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EP0770119A1 - Utilisation de benzaldehydes pour marquer des hydrocarbures - Google Patents

Utilisation de benzaldehydes pour marquer des hydrocarbures

Info

Publication number
EP0770119A1
EP0770119A1 EP95924960A EP95924960A EP0770119A1 EP 0770119 A1 EP0770119 A1 EP 0770119A1 EP 95924960 A EP95924960 A EP 95924960A EP 95924960 A EP95924960 A EP 95924960A EP 0770119 A1 EP0770119 A1 EP 0770119A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
benzaldehydes
radical
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.)
Withdrawn
Application number
EP95924960A
Other languages
German (de)
English (en)
Inventor
Claudia Kräh
Ulrike Schlösser
Karin Heidrun Beck
Udo Mayer
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 SE
Original Assignee
BASF SE
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 SE filed Critical BASF SE
Publication of EP0770119A1 publication Critical patent/EP0770119A1/fr
Withdrawn legal-status Critical Current

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Definitions

  • the present invention relates to the use of benzaldehyde of the formula I.
  • ring A can be fused to benzo
  • R 1 , R 2 and R 3 each independently represent hydrogen, hydroxyl, C_-C_ 5- alkyl, Ci-Cis-alkoxy, cyano, nitro or a radical of the formula NR 4 R 5 or COOR 6 , in which
  • R 4 is hydrogen or Ci-Cis-alkyl, which is by 1 to
  • oxygen atoms can be interrupted in ether function and is optionally substituted by phenyl
  • R 5 for C 1 -C 5 alkyl which can be interrupted by 1 to 4 oxygen atoms in ether function and is optionally substituted by phenyl, or a radical of the formula L-NX i X 2 , in which L has the meaning of C 2 -C ⁇ - Alkylene and X 1 and X 2 independently of one another each have the meaning of Ci-C ⁇ -alkyl or, together with the nitrogen atom connecting them, the meaning of a 5- or 6-membered saturated heterocyclic radical which also has an oxygen atom in the ring may contain, own, and
  • R 6 for hydrogen, C_-Ci 5 alkyl, which can be interrupted by 1 to 4 oxygen atoms in ether function, or for a radical of the formula L-NX X X 2 , where L, X 1 and X 2 each have the above meaning, as a marking agent for hydrocarbons, a method for the detection of these benzaldehydes in hydrocarbons and hydrocarbons, containing the above-mentioned benzaldehydes.
  • Azo dyes which serve as marking agents for mineral oils are already known from US Pat. No. 5,145,573, US Pat. No. 5,182,372 and EP-A-499 845.
  • US Pat. No. 4,009,008 describes a method for marking mineral oils using disazo dyes, in which the dye added to the mineral oil is made visible by adding an adsorbent to the marked mineral oil that binds other colored components of the mineral oil .
  • DE-A-3 608 215 and DE-A-3 724 757 describe benzopyran derivatives and their use in recording systems.
  • Example 1 of DE-A-3 608 215 is the reaction of 2,3-dimethylbenzopyrylium trichlorozincate with 4-dimethylaminobenzaldehyde in methanol to form the color salt of the formula
  • WO-A-11 466/1994 describes the use of substituted anilines for marking mineral oils.
  • the object of the present invention was to provide new means for marking hydrocarbons.
  • the new agents should be easily accessible and readily soluble in hydrocarbons.
  • should 'they can be detected in a simple manner. Even very small amounts of marking material should be made visible by a strong color reaction.
  • All alkyl and alkylene radicals occurring in the above-mentioned formula I can be either straight-chain or branched. If X 1 and X 2 together with the nitrogen atom connecting them represent a 5- or 6-membered saturated heterocyclic radical which may also contain an oxygen atom in the ring, then pyrrolidinyl, piperidinyl or morpholinyl can be considered .
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , ⁇ i and X 2 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert -Pentyl, hexyl or 2-methylpentyl.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are, for example, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, ündecyl, dodecyl, tridecyl, 3,5,5 , 7-tetramethylnonyl, isotride ⁇ cyl, tetradecyl or pentadecyl (the above terms isoctyl, isononyl, isodecyl and isotridecyl are trivial names and come from the alcohols obtained after oxosynthesis - see also Üllmann's Encyclopedia of Industrial Chemistry, 5th Edition , Vol. AI, pages 290 to 293, and vol. A 10, pages 284 and 285).
  • R 1 , R 2 and R 3 are furthermore, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, 2-methylpentyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, isooctyloxy, nonyloxy, isononyloxy, decyloxy, isodecyloxy, undecyloxy, dodecyloxy, tridecyloxy, 3,5, 5,7-tetramethylnonyloxy, isotridecyloxy, tetradecyloxy or pentadecyloxy.
  • R 4 and R 5 are furthermore, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3- Propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxy-butyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6 -Dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl ', 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3, 6,8-trioxadecyl, 3,
  • L are, for example, (CH 2 ) 2 , (CH 2 ) 3 , (CH 2 ) 4 , (CH 2 ) 5 , (CH 2 ) 6 , (CH 2 ) 7 , (CH 2 ) 8 , CH (CH 3 ) CH 2 or CH (CH 3 ) CH (CH 3 ).
