Tracers and method of marking liquids
Method of marking a hydrocarbon liquid includes: adding thereto, a tracer compound of Formula I: wherein, each A is independently selected from the group consisting of (i) a phenyl group, (ii) a phenyl group substituted with one or more halogen atoms, an aliphatic group or a halogenated aliphatic group, (iii) a partially or fully halogenated alkyl group or (iv) a linear branched or cyclic C 1 -C 20 alkyl group, and each B is independently selected from the group consisting of a (i) phenyl, (ii) phenylmethyl group, (iii) a cyclohexyl group, (iv) a cyclohexylmethyl group, (v) a substituted phenyl or phenylmethyl group in which the benzene ring is substituted by at least one substituent selected from the group consisting of a fluorine atom, a partially or fully halogenated alkyl group and a linear, branched or cyclic C 1 -C 20 alkyl group or (vi) a linear, branched or cyclic C 1 -C 20 alkyl group.
1. A method of marking a hydrocarbon liquid, comprising the step of adding to said liquid, as a tracer compound, a compound of Formula I:
wherein,
each A is independently selected from the group consisting of (i) a phenyl group, (ii) a phenyl group substituted with one or more halogen atoms, an aliphatic group or a halogenated aliphatic group, (iii) a partially or fully halogenated alkyl group and (iv) a linear branched or cyclic C1-C20 alkyl group,
and each B is independently selected from the group consisting of (i) a phenyl group, (ii) an unsubstituted phenylmethyl group, (iii) a substituted phenyl or phenylmethyl group in which the benzene ring is substituted by at least one of the substituents selected from the group consisting of a fluorine atom, a partially or fully halogenated alkyl group and a linear, branched or cyclic C1-C20 alkyl group and (iv) a linear, branched or cyclic C1-C20 alkyl group,
wherein said tracer compound is added to the liquid at a concentration in the range of from 1-1000 micrograms per liter.
2. The method according to claim 1 , wherein after adding the tracer compound to said hydrocarbon liquid and mixing, at least 10% of the tracer compound is retained in the hydrocarbon liquid after a 10 ml sample of the liquid containing from 50 to 1000 μg/l of the tracer compound has been shaken for 2 minutes with 0.5 g of fresh activated charcoal.
3. The method according to claim 1 , wherein after adding the tracer compound to said hydrocarbon liquid and mixing, at least 50% of the tracer compound is retained in the hydrocarbon liquid after a 10 ml sample of the liquid containing from 50 to 1000 μg/l of the tracer compound has been shaken for 2 minutes with 0.5 g of fresh powdered sepiolitic clay.
4. The method according to claim 1 , wherein after adding the tracer compound to said hydrocarbon liquid and mixing, at least 50% of the tracer compound is retained in the hydrocarbon liquid after a sample of the liquid containing from 50 to 1000 μg/l of the tracer compound has been vigorously agitated in contact with an equal volume of up to 5% aqueous HCl.
5. The method according to claim 1 , wherein after adding the tracer compound to said hydrocarbon liquid and mixing, at least 50% of the tracer compound is retained in the hydrocarbon liquid after a sample of the liquid containing from 50 to 1000 μg/l of the tracer compound has been vigorously agitated in contact with an equal volume of up to 5% aqueous H 2 SO 4 .
6. The method according to claim 1 , wherein after adding the tracer compound to said hydrocarbon liquid and mixing, at least 50% of the tracer compound is retained in the hydrocarbon liquid after a sample of the liquid containing from 50 to 1000 μg/l of the tracer compound has been vigorously agitated in contact with an equal volume of up to 5% aqueous HNO 3 .
7. The method according to claim 1 , wherein after adding the tracer compound to said hydrocarbon liquid and mixing, at least 50% of the tracer compound is retained in the hydrocarbon liquid after a sample of the liquid containing from 50 to 1000 μg/l of the tracer compound has been vigorously agitated in contact with 2 Molar aqueous sodium hydroxide solution.
8. The method according to claim 1 , wherein each A is selected from the group consisting of (i) a phenyl group, and (ii) a substituted phenyl group substituted with at least one halogen, alkyl group or halogenated alkyl group.
