Fuel lubricity additives

Abstract

A fuel lubricity additive is disclosed comprising an imidazoline. The fuel lubricity additive may be prepared by reacting an optionally substituted organic acid with an optionally substituted polyamine. Fuel compositions are also disclosed, comprising a fuel and the fuel lubricity additive. Processes for reducing wear in an engine, for example an internal combustion engine, using the fuel lubricity additive are disclosed.

1 . A fuel lubricity additive comprising an imidazoline of the following formula:  
       
         
           
           
               
               
           
         
       
       wherein: 
 R is chosen from saturated and unsaturated, linear, aromatic, branched, and cyclic hydrocarbyl groups, which are unsubstituted or substituted with at least one of hydroxyl, nitro, amino, and cyano groups;  
 R′ is independently chosen from hydrogen, hydroxyl, nitro, amino, cyano, and saturated and unsaturated, linear, aromatic, branched and cyclic hydrocarbyl groups;  
 A is chosen from SH, OH and NY 2  groups; and  
 Y is independently chosen from hydrogen and saturated and unsaturated, linear, aromatic, branched and cyclic hydrocarbyl groups, which are unsubstituted or substituted with at least one of hydroxyl, nitro, amino, and cyano groups.  
 
     
     
         2 . The fuel lubricity additive according to  claim 1 , wherein R is chosen from hydrocarbyl groups having from 10 to 20 carbon atoms, and A is an amino group.  
     
     
         3 . The fuel lubricity additive according to  claim 1 , wherein R′ is hydrogen, and A is NH 2 .  
     
     
         4 . The fuel lubricity additive according to  claim 1 , wherein A is chosen from —SH, —OH and —NY 2  groups.  
     
     
         5 . A fuel lubricity additive comprising an imidazoline, wherein said imidazoline is prepared by a process comprising reacting a compound of formula (I):  
       
         
           
           
               
               
           
         
         with a compound of formula (II):  
         
           
             
             
                 
                 
             
           
         
         to yield an imidazoline of formula (III):  
         
           
             
             
                 
                 
             
           
         
         wherein:  
         R is chosen from saturated and unsaturated, linear, aromatic, branched, and cyclic hydrocarbyl groups, and is unsubstituted or substituted with at least one of hydroxyl, nitro, amino, and cyano groups;  
         R′ is independently chosen from hydrogen, hydroxyl, nitro, amino, cyano, and saturated and unsaturated, linear, aromatic, branched and cyclic hydrocarbyl groups;  
         A is chosen from —SH, OH and NY 2  groups; and  
         Y is independently chosen from hydrogen and saturated and unsaturated, linear, aromatic, branched and cyclic hydrocarbyl groups, each of which is unsubstituted or substituted with at least one of hydroxyl, nitro, amino, and cyano groups.  
       
     
     
         6 . The fuel lubricity additive according to  claim 5 , wherein R is chosen from hydrocarbyl groups having from 10 to 20 carbon atoms.  
     
     
         7 . The fuel lubricity additive according to  claim 5 , wherein R′ is hydrogen.  
     
     
         8 . The fuel lubricity additive according to  claim 5 , wherein A is chosen from —SH, —OH and —NH 2  groups.  
     
     
         9 . The fuel lubricity additive according to  claim 5 , wherein compounds (I) and (II) are reacted together in a molar ratio ranging from 1:2 to 2:1.  
     
     
         10 . The fuel lubricity additive according to  claim 5 , wherein compounds (I) and (II) are reacted together in a molar ratio ranging from 0.8:1 to 1:0.8.  
     
     
         11 . The fuel lubricity additive according to  claim 5 , wherein the fuel is a diesel fuel.  
     
     
         12 . The fuel lubricity additive according to  claim 5 , wherein the fuel is a biodiesel fuel.  
     
     
         13 . The fuel lubricity additive according to  claim 5 , wherein the fuel is gasoline.  
     
     
         14 . The fuel lubricity additive according to  claim 5 , wherein the R is chosen from linear alkenyl groups.  
     
     
         15 . The fuel lubricity additive according to  claim 5 , wherein the compound of formula (I) is chosen from 9,10-decylenic acid, octenoic acid, linoleic acid, naphthenic acid, and a tall oil fatty acid.  
     
     
         16 . The fuel lubricity additive according to  claim 5 , wherein the compound of formula (II) is chosen from ethylene diamine, aminoethyl ethanolamine, and diethylenetriamine.  
     
     
         17 . The fuel lubricity additive according to  claim 5 , wherein the compound of formula (I) is isostearic acid and the compound of formula (II) is aminoethyl ethanolamine.  
     
     
         18 . The fuel lubricity additive according to  claim 5 , wherein the compound of formula (I) is naphthenic acid and the compound of formula (II) is aminoethyl ethanolamine.  
     
     
         19 . The fuel lubricity additive according to  claim 5 , wherein the compound of formula (I) is isostearic acid and the compound of formula (II) is diethylenetriamine.  
     
