IP Library › Granted Patent US 11,795,374
Granted Patent B2
US 11,795,374 · App. 17/490,686 · Granted Oct 24, 2023

Composition and method of making cationic surfactants with two quaternary ammonium head groups

Inventors: Xuan Zhang (Beijing, CN); Ming Han (Beijing, CN); Jinxun Wang (Dhahran, SA); Dongqing Cao (Beijing, CN)
Assignee: SAUDI ARABIAN OIL COMPANY
C09K8/584
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Quick Facts
Patent No.
US 11,795,374
App. No.
17/490,686
Granted
Oct 24, 2023
Kind
B2
Abstract

A surfactant composition is provided. The composition includes chemical structure represented by Formula (1): where R 1 represents a hydrocarbon group, a substituted hydrocarbon group, an alkyl ester group, or an alkyl amine having from 4 to 28 carbon atoms, and R 2 and R 3 represent hydrocarbon groups having from 1 to 5 carbon atoms. Also provided is a composition including a brine comprising a total salinity of at least 20,000 mg/L and the chemical structure shown in Formula (1). Methods of making a composition including the chemical structure represented by Formula (1) are also provided.

Claims (26)

1. A composition of matter comprising:

a chemical structure as shown in Formula (1);

wherein R 1 represents, an alkyl ester group or an alkyl amine having from 4 to 28 carbon atoms; and

wherein R 2 and R 3 represent hydrocarbon groups having from 1 to 5 carbon atoms.

2. The composition of claim 1 , wherein R 1 is a hydrophobic group.

3. The composition of claim 1 , wherein R 1 is selected from the group consisting of an erucyl amidopropyl group, an oleyl amidopropyl group, and combinations thereof.

4. A method of making a surfactant comprising:

providing a mixture of a tertiary amine having a chemical structure shown in Formula (2), a tertiary amine hydrochloride having a chemical structure shown in Formula (3), epichlorohydrin, and a solvent; and

maintaining the mixture at an elevated temperature to produce the surfactant;

wherein R 1 represents a hydrocarbon group, a substituted hydrocarbon group, an alkyl ester group, or an alkyl amine having from 4 to 28 carbon atoms; and

wherein R 2 and R 3 represent hydrocarbon groups having from 1 to 5 carbon atoms.

5. The method of claim 4 , wherein the tertiary amine is selected from the group consisting of N,N-Dimethylerucylamine; N, N-dimethyl-oleyl-1, 3-propylenediamine; N, N-dimethyloctadecylamine, and combinations thereof.

6. The method of claim 4 , wherein the tertiary amine hydrochloride is trimethylamine hydrochloride.

7. The method of claim 4 , wherein the mixture is maintained at a temperature of from about 30 to 100° C.

8. A composition comprising:

a brine comprising a total salinity of at least 20,000 mg/L; and

a chemical structure as shown in Formula (1);

wherein R 1 represents a hydrocarbon group, a substituted hydrocarbon group, an alkyl ester group, or an alkyl amine having from 4 to 28 carbon atoms; and

wherein R 2 and R 3 represent hydrocarbon groups having from 1 to 5 carbon atoms.

9. The composition of claim 8 , wherein R 1 is a hydrophobic group.

10. The composition of claim 9 , wherein the composition is stable in seawater at 95° C. for 2 days.

11. The composition of claim 9 , wherein an interfacial tension of a crude oil surfactant solution the is less than 0.1 mN/m.

12. The composition of claim 8 , wherein R 1 is selected from the group consisting of an erucyl amidopropyl group, an octadeyl dimethyl group, an oleyl amidopropyl group, and combinations thereof.

13. The composition of claim 8 , comprising from 200 mg/L to 2,000 mg/L of the compound shown in formula (1).

14. The composition of claim 8 , wherein the total salinity is at least 50,000 mg/L.

15. The composition of claim 8 , wherein the composition is stable in seawater at 25° C. for 2 days.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 27, 2022
From: ARAMCO FAR EAST (BEIJING) BUSINESS SERVICES CO., LTD.
To: SAUDI ARABIAN OIL COMPANY
Reel/Frame 060205/0594 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2021
From: ZHANG, XUAN; CAO, DONGQING
To: ARAMCO FAR EAST (BEIJING) BUSINESS SERVICES CO., LTD.
Reel/Frame 057669/0795 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2021
From: HAN, MING; WANG, JINXUN
To: SAUDI ARABIAN OIL COMPANY
Reel/Frame 057684/0552 →
Continuity (1)
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