IP Library Granted Patent US 8,288,323
Granted Patent B2
US 8,288,323 · App. 12/396,076 · Granted Oct 16, 2012

Compositions containing amide surfactants and methods for inhibiting the formation of hydrate agglomerates

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Quick Facts
Patent No.
US 8,288,323
App. No.
12/396,076
Granted
Oct 16, 2012
Kind
B2
Abstract

One or more compositions and methods for inhibiting the formation of hydrate agglomerates in a fluid comprising water, gas, and optionally liquid hydrocarbon are disclosed. The fluid can be contained in an oil or gas pipeline or refinery.

Claims (33)

1. 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 amount of a composition comprising the following formula and optionally salts thereof:

wherein R 1 is C 4 H 9 , C 6 H 13 , C 8 H 17 , or benzyl;

wherein R 2 is a C 8 H 17 , C 12 H 25 , or C 18 H 35 ;

wherein R 3 is CH 3 or C 2 H 5 ;

wherein R 4 is C n H 2n+1 , wherein n=0 to 22; or H

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

wherein Y═(CH 2 ) n , wherein n=1 to 8.

2. The method of claim 1 , wherein R 1 and/or R 2 and/or R 4 are linear, branched, and/or cyclic.

3. The method of claim 1 , wherein the halogen is selected from chlorine, bromine, iodine, or combinations thereof.

4. The method of claim 1 , wherein Y═(CH 2 ) n , wherein n=1 to 4.

5. The method of claim 1 , where Y═(CH 2 ) n , wherein n=1 to 2.

6. The method of claim 1 , comprising the following formula and optionally salts thereof:

7. The method of claim 1 , comprising the following formula:

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

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

10. The method 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.

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

12. The method 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, kerosene, diesel, isobutanol, heptane, or a combination thereof.

13. The method of claim 1 , wherein R 2 and R 4 are independently linear, branched, and/or cyclic.

14. The method of claim 1 , wherein Y═(CH 2 ) n , wherein n=1 to 4.

15. The method of claim 1 , wherein said fluid has a salinity of 1 to 20 w/w percent total dissolved solids.

16. The method of claim 1 , wherein said fluid has a water cut from 1 to 60 v/v percent.

17. The method of claim 1 , wherein the fluid is contained in an oil or gas pipeline.

18. 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 amount of a composition produced by reacting an alkyl acrylate with 1-methylpiperazine and then subsequently reacting the resulting product with an amine to form an amide and reacting said amide with an alkyl halide.

19. The composition of claim 18 , wherein said amine is oleylamine.

20. The composition of claim 18 , wherein the alkyl halide is a 1-bromohexane.

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

wherein R 1 is C 4 H 9 , C 6 H 13 , C 8 H 17 , or benzyl;

wherein R 2 is a C 8 H 17 , C 12 H 25 , or C 18 H 35 ;

wherein R 3 is CH 3 or C 2 H 5 ;

wherein R 4 is C n H 2n+1 , wherein n=0 to 22; or H

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

wherein Y═(CH 2 ) n , wherein n=1 to 8.

Assignments (11)
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 →
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 Apr 4, 2017
From: NALCO COMPANY
To: ECOLAB USA INC.
Reel/Frame 042147/0420 →
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 →
CHANGE OF NAME Recorded Feb 28, 2017
From: NALCO COMPANY
To: NALCO COMPANY LLC
Reel/Frame 041835/0903 →
RELEASE OF SECURITY INTEREST Recorded Feb 24, 2017
From: BANK OF AMERICA, N.A.
To: NALCO COMPANY
Reel/Frame 041808/0713 →
RELEASE OF SECURITY INTEREST Recorded Jun 18, 2015
From: BANK OF AMERICA, N.A.
To: NALCO COMPANY
Reel/Frame 035976/0609 →
SECURITY AGREEMENT Recorded May 18, 2009
From: NALCO COMPANY; CALGON LLC; NALCO ONE SOURCE LLC; NALCO CROSSBOW WATER LLC
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 022703/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 2, 2009
From: ACOSTA, ERICK J.; WEBBER, PETER A.
To: NALCO COMPANY
Reel/Frame 022332/0242 →