  • benzaldehydes of the formula I in which at least one of the radicals R 1 to R 3 is a radical of the formula NRR 5 , in which R 4 and R 5 each have the abovementioned meaning.
  • Benzaldehydes of the formula la are particularly preferred
  • R 1 , R 2 , R 4 and R 5 each have the abovementioned meaning, used for marking hydrocarbons.
  • Benzaldehydes of the formula Ia in which R 4 and R 5 independently of one another are each C 1 -C 3 -alkyl, and R 1 and R 2 are each hydrogen, are particularly preferably used for marking hydrocarbons.
  • the invention also relates to a method for detecting the presence of benzaldehydes of the formula I in hydrocarbons, the hydrocarbon being treated with an aqueous-alcoholic or alcoholic medium which is a protonic acid, at least one compound from the group of Compounds consisting of substituted benzopyrylium salts of formula II
  • R 7 is Ci-C ⁇ -alkyl, phenyl, Ci-Cs-alkoxy or halogen and R ⁇ for methyl or R 7 and R 8 together represent 1,4-butylene and the ring B can be fused by a benzene ring and if appropriate by C ⁇ -C 4 alkyl, pyrrolidino, piperidino, morpholino, chlorine or bromine or in ring position 7 possibly also by hydroxy, C. -C ⁇ alkoxy, Ci-Cs-mono- or dialkylamino, which in turn can be substituted by chlorine or phenyl, is substituted and ® means any anion, and indoles of the formula III
  • R 9 and R 10 independently of one another each represent hydrogen, hydroxy, a radical of the formula NR 4 R 5 , in which R 4 and R 5 each have the abovementioned meaning, Ci-C ⁇ -alkyl, phenyl, Ci-Cs-alkoxy or Halogen stand,
  • indoles of the formula III preference is given to using indoles of the formula III, in particular 2-phenylindole.
  • Suitable anions X® are tetrachlorozincate, halide, sulfate, tetrafluoroborate or phosphate.
  • the benzaldehydes I, the benzopyrylium salts II and the indoles III are generally known per se.
  • Labeling in the sense of the invention means an addition of the benzaldehydes of the formula I to hydrocarbons in such a concentration that the hydrocarbons are either not colored at all or only slightly visible to the human eye, but the benzaldehydes of the formula I can be easily and clearly detected by the detection methods described in more detail here.
  • the present invention further provides hydrocarbons containing one or more of the benzaldehydes of the formula I.
  • Hydrocarbons in the sense of the invention are understood to mean aliphatic or aromatic hydrocarbons which are present in the liquid state under normal conditions.
  • These are in particular mineral oils, for example fuels, such as gasoline, kerosene or diesel oil, or oils, such as heating oil or engine oil.
  • the benzaldehydes of the formula I are particularly suitable for marking mineral oils for which labeling 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 benzaldehydes 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® AB
  • a concentration of benzaldehydes I of 5 to 80% by weight, based on the solution, is generally chosen.
  • Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol or cyclohexanol
  • glycols such as butyl ethylene glycol or methyl propylene 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 or p-cresol
  • ketones such as diethyl ketone or cyclohexanone
  • Lactams such as 3-
  • aqueous alcoholic or alcoholic medium which is a pyrylium salt of the formula II and / or an indole of the formula III, a protonic acid and optionally a halide of the metals zinc, aluminum or tin.
  • aqueous-alcoholic media the weight ratio water: alcohol is 0.5: 1 to 4: 1, preferably about 1: 1.
  • Suitable alcohols are, for example, ethanol, propanol, isopropanol, l-methoxypropan-2-ol, ethylene glycol or 1,2- or 1,3-propylene glycol. The use of ethanol is preferred.
  • Suitable protonic acids for the processes according to the invention are in particular so-called strong acids, i.e. Protonic acids whose pKa is ⁇ .3.5.
  • strong acids i.e. Protonic acids whose pKa is ⁇ .3.5.
  • examples of such acids are inorganic or organic acids, such as perchloric acid, hydroiodic acid, hydrochloric acid, hydrobromic acid, hydrofluoric acid, sulfuric acid, nitric acid, phosphoric acid, benzenesulfonic acid, toluenesulfonic acid, naphthalenesulfonic acid, methanesulfonic acid, oxalic acid, maleic acid , Dichloroacetic acid or bromoacetic acid. In some cases it may be advantageous to use these acids e.g. by adding acetic acid.
  • Suitable halides of the metals zinc, aluminum or tin are e.g. Zinc chloride, zinc bromide, aluminum chloride, aluminum bromide or tin tetrachloride. Zinc chloride is particularly noteworthy.
  • the concentration of the protonic acid in the aqueous-alcoholic or alcoholic solution is usually 5 to 50% by weight, preferably 10 to 30% by weight.
  • the concentration of metal halide is generally 0 to 50% by weight, preferably 5 to 20% by weight, in each case based on the weight of the solution.
  • a great advantage of the invention is that two different methods for the detection of the benzaldehydes of the formula I can be used.
  • the detection can therefore also be carried out very reliably in the event of possible interference (for example additives in diesel fuel).
  • possible interference for example additives in diesel fuel.

