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WO1996002613A1 - Utilisation de benzaldehydes pour marquer des hydrocarbures - Google Patents

Utilisation de benzaldehydes pour marquer des hydrocarbures Download PDF

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Publication number
WO1996002613A1
WO1996002613A1 PCT/EP1995/002558 EP9502558W WO9602613A1 WO 1996002613 A1 WO1996002613 A1 WO 1996002613A1 EP 9502558 W EP9502558 W EP 9502558W WO 9602613 A1 WO9602613 A1 WO 9602613A1
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WO
WIPO (PCT)
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.)
Ceased
Application number
PCT/EP1995/002558
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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
Priority to KR1019970700194A priority Critical patent/KR970704860A/ko
Priority to FI970108A priority patent/FI970108A7/fi
Priority to SK51-97A priority patent/SK5197A3/sk
Priority to BR9508401A priority patent/BR9508401A/pt
Priority to MX9700365A priority patent/MX9700365A/es
Priority to AU29263/95A priority patent/AU686838B2/en
Application filed by BASF SE filed Critical BASF SE
Priority to EP95924960A priority patent/EP0770119A1/fr
Priority to JP8504633A priority patent/JPH10502693A/ja
Publication of WO1996002613A1 publication Critical patent/WO1996002613A1/fr
Priority to NO970126A priority patent/NO970126L/no
Anticipated expiration legal-status Critical
Priority to BG101156A priority patent/BG101156A/xx
Ceased 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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  • Chemical & Material Sciences (AREA)
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  • Medicinal Chemistry (AREA)
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  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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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, R2 et R3¿ désignent hydrogène, hydroxy, alkyle C¿1?-C15, alcoxy C1-C15, cyano, nitro ou un reste de la formule NR?4R5¿ ou COOR6, R4 désignant hydrogène ou alkyle C¿1?-C15 éventuellement substitué, R?5¿ désignant alkyle C¿1?-C15 éventuellement substitué ou un reste de la formule L-NX?1X2¿, dans laquelle L désigne alkylène C¿2?-C8 et X?1 et X2¿ désignent, indépendamment l'un de l'autre, alkyle C¿1?-C6 ou conjointement avec l'atome d'azote qui les lie, un reste hétérocyclique, et R?6¿ désignant hydrogène, alkyle C¿1?-C15 éventuellement substitué ou un reste de la formule L-NX?1X2¿, dans laquelle L, X1 et X2 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.
PCT/EP1995/002558 1994-07-13 1995-07-03 Utilisation de benzaldehydes pour marquer des hydrocarbures Ceased WO1996002613A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
EP95924960A EP0770119A1 (fr) 1994-07-13 1995-07-03 Utilisation de benzaldehydes pour marquer des hydrocarbures
FI970108A FI970108A7 (fi) 1994-07-13 1995-07-03 Bentsaldehydien käyttö hiilivetyjen merkitsemiseen
SK51-97A SK5197A3 (en) 1994-07-13 1995-07-03 Use of benzaldehyde derivative to mark hydrocarbons, proofing method for the benzaldehyde derivative presence in hydrocarbons and hydrocarbons containing the benzaldehyde derivative
BR9508401A BR9508401A (pt) 1994-07-13 1995-07-03 Uso de benzaldeídos processo de detecção de benzaldeídos e hidrocarboneto com um marcador
MX9700365A MX9700365A (es) 1994-07-13 1995-07-03 Uso de benzaldehidos para asignar hidrocarburos.
KR1019970700194A KR970704860A (ko) 1994-07-13 1995-07-03 탄화 수소 표지용 벤즈알데히드의 용도
JP8504633A JPH10502693A (ja) 1994-07-13 1995-07-03 炭化水素をマーキングするためのベンズアルデヒドの使用
AU29263/95A AU686838B2 (en) 1994-07-13 1995-07-03 Use of benzaldehydes to mark hydrocarbons
NO970126A NO970126L (no) 1994-07-13 1997-01-10 Anvendelse av benzaldhyder for markering av hydrokarboner
BG101156A BG101156A (bg) 1994-07-13 1997-01-21 Използване на бензалдехиди за маркиране на въглеводороди

