IP Library Granted Patent US 8,334,240
Granted Patent B2
US 8,334,240 · App. 12/400,428 · Granted Dec 18, 2012

Compositions and methods for inhibiting the agglomeration of hydrates in a process

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Quick Facts
Patent No.
US 8,334,240
App. No.
12/400,428
Granted
Dec 18, 2012
Kind
B2
Abstract

One or more compositions and methods for inhibiting the formation of hydrate agglomerates in a fluid that contain a specified generic formula are disclosed. The fluid can be contained in an oil or gas pipeline or refinery.

Claims (37)

1. A composition comprising the following formula and optionally salts thereof:

where R 1 is C n H 2n+1 , wherein n=0 to 12; benzyl; or II;

where R 2 is a C 4 to C 22 alkyl;

where R 3 is C n H 2n+1 , wherein n=0 to 12; benzyl; or II;

where X − is an anion or a sulfate and wherein X − is only present when both R 1 and R 3 are present;

where Y=(CH 2 ) n , wherein n is 1 to 8; and

wherein R 3 and R 1 can not be Hydrogen at the same time.

2. The composition of claim 1 , wherein the alkyl group of R 1 is liner and/or branched.

3. The composition of claim 1 , wherein R 3 is a methyl or an ethyl group.

4. The method of claim 1 , wherein Y=(CH 2 ) n , wherein n is 1 to 4, optionally wherein Y is linear or branched.

5. The composition of claim 1 , wherein R 1 is a C 4 -C 6 alkyl.

6. The composition of claim 1 , wherein R 2 is a C 6 -C 12 alkyl.

7. The composition of claim 1 comprising the following formula and optionally salts thereof:

8. The composition of claim 1 comprising the following formula:

9. The composition of claim 1 , wherein the composition further comprises one or more hydrate inhibitors.

10. The composition of claim 1 , wherein the composition farther comprises one or more thermodynamic hydrate inhibitors, one or more kinetic hydrate inhibitors, one or more anti-agglomerants, or a combination thereof.

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

12. The composition of claim 1 , wherein the composition further comprises one or more polar or nonpolar solvents or a mixture thereof.

13. The composition of claim 1 , wherein the composition further comprises one or more solvents selected from isopropanol, methanol, ethanol, heavy aromatic naptha, toluene, ethylene glycol, ethylene glycol monobutyl ether (EGMBE), diethylene glycol monoethyl ether, xylene, or a combination thereof.

14. The composition of claim 1 , wherein the alkyl group of R 2 is linear, branched, cyclic, and/or unsaturated.

15. A hydrate inhibitor comprising a quaternary ammonium salt prepared by reacting dodecyl 3-(4-methylpiperazin-1-yl) with an alkyl or a benzyl halide.

16. A method of inhibiting the formation of hydrate agglomerates in a fluid comprising water, gas, and optionally liquid hydrocarbon comprising adding to the fluid an effective anti-agglomerant amount of a composition comprising the following formula:

where R 1 is C n H 2n+1 , wherein n=0 to 12; benzyl; or H and wherein R 1 is linear;

where R 2 is a C 4 to C 12 alkyl;

where R 3 is C n H 2n+1 , wherein n=0 to 12; benzyl; or H and wherein R 3 is linear;

where X − is an anion, or sulfate and wherein X − is only present when both R 1 and R 3 are present;

where Y=(CH 2 ) n , wherein n is 1 to 6; and

wherein R 3 and R 1 can not be hydrogen at the same time.

17. The method of claim 16 , wherein the alkyl groups of R 2 are linear, branched, cyclic, and/or unsaturated.

18. The method of claim 16 , wherein R 3 is a methyl or ethyl group.

19. The method of claim 16 , wherein Y=(CH 2 ) n , wherein n is 1 to 4, optionally wherein Y is linear or branched.

20. The method of claim 16 , wherein R 1 is a C 4 -C 6 alkyl.

21. The method of claim 16 , wherein R 2 is a C 6 -C 12 alkyl.

22. The method of claim 16 , wherein said fluid has a salinity of 1% to 20% w/w percent TDS.

23. The method of claim 16 wherein said fluid has a water cut from 1 to 60% v/v total dissolved solids.

24. The method of claim 16 , wherein the fluid is contained in an oil or gas pipeline or refinery.

25. The method of claim 16 , wherein the composition comprises the following formula:

Assignments (9)
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 Mar 24, 2022
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 059496/0219 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 053250/0001 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 052848/0368 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2017
From: NALCO COMPANY
To: ECOLAB USA INC.
Reel/Frame 042147/0420 →
CHANGE OF NAME Recorded Feb 28, 2017
From: NALCO COMPANY
To: NALCO COMPANY LLC
Reel/Frame 041835/0903 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2017
From: NALCO COMPANY LLC; CALGON CORPORATION; CALGON LLC; ONDEO NALCO ENERGY SERVICES, L.P.
To: ECOLAB USA INC.
Reel/Frame 041836/0437 →
RELEASE OF SECURITY INTEREST Recorded Feb 24, 2017
From: BANK OF AMERICA, N.A.
To: NALCO COMPANY
Reel/Frame 041808/0713 →