Fuel additives for reducing low speed pre-ignition events

Abstract

Method for preventing or reducing low speed pre-ignition events in a spark-ignited internal combustion engine is provided. The method includes supplying to the engine a fuel composition comprising a primary additive having a structure given by or a salt thereof. R 1 and R 2 are independently H, C 1 -C 20 hydrocarbyl group, carboxyl group, ester, amide, ketone, ether, or hydroxyl group. R 3 and R 4 are independently H, C 1 -C 20 hydrocarbyl group, carboxyl group, ester, amide, ketone, ether, amino, or hydroxyl group or wherein R 3 and R 4 are part of a cyclic group. R 5 is C 1 -C 100 hydrocarbyl group, carboxyl group, ether, or hydroxyl group. Lastly, p is 0 to 2, n is 1 to 5, m is 0 to 2, and p+n+m is less than 6.

1 . A method for preventing or reducing low speed pre-ignition events in a spark-ignited internal combustion engine, the method comprising:
 supplying to the engine a fuel composition comprising a primary additive having a structure given by   
       
         
           
           
               
               
           
         
       
       or a salt there of;
 wherein R 1  and R 2  are independently H, C 1 -C 20  hydrocarbyl group, carboxyl group, ester, amide, ketone, ether, or hydroxyl group; 
 wherein R 3  and R 4  are independently H, C 1 -C 20  hydrocarbyl group, carboxyl group, ester, amide, ketone, ether, amino, or hydroxyl group or wherein R 3  and R 4  are part of a cyclic group; 
 wherein R 5  is C 1 -C 100  hydrocarbyl group, carboxyl group, ether, or hydroxyl group; and 
 wherein p is 0 to 2, n is 1 to 5, m is 0 to 2, and p+n+m is less than 6. 
 
     
     
         2 . The method of  claim 1 , wherein the carboxyl group is a carboxylic acid. 
     
     
         3 . The method of  claim 1 , wherein the cyclic group contains one or more nitrogens or one or more oxygens. 
     
     
         4 . The method of  claim 1 , wherein the primary additive is 2,4,6-tris(dimethyl aminomethyl)phenol, 2-[(dimethylamino)methyl]phenol, 4-(tert-butyl)-2,6-bis((dimethylamino)methyl)phenol, or 2-(tert-butyl)-4,6-bis((dimethylamino)methyl)phenol. 
     
     
         5 . The method of  claim 1 , further comprising:
 a secondary additive or a salt thereof.   
     
     
         6 . The method of  claim 5 , wherein the secondary additive is an acid, phenol, 1,3 dicarbonyl, hydroxyamide, antioxidant, salicylate, or amidine. 
     
     
         7 . The method of  claim 5 , wherein the secondary additive is 2-ethylhexanoic acid, or 1,8-diazabicyclo[5.4.0]-undeca-7-ene. 
     
     
         8 . The method of  claims 1 , R 1  and R 2  are both hydrogen. 
     
     
         9 . The method of  claim 1 , wherein at least one of R 3  and R 4  is a methyl group. 
     
     
         10 . The method of  claim 1 , wherein n is 2 or 3. 
     
     
         11 . A method for preventing or reducing low speed pre-ignition events in a spark-ignited internal combustion engine, the method comprising:
 supplying the engine a fuel composition comprising a phenolic amine having a structure given by   
       
         
           
           
               
               
           
         
       
       or a salt there of;
 wherein R 1  and R 2  are independently H, C 1 -C 20  hydrocarbyl group, carboxyl group, ester, amide, ketone, ether, or hydroxyl group; 
 wherein R 3  and R 4  are independently H, C 1 -C 20  hydrocarbyl group, carboxyl group, ester, amide, ketone, ether, amino, or hydroxyl group or wherein R 3  and R 4  are part of a cyclic group; 
 wherein R 5  is C 1 -C 100  hydrocarbyl group, carboxyl group, ether, or hydroxyl group; 
 wherein p is 0 to 2, n is 1 to 5, m is 0 to 2, and p+n+m is less than 6; and 
 a secondary additive or a salt thereof, wherein the secondary additive is an acid, phenol, 1,3 dicarbonyl, hydroxyamide, antioxidant, salicylate, or amidine. 
 
     
     
         12 . The method of  claim 11 , wherein the carboxyl group is a carboxylic acid. 
     
     
         13 . The method of  claim 11 , wherein the cyclic group contains one or more nitrogens or one or more oxygens. 
     
     
         14 . The method of  claim 11 , wherein the phenolic amine is 2,4,6-tris(dimethyl aminomethyl)phenol, 2-[(dimethylamino)methyl]phenol, 4-(tert-butyl)-2,6-bis((dimethylamino)methyl)phenol, or 2-(tert-butyl)-4,6-bis((dimethylamino)methyl)phenol. 
     
     
         15 . The method of  claim 11 , wherein the secondary additive is 2-ethylhexanoic acid, or 1,8-diazabicyclo[5.4.0]-undeca-7-ene. 
     
     
         16 . The method of  claims 11 , R 1  and R 2  are both hydrogen. 
     
     
         17 . The method of  claim 11 , wherein at least one of R 3  and R 4  is a methyl group. 
     
     
         18 . The method of  claim 11 , wherein n is 2 or 3.