the carbonyl compounds of the formula I and / or II, the reagent solution then has a red or violet-brown color.
  • Example 1 was carried out with unmarked liquid gas.
  • the reagent was yellow in color.
  • Example 2 The test described in Example 1 was repeated. The reagent was clearly purple in color.
  • Example 5 20 ml of diesel oil marked with 50 ppm acetylacetone were placed in a separatory funnel. Then 2 ml of the reagent described in Example 1 were added and the mixture was shaken vigorously for 20 seconds. They were then allowed to sit down. The phases separated after 5 minutes. The lower aqueous phase was clearly red in color.
  • Example 5 20 ml of diesel oil marked with 50 ppm acetylacetone were placed in a separatory funnel. Then 2 ml of the reagent described in Example 1 were added and the mixture was shaken vigorously for 20 seconds. They were then allowed to sit down. The phases separated after 5 minutes. The lower aqueous phase was clearly red in color. Example 5
  • Example 4 1 ml of the labeled diesel oil from Example 4 was diluted with 9 ml of unlabeled diesel oil. The procedure described in Example 4 was repeated with this mixture. The lower aqueous phase was slightly red in color.
  • Example 4 The procedure described in Example 4 was carried out with 20 ml of unlabeled diesel oil. The lower aqueous phase remained yellow.

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Abstract

L'invention concerne l'utilisation de composés beta -dicarbonyle ou de composés ortho-hydroxycarbonyle aromatiques pour marquer des hydrocarbures, des hydrocarbures contenant comme marqueurs des composés beta -dicarbonyle ou des composés ortho-hydroxycarbonyle aromatiques. L'invention concerne également un procédé de dosage de composés beta -dicarbonyle ou de composés ortho-hydroxycarbonyle aromatiques dans des hydrocarbures.
PCT/EP1995/002330 1994-06-24 1995-06-16 Utilisation de composes carbonyle pour marquer des hydrocarbures Ceased WO1996000271A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
PL95317941A PL317941A1 (en) 1994-06-24 1995-06-16 Application od carbonyl compounds for labelling hydrocarbons
JP8502759A JPH10502111A (ja) 1994-06-24 1995-06-16 炭化水素の標識のためのカルボニル化合物の使用
MX9700119A MX9700119A (es) 1994-06-24 1995-06-16 Uso de compuestos de carbonilo como marcadores para hidrocarburos.
BR9508104A BR9508104A (pt) 1994-06-24 1995-06-16 Uso de composto de carbonila hidrocarboneto e processo para detectar composto de carbonila
EP95923333A EP0766724A1 (fr) 1994-06-24 1995-06-16 Utilisation de composes carbonyle pour marquer des hydrocarbures
AU27928/95A AU2792895A (en) 1994-06-24 1995-06-16 Use of carbonyl compounds for marking hydrocarbons
NO965554A NO965554L (no) 1994-06-24 1996-12-23 Anvendelse av karbonylforbindelser for markering av hydrokarboner

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI941320A IT1269947B (it) 1994-06-24 1994-06-24 Composizione marcante-denaturante particolarmente adatta per marcare e denaturare combustibili
ITMI94A001320 1994-06-24

Publications (1)

Publication Number Publication Date
WO1996000271A1 true WO1996000271A1 (fr) 1996-01-04

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Country Status (14)

Country Link
EP (1) EP0766724A1 (fr)
JP (1) JPH10502111A (fr)
AU (1) AU2792895A (fr)
BR (1) BR9508104A (fr)
CA (1) CA2193886A1 (fr)
CO (1) CO4410389A1 (fr)
CZ (1) CZ379296A3 (fr)
HU (1) HUT76753A (fr)
IL (1) IL114195A0 (fr)
IT (1) IT1269947B (fr)
MX (1) MX9700119A (fr)
NO (1) NO965554L (fr)
PL (1) PL317941A1 (fr)
WO (1) WO1996000271A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1010978A1 (fr) * 1998-12-16 2000-06-21 Total Raffinage Distribution S.A. Indicateur coloré pour la mesure de la répartition des familles d'hydrocarbures

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2971254B1 (fr) * 2011-02-08 2014-05-30 Total Raffinage Marketing Compositions liquides pour marquer les carburants et combustibles hydrocarbones liquides, carburants et combustibles les contenant et procede de detection des marqueurs
EP2738154A1 (fr) * 2012-11-30 2014-06-04 Inter-Euro Technology Limited Marqueurs de combustible améliorés

Citations (10)

