Bis-quaternary ammonium salt corrosion inhibitors
View Patent ↗Bis-quaternary ammonium salts of formula wherein Y is a group of formula NR 11 R 12 + X − or NR 7 ; n is 0 or 1; p is 1 or 2; r and q are independently 2, 3 or 4; X is an anionic counterion and R 1 R 2 R 3 N— and R 4 R 5 R 6 N— are independently selected from groups of formula —N(R 13 ) 2 R 8 , —N(R 14 ) 3 , —N(R 13 ) 3 , —N(R 13 ) 2 (CH 2 ) q OC(O)R 9 , and wherein R 7 , R 11 and R 12 are independently selected from C 1 -C 18 alkyl; R 8 , R 9 , R 10 and R 15 are independently selected from C 8 -C 18 alkyl and C 8 -C 18 alkenyl; R 13 is C 1 -C 4 alkyl; R 14 is C 2 -C 4 hydroxyalkyl; and R 11 is selected from C 2 -C 4 hydroxyalkyl, C 2 -C 4 aminoalkyl and groups of formula —CH 2 ) r NHC(O)R 15 are effective inhibitors of corrosion and biofouling of metallic surfaces in contact with gas- and oil-field fluids.
1. A method of inhibiting corrosion and biofouling of metallic surfaces in contact with a fluid encountered in petroleum operations comprising adding to the fluid up to about 1,000 ppm of one or more bis-quaternary ammonium salts of formula
wherein Y is a group of formula NR 11 R 12 + X − or NR 7 ; n is 1; p is 1 or 2; r and q are independently 2, 3 or 4; X is an anionic counterion, Z is an anionic counterion, and R 1 R 2 R 3 N— and R 4 R 5 R 6 N— are independently selected from groups of formula—N(R 13 ) 2 R 8 , —N(R 14 ) 3 , —N(R 13 ) 3 , —N(R 13 ) 2 (CH 2 ) q OC(O)R 9 ,
wherein R 7 , R 11 and R 12 are independently selected from C 1 -C 18 alkyl; R 8 , R 9 , R 10 and R 15 are independently selected from C 8 -C 18 alkyl and C 8 -C 18 alkenyl; R 13 is C 1 -C 4 alkyl; R 14 is C 2 -C 4 hydroxyalkyl; and wherein said petroleum operation is primary, secondary, and/or tertiary oil recovery.
2. The method of claim 1 wherein R 1 R 2 R 3 N— and R 4 R 5 R 6 N— are independently selected from groups of formula —N(CH 3 ) 2 R 8 , —N(CH 2 CH 2 OH) 3 , —N(CH 2 CH 3 ) 3 , —N(CH3) 2 CH 2 CH 2 OC(O)R 9 ,
wherein R 7 , R 11 and R 12 are independently selected from C 1 -C 18 alkyl; R 8 , R 9 , R 10 and R 15 are independently selected from C 8 -C 18 alkyl and C 8 -C 18 alkenyl; and R 11 is selected from groups of formula —CH 2 CH 2 OH, —CH 2 CH 2 NH 2 and —CH 2 CH 2 NHC(O)R 15 .
3. The method of claim 2 wherein R 1 R 2 R 3 N— and R 4 R 5 R 6 N— are independently selected from groups of formula
—N(CH 3 ) 2 R 8 ;
4. The method of claim 3 wherein R 8 is C 8 -C 18 alkyl.
5. The method of claim 3 wherein R 8 is C 8 -C 18 alkenyl.
6. The method of claim 3 wherein R 10 is C 8 -C 18 alkenyl.
7. The method of claim 1 wherein n is 1.
8. The method of claim 7 wherein R 1 R 2 R 3 N— and R 4 R 5 R 6 N— are groups of formula —N(CH 3 ) 2 R s , —N(CH 2 CH 2 OH) 3 , —N(CH 2 CH 3 ) 3 or —N(CH 3 ) 2 CH 2 CH 2 OC(O)R 9 .
9. The method of claim 1 wherein the bis-quaternary ammonium salts are selected from the group consisting of salts of formula
10. The method of claim 1 wherein the fluid is an oil field fluid comprising oil and water.
11. The method of claim 1 wherein Z is chloride or sulfate.
12. The method of claim 1 wherein Z is chloride.