Corrosion inhibitor formulations based on compounds with both pyridinium and hydroxy substituents

Abstract

Compounds for inhibiting corrosion are provided that include a pyridinium substituent and a hydroxy substituent. Also provided are methods of making the compounds. Also provided are corrosion inhibitor formulations including the compounds. Also provided are processes for inhibiting corrosion of a metallic surface using the corrosion inhibitor formulations.

1 . A compound for inhibiting corrosion, the compound comprising: 
       
         
           
           
               
               
           
         
         or a salt thereof, where: 
         R 1 , R 2 , R 3 , R 4 , and R 5  are independently hydrogen, substituted or unsubstituted C 1  to C 24  alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, sulfonate, aryl sulfonate, C 1  to C 24  alkyl sulfonate, taurine, carboxylate, amine, alkylamine, arylamine, alkylammonium, arylammonium, sulfonamide, halogen, hydroxy, amide, nitro, cyano, azide, O-alkyl, S-alkyl, silyl, trialkylsilyl, O-silyl, haloalkyl, alkylsulfhydryl, trifluoromethyl, hydrazide, substituted or unsubstituted aryl, heteroaryl, or heterocyclic alkynyl, carboxyalkyl, aminoalkyl, haloalkyl, azidoalkyl, amide, amino acid, or peptide; and 
         R 6  is a substituted or unsubstituted C 1  to C 24  alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, sulfonate, aryl sulfonate, C 1  to C 24  alkyl sulfonate, taurine, carboxylate, amine, alkylamine, arylamine, alkylammonium, arylammonium, sulfonamide, halogen, hydroxy, amide, nitro, cyano, azide, O-alkyl, S-alkyl, silyl, trialkylsilyl, O-silyl, haloalkyl, alkylsulfhydryl, trifluoromethyl, hydrazide, substituted or unsubstituted aryl, heteroaryl, or heterocyclic alkynyl, carboxyalkyl, aminoalkyl, haloalkyl, azidoalkyl, amide, amino acid, or peptide. 
       
     
     
         2 . The compound of  claim 1 , where R 6  is a substituted or unsubstituted C 1  to C 24  alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, or a substituted or unsubstituted alkynyl. 
     
     
         3 . The compound of  claim 1 , where R 6  is a substituted or unsubstituted C 1  to C 24  alkyl. 
     
     
         4 . The compound of  claim 1 , where R 6  is a substituted or unsubstituted C 5  to C 15  alkyl. 
     
     
         5 . The compound of  claim 1 , where:
 R 1 , R 2 , R 3 , R 4 , and R 5  are independently hydrogen; and   R 6  is an unsubstituted C 5  to C 15  alkyl.   
     
     
         6 . A method of making the compound of  claim 1  comprising:
 reacting a pyridine comprising Formula (II): 
 
       
         
           
           
               
               
           
         
         or a salt thereof, with an epoxide comprising Formula (III): 
       
       
         
           
           
               
               
           
         
         in the presence of an acid to produce the compound; 
       
       where:
 R 1 , R 2 , R 3 , R 4 , and R 5  are independently hydrogen, substituted or unsubstituted C 1  to C 24  alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, sulfonate, aryl sulfonate, C 1  to C 24  alkyl sulfonate, taurine, carboxylate, amine, alkylamine, arylamine, alkylammonium, arylammonium, sulfonamide, halogen, hydroxy, amide, nitro, cyano, azide, O-alkyl, S-alkyl, silyl, trialkylsilyl, O-silyl, haloalkyl, alkylsulfhydryl, trifluoromethyl, hydrazide, substituted or unsubstituted aryl, heteroaryl, or heterocyclic alkynyl, carboxyalkyl, aminoalkyl, haloalkyl, azidoalkyl, amide, amino acid, or peptide; and 
 R 6  is a substituted or unsubstituted C 1  to C 24  alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, sulfonate, aryl sulfonate, C 1  to C 24  alkyl sulfonate, taurine, carboxylate, amine, alkylamine, arylamine, alkylammonium, arylammonium, sulfonamide, halogen, hydroxy, amide, nitro, cyano, azide, O-alkyl, S-alkyl, silyl, trialkylsilyl, O-silyl, haloalkyl, alkylsulfhydryl, trifluoromethyl, hydrazide, substituted or unsubstituted aryl, heteroaryl, or heterocyclic alkynyl, carboxyalkyl, haloalkyl, azidoalkyl, amide, amino acid, or peptide. 
 
     
     
         7 . The method of  claim 6 , where R 6  is a substituted or unsubstituted C 1  to C 24  alkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkenyl, or a substituted or unsubstituted alkynyl. 
     
     
         8 . The method of  claim 6 , where R 6  is a substituted or unsubstituted C 1  to C 24  alkyl. 
     
     
         9 . The method of  claim 6 , where R 6  is a substituted or unsubstituted C 5  to C 15  alkyl. 
     
     
         10 . The method of  claim 6 , where:
 R 1 , R 2 , R 3 , R 4 , and R 5  are independently hydrogen; and   R 6  is an unsubstituted C 5  to C 15  alkyl.   
     
     
         11 . A sour well fluid comprising the compound of  claim 1  at a concentration by weight of 0.1 parts per million to 100 parts per million of the well fluid. 
     
     
         12 . The well fluid of  claim 11 , where the compound of  claim 1  is present at a concentration by weight of 0.2 parts per million to 20 parts per million. 
     
     
         13 . The well fluid of  claim 11  comprising petroleum hydrocarbons. 
     
     
         14 . A formulation for inhibiting corrosion comprising:
 the compound of  claim 1 ; and   water.   
     
     
         15 . The formulation of  claim 14  further comprising a synergist. 
     
     
         16 . The formulation of  claim 15  further comprising a nonionic surfactant, imidazoline, a secondary solvent, a coupling agent, and an ethoxylated amine. 
     
     
         17 . The formulation of  claim 16  where:
 the compound is present t a concentration of from 5 to 25 weight percent; 
 the water is present at a concentration of from 40 to 90 weight percent; 
 the imidazoline is present at a concentration of from 1 to 10 weight percent; and 
 the synergist comprises thioglycollic acid, 2-mercaptoethanol, or a mixture thereof. 
 
     
     
         18 . A process for inhibiting corrosion comprising contacting a metallic surface with the formulation of  claim 14 . 
     
     
         19 . The process of  claim 18 , where the metallic surface comprises steel. 
     
     
         20 . A process for inhibiting corrosion comprising adding the formulation of  claim 14  to a well fluid to effect a concentration by weight of the formulation in the well fluid of from 0.5 parts per million to 500 parts per million.