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4424712A DE4424712A1 (de) 1994-07-13 1994-07-13 Verwendung von Benzaldehyden zum Markieren von Kohlenwasserstoffen
DEP4424712.5 1994-07-13

Publications (1)

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WO1996002613A1 true WO1996002613A1 (fr) 1996-02-01

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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)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2738154A1 (fr) * 2012-11-30 2014-06-04 Inter-Euro Technology Limited Marqueurs de combustible améliorés
WO2022161960A1 (fr) 2021-01-29 2022-08-04 Basf Se Procédé de marquage de carburants
WO2022223384A1 (fr) 2021-04-20 2022-10-27 Basf Se Procédé de détection d'un ou de plusieurs marqueurs dans un carburant pétrolier à l'aide d'un détecteur photoacoustique

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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
NZ535892A (en) * 2002-04-26 2006-11-30 Bp Oil Int Method and apparatus for improving the oxidative thermal stability of jet fuel
JP2006523681A (ja) 2003-03-24 2006-10-19 ルイトポルド・ファーマシューティカルズ・インコーポレーテッド Ｄｎａ−ｐｋ阻害剤としてのキサントン、チオキサントンおよびアクリジノン
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

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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
EP0236973A2 (fr) * 1986-03-12 1987-09-16 BASF Aktiengesellschaft Benzopyranes et leur usage dans un système d'enregistrement
JPS6428559A (en) * 1987-07-24 1989-01-31 Terumo Corp Reagent for inspection of indole production capacity
EP0304613A1 (fr) * 1987-07-25 1989-03-01 BASF Aktiengesellschaft Dérivés de benzopyranne
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
US5079128A (en) * 1982-04-06 1992-01-07 Canon Kabushiki Kaisha Optical recording medium and process for recording thereupon
DE4238994A1 (de) * 1992-11-19 1994-05-26 Basf Ag Aniline als Markierungsmittel für Mineralöle

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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
US5079128A (en) * 1982-04-06 1992-01-07 Canon Kabushiki Kaisha Optical recording medium and process for recording thereupon
EP0236973A2 (fr) * 1986-03-12 1987-09-16 BASF Aktiengesellschaft Benzopyranes et leur usage dans un système d'enregistrement
JPS6428559A (en) * 1987-07-24 1989-01-31 Terumo Corp Reagent for inspection of indole production capacity
EP0304613A1 (fr) * 1987-07-25 1989-03-01 BASF Aktiengesellschaft Dérivés de benzopyranne
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
DE4238994A1 (de) * 1992-11-19 1994-05-26 Basf Ag Aniline als Markierungsmittel für Mineralöle

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2738154A1 (fr) * 2012-11-30 2014-06-04 Inter-Euro Technology Limited Marqueurs de combustible améliorés
WO2014083186A3 (fr) * 2012-11-30 2014-09-12 Inter-Euro Technology Limited Marqueurs de combustible améliorés
WO2022161960A1 (fr) 2021-01-29 2022-08-04 Basf Se Procédé de marquage de carburants
WO2022223384A1 (fr) 2021-04-20 2022-10-27 Basf Se Procédé de détection d'un ou de plusieurs marqueurs dans un carburant pétrolier à l'aide d'un détecteur photoacoustique

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FI970108A0 (fi) 1997-01-10
JPH10502693A (ja) 1998-03-10
AU686838B2 (en) 1998-02-12
CZ9597A3 (en) 1997-06-11
AU2926395A (en) 1996-02-16
KR970704860A (ko) 1997-09-06
HUT76687A (en) 1997-10-28
CA2195019A1 (fr) 1996-02-01
IL114442A0 (en) 1995-11-27
CO4600746A1 (es) 1998-05-08
NO970126L (no) 1997-03-10
EP0770119A1 (fr) 1997-05-02
PL318378A1 (en) 1997-06-09
BG101156A (bg) 1997-08-29
MX9700365A (es) 1997-04-30
BR9508401A (pt) 1998-05-19
DE4424712A1 (de) 1996-01-18
TR199500823A2 (tr) 1996-06-21
FI970108A7 (fi) 1997-03-12
NO970126D0 (no) 1997-01-10
SK5197A3 (en) 1997-08-06

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