Fuel Markers and Methods of Producing and Using Same

Abstract

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.

What is claimed is: 
     
         1 . A 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 greater than about 300 at an ionization energy of equal to or greater than about 70 eV. 
       
     
     
         2 . The compound of  claim 1  wherein X is O or S and R 1  and R 2  are lone non-bonding electron pairs. 
     
     
         3 . The compound of  claim 1  wherein the compound characterized by Formula I has Structure A: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The compound of  claim 1  wherein the compound characterized by Formula I has Structures B-F: 
       
         
           
           
               
               
           
         
       
     
     
         5 . The compound 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 nonyl 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 compound of  claim 1  wherein the compound characterized by Formula I has any of Structures G-O: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         7 . The compound 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 compound 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 compound of  claim 7  wherein the compound characterized by Formula I has Structure P: 
       
         
           
           
               
               
           
         
       
     
     
         10 . The compound of  claim 1  wherein X is C and R 3  and R 3′  can each independently be a methyl group or hydrogen. 
     
     
         11 . The compound of  claim 1  wherein X is C and R 4  and R 4′  can each independently be 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. 
     
     
         12 . The compound 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 compound of  claim 1  wherein R 4  and R 4′  are hydrogen. 
     
     
         14 . The compound of  claim 1  wherein R 4  and R 4′  can each independently be hydrogen or a tert-butyl group. 
     
     
         15 . The compound of  claim 1  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 compound of  claim 1  wherein R 5  and R 5′  are both a pentyl group or a heptyl group. 
     
     
         17 . The compound 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 compound of  claim 1  wherein X is O and R 5  and R 5′  are a heptyl group. 
     
     
         19 . The compound of  claim 1  wherein X is O or S and R 3 , R 3′ , R 7  and R 7′  can each independently be hydrogen or a methyl group. 
     
     
         20 . The compound 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.; wherein the solvent is miscible with a fuel; and 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.