Azo dyes and a method of making a hydrocarbon using an azo dye

Fuel and related compositions – Liquid fuels – Organic azide compound – or organic compound having acyclic...

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208 12, 208 15, 208 16, 534797, 534802, 534804, 534832, 534831, 534843, 534851, 534876, 534852, 534860, 534DIG1, C10L 122, C10L 104, C09B 29095, C09B 29085, G09B 21053

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058273328

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP94/04091 filed Dec. 9, 1994.


BACKGROUND OF THE INVENTION



FIELD OF THE INVENTION

The present invention relates to the use of azo dyes of the formula I ##STR2## where the ring A may be benzofused, from 1 to 4 ether oxygen atoms, ether oxygen atoms, or a radical of the formula L--NX.sup.1 X.sup.2, where L is C.sub.2 -C.sub.8 -alkylene and X.sup.1 and X.sup.2 independently of one another are each C.sub.1 -C.sub.6 -alkyl or, together with the nitrogen atom linking them, form a 5-membered or 6-membered saturated heterocyclic radical which may furthermore contain an oxygen atom in the ring, are each hydrogen, C.sub.1 -C.sub.15 -alkyl or C.sub.1 -C.sub.15 -alkoxy and cyano, nitro or a radical of the formula COOX.sup.3, where X.sup.3 is hydrogen, C.sub.1 -C.sub.15 -alkyl which may be interrupted by from 1 to 4 ether oxygen atoms, or is a radical of the formula L--NX.sup.1 X.sup.2, where L, X.sup.1 and X.sup.2 each have the abovementioned meanings, abovementioned azo dyes, a process for detecting these azo dyes in hydrocarbons and novel azo dyes.


DISCUSSION OF THE BACKGROUND

U.S. Pat. No. 5,145,573, U.S. Pat. No. 5,182,372 and EP-A-499 845 disclose azo dyes which serve as markers for mineral oils. However, it has been found that the dyes described there exhibit insufficient dilutability in hydrocarbons.
U.S. Pat. No. 4,009,008 furthermore describes a process for marking mineral oils by means of azo dyes, in which the dye added to the mineral oil is rendered visible by adding to the marked mineral oil an adsorbent which binds other colored components of the mineral oil.
It is an object of the present invention to provide novel markers for hydrocarbons. The novel markers should be easily obtainable and readily soluble in hydrocarbons. Moreover, they should be detectable in a simple manner. Even very small amounts of marker should be capable of being rendered visible by a strong color reaction.


SUMMARY OF THE INVENTION

We have found that this object is achieved and that the azo dyes of the formula I which are defined at the outset can advantageously be used as pH-dependent markers for hydrocarbons.


DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

All alkyl and alkylene radicals occurring in the formula stated here may be either straight-chain or branched.
If X.sup.1 and X.sup.2, together with the nitrogen atom linking them, form a 5-membered or 6-membered saturated heterocyclic radical which may furthermore contain an oxygen atom in the ring, examples of said radicals which are suitable are pyrrolidinyl, piperidinyl and morpholinyl.
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, X.sup.1, X.sup.2 and X.sup.3 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and X.sup.3 are furthermore, for example, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl, tetradecyl or pentadecyl (the above names isooctyl, isononyl, isodecyl and isotridecyl are trivial names and originate from the alcohols obtained by the oxo synthesis; cf. Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A1, pages 290 to 293, and Vol. A 10, pages 284 and 285).
R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 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.
L is, for example, (CH.sub.2).sub.2, (CH.sub.2).sub.3, (CH.sub.2).sub.4, (CH.sub.2).sub.5, (CH.sub.2).sub.6, (CH.sub.2).sub.7, (CH.sub.2).sub.8, CH(CH.sub.3)CH.sub.2 or CH(CH.sub.3)CH(CH.sub.3).
R.sup.1, R.sup.2 and X

REFERENCES:
patent: 3218309 (1965-11-01), Elslager et al.
patent: 4011209 (1977-03-01), Defeo et al.
patent: 4037007 (1977-07-01), Wood
patent: 4186243 (1980-01-01), Astbury et al.
patent: 4268439 (1981-05-01), Kruckenberg
patent: 4315756 (1982-02-01), Zeidler et al.
patent: 4840884 (1989-06-01), Mooberry et al.
patent: 4904765 (1990-02-01), Derber et al.
patent: 5247071 (1993-09-01), Hansen et al.
patent: 5266227 (1993-11-01), Reichelt et al.
patent: 5364745 (1994-11-01), Mooberry et al.

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