Method for inhibiting gas hydrate blockage in oil and gas pipelines

Patent metadata

Field	Value
Publication number	US-11753577-B2
Application number	US-201916424241-A
Country	US
Kind code	B2
Filing date	May 28, 2019
Priority date	May 28, 2019
Publication date	Sep 12, 2023
Grant date	Sep 12, 2023

Abstract

This invention relates to a method for inhibiting the agglomeration of gas hydrates, comprising the injection of an anti-agglomerant comprising a N,N-dialkyl-ammoniumalkyl fatty acid amide represented by the formula (I)whereinR1 is an alkyl or alkenyl group having from 7 to 21 carbon atoms,R2 and R3 are each independently an alkyl group containing 1 to 10 carbon atoms, or together form an optionally substituted ring having 5 to 10 ring atoms, wherein the ring may carry up to 3 substituents,R4 is hydrogen or an alkyl group having 1 to 6 carbon atoms,R5 is hydrogen or an optionally substituted hydrocarbyl group having 1 to 22 carbon atoms andA is an alkylene group having two or three carbon atoms,into a fluid comprising gas, water and oil under conditions prone to the formation of gas hydrates,wherein the N,N-dialkyl-ammoniumalkyl fatty acid amide represented by formula (I) is produced by the aminolysis of an ester of a fatty acid and a C1- to C4-alcohol with an N,N-dialkylamino alkyl amine and subsequent neutralization with a carboxylic acid.

First claim

The invention claimed is:

1. A method for inhibiting the agglomeration of gas hydrates, comprising the step of injecting at least one anti-agglomerant comprising at least one N,N-dialkyl-ammoniumalkyl fatty acid amide represented by the formula (I)

wherein
R 1 is an alkyl or alkenyl group having from 7 to 21 carbon atoms,
R 2 and R 3 are each independently an alkyl group containing 1 to 10 carbon atoms, or together form an optionally substituted ring having 5 to 10 ring atoms, wherein the ring may carry up to 3 substituents,
R 4 is hydrogen or an alkyl group having 1 to 6 carbon atoms,
R 5 is hydrogen or an optionally substituted hydrocarbyl group having 1 to 22 carbon atoms and
A is an alkylene group having two or three carbon atoms,

into a fluid comprising gas, water and oil under conditions prone to the formation of gas hydrates,
wherein the at least one N,N-dialkyl-ammoniumalkyl fatty acid amide represented by formula (I) is produced by the aminolysis of a fatty acid ester of at least one fatty acid and at least one monohydric C 1 to C 4 -alcohol with at least one N,N-dialkylamino alkyl amine and subsequent neutralization with at least one carboxylic acid,
wherein the fatty acid ester of the at least one fatty acid with the at least one monohydric C 1 -C 4 -alcohol has the formula (III)
R 1 —COOR 6   (III)

wherein
R 1 is defined above, and
R 6 is an alkyl group having 1 to 4 carbon atoms,

and wherein the at least one N,N-dialkylamino alkyl amine has the general formula (V)

wherein
R 2 , R 3 , R 4 and A are each independently defined above.

2. The method according to claim 1 , wherein R 1 is an alkyl or alkenyl group having 12 or 14 carbon atoms.

3. The method according to claim 1 , wherein at least 60 mol-% of the at least one fatty acid has 12 to 14 carbon atoms.

4. The method according to claim 2 , wherein the molar ratio of the fatty acid having 12 carbon atoms and the fatty acid having 14 carbon atoms is between 1:9 and 9:1.

5. The method according to claim 1 , wherein R 1 is a linear alkyl or alkenyl group having from 7 to 21 carbon atoms.

6. The method according to claim 1 , wherein the at least one monohydric C 1 -C 4 -alcohol is selected from the group consisting of methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, tert.-butanol and mixtures thereof.

7. The method according to claim 1 , wherein the at least one fatty acid and the at least one N,N-dialkylaminoalkylamine are reacted in a molar ratio of between 3:1 and 1:3.

8. The method according to claim 1 , wherein the at least one carboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid, butyric acid, pivalic acid, hexanoic acid, octanoic acid, 2-ethyl hexanoic acid, decanoic acid neodecanoic acid, undecanoic acid, neoundecanoic acid, dodecanoic acid, neododecanoic acid, tridecanoic acid, iso-tridecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, acrylic acid, methacrylic acid and mixtures thereof.

9. The method according to claim 1 , wherein the at least one fatty acid and the at least one carboxylic acid are different.

10. The method according to claim 9 , wherein the at least one fatty acid and the at least one carboxylic acid differ in at least one parameter, wherein the parameter is selected from the group consisting of alkyl chain length, acid value, degree of branching, and degree of unsaturation.

11. The method according to claim 1 , wherein the at least one anti-agglomerant is essentially free of glycerol.

12. The method according to claim 1 , wherein the at least one anti-agglomerant is injected into the fluid prone to the formation of gas hydrates prior to formation of hydrates.

13. The method according to claim 1 , wherein the compound according to formula (I) is combined with at least one polymeric gas hydrate inhibitor.

14. The method according to claim 1 , wherein the compound according to formula (I) is combined with at least one thermodynamic gas hydrate inhibitor.

15. The method according to claim 1 , wherein the fluid has a pH value of below 8.0.

Assignees

• Clariant Int Ltd

Inventors

• Bodnar Scot
• Smith Dan
• Hoevelmann Felix
• Krüger Corinna
• Krull Matthias
• WYLDE Jonathan James
• Tejada Lisa Greaney

Classifications

• C09K8/524 Primary

  organic depositions, e.g. paraffins or asphaltenes · CPC title

• C09K8/52 Primary

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

• C10L3/107

  Limiting or prohibiting hydrate formation · CPC title

• C09K2208/22

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

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title