IP Library Granted Patent US 8,329,620
Granted Patent B2
US 8,329,620 · App. 12/245,849 · Granted Dec 11, 2012

Compositions and methods for inhibiting the agglomeration of hydrates

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Quick Facts
Patent No.
US 8,329,620
App. No.
12/245,849
Granted
Dec 11, 2012
Kind
B2
Abstract

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

Claims (39)

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

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

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

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

wherein X − is optional and is a halogen or a carboxylate and wherein X − is only present when both R 1 and R 3 are present;

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

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

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

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

4. The composition claim 1 , wherein the halogen is chlorine, bromine, or iodine.

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

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

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

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

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

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

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

12. 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.

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

14. 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.

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

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

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

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

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

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

wherein X − is a halogen or a carboxylate and wherein X − is only present when both R 1 and R 3 are present;

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

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

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

19. The method of claim 17 , wherein R 3 is a methyl or ethyl group.

20. The method of claim 17 , wherein the halogen is chlorine, bromine, or iodine.

21. The method of claim 17 , wherein Y═(CH 2 ) n , wherein n is 1 to 4, optionally wherein Y is linear or branched.

22. The method of claim 17 , wherein R 1 is a C 4 -C 6 alkyl.

23. The method of claim 17 , wherein R 2 is a C 6 -C 12 alkyl.

24. The method of claim 17 , wherein said fluid has a salinity of 1% to 20% w/w percent TDS.

25. The method of claim 17 , wherein said aqueous medium has a water cut from 1 to 60% w/w or v/v total dissolved solids.

26. The method of claim 17 , wherein the aqueous medium is contained in an oil or gas pipeline or refinery.

27. The method of claim 17 , wherein the composition comprises the following formula:

Assignments (1)
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 →