Fuel markers and methods of producing and using same
View Patent ↗A composition comprising a fuel and at least one compound characterized by Formula I: wherein X is carbon, oxygen, or sulfur; R 1 and R 2 each independently are hydrogen, a C 1 to C 20 alkyl, or a C 6 to C 10 aryl; R 3 and R 3′ each independently are hydrogen or a C 1 to C 4 alkyl; R 4 and R 4′ each independently are hydrogen, a C 1 to C 4 alkyl, a C 4 to C 10 cycloalkyl, or a C 6 to C 10 aryl; R 5 and R 5′ each independently are a C 4 to C 10 alkyl; R 6 and R 6′ each independently are hydrogen or a C 1 to C 6 alkyl; and R 7 and R 7′ each independently are hydrogen or a C 1 to C 4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than about 70 eV produces at least one ion having a mass-to-charge ratio of from 300 to 600.
1. A composition comprising (a) a fuel and (b) at least one compound characterized by Formula I:
wherein X can be carbon (C), oxygen (O), or sulfur (S); R 1 and R 2 can each independently be hydrogen, a C 1 to C 20 alkyl group, or a C 6 to C 10 aryl group; R 3 and R 3′ can each independently be hydrogen or a C 1 to C 4 alkyl group; R 4 and R 4′ can each independently be hydrogen, a C 1 to C 4 alkyl group, a C 4 to C 10 cycloalkyl group, or a C 6 to C 10 aryl group; R 5 and R 5′ can each independently be a C 4 to C 10 alkyl group; R 6 and R 6′ can each independently be hydrogen or a C 1 to C 6 alkyl group; and R 7 and R 7′ can each independently be hydrogen or a C 1 to C 4 alkyl group; and wherein the compound characterized by Formula I when subjected to gas chromatography mass spectrometry (GC-MS) using electron ionization produces at least one ion having a mass-to-charge ratio of from about 300 to about 600 at an ionization energy of equal to or greater than about 70 eV.
2. The composition of claim 1 wherein X is O or S and R 1 and R 2 are lone non-bonding electron pairs.
3. The composition of claim 1 wherein the compound characterized by Formula I has Structure A:
4. The composition of claim 1 wherein the compound characterized by Formula I has Structures B-F:
5. The composition of claim 1 . wherein X is C and R 1 and R 2 each independently are selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a n-pentyl group, an iso-pentyl group, a sec-pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyi group, a decyl group, a undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group and a nonadecyl group.
6. The composition of claim 1 wherein the compound characterized by Formula I has any of Structures G-O:
7. The composition of claim 1 wherein X is C and R 1 and R 2 can each independently be hydrogen, a C 1 to C 10 alkyl group, or a C 6 to C 10 aryl group.
8. The composition of claim 7 wherein the C 6 to C 10 aryl group is phenyl, a substituted phenyl, tolyl, a substituted tolyl, xylyl or a substituted xylyl.
9. The composition of claim 7 wherein the compound characterized by Formula I has Structure P:
10. The composition of claim 1 wherein X is C and R 3 and R 3′ can each independently be a methyl group or hydrogen.
11. The composition of claim 1 wherein X is C and R 4 , and R 4′ can each independently be a C 1 to C 10 alkyl group, a C 4 to C 10 cycloalkyl group, or a C 6 to C 10 aryl group.
12. The composition of claim 11 wherein the C 4 to C 10 cycloalkyl group is a cyclobutyl group, a substituted cyclobutyl group, a cyclopentyl group, a substituted cyclopentyl group, a cyclohexyl group, a substituted cyclohexyl group, a cycloheptyl group, a substituted cycloheptyl group, a cyclooctyl group, or a substituted cyclooctyl group.
13. The composition of claim 1 wherein R 4 and R 4′ are hydrogen.
14. The composition of claim 1 wherein R 4 and R 4′ can each independently be hydrogen or a tent-butyl group.
15. The composition of claim wherein X is C, R 1 and R 2 are a methyl group, and R 5 and R 5′ are both a C 4 to C 10 alkyl group.
16. The composition of claim 15 wherein R 5 and R 5′ are both a pentyl group or a heptyl group.
17. The composition of claim 1 wherein R 6 and R 6′ each independently are selected from the group consisting of a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a n-pentyl group, an iso-pentyl group, a sec-pentyl group and a hexyl group.
18. The composition of claim 1 wherein the fuel comprises gasoline, diesel, jet fuel, kerosene, non-petroleum derived fuels, alcohol fuels, ethanol, methanol, propanol, butanol, biodiesel, maritime fuels, or combinations thereof.
19. The composition of claim 1 wherein the compound characterized by Formula I is present in an amount of from about 1 ppb to about 50 ppm, based on the total weight of the composition.
20. The composition of claim 1 wherein R 3 and R 3′ are hydrogen.
21. The composition of claim 1 wherein R 6 and R 6′ are hydrogen.
22. The composition of claim 1 wherein R 7 and R 7′ are hydrogen.
23. The composition of claim 2 wherein R 3 , R 3′ , R 7 and R 7′ are hydrogen.
24. The composition of claim 1 wherein X is S and R 6 and R 6′ can each independently be hydrogen or a Cert-butyl group.
25. The composition of claim 1 wherein X is S and R 4 and R 4′ are a methyl group.
26. The composition of claim 1 wherein X is O and R 5 and R 5′ are a heptyl group.
27. The composition of claim 26 wherein the compound characterized by Formula I has Structure A:
28. The composition of claim 1 wherein X is S and R 7 and R 7′ can each independently be hydrogen or a methyl group.
29. The composition of claim 28 wherein the compound characterized by Formula I. has Structure F:
30. The composition of claim 1 wherein the C 1 to C 4 alkyl group is a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a sec-butyl group, or a tort-Butyl group.
31. The composition of claim 1 wherein the C 6 to 10 aryl group is a phenyl group.
32. The composition of claim 1 wherein the compound characterized by Formula I is soluble in a solvent characterized by a flash point greater than about 60° C., and wherein the solvent is miscible with the fuel.
33. The composition of claim 32 wherein the compound characterized by Formula I is characterized by a solubility in the solvent of equal to or greater than about 50% at 25°C.
34. The composition of claim 32 wherein the solvent comprises non-polar solvents, hydrocarbons, aromatic hydrocarbons, mineral spirits, halogenated hydrocarbons, polar solvents, aprotic polar solvents, N-methylpyrollidone, ethers, carbonates, esters, ketones, aldehydes, alcohols, 2-ethylhexanol, nitriles, or combinations thereof.
35. The composition of claim 1 wherein the compound characterized by Formula I is resistant to laundering.
36. The composition of claim 35 wherein the compound characterized by Formula I is resistant to extraction and/or masking.