IP Library Granted Patent US 11,897,796
Granted Patent B2
US 11,897,796 · App. 17/157,770 · Granted Feb 13, 2024

Compositions of heterocyclic compounds and uses as sulfidogenesis inhibitors

Inventors: Timothy James Tidwell (Angleton, TX); Alicia Dinges (Houston, TX); Ashish Dhawan (Aurora, IL)
Assignee: ChampionX USA Inc.
C02F1/68C07D413/06C09K8/575C02F2103/365C02F2307/14
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Quick Facts
Patent No.
US 11,897,796
App. No.
17/157,770
Granted
Feb 13, 2024
Kind
B2
Abstract

The present disclosure generally relates to compositions and uses of sulfidogenesis inhibitor compounds of Formulae 1 and 2 for preventing sulfidogenesis, i.e., the reduction reaction of a sulfur-containing compound by sulfur-utilizing prokaryotes that produce sulfide species such as hydrogen sulfide, during enhanced oil recovery processes. A method for inhibiting or decreasing microbial sulfide production by sulfur-utilizing prokaryotes includes addition of an effective amount of sulfidogenesis inhibitor compounds of Formulae 1 and 2 to the fluid that is injected into a sulfidogenic reservoir system during enhanced oil recovery. For example, the compounds can be used as sulfidogenesis inhibitors in a water injection system for use in a hydrocarbon extraction system or a hydrocarbon production system. Thus, these compositions can be effectively used as inhibitors of biogenic hydrogen sulfide generation in oilfield fluids.

Claims (25)

1. A method of sulfidogenesis inhibition in a hydrocarbon-containing system comprising a water injection system, a hydrocarbon extraction system, or a hydrocarbon production system, the method comprising administering an effective amount of a sulfidogenesis inhibitor compound of Formula 1 into the water injection system, the hydrocarbon extraction system, or the hydrocarbon production system, the compound of Formula 1 having a structure corresponding to:

wherein

A is a nitrogen-containing heterocycle of 1,3-oxazetidine, 1,3-diazetidine, 1,3-thiazetidine, oxazolidine, imidazolidine, thiazolidine, 1,3-oxazinane, hexahydropyrimidine, 1,3-thiazinane, 1,3-oxazepane, 1,3-diazepane, 1,3-thiazepane, 1,3-oxazocane, 1,3-diazocane, 1,3-thiazocane;

R 1 , R 2 , R 4 , and R 5 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, or substituted or unsubstituted alkaryl;

R 3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted alkaryl; and

n is an integer from 1 to 10.

2. The method of claim 1 , wherein the sulfidogenesis inhibitor compound of formula 1 inhibits the production of hydrogen sulfide by a sulfur-utilizing prokaryote.

3. The method of claim 2 , wherein the sulfur-utilizing prokaryote produces sulfide through reduction of sulfate, thiosulfate, sulfur, bisulfite, an organosulfur compound, or a combination thereof.

4. The method of claim 1 , wherein the sulfidogenesis inhibitor compound of Formula 1 is administered by contacting the compound of Formula 1 with water in the water injection system or the sulfidogenesis inhibitor compound of Formula 1 is administered by injecting an injection fluid into the hydrocarbon extraction system or the hydrocarbon production system.

5. The method of claim 1 , wherein the hydrocarbon extraction system or the hydrocarbon production system is a subterranean hydrocarbon-containing formation.

6. The method of claim 1 , wherein the sulfidogenesis inhibitor compound of Formula 1 has a structure corresponding to Formula 2

wherein

R 1 , R 2 , R 4 , and R 5 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, or substituted or unsubstituted alkaryl.

7. The method of claim 6 , wherein R 2 and R 4 are hydrogen and R 1 and R 5 are independently hydrogen, substituted or unsubstituted C 1 to C 6 alkyl, or substituted or unsubstituted phenyl.

8. The method of claim 6 , wherein R 2 and R 4 are hydrogen and R 1 and R 5 are independently hydrogen, unsubstituted C 1 to C 6 alkyl, or unsubstituted phenyl.

9. The method of claim 6 , wherein R 2 and R 4 are hydrogen and R 1 and R 5 are independently hydrogen, methyl, ethyl, propyl, butyl, phenyl, or benzyl.

10. The method of claim 9 , wherein the effective amount of the sulfidogenesis inhibitor compound of Formula 2 is from about 1 to about 500 ppm based on the total amount of injection fluid injected into the formation or production system.

11. The method of claim 10 , wherein the effective amount of the sulfidogenesis inhibitor compound of Formula 2 is from about 1 to about 250 ppm based on the total amount of injection fluid injected into the formation or production system.

12. The method of claim 10 , wherein the effective amount of the sulfidogenesis inhibitor compound of Formula 2 is from about 1 to about 100 ppm based on the total amount of injection fluid injected into the formation or production system.

13. The method of claim 1 , wherein the sulfidogenesis inhibitor compound of Formula 1 is injected into the water injection system, the hydrocarbon extraction system, or the hydrocarbon production system continuously with the injection fluid.

14. The method of claim 1 , wherein the sulfidogenesis inhibitor compound of Formula 1 is injected into the water injection system, the hydrocarbon extraction system, or the hydrocarbon production system intermittently with the injection fluid.

15. The method of claim 14 , wherein the injection of the sulfidogenesis inhibitor compound of Formula 1 is intermittently injected every one to three hours.

16. The method of claim 14 , wherein the injection of the sulfidogenesis inhibitor compound of Formula 1 is intermittently injected every one to three days.

17. The method of claim 14 , wherein the injection of the sulfidogenesis inhibitor compound of Formula 1 is intermittently injected every one to three weeks.

18. The method of claim 16 , further comprising administering an organic solvent, a corrosion inhibitor, an asphaltene inhibitor, a paraffin inhibitor, a scale inhibitor, an emulsifier, a water clarifier, a dispersant, an emulsion breaker, a gas hydrate inhibitor, a biocide, a pH modifier, a surfactant, or a combination thereof.

Assignments (3)
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 →
SECURITY INTEREST Recorded Apr 30, 2021
From: APERGY ESP SYSTEMS, LLC; APERGY BMCS ACQUISITION CORPORATION; CHAMPIONX USA INC.; HARBISON-FISCHER, INC.; NORRIS RODS, INC.; NORRISEAL-WELLMARK, INC.; PCS FERGUSON, INC.; QUARTZDYNE, INC.; US SYNTHETIC CORPORATION; WINDROCK, INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 056106/0007 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 25, 2021
From: DHAWAN, ASHISH; TIDWELL, TIMOTHY JAMES; DINGES, ALICIA
To: CHAMPIONX USA INC.
Reel/Frame 055024/0120 →
Continuity (2)
Provisional Application 62964968 · Jan 23, 2020
Related Publication 20210238068A1 · Aug 5, 2021