Fuel and related compositions – Liquid fuels – Organic nitrogen compound containing
Patent
1996-03-04
1998-04-14
Raymond, Richard L.
Fuel and related compositions
Liquid fuels
Organic nitrogen compound containing
252401, 436 56, 436 60, 436111, 436112, 508563, 564428, G01N 3328, G01N 3122, C10L 100
Patent
active
057386935
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP94/02824 filed Aug. 25, 1994.
The present invention relates to a novel method for detecting naphthylamines which are present as tracers in mineral oils, wherein the naphthylamine is extracted by treating the mineral oil with an aqueous medium, and is coupled in the aqueous phase with a diazonium salt of an aromatic amine to form an azo dye.
The present invention also relates to the use of specific naphthylamines as tracers for mineral oils and to mineral oils containing these naphthylamines.
U.S. Pat. No. 4,209,302 discloses the use of 1- or 2-(3-morpholinopropylamino)naphthalene, 1- or 2-(3-dimethylaminopropylamino)naphthalene or 1- or 2-(3-diethylaminopropylamino)naphthalene as tracers.
The detection of these compounds is in this case carried out by reacting the appropriate naphthylamines with diazotized 2-chloro-4-nitroaniline. However, it has emerged that this tracer and detection method is not yet completely satisfactory because, inter alia, the stability of the diazonium salt is low.
Anal. Chem., 54 (1982), 91-96, discloses that mineral oils can contain, inter alia, 1- or 2-aminonaphthalenes.
It is an object of the present invention to provide a novel method for detecting mineral oils having naphthylamines as tracers. The novel method ought to be simple to carry out. Moreover, it ought to be possible to render even very small amounts of tracer visible by a strong color reaction. Finally, the tracer should not be removable from the mineral oil by simple extraction with water.
We have found that this object is achieved by detecting the presence of naphthylamines of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted and can be interrupted by 1 to 3 oxygen atoms in ether functionalities or 1 to 3 C.sub.1 -C.sub.4 -alkylimino groups, or C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.18 -alkenyl or unsubstituted or substituted phenyl, or R.sup.1 and R.sup.2 form, together with the nitrogen atom connecting them, a 5- or 6-membered saturated heterocyclic radical which may have another hetero atom, and another, C.sub.1 -C.sub.8 -alkyl, benzyl, cyano, nitro, C.sub.1 -C.sub.4 -alkanoyl, C.sub.1 -C.sub.4 -alkanoylamino, benzoylamino, hydroxysulfonyl or a radical of the formula OL.sup.1, COOL.sup.1, NL.sup.1 L.sup.2 or CONL.sup.1 L.sup.2, where L.sup.1 and L.sup.2 are each hydrogen, unsubstituted or substituted C.sub.1 -C.sub.18 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl or unsubstituted or substituted phenyl, or R.sup.3 together with R.sup.2 is C.sub.3 -alkylene which is unsubstituted or substituted by hydroxyl, and, when the radicals NR.sup.1 R.sup.2 and NL.sup.1 L.sup.2 are in the peri positions, R.sup.1 and L.sup.1 can together also be isopropylidene, the formula I by treating the mineral oil with an aqueous medium and coupling it in the aqueous phase, in the presence or absence of a buffer, with a diazonium salt derived from an amine from the aminoanthraquinone series to form an azo dye.
All alkyl and alkenyl groups occurring in the naphthylamines may be straight-chain or branched.
For the purposes of the invention, alkenyl radicals essentially have from 1 to 3 double bonds.
Examples of suitable substituents for substituted alkyl groups in the abovementioned formula I are, unless otherwise indicated, hydroxyl, amino, morpholinyl or phenyl. These alkyl groups have, as a rule, 1 or 2 substituents.
Examples of suitable substituents for substituted phenyl groups in the abovementioned formula I are C.sub.1 -C.sub.12 -alkyl, hydroxyl or C.sub.1 -C.sub.4 -alkoxy. These phenyl groups have, as a rule, 1 to 3 substituents.
If R.sup.1 and R.sup.2 form, together with the connecting nitrogen atom, a 5- or 6-membered saturated heterocyclic radical, which may have another hetero atom, suitable examples thereof are pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N-(C.sub.1 -C.sub.4 -alkyl.sub.) -piperazinyl.
Examples of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1,
REFERENCES:
patent: 4209302 (1980-06-01), Orelup
patent: 4735631 (1988-04-01), Orelup
patent: 4770802 (1988-09-01), Ishida et al.
Tomkins et al., Anal. Chem. (1982), 54(1), 91-96.
Dyllick-Brenzinger Rainer
Kurtz Walter
Lamm Gunther
Schlosser Ulrike
BASF - Aktiengesellschaft
Raymond Richard L.
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