IP Library Granted Patent US 10,774,281
Granted Patent B2
US 10,774,281 · App. 15/778,033 · Granted Sep 15, 2020

Use of a particular carboxylic amino acid in order to limit the formation and/or agglomeration of gas hydrates

Inventors: Tong Eak Pou (Irigny, FR); Frédéric Moser (Pierre-Benite, FR); Gilles Barreto (Messimy, FR); Jean-Philippe Gillet (Brignais, FR)
Assignee: Arkema France
C10L3/107C09K8/52C09K8/86C09K2208/22
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Quick Facts
Patent No.
US 10,774,281
App. No.
15/778,033
Granted
Sep 15, 2020
Kind
B2
Abstract

Provided is a process for limiting or preventing the formation and/or agglomeration of gas hydrates, comprising combining (1) a production fluid comprising an aqueous phase and one or more gasses and (2) at least one compound represented by formula (I) or a salt thereof as defined herein.

Claims (44)

1. A process for limiting or preventing the formation and/or agglomeration of gas hydrates, comprising combining (1) a production fluid comprising an aqueous phase and one or more gasses and (2) at least one compound represented by formula (I) or a salt thereof:

wherein

R 1 represents a linear or branched, saturated or unsaturated C 6 to C 30 alkyl chain, wherein the alkyl chain is optionally interrupted with one or more hydrocarbon-based rings,

R 2 represents a hydrogen atom or a group —(CHR a —CHR b )—COOR 5 , wherein R a and R b , which may be identical or different, represent, independently of each other, a hydrogen atom or a methyl group,

R 3 represents a hydrogen atom or a group —(CHR a —CHR b )—COOR 6 , wherein R a and R b , which may be identical or different, represent, independently of each other, a hydrogen atom or a methyl group,

R 4 represents a hydrogen atom or a group —(CHR a —CHR b )—COOR 7 , wherein R a and R b , which may be identical or different, represent, independently of each other, a hydrogen atom or a methyl group,

R 5 , R 6 and R 7 , which may be identical or different, represent, independently of each other, a hydrogen atom or a linear or branched, saturated or unsaturated C 1 to C 12 alkyl chain,

wherein at least one of the radicals R 2 , R 3 or R 4 comprises a carboxylic acid function (—COOH),

m represents an integer ranging from 1 to 6,

n represents an integer ranging from 0 to 10, and

p is 0 or 1.

2. The process of claim 1 , wherein

p is 0,

R 2 represents a group —(CH 2 ) 2 —COOR 5 ,

R 3 represents a group —(CH 2 ) 2 —COOR 6 , and

R 4 represents a group —(CH 2 ) 2 —COOR 7 ,

wherein R 5 , R 6 and R 7 , which may be identical or different, represent, independently of each other, a hydrogen atom or a linear or branched, saturated or unsaturated C 1 to C 12 alkyl chain, wherein at least one of the radicals R 5 , R 6 and R 7 represents a hydrogen atom.

3. The process of claim 1 , wherein R 5 , R 6 and R 7 each represent a hydrogen atom.

4. The process of claim 1 , wherein n is an integer ranging from 0 to 4.

5. The process of claim 1 , wherein

p is 0,

n is 0,

R 1 represents a linear or branched, saturated or unsaturated C 8 to C 18 alkyl chain,

R 2 represents a hydrogen atom, and

R 3 represents a group —(CHR a —CHR b )—COOR 6 ,

wherein R a and R b , which may be identical or different, represent, independently of each other, a hydrogen atom or a methyl group, and wherein R 6 represents a hydrogen atom.

6. The process of claim 1 , wherein

p is equal to 0 and

n is equal to 0,

R 1 represents a linear or branched, saturated or unsaturated C 8 to C 18 alkyl chain,

R 2 represents a group —(CHR a —CHR b )—COOR 5 ,

wherein R a and R b , which may be identical or different, represent, independently of each other, a hydrogen atom or a methyl group, and wherein R 5 represents a hydrogen atom, and

R 3 represents a group —(CHR a —CHR b )—COOR 6 ,

wherein R a and R b , which may be identical or different, represent, independently of each other, a hydrogen atom or a methyl group, and wherein R 6 represents a hydrogen atom.

7. The process of claim 1 , wherein the formation and/or agglomeration of the gas hydrates is limited or prevented in a process for extracting petroleum, condensates or gas, during drilling, the completion operation or during production.

8. The process of claim 1 , wherein the compound represented by formula (I) is predissolved in a liquid chosen from water and organic solvents, and mixtures thereof.

9. The process of claim 8 , wherein the organic solvents are chosen from methanol, ethanol, isopropanol, n-butanol, isobutanol, 2-ethylhexanol, glycerol, ethylene glycol (or monoethylene glycol), 1,2-propylene glycol, 1,3-propylene glycol, hexylene glycol, butylglycol, ethylene glycol dibutyl ether, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, N-methylpyrrolidone, cyclohexanone, xylenes, toluene, 1-octanol and 2-octanol, and mixtures of two or more thereof in all proportions.

10. The process of claim 8 , wherein the amount of the compound represented by formula (I) dissolved in the liquid is greater than or equal to 10%, relative to the total weight of the resulting solution.

11. The process of claim 1 , wherein the compound represented by formula (I) is combined with the production fluid in an amount ranging from 0.1% to 10% by weight, relative to the total weight of the aqueous phase of the production fluid.

12. The process of claim 1 , wherein the compound represented by formula (I) is combined with the production fluid in an amount ranging from 0.3% to 8% by weight, relative to the total weight of the aqueous phase of the production fluid.

13. The process of claim 1 , wherein the compound represented by formula (I) is combined with the production fluid in an amount ranging from 0.4% to 4% by weight, relative to the total weight of the aqueous phase of the production fluid.

14. The process of claim 1 , wherein the compound represented by formula (I) is in the form of a salt.

15. The process of claim 1 , wherein the proportion of the aqueous phase in the production fluid is from 10% to 90%, relative to the total weight of the production fluid.

16. The process of claim 1 , wherein the production fluid comprises at least one gas selected from the group consisting of methane, ethane, propane, butane, carbon dioxide, hydrogen sulfide, and mixtures thereof.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2018
From: POU, TONG EAK; MOSER, FRÉDÉRIC; BARRETO, GILLES; GILLET, JEAN-PHILIPPE
To: ARKEMA FRANCE
Reel/Frame 046120/0362 →
Priority Claims (1)
FR 15 61490 · Nov 27, 2015 · national
Continuity (1)
Related Publication 20180340127A1 · Nov 29, 2018