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Abstract

L'invention concerne l'utilisation, comme agents de marquage d'hydrocarbures, de benzaldéhydes de la formule (I), dans laquelle le composé cyclique A peut être benzon-annelé et R<1>, R<2> et R<3> désignent hydrogène, hydroxy, alkyle C1-C15, alcoxy C1-C15, cyano, nitro ou un reste de la formule NR<4>R<5> ou COOR<6>, R<4> désignant hydrogène ou alkyle C1-C15 éventuellement substitué, R<5> désignant alkyle C1-C15 éventuellement substitué ou un reste de la formule L-NX<1>X<2>, dans laquelle L désigne alkylène C2-C8 et X<1> et X<2> désignent, indépendamment l'un de l'autre, alkyle C1-C6 ou conjointement avec l'atome d'azote qui les lie, un reste hétérocyclique, et R<6> désignant hydrogène, alkyle C1-C15 éventuellement substitué ou un reste de la formule L-NX<1>X<2>, dans laquelle L, X<1> et X<2> correspondent chacun à la définition donnée ci-dessus. L'invention concerne en outre un procédé de détection de ces benzaldéhydes dans des hydrocarbures, ainsi que des hydrocarbures qui contiennent les benzaldéhydes précités.
EP95924960A 1994-07-13 1995-07-03 Utilisation de benzaldehydes pour marquer des hydrocarbures Withdrawn EP0770119A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4424712 1994-07-13
DE4424712A DE4424712A1 (de) 1994-07-13 1994-07-13 Verwendung von Benzaldehyden zum Markieren von Kohlenwasserstoffen
PCT/EP1995/002558 WO1996002613A1 (fr) 1994-07-13 1995-07-03 Utilisation de benzaldehydes pour marquer des hydrocarbures

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EP (1) EP0770119A1 (fr)
JP (1) JPH10502693A (fr)
KR (1) KR970704860A (fr)
AU (1) AU686838B2 (fr)
BG (1) BG101156A (fr)
BR (1) BR9508401A (fr)
CA (1) CA2195019A1 (fr)
CO (1) CO4600746A1 (fr)
CZ (1) CZ9597A3 (fr)
DE (1) DE4424712A1 (fr)
FI (1) FI970108A7 (fr)
HU (1) HUT76687A (fr)
IL (1) IL114442A0 (fr)
MX (1) MX9700365A (fr)
NO (1) NO970126L (fr)
PL (1) PL318378A1 (fr)
SK (1) SK5197A3 (fr)
TR (1) TR199500823A2 (fr)
WO (1) WO1996002613A1 (fr)

