Fuel additive compounds and method of making the compounds

Abstract

The present application is directed to detergent base products and processes for forming the detergent base products. One embodiment of the process comprises forming a bis-Mannich intermediate compound by reacting (i) at least one hydroxyl substituted aromatic ring compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight of about 500 to about 3000; (ii) at least one primary amine; and (iii) at least one aldehyde. The resulting bis-Mannich intermediate compound is then reacted with at least one second amine compound chosen from primary and secondary amines to form the detergent base product.

1 . A process for forming a detergent base product, the process comprising:
 forming a bis-Mannich intermediate compound by reacting (i) at least one hydroxyl substituted aromatic ring compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight of about 500 to about 3000; (ii) at least one primary amine; and (iii) at least one aldehyde; and   reacting the bis-Mannich intermediate compound with at least one second amine compound chosen from primary and secondary amines to form the detergent base product.   
     
     
         2 . The process of  claim 1 , wherein at least one hydroxyl substituted aromatic ring compound has a formula 1, 
       
         
           
           
               
               
           
         
         where R 1 , R 2  and R 3  are substituents independently chosen from a hydrogen radical, C 1-6  alkyls and hydrocarbyl substituents having a number average molecular weight in the range of about 500 to about 3000, with the proviso that at least one of R 1 , R 2  and R 3  is a hydrocarbyl substitutent. 
       
     
     
         3 . The process of  claim 2 , wherein one of R 1 , R 2  and R 3  is a C 1-6  alkyl chosen from methyl, ethyl, propyl, isopropyl, butyl, and isobutyl. 
     
     
         4 . The process of  claim 2 , wherein the hydrocarbyl substituent is a group chosen from polypropylene groups, polybutylene groups, polyalpha-olefin groups, and ethylene/alpha-olefin copolymer groups. 
     
     
         5 . The process of  claim 2 , wherein the hydrocarbyl substituent is a copolymer group having at least one monomer chosen from butylene, isobutylene, and propylene, and at least one monomer chosen from mono-olefinic comonomers. 
     
     
         6 . The process of  claim 2 , wherein the hydrocarbyl substituent is a polyisobutylene group. 
     
     
         7 . The process of  claim 2 , wherein R 1  is methyl, R 2  is a hydrogen radical and R 3  is a polyisobutylene group. 
     
     
         8 . The process of  claim 1 , wherein the at least one primary amine is a compound of formula (II), 
       
         
           
           
               
               
           
         
         where R 4  is a substituent chosen from alkyl, aryl, alkenyl, alkyl amino, dialkyl amino, alkylaminoalkyl, and dialkylaminoalkyl groups. 
       
     
     
         9 . The process of  claim 8 , wherein R 4  is a -C 1-8 NR′R″ group, where the C 1-8  portion of the group is a straight or branched chain alkyl, and R′ and R″ are independently chosen from hydrogen radicals, methyl, ethyl, propyl and butyl groups. 
     
     
         10 . The process of  claim 1 , wherein at least one primary amine is chosen from dimethylaminopropyl amine, diethylaminopropyl amine, and dimethylaminobutyl amine. 
     
     
         11 . The process of  claim 1 , wherein the at least one aidehyde is chosen from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, heptaldehyde, stearaldehyde, benzaldehyde, salicylaldehyde, furfural aldehyde, thiophene aldehyde, and paraformaldehyde. 
     
     
         12 . The process of  claim 1 , wherein at least one hydroxyl substituted aromatic ring compound, the at least one primary amine and the at least one aldehyde are mixed in a ratio of about 1 mole of hydroxyl substituted aromatic ring compound; about 0.3 to about 0.7 moles of primary amine; and from about 0.8 to about 1.5 moles aldehyde. 
     
     
         13 . The process of  claim 1 , wherein at least one second amine is a compound of formula (IV), 
       
         
           
           
               
               
           
         
         wherein R 5  and R 6  are each independently chosen from a hydrogen radical, alkyl, cycloalkyl, aryl, alkaryl, and aralkyl groups, with the proviso that at least one of R 5  and R 6  is not a hydrogen radical. 
       
     
     
         14 . The process of  claim 1 , wherein at least one second amine is a compound of formula (V): 
       
         
           
           
               
               
           
         
         where R 7  is a linear, branched, or cyclic alkyl group having from 1 to 10 carbon atoms. 
       
     
     
         15 . The process of  claim 14 , where R 7  is a saturated, straight chain hydrocarbon having 1 to 6 carbon atoms. 
     
     
         16 . The process of  claim 14 , where R 7  is a substituted or unsubstituted cycloalkane having a 4 to 8 carbon member ring that is optionally substituted with one or more methyl, ethyl or propyl groups. 
     
     
         17 . The process of  claim 1 , wherein the at least one second amine is chosen from dimethylamine, diethylamine, dipropylamine, dibutylamine, and dipentylamine. 
     
     
         18 . The process of  claim 1 , wherein the at least one second amine is chosen from cyclohexaneamine; 1,3-propanediamine; 1,2 ethane diamine; 1,4-butanediamine; 1,6-hexanediamine; 1,2-diaminocyclohexane; 1,2-amino-3 methyl cyclohexane; 1,2 amino 4 methyl cyclohexane; N-methylamine methanediamine and 3,3 dimethyl amino propyl amine. 
     
     
         19 . A detergent base product formed by the method of  claim 1 . 
     
     
         20 . A process for forming a Mannich reaction product, the process comprising:
 reacting at least one amine compound chosen from primary and secondary amines with a bis-Mannich compound having a formula III,   
       
         
           
           
               
               
           
         
         where R 1  is chosen from a hydrogen radical and C 1-6  alkyl; 
         R 3  is a hydroxyaromatic compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight of about 500 to about 3000; and 
         R 4  is a linear, branched, or cyclic, substituted or unsubstituted, saturated or unsaturated alkyl amine group. 
       
     
     
         21 . A fuel composition comprising:
 a base fuel; and   a detergent base product comprising a mixture of formulae (VI) and (VII),   
       
         
           
           
               
               
           
         
         where R 1 and R 3  are substituents independently chosen from a hydrogen radical, C 1-6  alkyls and hydrocarbyl substituents having a number average molecular weight in the range of about 500 to about 3000, with the proviso that at least one of R 1 and R 3  is a hydrocarbyl substitutent, 
         R 4  is a substituent chosen from alkyl, aryl, alkenyl, alkyl amino, dialkyl amino, alkylaminoalkyl, and dialkylaminoalkyl groups, 
         R 5  and R 6  are each independently chosen from a hydrogen radical, alkyl, cycloalkyl, aryl, alkaryl, and aralkyl groups, with the proviso that at least one of R 5  and R 6  is not a hydrogen radical.