Synthesis of a cationic surfmer and its copolymers for enhanced oil recovery

Patent metadata

Field	Value
Publication number	US-12049529-B2
Application number	US-202318325989-A
Country	US
Kind code	B2
Filing date	May 30, 2023
Priority date	Jul 22, 2020
Publication date	Jul 30, 2024
Grant date	Jul 30, 2024

Abstract

Provided is a quaternary ammonium surfmer and copolymers thereof. The surfmer may have the following general formula (I): N + —R 1 R 2 R 3 R 4 (X − ), where: R 1 and R 2 may independently be H or a C 1 -C 3 alkyl, R 3 may be a C 19+ amidoalkyl group, R 4 may be a C 3 -C 6 alkyl having a terminal olefin double bond group, and X may be a halogen. Further provided is a method for synthesizing the quaternary ammonium surfmer, copolymers thereof, and a method for recovering hydrocarbons from a subterranean formation that may include injecting a treatment fluid comprising the quaternary ammonium surfmer or copolymers thereof into the subterranean formation.

First claim

What is claimed:

1. A subterranean formation treatment fluid for treating a subterranean formation, comprising a surfmer copolymer comprising an acrylamide compound comonomer and a quaternary ammonium surfmer, wherein the quaternary ammonium surfmer has the following general formula (I):
N + —R 1 R 2 R 3 R 4 (X − )  (I)

where:
R 1 and R 2 are independently H or a C 1 -C 3 alkyl,
R 3 is a C 19+ amidoalkyl group,
R 4 is a C 3 -C 6 alkyl having a terminal olefin double bond group, and
X is a halogen.

2. The subterranean formation treatment fluid of claim 1 , wherein R 3 is an erucyl-amidoalkyl group.

3. The subterranean formation treatment fluid of claim 2 , wherein R 3 is an erucyl-amidopropyl group.

4. The subterranean formation treatment fluid of claim 1 , wherein R 1 and R 2 are each a methyl group, R 4 is an allyl group (—CH 2 —CH═CH 2 ), and X is bromide or chloride.

5. The subterranean formation treatment fluid of claim 1 , wherein the quaternary ammonium surfmer has the following general formula (II):
R 5 —CH═CH—R 6 —COHN—R 7 —N + R 1 R 2 R 4 (Br)  (II)

where:
R 5 is a C 8 -C 16 alkyl,
R 6 is a C 9 -C 16 alkyl,
R 7 is a C 2 -C 6 alkyl, and
R 1 , R 2 , and R 4 are as defined in claim 1 .

6. The subterranean formation treatment fluid of claim 5 , wherein R 5 is a C 8 alkyl, R 6 is a Co alkyl, R 7 is propyl, R 1 and R 2 are each methyl, and R 4 is an allyl group (−CH 2 —CH═CH 2 ) or a 1-butene group (—CH 2 —CH 2 —CH═CH 2 ).

7. The subterranean formation treatment fluid of claim 1 , wherein the quaternary ammonium surfmer is a reaction product of N,N-dimethyl-erucyl-1,3-propylenediamine and allyl bromide.

8. The subterranean formation treatment fluid of claim 1 , wherein the acrylamide compound comonomer is one or more selected from the group consisting of acrylamide and 2-acrylamido-2-methyl-1-propanesulfonic acid sodium salt.

9. The subterranean formation treatment fluid of claim 1 , wherein the copolymer is partially hydrolyzed and includes one or more sodium carboxylate subunits.

10. A surfmer copolymer comprising an acrylamide compound comonomer and a quaternary ammonium surfmer, wherein the quaternary ammonium surfmer has the following general formula (I):
N + −R 1 R 2 R 3 R 4 (X − )  (I)

where:
R 1 and R 2 are independently H or a C 1 -C 3 alkyl,
R 3 is a C 19+ amidoalkyl group,
R 4 is a C 3 -C 6 alkyl having a terminal olefin double bond group, and
X is a halogen.

Assignees

• Saudi Arabian Oil Co

Inventors

• Zhang Xuan
• Han Ming
• Xu Limin

Classifications

• E21B43/16

  Enhanced recovery methods for obtaining hydrocarbons · CPC title

• C09K8/588

  characterised by the use of specific polymers {(polymeric surfactants C09K8/584)} · CPC title

• C09K8/584 Primary

  characterised by the use of specific surfactants · CPC title

• C08F220/56

  Acrylamide; Methacrylamide · CPC title

• C07C233/38

  having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton · CPC title