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DE19538121C1 (de) * 1995-10-13 1997-02-27 Dornier Gmbh Lindauer Ungesteuerte Spanneinheit für die Webkette einer Webmaschine
WO2002020500A2 (fr) * 2000-09-01 2002-03-14 Icos Corporation Substances potentialisant un traitement anticancereux et methodes a cet effet
CN1329485C (zh) * 2002-04-26 2007-08-01 英国石油国际有限公司 改善馏分燃料热氧化稳定性的方法和装置
US8404681B2 (en) 2003-03-24 2013-03-26 Luitpold Pharmaceuticals, Inc. Xanthones, thioxanthones and acridinones as DNA-PK inhibitors
EP2738154A1 (fr) * 2012-11-30 2014-06-04 Inter-Euro Technology Limited Marqueurs de combustible améliorés
US9594070B2 (en) * 2013-11-05 2017-03-14 Spectrum Tracer Services, Llc Method using halogenated benzoic acid esters and aldehydes for hydraulic fracturing and for tracing petroleum production
US10017684B2 (en) 2016-04-20 2018-07-10 Spectrum Tracer Services, Llc Method and compositions for hydraulic fracturing and for tracing formation water
WO2022161960A1 (fr) 2021-01-29 2022-08-04 Basf Se Procédé de marquage de carburants
US20240219366A1 (en) 2021-04-20 2024-07-04 Basf Se A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector

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FR1450273A (fr) * 1965-10-18 1966-05-06 Warner Lambert Pharmaceutical Préparation utilisable pour la recherche de l'indole produit par les microorganismes
US3930108A (en) * 1974-11-21 1975-12-30 Moore Business Forms Inc 9-(4-Aminophenyl polymethine)-9-xanthenol compounds and pressure sensitive system therewith
US5079127A (en) * 1982-04-06 1992-01-07 Canon Kabushiki Kaisha Optical recording medium and process for recording thereupon
DE3608215A1 (de) * 1986-03-12 1987-09-17 Basf Ag Neue benzopyrane und deren verwendung in aufzeichnungssystemen
JPH0630626B2 (ja) * 1987-07-24 1994-04-27 テルモ株式会社 インド−ル産生能検査用試薬
DE3724757A1 (de) * 1987-07-25 1989-02-09 Basf Ag Benzopyranderivate
GB8802237D0 (en) * 1988-02-02 1988-03-02 Shell Int Research Detection of chemicals by immunoassay
FR2650606B1 (fr) * 1989-08-07 1992-04-30 Aussedat Rey Papier de securite infalsifiable et composition aqueuse ou organique utile, notamment pour rendre un papier infalsifiable
DE4238994A1 (de) * 1992-11-19 1994-05-26 Basf Ag Aniline als Markierungsmittel für Mineralöle

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SK5197A3 (en) 1997-08-06
AU686838B2 (en) 1998-02-12
FI970108L (fi) 1997-03-12
CA2195019A1 (fr) 1996-02-01
IL114442A0 (en) 1995-11-27
CZ9597A3 (en) 1997-06-11
AU2926395A (en) 1996-02-16
BR9508401A (pt) 1998-05-19
TR199500823A2 (tr) 1996-06-21
NO970126L (no) 1997-03-10
WO1996002613A1 (fr) 1996-02-01
HUT76687A (en) 1997-10-28
JPH10502693A (ja) 1998-03-10
BG101156A (bg) 1997-08-29
NO970126D0 (no) 1997-01-10
CO4600746A1 (es) 1998-05-08
FI970108A7 (fi) 1997-03-12
KR970704860A (ko) 1997-09-06
DE4424712A1 (de) 1996-01-18
FI970108A0 (fi) 1997-01-10
PL318378A1 (en) 1997-06-09
MX9700365A (es) 1997-04-30

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