Hydrate inhibitors

Patent metadata

Field	Value
Publication number	US-11780940-B2
Application number	US-202016915214-A
Country	US
Kind code	B2
Filing date	Jun 29, 2020
Priority date	Jun 29, 2020
Publication date	Oct 10, 2023
Grant date	Oct 10, 2023

Abstract

An N-vinyl amide polymer is disclosed. The N-vinyl amide polymer is a reaction product of: a monomer component comprising an N-vinyl amide; and a chain transfer agent of the formula:

wherein each occurrence of R 1 is independently a C 1-20 alkylene, a C 1-20 heteroalkylene, a C 3-20 cycloalkylene, a C 3-20 heterocycloalkylene, a C 6-20 arylene, or a combination thereof, and R 1 is substituted or unsubstituted; R 2 is a divalent or multivalent organic group having 2 to 40 carbon atoms; and n is at least 2.

First claim

What is claimed is:

1. An N-vinyl amide polymer which is a reaction product of:
a monomer component comprising an N-vinyl amide; and
a chain transfer agent of Formula (I):

wherein
each occurrence of R 1 is independently a C 1-20 alkylene, a C 1-20 heteroalkylene, a C 3-20 cycloalkylene, a C 3-20 heterocycloalkylene, a C 6-20 arylene, or a combination thereof, and R 1 is substituted or unsubstituted;
R 2 is a multivalent organic group having 2 to 40 carbon atoms; and
n is at least 2.

2. The N-vinyl amide polymer of claim 1 , wherein each occurrence of R 1 is independently a C 1-10 alkylene, a C 6-12 arylene, or a combination thereof.

3. The N-vinyl amide polymer of claim 1 , wherein R 2 is a substituted or unsubstituted C 2-30 alkyl, C 3-30 cycloalkyl, C 2-30 heteroalkyl, C 3-30 heterocycloalkyl, or a combination comprising at least one of the foregoing.

4. The N-vinyl amide polymer of claim 1 , wherein R 2 has one or more hydroxyl substituents.

5. The N-vinyl amide polymer of claim 1 , wherein the N-vinyl amide is of Formula (II) or Formula (III)

wherein
each R 4 is independently a halogen atom or a C 1-10 alkyl,
each of R 5 and R 6 is independently hydrogen or a C 1-10 alkyl,
n is 1 to 5, and
m is 2+n.

6. The N-vinyl amide polymer of claim 5 , wherein the N-vinyl amide is of Formula (II), m is 0, and n is 1 to 2.

7. The N-vinyl amide polymer of claim 1 , wherein the monomer component further comprises at least one of an acrylate or an acrylamide.

8. The N-vinyl amide polymer of claim 1 , wherein the N-vinyl amide polymer is a reaction product of the monomer component, the chain transfer agent, and a crosslinking agent.

9. The N-vinyl amide polymer of claim 8 , wherein the crosslinking agent comprises glycerol dimethacrylate, ethylene glycol dimethacrylate, di(ethylene glycol) dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, poly(ethylene glycol) dimethacrylate, 1,3-butanediol dimethacrylate, 1,4-butanediol dimethacrylate, glycerol 1,3-diglycerolate diacrylate, ethylene glycol diacrylate, di(ethylene glycol) diacrylate, tri(ethyleneglycol) diacrylate, tetra(ethylene glycol) diacrylate, poly(ethylene glycol) diacrylate, or 1,4-butanediol diacrylate, or a combination comprising at least one of the foregoing.

10. The N-vinyl amide polymer of claim 8 , wherein the monomer component comprises 1-vinyl-2-pyrrolidinone and at least one of N-vinylcaprolactam and butyl acrylate.

11. A hydrate inhibitor composition comprising the N-vinyl amide polymer of claim 1 .

12. The hydrate inhibitor composition of claim 11 , further comprising a solvent.

13. The hydrate inhibitor composition of claim 12 , wherein the solvent comprises methanol, ethanol, propanol, butanol, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, glycerin, diethylene glycol monoethyl ether, ethoxylated propylene glycols, ethylene glycol monobutyl ether, 2-ethoxyethanol, 2-propoxyethanol, 2-i sopropoxyethanol, 2-butoxyethanol, 2-i sobutoxyethanol, 2-methoxyethanol, a ketone, or a combination comprising at least one of the foregoing.

14. The hydrate inhibitor composition of claim 11 , wherein the N-vinyl amide polymer is present in an amount of about 5 to about 50 wt % based on the total weight of the hydrate inhibitor composition.

15. A method of controlling hydrate formation in a fluid comprising water and a hydrate-forming guest molecule, the method comprising contacting the fluid with an inhibitor composition comprising the polymer of claim 1 .

16. The method of claim 15 , wherein the hydrate-forming guest molecule comprises methane, ethane, ethylene, acetylene, propane, propylene, methylacetylene, n-butane, isobutane, 1-butene, trans-2-butene, cis-2-butene, isobutene, butene mixtures, isopentane, pentenes, natural gas, carbon dioxide, hydrogen sulfide, nitrogen, oxygen, argon, krypton, and xenon, or a combination comprising at least one of the foregoing.

17. The N-vinyl amide polymer of claim 1 , wherein in Formula (I), each occurrence of R 1 is independently —CH 2 —, —CH(CH 3 )—, —CH(C 2 H 5 )—, —C(CH 3 ) 2 —, —CH 2 CH 2 —, —CH(CH 3 )CH 2 —, —CH 2 CH(NH 2 )—, —CH 2 CH(COOH)—, —CH 2 CH 2 CH 2 —, or —C 6 H 5 CH 2 —.

18. The N-vinyl amide polymer of claim 1 , wherein R 2 is a C 2-40 alkyl, a C 2-40 heteroalkyl, a C 3-40 cycloalkyl, a C 3-40 heterocycloalkyl, a C 6-40 aryl, or a combination thereof.

19. The N-vinyl amide polymer of claim 1 , wherein R 2 is substituted with one or more hydroxyl groups.

20. The N-vinyl amide polymer of claim 1 , wherein R 2 contains up to 10 ether bonds.

Assignees

• Xu Kui
• Panchalingam Vaithilingam
• Jakubowski Wojciech J
• Jankowski Szymon
• Stewart Ayala Jonathan Raymond
• Jackson Steven
• Sanders Christina
• Baker Hughes Oilfield Operations Llc

Inventors

• Xu Kui
• Panchalingam Vaithilingam
• Jakubowski Wojciech J
• Jankowski Szymon
• Stewart-Ayala Jonathan Raymond
• Jackson Steven
• Sanders Christina

Classifications

• C08F20/54 Primary

  Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide} · CPC title

• C08F2/44

  Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers · CPC title

• C08F26/10

  N-Vinyl-pyrrolidone · CPC title

• C08K5/37

  Thiols · CPC title

• C09K8/52

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