IP Library Granted Patent US 10,281,086
Granted Patent B2
US 10,281,086 · App. 15/231,424 · Granted May 7, 2019

Anti-agglomerants for controlling gas hydrates

Inventors: Peter A. Webber (Sugar Land, TX); Sahana Nagappayya (Houston, TX)
Assignee: Ecolab USA Inc.
F17D1/16C09K8/52C10G75/04C09K2208/22
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Quick Facts
Patent No.
US 10,281,086
App. No.
15/231,424
Granted
May 7, 2019
Kind
B2
Abstract

The present invention generally relates to one or more compositions and methods for inhibiting the formation of gas hydrate agglomerates in a fluid. The fluid may be contained, for example, in an oil or gas pipeline or refinery.

Claims (34)

1. A method for inhibiting gas hydrate agglomeration in a fluid comprising a hydrocarbon and water, the method comprising adding to the fluid an effective amount of a compound of formula 2A, 3A, 4A, 5A, or 7A to inhibit gas hydrate agglomeration in the fluid, wherein the compound of Formula 2A, 3A, 4A, 5A, or 7A corresponds to the following structures:

wherein

R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , and R 29 are each independently hydrogen, alkyl, alkoxy, aminoalkyl, carboxyl, carboxyalkyl, alkenyl, alkenoxy; carboxyalkenyl, aryl, aryloxy, or carboxyaryl;

R 31 , R 32 , R 33 , and R 34 are each independently hydrogen, alkyl, alkoxy, aminoalkyl, carboxyl, carboxyalkyl, alkenyl, alkenoxy; carboxyalkenyl, aryl, aryloxy, or carboxyaryl;

R 2 is optionally substituted alkyl, alkenyl, or alkynyl;

Z is —NR 3 —C(O)—, —C(O)—NR 3 —, —O—C(O)—, —C(O)—O—, —S—C(O)—, —C(O) —S—, —O—C(O) —NR 3 —, —NR 3 —C(O)—O—, or —NR 3 —C(O) —NR 3 —;

R 3 is hydrogen or optionally substituted alkyl, alkenyl, alkynyl, or aryl; and

n is an integer from 0 to 25.

2. The method of claim 1 wherein

R 2 is C 10 -C 24 alkyl or alkenyl;

Z is —NR 3 —C(O) —or —C(O)—NR 3 —,

n is an integer from 0 to 12.

3. The method of claim 1 wherein Z is —C(O)—NR 3 —and R 3 is hydrogen.

4. The method of claim 3 wherein R 2 is C 10 -C 20 alkyl or alkenyl, and n is 2 or 3.

5. The method of claim 1 wherein the compound has the structure of Formula 3A

6. The method of claim 5 wherein R 31 , R 32 , R 33 , and R 34 are hydrogen, Z is —NR 3 —C(O)— or —C(O)—NR 3 —, R 3 is hydrogen, R 2 is C 10 -C 20 alkyl or alkenyl, and n is 2 or 3.

7. The method of claim 6 wherein Z is —C(O)—NR 3 —, and n is 2.

8. The method of claim 6 wherein Z is —NR 3 —C(O)—, and n is 3.

9. The method of claim 1 wherein the compound has the structure of Formula 4A

10. The method of claim 9 wherein R 32 , R 33 , and R 34 are hydrogen, Z is —NR 3 —C(O)—or —C(O)—NR 3 —, R 3 is hydrogen, R 2 is C 10 -C 20 alkyl or alkenyl, and n is 2 or 3.

11. The method of claim 9 wherein Z is —C(O)—NR 3 —, and n is 2.

12. The method of claim 9 wherein Z is —NR 3 —C(O)—, and n is 3.

13. A method for inhibiting gas hydrate agglomeration in a fluid comprising a hydrocarbon and water, the method comprising adding to the fluid an effective amount of a compound of formula 2A to inhibit gas hydrate agglomeration in the fluid, the compound having the structure

wherein

R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , and R 29 are each independently hydrogen, alkyl, alkoxy, aminoalkyl, carboxyl, carboxyalkyl, alkenyl, alkenoxy; carboxyalkenyl, aryl, aryloxy, or carboxyaryl;

R 31 , R 32 , R 33 , and R 34 are each independently hydrogen, alkyl, alkoxy, aminoalkyl, carboxyl, carboxyalkyl, alkenyl, alkenoxy; carboxyalkenyl, aryl, aryloxy, or carboxyaryl;

R 2 is optionally substituted alkyl, alkenyl, or alkynyl;

Z is —NR 3 —C(O)—, —C(O)—NR 3 —, —O—C(O)—, —C(O)—O—, —S—C(O)—, —C(O)—S—, —O—C(O)—NR 3 —, —NR 3 —C(O)—O—, or —NR 3 —C(O)—NR 3 —;

R 3 is hydrogen or optionally substituted alkyl, alkenyl, alkynyl, or aryl; and

n is an integer from 0 to 25.

14. The method of claim 13 wherein R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 are hydrogen, Z is —NR 3 —C(O)—or —C(O)—NR 3 —, R 2 is C 10 -C 20 alkyl or alkenyl, and n is 2 or 3.

15. The method of claim 14 wherein Z is —C(O)—NR 3 —, R 3 is hydrogen, and n is 2.

16. The method of claim 14 wherein Z is —NR 3 —C(O)—, R 3 is hydrogen, and n is 3.

17. The method of claim 14 wherein R 3 is hydrogen.

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 Aug 8, 2016
From: WEBBER, PETER A.; NAGAPPAYYA, SAHANA
To: ECOLAB USA INC.
Reel/Frame 039372/0631 →
Continuity (2)
Continuation 14090621 · Nov 26, 2013
Related Publication 20160348848A1 · Dec 1, 2016