IP Library › Granted Patent US 12,331,244
Granted Patent B2
US 12,331,244 · App. 18/678,158 · Granted Jun 17, 2025

Alkyl lactone-derived hydroxyamides and alkyl lactone-derived hydroxyesters for the control of natural gas hydrates

Inventors: Jeremy Wayne Bartels (Sugar Land, TX); Jeffrey M. Servesko (Bend, OR)
C09K8/524C07C237/10C07D223/04C09K8/52C09K2208/22
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Quick Facts
Patent No.
US 12,331,244
App. No.
18/678,158
Granted
Jun 17, 2025
Kind
B2
Abstract

Disclosed are alkyl lactone-derived hydroxyamides and alkyl lactone-derived hydroxyesters used in compositions and methods for inhibiting natural gas hydrate agglomerates. The alkyl lactone-derived hydroxyamides and alkyl lactone-derived hydroxyesters are reaction products of an alkyl lactone and an amine, and an alkyl lactone and an alcohol, respectively.

Claims (11)

1. A method of inhibiting formation of agglomerates of natural gas hydrates, the method comprising:

introducing into a fluid a composition comprising an alkyl lactone-derived hydroxyester to inhibit formation of the agglomerates of the natural gas hydrates, wherein the alkyl lactone-derived hydroxyester comprises:

2. The method of claim 1 , wherein the alkyl lactone-derived hydroxyester is a reaction product of an alkyl lactone and an alcohol, wherein the alkyl lactone comprises γ-undecalactone and the alcohol comprises dibutylaminomethanol or dibutylaminoethanol, wherein the alkyl lactone-derived hydroxyester comprises:

3. The method of claim 1 , wherein the alkyl lactone-derived hydroxyester is a reaction product of an alkyl lactone and an alcohol, wherein the alkyl lactone comprises δ-dodecalactone and the alcohol comprises dibutylaminomethanol or dibutylaminoethanol, wherein the alkyl lactone-derived hydroxyester comprises:

4. The method of claim 1 , wherein the fluid is contained in an oil or natural gas production operation or pipeline.

5. The method of claim 1 , wherein the fluid comprises water, natural gas, and liquid hydrocarbon.

6. The method of claim 5 , wherein the fluid comprises water in a range of from about 1 wt % to about 80 wt % based on a weight of the liquid hydrocarbon.

7. The method of claim 5 , wherein the alkyl lactone-derived hydroxyester is present in a range of from about 1,000 ppm to about 50,000 ppm based on a total weight of the composition.

8. The method of claim 1 , wherein the composition further comprises one or more thermodynamic gas hydrate inhibitors, kinetic gas hydrate inhibitors, anti-agglomerants, asphaltene inhibitors, paraffin inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, or any combination thereof.

9. The method of claim 1 , wherein the alkyl lactone-derived hydroxyester has a 48-hour EC5o value with Daphnia magna in a range of from 10 to 100 mg/ml.

10. The method of claim 1 , wherein the alkyl lactone-derived hydroxyester has biodegradation of greater than 10%, greater than 20%, greater than 30%, greater than 40%, greater than 50%, or greater than 60% when measured in a 28 day degradation test.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2024
From: CHAMPIONX USA INC.
To: CHAMPIONX LLC
Reel/Frame 067754/0348 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 17, 2024
From: BARTELS, JEREMY WAYNE; SERVESKO, JEFFREY M.
To: ECOLAB USA INC.
Reel/Frame 067748/0168 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 17, 2024
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 067768/0197 →
Continuity (4)
Continuation 17861360 · Jul 11, 2022
Continuation 16507873 · Jul 10, 2019
Provisional Application 62697153 · Jul 12, 2018
Related Publication 20240318065A1 · Sep 26, 2024
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