     
         20 . The fuel lubricity additive according to  claim 5 , wherein the compound of formula (I) is a tall oil fatty acid and the compound of formula (II) is diethylenetriamine.  
     
     
         21 . The fuel lubricity additive according to  claim 5 , wherein the compound of formula (I) is isostearic acid and the compound of formula (II) is diethylenetriamine.  
     
     
         22 . The fuel lubricity additive according to  claim 5 , wherein the compound of formula (I) is a tall oil fatty acid and the compound of formula (II) is aminoethyl ethanolamine.  
     
     
         23 . The fuel lubricity additive according to  claim 5 , wherein said imidazoline is prepared under batch process conditions.  
     
     
         24 . The fuel lubricity additive according to  claim 5 , wherein said imidazoline is prepared under continuous process conditions.  
     
     
         25 . A fuel composition comprising: 
 (A) a fuel in major amount; and    (B) a fuel lubricity additive according to  claim 1  in a minor amount.    
     
     
         26 . The fuel composition according to  claim 25 , wherein the fuel is gasoline, or a gasoline-alcohol blend.  
     
     
         27 . The fuel composition according to  claim 25 , wherein the fuel is a diesel fuel, or diesel fuel-alcohol blend.  
     
     
         28 . The fuel composition according to  claim 25 , wherein the fuel is a biodiesel fuel.  
     
     
         29 . The fuel composition according to  claim 25 , wherein the fuel comprises an emulsion of diesel fuel and water or ethanol.  
     
     
         30 . The fuel composition according to  claim 25 , further comprising at least one of dispersants, detergents, oxygenates, antioxidants, carrier fluids, metal deactivators, dyes, markers, pour-point depressants, corrosion inhibitors, biocides, cetane improvers, antistatic additives, stabilizers, anti-foam agents, drag-reducing agents, demulsifiers, dehazers, anti-icing additives, anti-knock additives, anti-valve-seat recession additives, additional lubricity additives, and combustion improvers.  
     
     
         31 . An anti-wear composition comprising the fuel lubricity additive according to  claim 1 , wherein said fuel lubricity additive is present in an amount sufficient to reduce the wear in an internal combustion engine.  
     
     
         32 . A friction modifying composition comprising the fuel lubricity additive according to  claim 1 , wherein said fuel lubricity additive is present in a fuel in an amount sufficient to modify the friction of the fuel.  
     
     
         33 . A process for improving the lubricity of a fuel composition in an engine, comprising operating said engine with a fuel comprising a fuel lubricity additive according to  claim 1 .  
     
     
         34 . A process for improving the lubricity of a fuel composition in an engine, comprising operating said engine with a fuel composition according to  claim 25 .  
     
     
         35 . The process according to  claim 34 , wherein said fuel composition comprises gasoline.  
     
     
         36 . The process according to  claim 34 , wherein said fuel composition comprises a diesel fuel.  
     
     
         37 . The process according to  claim 34 , wherein said fuel composition comprises a biodiesel fuel.  
     
     
         38 . A process for improving the fuel economy of an internal combustion engine comprising using as a fuel in the internal combustion engine the fuel composition according to  claim 25 , wherein the fuel lubricity additive is present in an amount sufficient to improve the fuel economy of the internal combustion engine using the fuel composition, as compared to the engine operated in the same manner and using the same fuel except that the fuel is devoid of the fuel lubricity additive.  
     
     
         39 . The process according to  claim 38 , wherein the fuel lubricity additive is present in the fuel composition in an amount ranging from 25 to 150 ptb.  
     
     
         40 . The process according to  claim 38 , wherein the fuel lubricity additive is present in the fuel composition in an amount ranging from 40 to 60 ptb.  
     
     
         41 . A process for reducing wear in an internal combustion engine comprising using as a fuel for the internal combustion engine the fuel composition of  claim 25 , wherein the fuel lubricity additive is present in an amount sufficient to reduce the wear in an internal combustion engine operated using the fuel composition, as compared to the wear in the engine operated in the same manner and using the same fuel except that the fuel is devoid of the fuel lubricity additive.  
     
     
         42 . The process according to  claim 41 , wherein the fuel lubricity additive is present in the fuel composition in an amount ranging from 25 to 150 ptb.  
     
     
         43 . The process according to  claim 41 , wherein the fuel lubricity additive is present in the fuel composition in an amount ranging from 40 to 60 ptb.  
     
     
         44 . A process for providing friction modification in an internal combustion engine comprising using as a fuel for the internal combustion engine the fuel composition of  claim 25 , wherein the fuel lubricity additive is present in an amount sufficient to reduce the wear in an internal combustion engine operated using the fuel composition, as compared to the wear in the engine operated in the same manner and using the same fuel except that the fuel is devoid of the fuel lubricity additive.  
     
     
         45 . The process according to  claim 44 , wherein the fuel lubricity additive is present in the fuel composition in an amount ranging from 25 to 150 ptb.  
     
     
         46 . The process according to  claim 44 , wherein the fuel lubricity additive is present in the fuel composition in an amount ranging from 40 to 60 ptb.