Mannich condensation products as sequestering agents for fuels and lubricating oils

Abstract

Sequestering agents for use in fuels and lubricating oils derived from Mannich condensation reaction utilizing a polyisobutyl-substituted hydroxyaromatic compound, an aldehyde, an alkali metal base, and glycine or aspartic acid, or an ester thereof.

What is claimed is: 
     
         1 . A compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein PIB is a polyisobutyl group having a number average molecular weight of about 1600 to about 3000; 
         X is, independently, hydrogen, an alkali metal ion, an ammonium ion, or alkyl having one to ten carbon atoms; 
         R′ is, independently, hydrogen or alkyl having one to 10 carbon atoms, cycloalkyl having from 3 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, alkaryl having 7 to 20 carbon atoms, or aralkyl having 7 to 20 carbon atoms; 
         Y is hydrogen, alkyl having 1 to 10 carbon atoms, or CHR′OH, or 
       
       
         
           
           
               
               
           
         
         Z is hydrogen, hydroxyl, 
       
       
         
           
           
               
               
           
         
         n is an integer from 0 to 20;
 wherein if n is 0, then Z is 
 
       
       
         
           
           
               
               
           
         
         and Y′ is H or —CHR′OH. 
       
     
     
         2 . The compound of  claim 1 , wherein the compound has the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         3 . The compound of  claim 1 , wherein the polyisobutyl group has a number average molecular weight of about 2100 to about 2500. 
     
     
         4 . The compound of  claim 1 , wherein X is ammonium, lithium, sodium, or potassium. 
     
     
         5 . The compound of  claim 1 , wherein R′ is hydrogen. 
     
     
         6 . The compound of  claim 1 , wherein Y is hydrogen or 
       
         
           
           
               
               
           
         
       
     
     
         7 . The compound of  claim 1 , wherein Z is 
       
         
           
           
               
               
           
         
       
     
     
         8 . The compound of  claim 1 , wherein Z is 
       
         
           
           
               
               
           
         
       
     
     
         9 . The compound of  claim 1 , wherein Y′ is H. 
     
     
         10 . The compound of  claim 1 , wherein n is an integer from 0 to 5. 
     
     
         11 . The compound of  claim 1 , wherein the polyisobutyl group contains at least 50 weight percent of methylvinylidene isomer. 
     
     
         12 . The compound of  claim 1 , wherein the polyisobutyl group contains at least 90 weight percent of methylvinylidene isomer. 
     
     
         13 . A compound prepared by the Mannich condensation of:
 (a) a polyisobutyl-substituted hydroxyaromatic compound having a number average molecular weight of about 1600 to about 3000;   (b) an aldehyde;   (c) aspartic acid, or an ester thereof; and   (d) an alkali metal base.   
     
     
         14 . The compound of  claim 13 , wherein the polyisobutyl-substituted hydroxyaromatic compound has a number average molecular weight of about 2100 to about 2500. 
     
     
         15 . The compound of  claim 13 , wherein the polyisobutyl-substituted hydroxyaromatic compound is derived from polyisobutene containing at least 50 weight percent methylvinylidene isomer. 
     
     
         16 . The compound of  claim 13 , wherein the polyisobutyl-substituted hydroxyaromatic compound is derived from polyisobutene containing at least 90 weight percent methylvinylidene isomer. 
     
     
         17 . The compound of  claim 13 , wherein the polyisobutyl-substituted hydroxyaromatic compound has the following formula: 
       
         
           
           
               
               
           
         
         wherein PIB is a polyisobutyl group derived from polyisobutene containing at least 50 weight percent methylvinylidene isomer and having a number average molecular weight in the range of about 1600 to about 3000; R 2  is hydrogen or alkyl having 1 to about 10 carbon atoms; and R 3  is hydrogen or hydroxyl. 
       
     
     
         18 . The compound of  claim 17 , wherein the polyisobutyl-substituted hydroxyaromatic compound has the following formula: 
       
         
           
           
               
               
           
         
       
     
     
         19 . The compound of  claim 13 , wherein the aldehyde is formaldehyde. 
     
     
         20 . The compound of  claim 13 , wherein the alkali metal base is sodium hydroxide, lithium hydroxide or potassium hydroxide. 
     
     
         21 . A method for preventing or controlling metal ion catalyzed oxidation and polymerization reactions in a hydrocarbon medium comprising sequestering the metal ion by the addition of an effective amount of the compound of  claim 1 . 
     
     
         22 . A fuel composition comprising a major amount of hydrocarbons boiling in the gasoline or diesel range and a minor effective amount of one or more of the compounds of  claim 1 . 
     
     
         23 . A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor effective amount of one or more of the compounds of  claim 1 .