# US 11,897,796 B2 · Compositions of heterocyclic compounds and uses as sulfidogenesis inhibitors

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- Number: US 11,897,796 B2
- Document ID: US11897796B2
- Status: Granted
- Kind: B2
- Application number: 17/157,770
- Filed: 2021-01-25
- Published: 2021-08-05
- Granted: 2024-02-13
- Earliest claimed: 2020-01-23
- Assignees: ChampionX USA Inc.
- Applicants: ChampionX USA Inc.
- Inventors: Timothy James Tidwell; Alicia Dinges; Ashish Dhawan
- Web page: https://patentgrep.com/patent/US11897796B2

## CPC

- C02F 1/68: by addition of specified substances, e.g. trace elements, for ameliorating potable water (medicinal water A61K)
- C09K 8/532: Sulfur
- C07D 413/06: linked by a carbon chain containing only aliphatic carbon atoms
- C09K 8/575: containing organic compounds
- C02F 2103/365: {from petrochemical industry (e.g. refineries)}
- C02F 2307/14: Treatment of water in water supply networks, e.g. to prevent bacterial growth
- C09K 8/524: organic depositions, e.g. paraffins or asphaltenes
- C09K 8/528: inorganic depositions, e.g. sulfates or carbonates
- C09K 2208/20: Hydrogen sulfide elimination
- C09K 2208/22: Hydrates inhibition by using well treatment fluids containing inhibitors of hydrate formers
- C09K 2208/32: Anticorrosion additives
- C02F: TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE (separation in general B01D; special arrangements on waterborne vessels of installations for treating water, waste water or sewage, e.g. for producing fresh water, B63J; adding materials to water to prevent corrosion C23F; treating radioactively-contaminated liquids G21F9/04; regeneration of reactants for recirculation into processes, see the relevant places for the processes)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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

### Claim 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;
R1, R2, R4, and R5 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, or substituted or unsubstituted alkaryl;
R3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted alkaryl; and
n is an integer from 1 to 10.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 2)

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.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

The method of claim 1, wherein the sulfidogenesis inhibitor compound of Formula 1 has a structure corresponding to Formula 2
wherein
R1, R2, R4, and R5 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, or substituted or unsubstituted alkaryl.

### Claim 7 (depends on 6)

The method of claim 6, wherein R2 and R4 are hydrogen and R1 and R5 are independently hydrogen, substituted or unsubstituted C1 to C6 alkyl, or substituted or unsubstituted phenyl.

### Claim 8 (depends on 6)

The method of claim 6, wherein R2 and R4 are hydrogen and R1 and R5 are independently hydrogen, unsubstituted C1 to C6 alkyl, or unsubstituted phenyl.

### Claim 9 (depends on 6)

The method of claim 6, wherein R2 and R4 are hydrogen and R1 and R5 are independently hydrogen, methyl, ethyl, propyl, butyl, phenyl, or benzyl.

### Claim 10 (depends on 9)

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.

### Claim 11 (depends on 10)

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.

### Claim 12 (depends on 10)

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.

### Claim 13 (depends on 1)

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.

### Claim 14 (depends on 1)

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.

### Claim 15 (depends on 14)

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

### Claim 16 (depends on 14)

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

### Claim 17 (depends on 14)

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

### Claim 18 (depends on 16)

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.