IP Library Granted Patent US 10,100,241
Granted Patent B2
US 10,100,241 · App. 15/504,996 · Granted Oct 16, 2018

Double-headed hydrate inhibitors and methods of use

Inventors: Qiang Lan (The Woodlands, TX); Deepak Steven Monteiro (Houston, TX); Mark Paul Ceglio, II (El Paso, TX); Pushkala Krishnamurthy (Pearland, TX); Erick J. Acosta (Sugar Land, TX)
Assignee: Multi-Chem Group, LLC
C09K8/524C07C211/63C07C233/04C09K2208/22
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Quick Facts
Patent No.
US 10,100,241
App. No.
15/504,996
Granted
Oct 16, 2018
Kind
B2
Abstract

Compositions and methods of using of such compositions to, for example, inhibit of the formation of gas hydrate agglomerates are provided. In one embodiment, the methods comprise: introducing a hydrate inhibitor composition comprising a compound into a fluid, wherein the compound comprises two hydrophobic cation moieties, a lipophilic tail, and two linking moieties.

Claims (30)

1. A method comprising:

introducing a hydrate inhibitor composition into a fluid located in a conduit through which the fluid is flowing, a wellbore, or a subterranean formation, wherein the hydrate inhibitor composition comprises at least one compound having the structural formula:

wherein each of R 1 and R 2 is independently a C 1 to C 6 hydrocarbon chain,

wherein R 3 is selected from the group consisting of hydrogen and any C 1 to C 6 hydrocarbon chain,

wherein R 4 is a C 1 to C 50 hydrocarbon chain,

wherein each of X − and Y − is independently a counter anion, and

wherein each of a and b is independently an integer from 1 to 10.

2. The method of claim 1 wherein each of X − and Y − is independently selected from the group consisting of: a carboxylate, a halide, a sulfate, an organic sulfonate, a hydroxide, and any combination thereof.

3. The method of claim 1 wherein the fluid comprises at least one component selected from the group consisting of: water, a gas, a liquid hydrocarbon, and any combination thereof.

4. The method of claim 1 wherein the fluid is located in the wellbore and the hydrate inhibitor composition is introduced into the fluid through the conduit or an injection point in fluid communication with the wellbore.

5. The method of claim 1 wherein the fluid is flowing through the subterranean formation when the hydrate inhibitor composition is introduced into the fluid.

6. The method of claim 1 wherein the fluid comprises water and has a water cut of about 50% or more.

7. The method of claim 1 wherein the fluid comprises water and the hydrate inhibitor composition is introduced into the fluid in an amount such that the compound is present in the fluid in an amount from about 0.1% to about 10% by volume based on the water cut of the fluid.

8. The method of claim 1 wherein R 4 is a C 1 to C 50 hydrocarbon chain resulting from a reaction between an acrylate or a methacrylate and an amine, the amine being selected from the group consisting of:

a synthetic primary amine selected from the group consisting of: butylamine, hexylamine, octylamine, dodecylamine, and any combination thereof;

a primary fatty amine derived from one or more fatty acids selected from the group consisting of: corn oil, canola oil, coconut oil, safflower oil, sesame oil, palm oil, cottonseed oil, soybean oil, olive oil, sunflower oil, hemp oil, wheat germ oil, palm kernel oil, vegetable oil, caprylic acid, capric acid, lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, sapienic acid, elaidic acid, vaccenic acid, linoleic acid, arachidic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, docosahexaenoic acid, behenic acid, lignoceric acid, cerotic acid, oleic acids (cis- and trans-), and any combination thereof; and

any combination thereof.

9. The method of claim 1 wherein the compound is a reaction product of a reaction between (i) an alkylating agent and (ii) a second intermediate resulting from a reaction between a dialkylaminoalkylamine and a first intermediate, the first intermediate resulting from a reaction between an acrylate or a methacrylate and an amine.

10. A method comprising:

introducing a hydrate inhibitor composition into a wellbore penetrating at least a portion of a subterranean formation, wherein the hydrate inhibitor composition comprises at least one compound having the structural formula:

wherein each of R 1 and R 2 is independently a C 1 to C 6 hydrocarbon chain,

wherein R 3 is selected from the group consisting of hydrogen and any C 1 to C 6 hydrocarbon chain,

wherein R 4 is a C 1 to C 50 hydrocarbon chain,

wherein each of X − and Y − is independently a counter anion, and

wherein each of a and b is independently an integer from 1 to 10.

11. The method of claim 10 wherein the hydrate inhibitor composition is introduced into the wellbore through a conduit or an injection point in fluid communication with the wellbore.

12. The method of claim 10 wherein each of X − and Y − is independently selected from the group consisting of: a carboxylate, a halide, a sulfate, an organic sulfonate, a hydroxide, and any combination thereof.

13. The method of claim 10 further comprising allowing the hydrate inhibitor composition to contact a fluid residing in the wellbore.

14. The method of claim 13 wherein the fluid comprises water and has a water cut of about 50% or more.

15. The method of claim 13 wherein the fluid comprises at least one component selected from the group consisting of: water, a gas, a liquid hydrocarbon, and any combination thereof.

Assignments (3)
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 5, 2018
From: HALLIBURTON ENERGY SERVICES, INC.
To: MULTI-CHEM GROUP, LLC
Reel/Frame 046788/0529 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 17, 2017
From: LAN, QIANG; MONTEIRO, DEEPAK STEVEN; CEGLIO, MARK PAUL, II; KRISHNAMURTHY, PUSHKALA; ACOSTA, ERICK J.
To: HALLIBURTON ENERGY SERVICES, INC.
Reel/Frame 041289/0451 →
Continuity (1)
Related Publication 20180155608A1 · Jun 7, 2018