Fuel Markers and Methods of Producing and Using Same

Abstract

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.

1 . A compound characterized by Formula I: 
       
         
           
           
               
               
           
         
         wherein X can be carbon (C), oxygen (O), or sulfur (S); wherein, when X is C, 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, and wherein the C 6  to C 10  aryl group is a hydrocarbon; wherein, when X is O or S, R 1  and R 2  are lone non-bonding electron pairs; 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 300 at an ionization energy of equal to or greater than 70 eV. 
       
     
     
         2 . (canceled) 
     
     
         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 8  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 10  alkyl group, a C 4  to C 10  cycloalkyl group, or a C 6  to C 10  aryl group. 
     
     
         12 . The compound of  claim 1  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 . A composition comprising a fuel and a marker compound wherein the marker compound 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 300 at an ionization energy of equal to or greater than 70 eV. 
     
     
         18 . The composition of  claim 17  wherein the marker compound is characterized by Formula I: 
       
         
           
           
               
               
           
         
         wherein X can be carbon (C), oxygen (O), or sulfur (S); wherein, when X is C, 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, and wherein the C 6  to C 10  aryl group is a hydrocarbon; wherein, when X is O or S, R 1  and R 2  are lone non-bonding electron pairs, 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 1  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. 
       
     
     
         19 . The composition of  claim 17  wherein the marker compound is characterized by Structure A: 
       
         
           
           
               
               
           
         
       
     
     
         20 . The composition of  claim 17  wherein the marker compound is characterized by Structures B-F: 
       
         
           
           
               
               
           
         
       
     
     
         21 . The compound of  claim 1  wherein R 3  and R 3′  are hydrogen.