Preparation of amine derivates from nitriles and phenols

Abstract

This application relates to fuel additive compositions and fuel compositions comprising an amine prepared from nitriles and phenolic compounds. Suitable nitrites include optionally substituted acrylonitrile, and suitable phenolic compounds include polyisobutylphenols and polyisobutyl cresols. The application also relates to methods for reducing intake valve deposits in engines.

1 . A fuel additive composition comprising an amine prepared by a process comprising: 
 (a) reacting a hydroxyaromatic compound of formula (I):                          wherein R may be independently chosen from hydrogen, halogen, hydroxyl, alkyl, alkenyl, alkynyl, nitro, and amino radicals, n is a number ranging from 0 to 4, and R 1 , may be chosen from alkyl and alkenyl radicals having from 10 to 1000 carbons atoms,    with an optionally substituted acrylonitrile of formula (II):                          wherein R 2  and R 3  may each independently be chosen from hydrogen, halogen, hydroxyl, nitro, amino, optionally substituted alkyl, optionally substituted alkenyl, and optionally substituted alkynyl radicals, to yield a compound of the formula (III):                          wherein R, n, R 1 , R 2 , and R 3  are as defined above; and    (b) reducing the compound of formula (III) to yield an amine of formula (IV):                          wherein R, n, R 1 , R 2 , and R 3  are as defined above.    
     
     
         2 . The fuel additive composition according to  claim 1 , wherein R 1  is chosen from polyalkylene radicals.  
     
     
         3 . The fuel additive composition according to  claim 1 , wherein n is 0.  
     
     
         4 . The fuel additive composition according to  claim 1 , wherein R 1  is chosen from polyolefin radicals.  
     
     
         5 . The fuel additive composition according to  claim 1 , wherein R 1  is chosen from polyisopropylene radicals and polyisobutylene radicals.  
     
     
         6 . The fuel additive composition according to  claim 1 , wherein the hydroxyaromatic compound is chosen from phenols.  
     
     
         7 . The fuel additive composition according to  claim 1 , wherein the hydroxyaromatic compound is chosen from alkyl phenols.  
     
     
         8 . The fuel additive composition according to  claim 7 , wherein the alkyl phenols are chosen from cresols.  
     
     
         9 . The fuel additive composition according to  claim 1 , wherein said amine is prepared under batch process conditions.  
     
     
         10 . The fuel additive composition according to  claim 1 , wherein said amine is prepared under continuous process conditions.  
     
     
         11 . The fuel additive composition according to  claim 1 , wherein the reduction of the nitrile to the amine is performed in the presence of a catalyst.  
     
     
         12 . The fuel additive composition according to  claim 11 , wherein the catalyst is chosen from Raney nickel and Group VIII metals.  
     
     
         13 . The fuel additive composition according to  claim 12 , wherein the catalyst is a Raney nickel catalyst.  
     
     
         14 . A fuel additive composition comprising a polyisobutyl-substituted aromatic amine, wherein said amine is prepared by: 
 (a) reacting an optionally substituted acrylonitrile with a polyolefin-substituted hydroxyaromatic compound to yield a 3-cyanopropane oxyaromatic compound; and    (b) reducing said 3-cyanopropane oxyaromatic compound with hydrogen in the presence of a catalyst to yield the polyolefin-substituted aromatic amine.    
     
     
         15 . The fuel additive composition according to  claim 14 , wherein the polyolefin-substituted hydroxyaromatic compound is a polyisobutylene-substituted phenol and the polyolefin-substituted aromatic amine is a polyisobutylene-substituted aromatic amine.  
     
     
         16 . The fuel additive composition according to  claim 14 , wherein the optionally substituted acrylonitrile is unsubstituted.  
     
     
         17 . The fuel additive composition according to  claim 14 , wherein the catalyst comprises Raney nickel.  
     
     
         18 . A fuel additive composition comprising an amine prepared by a process comprising: 
 reacting p-polyisobutylphenol with acrylonitrile to yield p-(polyisobutyl)phenoxy (3-cyano)propane; and    reducing said p-(polyisobutyl)phenoxy (3-cyano)propane with hydrogen in the presence of a catalyst comprising Raney nickel to yield p-(polyisobutyl)phenoxy (3-amino)propane.    
     
