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
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/56—Ring systems containing three or more rings
  • C07D209/80—[b, c]- or [b, d]-condensed
  • C07D209/82—Carbazoles; Hydrogenated carbazoles
  • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• • 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
  • C10L1/22—Organic compounds containing nitrogen
• • 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
  • C10L1/22—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
• • 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
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/064—Di- and triaryl amines
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
  • C10M2215/226—Morpholines
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
  • C10M2215/30—Heterocyclic compounds

Definitions

• the present invention relates to the use of leucotriarylmethanes of the formula I.
• Y stands for C * -Ci 6 alkyl
• R 1 , R 2 , R 3 and R 4 are the same or different and are each independently hydrogen, Ci-Cie-alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function and is optionally substituted, optionally substituted phenyl or optionally substituted naphthyl mean,
• hydrocarbons containing the above-mentioned leukotriarylmethanes hydrocarbons containing the above-mentioned leukotriarylmethanes, and a method for the detection of leukotriarylmethanes in hydrocarbons.
• the object of the present invention was to provide new means for marking hydrocarbons.
• the new funds should be easily accessible and in hydrocarbons be soluble.
• they should be able to be demonstrated in a simple manner. Even very small amounts of marking material should be made visible by a strong color reaction.
• the leukotriarylmethanes of the formula I described at the outset are advantageously suitable as marking agents for hydrocarbons.
• substituted phenyl or naphthyl radicals occur in the formulas mentioned here, these generally have 1 to 3 substituents.
• Z is substituted phenyl or naphthyl
• suitable substituents are, for example, C 1 -C 6 -alkyl, C 1 -C 6 alkoxy, halogen, amino or C 1 -C 6 mono- or dialkylamino.
• R 1 , R 2 , R3 or R 4 are substituted phenyl or substituted naphthyl, then as substituents, for example C 1 -C 6 -alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function, C 1 -C 6 -alkoxy or phenoxy be considered.
• R 1 , R 2 , R 3 and R 4 are substituted C 1 -C 6 -alkyl, substituents such as hydroxyl, halogen or cyano can be used.
• the alkyl radicals then usually have 1 or 2 substituents.
• R 1 , R 2 , R 3 , R 4 and Y are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, Octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl, tetradecyl, pentadecyl or hexadecyl (the above names isooctyl, isononyl , Isodecyl and Isotridecyl are trivial names and derive from
• R 1 , R 2 , R 3 and R 4 are furthermore, for example, 2-methoxethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or
• Suitable substituents for the Z radical are, in addition to the C 1 -C 6 -alkyl radicals already mentioned, for example fluorine, chlorine, bromine, mono- or dimethylamino, mono- or diethylamino, mono- or dipropylamino, mono- or diisopropylamino, mono- or dibutylamino , Mono- or dipentylamino, mono- or dihexylamino, mono- or diheptylamino, mono- or dioctylamino, mono- or bis (2-ethylhexyl) amino, mono- or dinonylamino, mono- or didecylamino, mono- or diundecyl-a ino, Mono- or didodecylamino, mono- or ditridecylamino, mono- or ditetradecylamino, mono- or dipentadecylamino, mono- or dihexadecylamino, N
• Leukotriarylmethanes of the formula I, in which Z represents optionally substituted phenyl, are preferably used for labeling hydrocarbons.
• Leukotriarylmethanes of the formula I in which R 1 , R 2 , R 3 , R 4 are each independently of the other C 1 -C 6 -alkyl are also preferably used for marking hydrocarbons.
• Leukotriarylmethanes of the formula II are particularly preferred.
• R 1 , R 2 , R 3 and R 4 each have the abovementioned meaning, used for marking hydrocarbons.
• Leukotriarylmethanes are very particularly preferred
• the leukotriarylmethanes of formula I are known per se and e.g. in K. Venkataraman "The Chemistry of Synthetic Dyes", Vol. II, Academic Press, New York, 1952, or can e.g. can be obtained by the methods mentioned there.
• Labeling in the sense of the invention means an addition of the leukotriarylmethanes of the formula I to hydrocarbons in such a concentration that the hydrocarbons are either not colored or only slightly visible to the human eye, but the leukotriarylmethanes of the formula I are characterized by the Detection methods described in more detail here can be detected easily and clearly visibly.
• Another object of the present invention are hydrocarbons containing one or more of the leukotriaryl methanes of the formula I.
