IP Library Granted Patent US 9,902,893
Granted Patent B2
US 9,902,893 · App. 15/706,903 · Granted Feb 27, 2018

Multiple hydrophilic head hydrate inhibitors

Inventors: Liangwei Qu (Spring, TX); Yangqiu Sun (Houston, TX); Funian Zhao (Tomball, TX); Curtis Conkle (Conroe, TX); Erick J. Acosta (Sugar Land, TX)
Assignee: Multi-Chem Group, LLC
C09K8/524C09K8/52C10L3/107C09K2208/22
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Quick Facts
Patent No.
US 9,902,893
App. No.
15/706,903
Granted
Feb 27, 2018
Kind
B2
Abstract

Compounds comprising multiple hydrophilic heads and a lipophilic tail may be employed into fluids to inhibit agglomeration of hydrates, among other things. Suitable hydrophilic heads may include secondary, tertiary, and/or quaternary ammonium cation moieties, phosphonium cation moieties, and combinations thereof. Such LDHI compounds may provide enhanced interactivity with hydrate crystals and/or hydrate-forming molecules. These compounds may be employed in fluids in various environments, such as a conduit penetrating a subterranean formation, or a conduit carrying fluid in an industrial setting.

Claims (26)

1. A composition comprising a compound having the structural formula:

wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of: hydrogen and a C 2 to C 8 hydrocarbon chain;

wherein each of X and X′ is an anion selected from the group consisting of halide, carboxylate, sulfate, organic sulfonate, hydroxide, and combinations thereof; and

wherein R comprises a hydrocarbon chain that comprises more carbon atoms than each one of R 1 , R 2 , and R 3 .

2. The composition of claim 1 wherein each of R 1 , R 2 , and R 3 is linear C 3 H 7 and R is a C 12 to C 16 hydrocarbon chain.

3. The composition of claim 1 , further comprising a solvent selected from the group consisting of: toluene, xylene, methanol, isopropyl alcohol, glycol, and combinations thereof.

4. The composition of claim 1 , wherein each of R 1 , R 2 , and R 3 is linear C 4 H 9 and R is a C 12 to C 16 hydrocarbon chain.

5. The composition of claim 1 , wherein R 1 is hydrogen, each of R 2 and R 3 is linear C 3 H 7 , and R is a C 12 to C 16 hydrocarbon chain.

6. The composition of claim 1 , wherein R is unsubstituted.

7. The composition of claim 1 , further comprising an acid selected from the group consisting of: acrylic acid, acetic acid, hydrochloric acid, citric acid, and combinations thereof.

8. A fluid comprising:

(i) water,

(ii) one of gas, liquid hydrocarbon, and combinations thereof, and

(iii) a hydrate inhibitor additive comprising a compound having the structural formula:

wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of: hydrogen and a C 2 to C 8 hydrocarbon chain;

wherein each of X and X′ is an anion selected from the group consisting of halide, carboxylate, sulfate, organic sulfonate, hydroxide, and combinations thereof; and

wherein R comprises a hydrocarbon chain that comprises more carbon atoms than each one of R 1 , R 2 , and R 3 .

9. The fluid of claim 8 , wherein each of R 1 , R 2 , and R 3 is linear C 3 H 7 and R is a C 12 to C 16 hydrocarbon chain.

10. The fluid of claim 8 , wherein R is unsubstituted.

11. The fluid of claim 8 , wherein each of R 1 , R 2 , and R 3 is linear C 4 H 9 and R is a C 12 to C 16 hydrocarbon chain.

12. The fluid of claim 8 , wherein R 1 is hydrogen, each of R 2 and R 3 is linear C 3 H 7 , and R is a C 12 to C 16 hydrocarbon chain.

13. The fluid of claim 8 , wherein the fluid has a water cut of 50% or more.

14. The fluid of claim 8 , wherein the fluid has a water cut of between about 30% and about 60%.

15. The fluid of claim 8 , further comprising a solvent selected from the group consisting of: toluene, xylene, methanol, isopropyl alcohol, glycol, and combinations thereof.

16. The fluid of claim 8 , further comprising an acid selected from the group consisting of: acrylic acid, acetic acid, hydrochloric acid, citric acid, and combinations thereof.

17. The fluid of claim 8 , wherein the compound is present in the fluid in an amount equal to about 0.1 to about 3.0% volume based on the water cut of the fluid.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2021
From: MULTI-CHEM GROUP, LLC
To: HALLIBURTON ENERGY SERVICES, INC.
Reel/Frame 056681/0849 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 18, 2017
From: QU, LIANGWEI; SUN, YANQIU; ZHAO, FUNIAN; CONKLE, CURTIS; ACOSTA, ERICK J.
To: MULTI-CHEM GROUP LLC
Reel/Frame 043611/0873 →
Continuity (2)
Division 14765460
Related Publication 20180010036A1 · Jan 11, 2018