IP Library Granted Patent US 10,900,128
Granted Patent B2
US 10,900,128 · App. 16/116,669 · Granted Jan 26, 2021

Use of sulfonium salts as corrosion inhibitors

Inventors: Brett Geissler (Richmond, TX); Ashish Dhawan (Aurora, IL); Alicia Dinges (Houston, TX); Carter Martin Silvernail (Burnsville, MN)
Assignee: ChampionX USA Inc.
C23F11/16C09K8/54C09K2208/22C09K2208/26C09K2208/32
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Quick Facts
Patent No.
US 10,900,128
App. No.
16/116,669
Granted
Jan 26, 2021
Kind
B2
Abstract

The present invention generally relates to the use of aryl sulfonium salts as a corrosion inhibitor in a water injection system, a hydrocarbon extraction system, or a hydrocarbon production system. Treating oilfield injection and produced fluids with aryl sulfonium salts can significantly decrease microbially induced corrosion. Thus, these aryl sulfonium salts can be effectively used as corrosion inhibitors in oilfield fluids.

Claims (20)

1. A method of inhibiting corrosion at a surface, the method comprising contacting the surface with an effective amount of an anticorrosion composition comprising an aryl sulfonium salt or mixture of aryl sulfonium salts, wherein the aryl sulfonium salt comprises (i) a cation of Formula 2 or (ii) a dication of Formula 3, and the mixture of aryl sulfonium salts comprises (iii) a cation of Formulae 1 and 2, (iv) a cation of Formula 1 and a dication of Formula 3, (v) a cation of Formula 2 and a dication of Formula 3, or (vi) a cation of Formulae 1 and 2, and a dication of Formula 3,

wherein R 1 -R 30 are independently hydrogen, alkyl, alkoxy, aryl, or heterocyclo, and wherein the surface is in contact with a hydrocarbon-containing fluid.

2. The method of claim 1 , wherein the anticorrosion composition inhibits microbially induced corrosion.

3. The method of claim 1 , wherein the aryl sulfonium salt comprises a cation of Formula 2.

4. The method of claim 1 , wherein the aryl sulfonium salt comprises a dication of Formula 3.

5. The method of claim 1 , wherein the mixture of aryl sulfonium salts comprises a cation of Formulae 1 and 2.

6. The method of claim 1 , wherein the mixture of aryl sulfonium salts comprises a cation of Formula 1 and a dication of Formula 3.

7. The method of claim 1 , wherein the mixture of aryl sulfonium salts comprises a cation of Formula 2 and a dication of Formula 3.

8. The method of claim 1 , wherein the mixture of aryl sulfonium salts comprises a cation of Formulae 1 and 2, and a dication of Formula 3.

9. The method of claim 8 , wherein one to three of R 1 -R 30 are independently alkyl and the balance are hydrogen.

10. The method of claim 8 , wherein R 1 -R 30 are hydrogen.

11. The method claim 1 , wherein the counterion for the cation of Formula 1, cation of Formula 2, or dication of Formula 3 is chloride, bromide, fluoride, iodide, nitrate, perchlorate, sulfonate, carbonate, chromate, hexafluoroarsenate, hexafluorophosphate, p-toluenesulfonate, acetate, formate, oxalate, phosphate, or a combination thereof.

12. The method of claim 1 , wherein the anticorrosion composition comprising the aryl sulfonium salt or mixture of aryl sulfonium salts in an aqueous solution is contacted with the surface and the aryl sulfonium salt or mixture of aryl sulfonium salts is administered in a concentration of from about 1 ppm to about 2000 ppm based on the total weight of the aqueous solution liquid.

13. The method of claim 12 , wherein the concentration of the aryl sulfonium salt or mixture of aryl sulfonium salts is from about 5 ppm to about 500 ppm.

