IP Library Granted Patent US 11,459,498
Granted Patent B2
US 11,459,498 · App. 17/234,601 · Granted Oct 4, 2022

Alkyl lactone-derived corrosion inhibitors

Inventors: Jeremy Moloney (Katy, TX); Jeremy Wayne Bartels (Sugar Land, TX); Jeffrey M. Servesko (Bend, OR)
Assignee: ChampionX USA Inc.
C09K8/54C07C69/675C07C235/10C09K8/524C09K15/22C23F11/145
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Quick Facts
Patent No.
US 11,459,498
App. No.
17/234,601
Granted
Oct 4, 2022
Kind
B2
Abstract

Disclosed are alkyl lactone-derived hydroxyamide and alkyl lactone-derived hydroxyester used in compositions and methods for inhibiting corrosion. The alkyl lactone-derived hydroxyamide and alkyl lactone-derived hydroxyester are reaction products of an alkyl lactone and an amine, and an alkyl lactone and an alcohol, respectively.

Claims (26)

1. A composition comprising

an alkyl lactone-derived hydroxyamide formed by a reaction between an alkyl lactone with N,N dimethylpropane-1,3-diamine,

wherein the alkyl lactone is selected from one or more of gamma-undecalactone, delta-undecalactone, and gamma-octalactone.

2. The composition of claim 1 , the composition comprising the alkyl lactone derived hydroxyamide selected from the group consisting of:

a compound having the structure

a compound having the structure

a compound having the structure

and any combination thereof.

3. The composition of claim 1 , wherein the composition further comprises one or more asphaltene inhibitors, paraffin inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, or any combination thereof.

4. The composition of claim 1 , wherein the composition comprising the alkyl lactone-derived hydroxyamide comprises a reduced toxicity compared to compositions not containing alkyl lactone derived hydroxyamide.

5. The composition of claim 1 , wherein the alkyl lactone derived hydroxyamide comprises a EC 5 o value with Daphnia magna greater than or equal to 10 mg/ml.

6. The composition of claim 1 , wherein the alkyl lactone derived hydroxyamide comprises a 48-hour EC 5 o value with Daphnia magna from about 10-100 mg/ml.

7. The composition of claim 1 , wherein the alkyl lactone derived hydroxyamide has an increased biodegradation compared to non-alkyl lactone-derived corrosion inhibitors.

8. The composition of claim 1 , the composition further comprising a fluid source, wherein the fluid source comprises a liquid hydrocarbon, gas, or a combination thereof.

9. The composition of claim 1 , wherein the alkyl lactone-derived hydroxyamide is acidified.

10. The composition of claim 1 , the composition further comprising produced water, the produced water comprising residual hydrocarbon products entrained therein and one or more of injectate, connate, brackish water, and sea water.

11. The composition of claim 1 , the composition further comprising an injectate.

12. The composition of claim 8 , wherein the fluid source comprises one or more of hydrogen sulfide, carbon dioxide, oxygen, sodium chloride, calcium chloride, and sulfur dioxide.

13. A composition comprising an alkyl lactone-derived hydroxyester to inhibit corrosion, the alkyl lactone-derived hydroxyester formed by a reaction between an alkyl lactone and an alcohol having the structure

14. The composition of claim 13 , wherein the composition further comprises one or more asphaltene inhibitors, paraffin inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, or any combination thereof.

15. The composition of claim 13 , wherein the composition comprising the alkyl lactone-derived hydroxyester comprises a reduced toxicity compared to compositions not containing alkyl lactone-derived hydroxyester.

16. The composition of claim 13 , wherein the alkyl lactone-derived hydroxyester comprises a EC 5 o value with Daphnia magna greater than or equal to 10 mg/ml.

17. The composition of claim 13 , wherein the alkyl lactone-derived hydroxyester comprises a 48-hour EC 5 o value with Daphnia magna from about 10-100 mg/ml.

18. The composition of claim 13 , wherein the alkyl lactone-derived hydroxyester has an increased biodegradation compared to non-alkyl lactone-derived corrosion inhibitors.

19. The composition of claim 13 , the composition further comprising a fluid source, wherein the fluid source comprises water, gas, liquid hydrocarbon, or any combination thereof.

20. The composition of claim 13 , wherein the alkyl lactone is gamma-undecalactone.

Assignments (5)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 21, 2024
From: CHAMPIONX USA INC.
To: CHAMPIONX LLC
Reel/Frame 067476/0580 →
SECURITY INTEREST Recorded Jun 8, 2022
From: APERGY BMCS ACQUISITION CORP.; APERGY ESP SYSTEMS, LLC; CHAMPIONX USA INC.; HARBISON-FISCHER, INC.; NORRIS-RODS, INC.; PCS FERGUSON, INC.; THETA OILFIELD SERVICES, INC.; US SYNTHETIC CORPORATION
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 060313/0456 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2021
From: MOLONEY, JEREMY; BARTELS, JEREMY WAYNE; SERVESKO, JEFFREY M.
To: ECOLAB USA INC.
Reel/Frame 055974/0666 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2021
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 055981/0035 →