Cationic ammonium surfactants as low dosage hydrate inhibitors

Patent metadata

Field	Value
Publication number	US-10435616-B2
Application number	US-201515522906-A
Country	US
Kind code	B2
Filing date	Oct 30, 2015
Priority date	Oct 30, 2014
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

This disclosure relates to anti-agglomerant low dosage hydrate inhibitors that can inhibit the formation of hydrate agglomerants and/or plugs. The anti-agglomerant low dosage hydrate inhibitors can be surfactants. The hydrate inhibitors can be used for inhibiting, retarding, mitigating, reducing, controlling and/or delaying formation of hydrocarbon hydrates, agglomerants of hydrates, and/or plugs. The hydrate inhibitors can be applied to prevent, reduce, and/or mitigate plugging of conduits, pipes, transfer lines, valves, and other places or equipment where hydrocarbon hydrate solids can form. The hydrate inhibitors can be zwitterionic or cationic ammonium surfactants.

First claim

What is claimed is:

1. A hydrate inhibitor composition comprising a hydrate-inhibiting effective amount of a compound of Formula (I), or an acid, a free base, a zwitterion, or a salt thereof:

wherein
R 1 is hydrogen, a C 1 to C 20 substituted or unsubstituted alkyl group, or a C 1 to C 20 substituted or unsubstituted alkenyl group;
R 2 is an alkylcarboxyl, or an alkylamido group;
R 4 is hydrogen, a C 1 to C 20 substituted or unsubstituted alkyl group, or a C 1 to C 20 substituted or unsubstituted alkenyl group;
R 5 is C 10 to C 20 alkyl or —R 50 —NR 6 R 7 , wherein R 50 is C 1 to C 5 alkylene, and R 6 and R 7 are independently C 1 to C 6 alkyl; and
R 8 is a C 2 to C 10 substituted or unsubstituted alkylene group.

2. The composition of claim 1 , wherein the substituted alkyl group of R 1 and R 4 has at least one of the —CH 2 — groups in the chain replaced with an ether, an amine, an amide, a carbonyl, or an ester functional group or at least one of the hydrogen atoms attached to a carbon atom of the chain is replaced with a hydroxy, a halo, or an amine group.

3. The composition of claim 2 , wherein the substituted alkyl group of R 1 and R 4 has at least one of the —CH 2 — groups in the chain replaced with an amine.

4. The composition of claim 1 , wherein R 8 is —C 2 H 4 —.

5. The composition of claim 4 , wherein R 1 is C 10 to C 20 alkyl or —R 10 —NR 6 R 7 , wherein R 10 is C 1 to C 5 alkylene, and R 6 and R 7 are independently substituted or unsubstituted C 1 to C 6 alkyl.

6. The composition of claim 1 , wherein R 2 is —R 20 —C(O)O − , wherein R 20 is C 1 to C 4 alkylene.

7. The composition of claim 1 , wherein R 4 is hydrogen.

8. The composition of claim 6 , wherein R 20 is C 2 H 4 , and R 50 is C 3 H 6 .

9. The composition of claim 1 , wherein when the compound is in its salt form, the counterion is selected from the group consisting of a halide, a carboxylate, hydrogen sulfate, dihydrogen phosphate, nitrate, and a combination thereof.

10. The composition of claim 9 , wherein the counterion is an acetate, an acrylate, or a combination thereof.

11. The composition of claim 1 , wherein the composition further comprises a thermodynamic hydrate inhibitor, a kinetic hydrate inhibitor, an anti-agglomerant, or a combination thereof.

12. The composition of claim 1 , wherein the composition further comprises a polar solvent, a nonpolar solvent, or a mixture thereof.

13. A method of inhibiting formation of hydrate agglomerants in a fluid comprising water, a gas, and optionally a liquid hydrocarbon, comprising contacting the fluid with an effective amount of a hydrate inhibitor composition of claim 1 .

14. The method of claim 13 , wherein the effective amount is from about 0.1 to about 10 volume %, based on an amount of water.

15. A hydrate inhibitor composition comprising a hydrate-inhibiting effective amount of:

wherein R 11 is C 8 to C 20 alkyl, and R 12 and R 13 are independently C 1 to C 6 alkyl.

16. The composition of claim 15 wherein the compound of Formula 1 is:

Assignees

• Ecolab Usa Inc

Inventors

• Lucente-Schultz Rebecca Michele
• Servesko Jeff

Classifications

• C07C237/10

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• C09K8/52 Primary

  Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning · CPC title

• C09K2208/22

  Hydrates inhibition by using well treatment fluids containing inhibitors of hydrate formers · CPC title

• C07C237/06

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title