IP Library Granted Patent US 11,339,320
Granted Patent B2
US 11,339,320 · App. 15/829,576 · Granted May 24, 2022

Thiol-formyl hemiacetal corrosion inhibitors

Inventors: Boyd Anthony Laurent (Pearland, TX); Prakasa Rao Anantaneni (Richmond, TX); Ryan Matthew Harrington (Houston, TX); Subhasis De (Webster, TX)
Assignee: ChampionX USA Inc.
C09K8/54C07C323/12C07C323/25C07C323/52C09K15/12C09K2208/32
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Quick Facts
Patent No.
US 11,339,320
App. No.
15/829,576
Granted
May 24, 2022
Kind
B2
Abstract

The present invention generally relates to compositions and methods for inhibiting corrosion at a surface in the production, transportation, storage, and separation of crude oil and natural gas.

Claims (30)

1. A method of inhibiting corrosion at a surface, the method comprising:

contacting the surface with an effective amount of an anti-corrosion composition, wherein the surface is part of equipment used in the production, transportation, storage, and/or separation of crude oil or natural gas; the composition comprising:

a compound of formula (IA)

wherein

R 1 is alkyl, aryl, or alkenyl;

n is an integer from 1 to 10;

R 2 is hydrogen, alkyl, alkenyl, or aryl; and

R 3 is hydrogen, alkyl, alkaryl, aryl, or heterocyclo.

2. The method of claim 1 , wherein the anti-corrosion composition comprises the compound of formula (IA).

3. The method of claim 2 , wherein R 1 of Formula (IA) is either:

C 1 -C 24 alkyl, C 1 -C 24 alkenyl, C 6 -C 12 aryl, or C 3 -C 8 cycloalkyl, wherein said alkyl, alkenyl, aryl, or cycloalkyl are each independently unsubstituted or substituted with 1 to 3 substituents independently selected from —F, —Cl, —NO 2 , —CN, —OH, —NH 2 , C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, —CO 2 R 10 , and —CON(R 11 ) 2 , wherein R 10 and R 11 , at each occurrence, are each independently hydrogen or C 1 -C 6 alkyl; or optionally one or more of the —CH 2 — groups of R 1 is replaced with a —C(O)O— group; or

C 1 -C 18 alkyl, or C 3 -C 8 cycloalkyl, wherein said alkyl, or cycloalkyl are each independently unsubstituted or substituted with 1 to 3 substituents independently selected from —OH, C 1 -C 6 alkoxy, or —CO 2 R 10 , wherein R 10 at each occurrence, is independently hydrogen or C 1 -C 6 alkyl; or optionally one or more of the —CH 2 — groups of R 1 is replaced with a —C(O)O— group.

4. The method of claim 2 , wherein R 1 of Formula (IA) is

C 1 -C 18 alkyl or C 3 -C 8 cycloalkyl.

5. The method of claim 4 , wherein R 2 of Formula (IA) is hydrogen.

6. The method of claim 5 , wherein n of Formula (IA) is 1 to 5.

7. The method of claim 6 , wherein R 3 of Formula (IA) is hydrogen, methyl, ethyl, propyl, or phenyl.

8. The method of claim 1 , wherein the anti-corrosion composition further comprises one or more additional corrosion inhibitors, solvents, asphaltene inhibitors, paraffin inhibitors, scale inhibitors, emulsifiers, water clarifiers, dispersants, emulsion breakers, gas hydrate inhibitors, biocides, pH modifiers, or surfactants.

9. The method of claim 1 , wherein the anti-corrosion composition comprises from about 0.1 to about 20 wt. % of one or more compounds of formula (IA) in a 1:1 water:glycol ether solvent system.

10. The method of claim 2 , wherein R 1 of Formula (IA) is C 1 -C 12 alkyl optionally substituted with 1 to 3 substituents of —OH or —CO 2 H; or R 1 is C 1 -C 12 alkyl wherein one or more of the —CH 2 — groups is replaced with a —C(O)O— group.

11. The method of claim 2 , wherein R 1 of Formula (IA) is C 1 -C 12 alkyl substituted with 1 to 3 substituents of —OH or —CO 2 H; or R 1 is C 1 -C 12 alkyl wherein one or more of the —CH 2 — groups is replaced with a —C(O)O— group.

12. The method of claim 2 , wherein R 1 of Formula (IA) is linear C 1 -C 10 alkyl substituted with a terminal —OH group.

13. The method of claim 2 , wherein R 1 of Formula (IA) is linear C 1 -C 10 alkyl substituted with a terminal —CO 2 H group.

14. The method of claim 2 , wherein R 1 of Formula (IA) is linear C 1 -C 10 alkyl wherein one of the —CH 2 — groups is replaced with a —C(O)O— group.

15. The method of claim 2 , wherein R 1 of Formula (IA) is —CH 2 —CH 2 —OH, cyclohexyl, —(CH 2 ) 6 —OH, propyl, dodecyl, —CH 2 CH(OH)CH 2 OH, —CH(C(O)OH)CH 2 C(O)OH, —(CH 2 ) 2 C(O)OCH 2 CH(C 2 H 5 )C 4 H 9 , or —(CH 2 ) 2 C(O)OH.

16. The method of claim 2 , wherein R 3 of Formula (IA) is hydrogen.

17. The method of claim 5 , wherein R 3 of Formula (IA) is hydrogen.

18. The method of claim 17 , wherein R 1 of Formula (IA) is —CH 2 —CH 2 —OH.

19. The method of claim 17 , wherein R 1 of Formula (IA) is cyclohexyl, propyl,

dodecyl, —CH 2 CH(OH)CH 2 OH, —CH(C(O)OH)CH 2 C(O)OH, —(CH 2 ) 2 C(O)OCH 2 CH(C 2 H 5 )C 4 H 9 , or —(CH 2 ) 2 C(O)OH.

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 Feb 28, 2018
From: LAURENT, BOYD ANTHONY; ANANTANENI, PRAKASA RAO; HARRINGTON, RYAN MATTHEW; DE, SUBHASIS
To: ECOLAB USA INC.
Reel/Frame 045062/0580 →