Carboxy alkyl-ester anti-agglomerants for the control of natural gas hydrates

Patent metadata

Field	Value
Publication number	US-11174235-B2
Application number	US-201916440663-A
Country	US
Kind code	B2
Filing date	Jun 13, 2019
Priority date	Jun 14, 2018
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

This disclosure relates to anti-agglomerant low dosage hydrate inhibitors that can inhibit the formation of hydrate agglomerants and/or plugs. Thus, provided herein are carboxy alkyl ester compounds that can be used in hydrate inhibitor compositions and methods of inhibiting formation of hydrate agglomerants in a fluid comprising water, a gas, and optionally a liquid hydrocarbon. Also provided herein are methods of making the carboxy alkyl ester compound.

First claim

The invention claimed is:

1. A compound having the structure of formula (Ia) or an acid, a free base, a zwitterion, or a salt thereof:

wherein
R 1 is C 10 to C 24 alkyl or alkenyl or straight or branched C 6 -C 24 alkyl and contains 1 to 12 ethylene oxide units;
R 5 is hydrogen;
R 2 is hydrogen;
R 4 is hydrogen; and
R 6 and R 7 are independently alkyl or R 6 and R 7 together with the nitrogen they are attached to form a ring.

2. The compound of claim 1 , wherein R 6 and R 7 are the same.

3. A compound having the structure of formula (Ie) or an acid, a free base, a zwitterion, or a salt thereof:

wherein
R 1 is hydrogen;
(ii) R 5 is C 10 to C 24 alkyl or alkenyl or straight or branched C 6 -C 24 alkyl and contains 1 to 12 ethylene oxide units;
R 4 is hydrogen;
A is a nitrogen-containing heterocycle, wherein the nitrogen-containing heterocycle is an optionally substituted pyrrolidine, piperidine, pyrazolidine, imidazolidine, isoxazolidine, oxazolidine, or azepane.

4. The compound of claim 3 , wherein the nitrogen-containing heterocycle is pyrrolidine, piperidine, pyrazolidine, imidazolidine, isoxazolidine, oxazolidine, or azepane.

5. A compound selected from the group consisting of:

6. A hydrate inhibitor composition comprising a hydrate-inhibiting effective amount of a compound of formula (I) of claim 1 .

7. A method of inhibiting formation of hydrate agglomerants in a fluid comprising water, a gas, and optionally a liquid hydrocarbon, the method comprising contacting the fluid with an effective amount of a hydrate inhibitor composition of claim 6 .

8. The compound of claim 1 , wherein R 1 is C 10 to C 24 alkyl.

9. The compound of claim 1 , wherein R 1 is C 10 to C 24 alkenyl.

10. The compound of claim 1 , wherein R 1 is straight or branched C 6 -C 24 alkyl and contains 1 to 12 ethylene oxide units.

11. The compound of claim 1 , wherein R 6 and R 7 are independently alkyl.

12. The compound of claim 1 , wherein R 6 and R 7 are independently C 1 to C 6 alkyl.

13. The compound of claim 5 , comprising:

14. The compound of claim 3 , wherein A is pyrrolidine.

15. The compound of claim 14 , wherein R 5 is C 10 to C 24 alkyl or alkenyl.

16. The compound of claim 14 , wherein R 5 is straight or branched C 6 -C 24 alkyl and contains 1 to 12 ethylene oxide units.

Assignees

• Championx Usa Inc

Inventors

• Servesko Jeff Michael
• Bartels Jeremy Wayne
• Jones Regan Andrew
• Metoyer Corbin

Classifications

• C10G2300/80

  Additives · CPC title

• C10L1/232

  containing nitrogen in a heterocyclic ring {(C10L1/221 takes precedence)} · CPC title

• C02F1/68

  by addition of specified substances, e.g. trace elements, for ameliorating potable water (medicinal water A61K) · CPC title

• C10L3/107 Primary

  Limiting or prohibiting hydrate formation · CPC title

• C07D295/15 Primary

  to an acyclic saturated chain · CPC title