14. The method of claim 1 , wherein the cation of Formula 1 is triarylsulfonium chloride, triarylsulfonium nitrate, triarylsulfonium bromide, triarylsulfonium fluoride, triarylsulfonium iodide, triarylsulfonium hexafluorophosphate, triarylsulfonium perchloroate, triaryl sulfonium sulfonate, triaryl sulfonium carbonate, triaryl sulfonium chromate, triarylsulfonium hexafluoroarsenate, triarylsulfonium p-toluenesulfonate, triarylsulfonium acetate, triarylsulfonium formate, triarylsulfonium oxalate, or triarylsulfonium phosphate; the cation of Formula 2 is diaryl (4-phenylthio)arylsulfonium chloride, diaryl (4-phenylthio)arylsulfonium fluoride, diaryl (4-phenylthio)arylsulfonium nitrate, diaryl (4-phenylthio)arylsulfonium bromide, diaryl (4-phenylthio)arylsulfonium iodide, diaryl (4-phenylthio)arylsulfonium hexafluorophosphate, diaryl (4-phenylthio)arylsulfonium perchloroate, diaryl (4-phenylthio)arylsulfonium sulfonate, diaryl (4-phenylthio)arylsulfonium hexafluoroarsenate, diaryl (4-phenylthio)arylsulfonium p-toluenesulfonate, diaryl (4-phenylthio)arylsulfonium acetate, diaryl (4-phenylthio)arylsulfonium formate, diaryl (4-phenylthio)arylsulfonium oxalate, or diaryl (4-phenylthio)arylsulfonium phosphate; and the dication of Formula 3 is (thiodi-4,1-phenylene)bis-diarylsulfonium dichloride, (thiodi-4,1-phenylene)bis-diarylsulfonium difluoride, (thiodi-4,1-phenylene)bis-diarylsulfonium dinitrate, (thiodi-4,1-phenylene)bis-diarylsulfonium dichloride dibromide, (thiodi-4,1-phenylene)bis-diarylsulfonium diiodide, (thiodi-4,1-phenylene)bis-diarylsulfonium dihexafluorophosphate, (thiodi-4,1-phenylene)bis-diarylsulfonium diperchloroate, (thiodi-4,1-phenylene)bis-diarylsulfonium disulfonate, (thiodi-4,1-phenylene)bis-diarylsulfonium dihexafluoroarsenate, diaryl (thiodi-4,1-phenylene)bis-diarylsulfonium di-p-toluenesulfonate, (thiodi-4,1-phenylene)bis-diarylsulfonium diacetate, (thiodi-4,1-phenylene)bis-diarylsulfonium diformate, (thiodi-4,1-phenylene)bis-diarylsulfonium dioxalate, or (thiodi-4,1-phenylene)bis-diarylsulfonium diphosphate.

15. The method of claim 14 , wherein the cation of Formula 1 is triphenyl sulfonium chloride, the cation of Formula 2 is diphenyl (4-phenylthio)phenylsulfonium chloride, and the dication of Formula 3 is (thiodi-4,1-phenylene)bis-diphenylsulfonium dichloride.

16. The method of claim 14 , wherein the cation of Formula 2 comprises diphenyl (4-phenylthio)phenylsulfonium chloride.

17. The method of claim 14 , wherein the dication of Formula 3 comprises (thiodi-4,1-phenylene)bis-diphenylsulfonium dichloride.

18. The method of claim 1 , wherein the hydrocarbon-containing fluid comprises natural gas or a liquid hydrocarbon.

19. The method of claim 18 , wherein the liquid hydrocarbon comprises crude oil, heavy oil, processed residual oil, bituminous oil, cocker oil, gas oil, fluid catalytic cracker feed or slurry, naphtha, diesel fuel, fuel oil, jet fuel, gasoline, or kerosene.

Assignments (6)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 17, 2025
From: JPMORGAN CHASE BANK, N.A.
To: CHAMPIONX LLC; APERGY ESP SYSTEMS, LLC; APERGY BMCS ACQUISITION CORP; HARBISON-FISCHER, INC.; NORRIS RODS, INC.,; NORRIS RODS, INC.,; NORRISEAL-WELLMARK, INC.; PCS FERGUSON, INC.; QUARTZDYNE, INC.; US SYNTHETIC CORPORATION
Reel/Frame 072004/0019 →
RELEASE OF SECURITY INTEREST Recorded Jun 7, 2022
From: BANK OF AMERICA, N.A.
To: CHAMPIONX USA INC.
Reel/Frame 060304/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 053849/0537 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 052848/0368 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 053250/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2019
From: GEISSLER, BRETT; DHAWAN, ASHISH; DINGES, ALICIA; SILVERNAIL, CARTER MARTIN
To: ECOLAB USA INC.
Reel/Frame 048479/0185 →