9. The method according to claim 8 , wherein each A is selected from phenyl, pentafluorophenyl, bis(trifluoromethyl)phenyl or bis(t-butyl)phenyl.
10. The method according to claim 1 , wherein each B is independently selected from:
a phenyl group;
an unsubstituted phenylmethyl group;
a phenylmethyl group in which the benzene ring is substituted by at least one C 1 -C 6 alkyl group, fluorine or halogenated alkyl group; or
a cyclohexylmethyl group.
11. The method according to claim 1 , wherein the tracer compounds are selected from the group consisting of:
(a) 3,6-diphenyl-2,5-di([pentafluorophenyl]methyl)pyrrolo[3,4-c]pyrrole-1,4-dione,
(b) 3,6-diphenyl-2,5-di([3,5-bistrifluoromethylphenyl]methyl)pyrrolo[3,4-c]pyrrole-1,4-dione,
(c) 3,6-diphenyl-2,5-di([3,5-bis(t-butyl)-phenyl]methyl)pyrrolo[3,4-c]pyrrole-1,4-dione, and
(d) 3,6-Di(3,5-bistrifluoromethylphenyl)-2,5-di(cyclohexylmethyl)pyrrolo[3,4-c]pyrrole-1,4-dione.
12. The method according to claim 1 , wherein the hydrocarbon liquid contains more than one tracer compound.
13. The method according to claim 1 , wherein the hydrocarbon liquid comprises a diesel fuel, a gasoline fuel or a solvent.
14. The method according to claim 1 , wherein the tracer compound is added to the hydrocarbon liquid in the form of a concentrated dosing solution of the tracer compound in a solvent.
15. A liquid composition comprising a mixture of a hydrocarbon liquid and from 1 μg/l to 10 mg/l of a tracer compound, wherein said tracer compound comprises a compound of Formula I:
wherein,
each A is independently selected from the group consisting of (i) a phenyl group, (ii) a phenyl group substituted with one or more halogen atoms, an aliphatic group or a halogenated aliphatic group, (iii) a partially or fully halogenated alkyl group or (iv) a linear branched or cyclic C 1 -C 20 alkyl group,
and each B is independently selected from the group consisting of (i) a phenyl group, (ii) an unsubstituted phenylmethyl group, (iii) a substituted phenyl or phenylmethyl group in which the benzene ring is substituted by at least one of the substituents selected from the group consisting of a fluorine atom, a partially or fully halogenated alkyl group and a linear, branched or cyclic C 1 -C 20 alkyl group and (iv) a linear, branched or cyclic C 1 -C 20 alkyl group.
16. The liquid composition according to claim 15 , wherein each A is selected from a phenyl group, a substituted phenyl group substituted with at least one halogen, alkyl group or halogenated alkyl group.
17. The liquid composition according to claim 16 , wherein each A is selected from pentafluorophenyl, bis(trifluoromethyl)phenyl or bis(t-butyl) phenyl.
18. The liquid composition according to claim 15 , wherein each B is independently selected from:
a phenyl group;
unsubstituted phenylmethyl group;
a phenylmethyl group in which the benzene ring is substituted by at least one C 1 -C 6 alkyl group, fluorine or halogenated alkyl group; or
a cyclohexylmethyl group.
19. The liquid composition according to claim 15 , wherein the tracer compound is selected from the group consisting of:
(a) 3,6-diphenyl-2,5-di([pentafluorophenyl]methyl)pyrrolo[3,4-c]pyrrole-1,4-dione
(b) 3,6-diphenyl-2,5-di([3,5-bistrifluoromethylphenyl]methyl)pyrrolo[3,4-c]pyrrole-1,4-dione
(c) 3,6-diphenyl-2,5-di([3,5-bis(t-butyl)-phenyl]methyl)pyrrolo[3,4-c]pyrrole-1,4-dione
(d) 3,6-di(3,5-bistrifluoromethylphenyl)-2,5-di(cyclohexylmethyl)pyrrolo[3,4-c]pyrrole-1,4-dione.
20. The liquid composition according to claim 15 , wherein the hydrocarbon liquid contains more than one tracer compound.
21. The liquid composition according to claim 15 , wherein the hydrocarbon liquid comprises a diesel fuel, a gasoline fuel or a solvent.
22. A liquid composition made by the method of claim 1 .