Mono and bis-ester derivatives of pyridinium and quinolinium compounds as environmentally friendly corrosion inhibitors
View Patent ↗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 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 the following formula:
wherein
is an aromatic, nitrogen-containing ring selected from oxazole, thiazole, acridine, cinnoline, quinoxazoline, pyridazine, pyridine, pyrimidine, quinazoline, quinoline, isoquinoline, and mixtures thereof;
Y is a group of formula —OC(O)R 1 or —C(O)OR 1 ;
L is —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 ; and
X is Br, Cl or I.
2. The method of claim 1 , wherein the quaternary nitrogen-containing corrosion inhibitors have the 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.
3. The method of claim 2 , 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.
4. The method of claim 1 , wherein the corrosion inhibitor compound is added in a composition comprising 5 to 50 weight percent of the one or more quaternary nitrogen-containing corrosion inhibitors dispersed or dissolved in one or more organic solvents.
5. The method of claim 4 , wherein the organic solvents are selected from alcohols, glycols and aliphatic and aromatic hydrocarbons.
6. The method of claim 5 , wherein the organic solvents comprise ethylene glycol monobutyl ether.
7. The method of claim 6 , comprising 5 to 20 weight percent of the one or more quaternary nitrogen-containing corrosion inhibitors.
8. The method of claim 1 , wherein the fluid comprises oil or gas and water.
9. 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 the following formula:
wherein
is an aromatic, nitrogen-containing ring, wherein the nitrogen-containing ring is a pyridine or quinoline 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;
Y is a group of formula —OC(O)R 1 or —C(O)OR 1 ;
L is C 1 -C 10 alkylene, C 2 -C 10 alkenylene 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 ; and
X is Br, Cl or I.
10. The method of claim 9 , wherein L is C 1 -C 10 alkylene or C 2 -C 10 alkenylene.
11. The method of claim 10 , wherein L is methylene.
12. The method of claim 9 , wherein the corrosion inhibitor compound is added in a composition comprising 5 to 50 weight percent of the one or more quaternary nitrogen-containing corrosion inhibitors dispersed or dissolved in one or more organic solvents.
13. The method of claim 12 , wherein the organic solvents are selected from alcohols, glycols and aliphatic and aromatic hydrocarbons.
14. The method of claim 13 , wherein the organic solvents comprise ethylene glycol monobutyl ether.
15. The method of claim 14 , comprising 5 to 20 weight percent of the one or more quaternary nitrogen-containing corrosion inhibitors.
16. The method of claim 9 , wherein the fluid comprises oil or gas and water.
17. 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 having the 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;
X is Br, Cl, or I;
R 1 is C 8 -C 20 alkyl or C 8 -C 20 alkenyl; and
R 2 is H or —C(O)R 1 .
18. The method of claim 17 , 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.