• the concentration of the leukotriaryl methanes of the formula I in the hydrocarbons is generally 1 to 500 ppm, preferably 5 to 50 ppm and in particular approx. 40 ppm.
• Hydrocarbons in the sense of the invention are to be understood as meaning aliphatic or aromatic hydrocarbons which are in a liquid state under normal conditions, e.g. Pentane, hexane, heptane, octane, isooctane, benzene, toluene, xylene, ethylbenzene, tetralin, decalin, dimethylnaphthalene, diisopropylnaphthalene, chlorobenzene or dichlorobenzene.
• these are mineral oils, for example fuels, such as gasoline, kerosene or diesel oil, or oils, such as heating oil or motor oil.
• the leukotriarylmethanes of the formula I are particularly suitable for marking mineral oils for which marking is required, for example for tax reasons. To reduce the cost of To keep this low, the aim is to use the smallest possible amount of marking agent for the marking.
• the leukotriaryl methanes of the formula I 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
• a concentration of leukotriarylmethane I 20 to 80% by weight, based on the solution, is generally chosen.
• Cosolvents e.g. 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 -Methylaniline, N, N-dimethylaniline, toluidine or xylidine, alkanolamines, such as 3- (2-methoxyethoxy) propylamine, o-cresol, m-cresol or p-cresol, ketones, such as diethyl ketone or cyclohexanone, lactones, such as ⁇ -butyro
• the leukotriarylmethanes of the formula I to be used according to the invention it is very easy to detect labeled hydrocarbons, even if, as already mentioned above, the labeling substances are only present in a concentration of approximately 10 ppm or less.
• the presence of the leukotriarylmethanes of the formula I used as markers in hydrocarbons can advantageously be demonstrated if the labeled hydrocarbon is treated with an oxidizing agent and optionally a protonic acid in the presence of water. This treatment results in a clearly visible color reaction and the leukotriarylmethane I passes into the aqueous phase with the formation of a triarylmethane dye.
• Z, R 1 , R 2 , R 3 and R 4 each have the abovementioned meaning and An ⁇ is the equivalent of an anion (for example sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, nitrate, acetate, lactate or citrate).
• an anion for example sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, nitrate, acetate, lactate or citrate.
• Suitable oxidizing agents are, for example, conventional, known inorganic or organic oxidizing agents, such as alkali permanganates, e.g. Potassium permangana, ammonium dichromate, alkali dichromates, e.g. Sodium or potassium dichromate, ammonium peroxodisulfate, alkali peroxodisulfates such as sodium or potassium peroxodisulfate, potassium peroxomonosulfate, iron (III) salts, e.g. Iron (III) chloride or iron (III) sulfate, hydrogen peroxide (in combination with suitable catalysts), quinones, e.g.
• alkali permanganates e.g. Potassium permangana
• ammonium dichromate alkali dichromates
• alkali dichromates e.g. Sodium or potassium dichromate
• ammonium peroxodisulfate alkali peroxodisulfates
• oxidizing agent can either be as an aqueous solution (inorganic oxidizing agent) or as
• organic solvent organic oxidizing agent
• Suitable organic solvents are e.g. Toluene, xylene, cyclohexanone, acetophenone, ⁇ -butyrolactone, 2-ethylhexyl acetate or esters of phthalic acid.
• the reaction is carried out in the presence of a dilute aqueous acid, for example 5 to 30% by weight aqueous acetic acid.
• a dilute aqueous acid for example 5 to 30% by weight aqueous acetic acid.
• the inorganic oxidizing agents can also be used in the presence of acid, for example sulfuric acid.
• the concentration of the oxidizing agents in the aqueous or organic solution is usually 0.001 to 5% by weight, preferably 0.01 to 1% by weight, in each case based on the weight of the solution.
• the amount of acid can be reduced to small amounts, e.g. a few drops, remain limited.
• the amount of acid used e.g. 5 to 30 wt .-% aqueous acetic acid larger, since the water contained in the acid serves as an aqueous phase.
• the amount of aqueous acid so that it approximately corresponds to the amount of the hydrocarbon to be investigated.
• the leukotriarylmethanes used according to the invention are easily accessible and readily soluble in hydrocarbons. In addition, they can be detected in a simple manner, and even very small amounts of marking material can be made visible by a strong color reaction.

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• Engineering & Computer Science (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
• Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

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• 1994
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