Mono and bis-ester derivatives of pyridinium and quinolinium compounds as environmentally friendly corrosion inhibitors

Abstract

A quaternary nitrogen-containing corrosion inhibitor of formula wherein is an aromatic, nitrogen-containing ring of 5 to 14 ring atoms, optionally containing an additional N, O or S ring atom and optionally substituted with one or more alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, amino, aminoalkyl, alkoxy, hydroxylalkyl, or cyano groups, or a mixture thereof, Y is a group of formula —OC(O)R 1 or —C(O)R 1 ; L is C 1 -C 10 alkyl, C 2 -C 10 alkenyl or a group of formula CH 2 CH(OR 2 )CH 2 —; R 1 is C 8 -C 20 alkyl or C 8 -C 20 alkenyl; R 2 is H or C(O)R 1 ; R 3 and R 4 are independently selected from H, alkyl, alkenyl, amino, alkoxy, hydroxylalkyl and cyano; and X is Br, Cl or I is particularly useful for inhibiting corrosion in oil and gas field applications.

1 . A quaternary nitrogen-containing corrosion inhibitor of formula 
       
         
           
           
               
               
           
         
       
       wherein 
       
         
           
           
               
               
           
         
       
       is an aromatic, nitrogen-containing ring of 5 to 14 ring atoms, optionally containing an additional N, O or S ring atom and optionally substituted with one or more alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, amino, aminoalkyl, alkoxy, hydroxylalkyl, or cyano groups, or a mixture thereof;
 Y is a group of formula —OC(O)R 1  or —C(O)R 1 ; 
 L is C 1 -C 10  alkyl, C 2 -C 10  alkenyl or a group of formula —CH 2 CH(OR 2 )CH 2 —; 
 R 1  is C 8 -C 20  alkyl or C 8 -C 20  alkenyl; 
 R 2  is H or <(O)R 1 ; and 
 X is Br, Cl or I. 
 
     
     
         2 . The corrosion inhibitor of  claim 1  wherein the aromatic, nitrogen-containing ring is selected from oxazole, thiazole, acridine, cinnoline, quinoxazoline, pyridazine, pyridine, pryimidine, quinazolinie, quinoline and isoquinoline. 
     
     
         3 . The corrosion inhibitor of  claim 2  wherein L is C 1 -C 10  alkylene or C 2 -C 10  alkenylene. 
     
     
         4 . The corrosion inhibitor of  claim 3  wherein L is methylene. 
     
     
         5 . The corrosion inhibitor of  claim 2  wherein L is a group of formula —CH 2 CH(OR 2 )CH 2 —. 
     
     
         6 . The corrosion inhibitor of  claim 1  wherein the aromatic, nitrogen-containing ring is selected from pyridine and quinoline. 
     
     
         7 . The corrosion inhibitor of  claim 6  wherein L is C 1 -C 10  alkylene, C 2 -C 10  alkenylene or a group of formula —CH 2 CH(OR 2 )CH 2 —. 
     
     
         8 . The corrosion inhibitor of  claim 7  wherein the pyridine or quinoline is substituted with 1-4 C 1 -C 6  alkyl, C 2 -C 6  alkenyl, or C 1 -C 6  aminoalkyl groups, or a mixture thereof. 
     
     
         9 . The corrosion inhibitor of  claim 8  wherein L is methylene. 
     
     
         10 . The corrosion inhibitor of  claim 1  of formula 
       
         
           
           
               
               
           
         
       
       wherein R 3 -R 6  are independently selected from H, alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, amino, aminoalkyl, alkoxy, hydroxylalkyl, or cyano groups, or a mixture thereof, or any two of R 3 -R 6  taken together with the ring atoms to which they are attached may form a fused cycloalkyl. 
     
     
         11 . The corrosion inhibitor of  claim 10  wherein R 3 -R 6  are independently selected from H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, or C 1 -C 6  aminoalkyl, or a mixture thereof. 
     
     
         12 . The corrosion inhibitor of  claim 1  of formula 
       
         
           
           
               
               
           
         
       
       wherein R 3 -R 6  are independently selected from H, alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, amino, aminoalkyl, alkoxy, hydroxylalkyl, or cyano groups, or a mixture thereof, or any two of R 3 -R 6  taken together with the ring atoms to which they are attached may form a fused cycloalkyl or fused heterocyclyl ring. 
     
     
         13 . The corrosion inhibitor of  claim 12  wherein R 3 -R 6  are independently selected from H, C 1 -C 6  alkyl, C 2 -C 6  alkenyl, or C 1 -C 6  aminoalkyl, or a mixture thereof. 
     
     
         14 . A corrosion inhibitor composition comprising 5 to 50 weight percent of the corrosion inhibitor of  claim 1  dispersed or dissolved in one or more organic solvents. 
     
     
         15 . The corrosion inhibitor composition of  claim 14  wherein the organic solvents are selected from alcohols, glycols and aliphatic and aromatic hydrocarbons. 
     
     
         16 . The corrosion inhibitor composition of  claim 15  wherein the organic solvents comprise ethylene glycol monobutyl ether. 
     
     
         17 . The corrosion inhibitor composition of  claim 16  comprising 5 to 20 weight percent of the corrosion inhibitor of  claim 1 . 
     
     
         18 . A method of inhibiting corrosion of a metallic surface in contact with a fluid in oil and gas applications comprising adding to the fluid an effective corrosion-inhibiting amount of one or more quaternary nitrogen-containing corrosion inhibitors according to  claim 1 . 
     
     
         19 . The method of  claim 18  wherein the fluid comprises oil or gas and water.