     
         19 . A fuel additive composition comprising an amine prepared by a process comprising: 
 reacting polyisobutylcresol with acrylonitrile to yield 2-methyl-4-polyisobutylphenoxy (3-cyano)propane; and    reducing said 2-methyl-4-polyisobutylphenoxy (3-cyano)propane with hydrogen in the presence of a catalyst comprising Raney nickel to yield 2-methyl-4-polyisobutylphenoxy (3-amino)propane.    
     
     
         20 . A fuel composition comprising: 
 (A) a fuel in a major amount; and    (B) an amine in a minor amount, wherein said amine is prepared by a process comprising: 
 reacting p-polyisobutylphenol with acrylonitrile to yield p-(polyisobutyl)phenoxy (3-cyano)propane; and  
 reducing said p-(polyisobutyl)phenoxy (3-cyano)propane with hydrogen in the presence of a catalyst comprising Raney nickel to yield p-(polyisobutyl)phenoxy (3-amino)propane.  
   
     
     
         21 . The fuel composition according to  claim 20 , wherein said fuel is a diesel fuel.  
     
     
         22 . The fuel composition according to  claim 20 , wherein said fuel is a biodiesel fuel.  
     
     
         23 . The fuel composition according to  claim 20 , wherein said fuel is gasoline.  
     
     
         24 . The fuel composition according to  claim 20 , wherein said fuel comprises at least one of diesel, biodiesel, and gasoline.  
     
     
         25 . The fuel composition according to  claim 20 , further comprising at least one additive chosen from dispersants, detergents, antioxidants, carrier fluids, metal deactivators, dyes, markers, corrosion inhibitors, biocides, antistatic additives, drag-reducing agents, demulsifiers, dehazers, anti-icing additives, anti-knock additives, anti-valve-seat recession additives, lubricity additives, and combustion improvers.  
     
     
         26 . The fuel composition according to  claim 20 , further comprising a Mannich product.  
     
     
         27 . A fuel composition comprising: 
 (A) a fuel in a major amount, and    (B) an amine in a minor amount, wherein said amine is prepared by a process comprising:    reacting polyisobutylcresol with acrylonitrile to yield 2-methyl-4-polyisobutylphenoxy (3-cyano)propane; and    reducing said 2-methyl-4-polyisobutylphenoxy (3-cyano)propane with hydrogen in the presence of a catalyst comprising Raney nickel to yield 2-methyl-4-polyisobutylphenoxy (3-amino)propane.    
     
     
         28 . The fuel composition according to  claim 27 , wherein said fuel is a diesel fuel.  
     
     
         29 . The fuel composition according to  claim 27 , wherein said fuel is a biodiesel fuel.  
     
     
         30 . The fuel composition according to  claim 27 , wherein said fuel is gasoline.  
     
     
         31 . The fuel composition according to  claim 27 , wherein said fuel comprises at least one of diesel, biodiesel, and gasoline.  
     
     
         32 . The fuel composition according to  claim 27 , further comprising at least one additive chosen from dispersants, detergents, antioxidants, carrier fluids, metal deactivators, dyes, markers, corrosion inhibitors, biocides, antistatic additives, drag-reducing agents, demulsifiers, dehazers, anti-icing additives, anti-knock additives, anti-valve-seat recession additives, lubricity additives, and combustion improvers.  
     
     
         33 . The fuel composition according to  claim 27 , further comprising a Mannich product.  
     
     
         34 . A process for controlling intake valve deposits in an engine, comprising operating said engine with a fuel comprising a fuel additive composition according to  claim 14 .  
     
     
         35 . A process for controlling intake valve deposits in an engine, comprising operating said engine with a fuel comprising a fuel additive composition according to  claim 18 .  
     
     
         36 . A process for controlling intake valve deposits in an engine, comprising operating said engine with a fuel comprising a fuel additive composition according to  claim 19 .  
     
     
         37 . A process for controlling intake valve deposits in an engine, comprising fueling and operating said engine with a fuel composition according to  claim 20 .  
     
     
         38 . The process according to  claim 37 , wherein said fuel composition comprises gasoline.  
     
     
         39 . A process for controlling intake valve deposits in an engine, comprising fueling and operating said engine with a fuel composition according to  claim 27 .  
     
     
         40 . The process according to  claim 39 , wherein said fuel composition comprises gasoline.