* 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
GB473653A (en) * 1936-04-15 1937-10-15 Ig Farbenindustrie Ag Improvements in the manufacture and production of carbon compounds of high molecularweight
US2205408A (en) * 1938-08-09 1940-06-25 Gen Aniline & Film Corp Fluorescent hydrocarbon oil
US3508875A (en) * 1967-10-03 1970-04-28 Union Oil Co Method for tracing the flow of water in subterranean formations
DE2111370A1 (de) * 1970-03-11 1971-09-23 Acna Verfahren zum Farben von aus der Erdoeldestillation stammenden Kohlenwasserstoffen und Farbstoffloesungen zur Durchfuehrung des Verfahrens
EP0310319A2 (fr) * 1987-09-28 1989-04-05 Acna Chimica Organica S.P.A. Utilisation d'alkyl (C1-C4)-phenyl-kétone pour marquer des produits pétroliérs et des solvants organiques
EP0327163A2 (fr) * 1988-02-02 1989-08-09 Biocode, Inc. Détection de produits chimiques par immunoessai
FR2650606A1 (fr) * 1989-08-07 1991-02-08 Aussedat Rey Papier de securite infalsifiable et composition aqueuse ou organique utile, notamment pour rendre un papier infalsifiable
WO1993016149A1 (fr) * 1992-02-14 1993-08-19 Basf Italia S.P.A. Sels metalliques utilises comme agents de marquage pour des bitumes combustibles
EP0565715A1 (fr) * 1990-04-26 1993-10-20 Yoshibi, Co., Ltd. Combustible a base de gaz liquefie donnant une flamme coloree tres lumineuse

Patent Citations (10)

* 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
GB473653A (en) * 1936-04-15 1937-10-15 Ig Farbenindustrie Ag Improvements in the manufacture and production of carbon compounds of high molecularweight
US2205408A (en) * 1938-08-09 1940-06-25 Gen Aniline & Film Corp Fluorescent hydrocarbon oil
US3508875A (en) * 1967-10-03 1970-04-28 Union Oil Co Method for tracing the flow of water in subterranean formations
DE2111370A1 (de) * 1970-03-11 1971-09-23 Acna Verfahren zum Farben von aus der Erdoeldestillation stammenden Kohlenwasserstoffen und Farbstoffloesungen zur Durchfuehrung des Verfahrens
EP0310319A2 (fr) * 1987-09-28 1989-04-05 Acna Chimica Organica S.P.A. Utilisation d'alkyl (C1-C4)-phenyl-kétone pour marquer des produits pétroliérs et des solvants organiques
EP0327163A2 (fr) * 1988-02-02 1989-08-09 Biocode, Inc. Détection de produits chimiques par immunoessai
FR2650606A1 (fr) * 1989-08-07 1991-02-08 Aussedat Rey Papier de securite infalsifiable et composition aqueuse ou organique utile, notamment pour rendre un papier infalsifiable
EP0565715A1 (fr) * 1990-04-26 1993-10-20 Yoshibi, Co., Ltd. Combustible a base de gaz liquefie donnant une flamme coloree tres lumineuse
WO1993016149A1 (fr) * 1992-02-14 1993-08-19 Basf Italia S.P.A. Sels metalliques utilises comme agents de marquage pour des bitumes combustibles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WINDHOLZ ET AL.: "THE MERCK INDEX", MERCK & CO., RAHWAY,N.J.,U.S.A. *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1010978A1 (fr) * 1998-12-16 2000-06-21 Total Raffinage Distribution S.A. Indicateur coloré pour la mesure de la répartition des familles d'hydrocarbures
FR2787577A1 (fr) * 1998-12-16 2000-06-23 Total Raffinage Distribution Indicateur colore pour la mesure de la repartition des familles d'hydrocarbures contenues dans un melange, son procede d'obtention et ses utilisations
US6451615B1 (en) 1998-12-16 2002-09-17 Total Raffinage Distribution S. A. Colored indicator to measure the distribution of the hydrocarbon families contained in a mixture, the procedure for obtaining it, and its uses

Also Published As

Publication number Publication date
EP0766724A1 (fr) 1997-04-09
ITMI941320A1 (it) 1995-12-24
BR9508104A (pt) 1997-08-12
IT1269947B (it) 1997-04-16
CO4410389A1 (es) 1997-01-09
HU9603550D0 (en) 1997-02-28
PL317941A1 (en) 1997-05-12
JPH10502111A (ja) 1998-02-24
AU2792895A (en) 1996-01-19
NO965554L (no) 1997-02-18
CA2193886A1 (fr) 1996-01-04
CZ379296A3 (en) 1997-06-11
ITMI941320A0 (it) 1994-06-24
HUT76753A (en) 1997-11-28
MX9700119A (es) 1997-04-30
NO965554D0 (no) 1996-12-23
IL114195A0 (en) 1995-10-31

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