IP Library Granted Patent US 10,113,128
Granted Patent B2
US 10,113,128 · App. 15/087,237 · Granted Oct 30, 2018

Fluorine-containing agents for enhancing hydrate inhibitors

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Quick Facts
Patent No.
US 10,113,128
App. No.
15/087,237
Granted
Oct 30, 2018
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 using a fluorine-containing agent and an anti-agglomerant. The fluid may be contained, for example, in an oil or gas pipeline or refinery.

Claims (23)

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 gas hydrate-inhibiting composition, the composition comprising an anti-agglomerant agent and a fluorine-containing agent comprising a fluoroalkyl moiety, the hydrate-inhibiting composition inhibiting gas hydrate agglomeration in the fluid.

2. The method of claim 1 , wherein the fluorine-containing agent is a perfluoropolyether, a perfluroalkylether, a perfluoropolyalkylether, a partially fluorinated betaine, a partially fluorinated amine oxide, a partially fluorinated non-ionic surfactant, a perfluroalkane, a partially fluorinated polybutylene, or a combination thereof.

3. The method of claim 1 , wherein the fluorine-containing agent is a compound of formula 1 having the structure of:

4. The method of claim 1 , wherein the fluorine-containing agent is a compound of formula 2 having the structure of:

wherein x is an integer from 10 to 60.

5. The method of claim 1 , wherein the fluorine-containing agent is a compound of formula 3 having the structure of:

wherein y is an integer from 1 to 275.

6. The method of claim 1 , wherein the fluorine-containing agent is a compound of formula 4 having the structure of:

7. The method of claim 1 , wherein the anti-agglomerant agent is an oxazolidinium compound; a quaternary ammonium compound with alkyl groups, alkoxylated alkyl groups, and fatty ester groups; tetrapropylene succinic acid-N,N-dibutylamino-N-ethyl ester; a quaternary ammonium compound with alkyl groups having alkoxy, amide, and ester substitution; a quaternary alkyl ammonium compounds; a quaternary ammonium, a quaternary phosphonium, a betaine, an amide, an amino alcohol, an ester, a sulphonium salt, or an amine oxide; an onium compound and amine salt; an amine compound having ether linkages; an alkoxylated diamine; an amine oxide salt; a zwitterionic quaternary ammonium compound; an ammonium or phosphonium alkylated hydrate; an alkylated ammonium, phosphonium, or sulphonium compound; a water-soluble alkoxide-based polymer or copolymer; an amino acid; a nonionic or anionic amphiphilic compound containing a polyol and a substituted or unsubstituted carboxylic acid; a hydroxycarbylamide; an organic amine and organic acid salt; a piperazine derivative; a quaternary ammonium substituted with an alkoxy group; an ion-pair amphiphilic complex; a rhamnolipid biosurfactant; a citric acid ester or citramide derivative; a quaternary amine having an amide group; a quaternary amine having an ester group; an ester quaternary ammonium compound; a reaction product of a polymerized unsaturated oil and an amino alcohol; an alkyl quaternary ammonium or phosphonium having alkoxylation; a quaternary sulphonium, phosphonium, ammonium salt combined with a corrosion inhibitor; an alkyl glycoside; an alkyl aryl sulphonic acid or an alkali metal or ammonium salt; a pyroglutamic acid ester; a tertiary amine salt; a quaternary ammonium polyoxyalkylene ester; a reaction product of a non-halide-containing inorganic acid, organic acid, or organic amine; a quaternary benzylammonium ion; a quaternary alkylammonium ion; a piperazinium amide/ester surfactant; an ammonium amide/ester surfactant; a cyclic ammonium amide/ester surfactant; or a combination thereof.

8. The method of claim 1 , wherein the anti-agglomerant agent is an amide, a quaternary benzylammonium ion, a quaternary alkylammonium ion, piperazinium amide/ester surfactant, an ammonium amide/ester surfactant, a cyclic ammonium amide/ester surfactant, or a combination thereof.

9. The method of claim 8 , wherein the anti-agglomerant agent is an amide, an ammonium amide/ester surfactant, a cyclic ammonium amide/ester surfactant, or a combination thereof.

10. The method of claim 1 , wherein an effective amount of the fluorine-containing agent is from about 0.1 to about 2 wt. % based on the total weight of the produced water in the well system.

11. The method of claim 10 , wherein the effective amount of the fluorine-containing agent is from about 0.5 to about 1.5 wt. %.

12. A method for inhibiting gas hydrate formation in a fluid comprising a hydrocarbon and water, the method comprising adding to the fluid an effective amount of a gas hydrate-inhibiting composition comprising a low dose hydrate inhibitor and a fluorine-containing agent, the gas hydrate-inhibiting composition inhibiting gas hydrate formation in the fluid, wherein the fluorine-containing agent comprises a fluoroalkyl moiety.

13. The method of claim 12 , wherein the fluorine-containing agent is a perfluoropolyether, a perfluroalkylether, a perfluoropolyalkylether, a partially fluorinated betaine, a partially fluorinated amine oxide, a partially fluorinated non-ionic surfactant, a perfluroalkane, a partially fluorinated polybutylene, or a combination thereof.

14. The method of claim 12 , wherein the fluorine-containing agent is a compound of formula 1 having the structure of:

15. The method of claim 12 , wherein the fluorine-containing agent is a compound of formula 2 having the structure of:

wherein x is an integer from 10 to 60.

16. The method of claim 12 , wherein the fluorine-containing agent is a compound of formula 3 having the structure of:

wherein y is an integer from 1 to 275.

17. The method claim 12 , wherein the fluorine-containing agent is a compound of formula 4 having the structure of:

18. The method of claim 1 , wherein the fluorine-containing agent comprises poly(vinylidene fluoride), poly(vinylidene-co-hexafluoro propylene), or a combination thereof.

19. The method of claim 12 , wherein the fluorine-containing agent comprises poly(vinylidene fluoride), poly(vinylidene-co-hexafluoro propylene), or a combination thereof.

Assignments (5)
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 →