IP Library Granted Patent US 9,458,373
Granted Patent B2
US 9,458,373 · App. 14/098,139 · Granted Oct 4, 2016

Composition and method for reducing hydrate agglomeration

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Quick Facts
Patent No.
US 9,458,373
App. No.
14/098,139
Granted
Oct 4, 2016
Kind
B2
Abstract

Compositions and methods of inhibiting the formation of hydrate agglomerates in fluids including water, gas, and optionally liquid hydrocarbons are disclosed. The compositions may include counterions, such as halides or carboxylates. The compositions may also include a thermodynamic hydrate inhibitor, a kinetic hydrate inhibitor, an additional anti-agglomerant, an asphaltene inhibitor, a paraffin inhibitor, a corrosion inhibitor, a scale inhibitor, an emulsifier, a water clarifier, a dispersant, an emulsion breaker, and combinations thereof.

Claims (32)

1. A composition comprising the following formula:

wherein R 1 is C 1 -C 10 alkyl or benzyl;

wherein R 2 is C 1 -C 10 alkyl, benzyl, or H;

wherein R 3 is C 1 -C 10 alkyl, benzyl, or H; and

wherein R 4 is C 4 -C 22 alkyl or alkenyl.

2. The composition of claim 1 , wherein each alkyl is independently selected from the group consisting of: a straight chain alkyl, a branched chain alkyl, a cyclic alkyl, and combinations thereof.

3. The composition of claim 1 , wherein the alkyl for each of R 1 , R 2 , and R 3 is independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and combinations thereof.

4. The composition of claim 1 , wherein the alkyl for R 4 is selected from the group consisting of butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and combinations thereof.

5. The composition of claim 1 , wherein the terminal nitrogen is further substituted with R 1 , and forms an ammonium ion, the composition further comprising a counterion X − as shown in the general formula below

6. The composition of claim 5 , wherein the counterion is a halide or a carboxylate.

7. The composition of claim 5 , comprising at least one or any combination of the following formulas (1) and (2), and optionally salts thereof:

8. The composition of claim 1 , further comprising at least one component selected from the group consisting of a thermodynamic hydrate inhibitor, a kinetic hydrate inhibitor, an additional anti-agglomerant, an asphaltene inhibitor, a paraffin inhibitor, a corrosion inhibitor, a scale inhibitor, an emulsifier, a water clarifier, a dispersant, an emulsion breaker, and combinations thereof.

9. The composition of claim 1 , further comprising at least one polar or nonpolar solvent or a mixture thereof.

10. A method of inhibiting the formation of hydrate agglomerates in a fluid comprising water, gas, and optionally liquid hydrocarbon comprising adding to the fluid the composition of claim 1 .

11. The method of claim 10 , wherein the fluid is contained in an oil or gas pipeline or refinery.

12. A composition comprising the following formula:

wherein R 1 is C 1 -C 10 alkyl, benzyl, or H;

wherein R 2 is C 5 -C 10 alkyl, benzyl, or H;

wherein R 3 is C 5 -C 10 alkyl, benzyl, or H; and

wherein R 4 is C 4 -C 22 alkyl or alkenyl.

13. A method of inhibiting the formation of hydrate agglomerates in a fluid comprising water, gas, and optionally liquid hydrocarbon comprising adding to the fluid the composition of claim 12 .

14. A method of inhibiting the formation of hydrate agglomerates in a fluid comprising water, gas, and optionally liquid hydrocarbon comprising adding to the fluid a composition comprising the following formula:

wherein R 1 is C 1 -C 10 alkyl, benzyl, or H;

wherein R 2 is C 1 -C 10 alkyl, benzyl, or H;

wherein R 3 is C 1 -C 10 alkyl, benzyl, or H; and

wherein R 4 is C 4 -C 22 alkyl or alkenyl.

15. The method of claim 14 , comprising at least one or any combination of the following formulas

16. The method of claim 14 , wherein R 1 is C 1 -C 10 alkyl or benzyl.

17. The method of claim 14 , wherein R 2 and R 3 are independently selected from C 5 -C 10 alkyl, benzyl, or H.

18. The method of claim 14 , wherein said fluid has a salinity of 1% to 25% w/w percent TDS.

19. The method of claim 14 , wherein said fluid has a water cut from 1 to 80% v/v total dissolved solids.

20. The method of claim 14 , wherein the fluid is contained in an oil or gas pipeline or refinery.

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 Jan 27, 2021
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 055141/0568 →
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 Dec 12, 2013
From: WEBBER, PETER A.
To: ECOLAB USA INC.
Reel/Frame 031773/0608 →