IP Library › Granted Patent US 12,435,280
Granted Patent B2
US 12,435,280 · App. 17/722,951 · Granted Oct 7, 2025

Crude oil demulsifier compositions and uses thereof

Inventors: Ashish Dhawan (Aurora, IL); Regan Andrew Jones (Sugar Land, TX)
Assignee: ECOLAB USA Inc.
C10G33/04B01D17/047C02F1/682C08F222/06C02F2101/32C02F2103/365
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Quick Facts
Patent No.
US 12,435,280
App. No.
17/722,951
Granted
Oct 7, 2025
Kind
B2
Abstract

The present disclosure relates to demulsifier compositions and methods of resolving emulsions using the compositions. The demulsifiers include modified hydroxy-succinimide copolymers. For example, the demulsifiers may include ethoxylated or propoxylated hydroxy-succinimide copolymers. The demulsifier compositions are useful for resolving oil-in-water, water-in-oil, and complex emulsions of water and oil.

Claims (44)

1. An emulsion, comprising water, an oil, and a composition, wherein the composition comprises an effective amount of a demulsifier, the demulsifier comprising a modified hydroxy-succinimide copolymer, wherein the modified hydroxy-succinimide copolymer comprises a structure selected from formula 1 or formula 2:

wherein R is a C 8 to C 36 alkyl group, X is linking group, each m is independently selected from 1 to 50, and n is selected from 5 to 200.

2. The emulsion of claim 1 , wherein the modified hydroxy-succinimide copolymer is an ethoxylated α-olefin hydroxy-succinimide copolymer.

3. The emulsion of claim 1 , wherein the emulsion excludes an alkylphenol compound.

4. A method of resolving an emulsion, comprising:

providing an emulsion including water and an oil,

adding a composition to the water, the oil, and/or the emulsion,

wherein the composition comprises an effective amount of a demulsifier, the demulsifier comprising a modified hydroxy-succinimide copolymer, and

separating the water from the oil,

wherein the modified hydroxy-succinimide copolymer comprises a structure selected from formula 1 or formula 2:

wherein R is a C 8 to C 36 alkyl group, X is linking group, each m is independently selected from 1 to 50, and n is selected from 5 to 200.

5. The method of claim 4 , further comprising mixing the oil with the water to obtain the emulsion.

6. The method of claim 4 , further comprising injecting the composition into a process stream comprising the oil, the water, and/or the emulsion.

7. The method of claim 4 , further comprising allowing the emulsion to stand in a quiescent state for a period of time sufficient to obtain separation into separate layers of water and oil prior to the separating.

8. The method of claim 4 , wherein the effective amount of the demulsifier is about 1 ppm to about 5,000 ppm, based on volume of the oil.

9. The method of claim 4 , wherein the oil comprises crude oil.

10. The method of claim 4 , wherein the modified hydroxy-succinimide copolymer comprises a weight average molecular weight from about 5,000 Da to about 300,000 Da.

11. The method of claim 4 , wherein the modified hydroxy-succinimide copolymer is an ethoxylated α-olefin hydroxy-succinimide copolymer.

12. The method of claim 4 , wherein the modified hydroxy-succinimide copolymer is an ethoxylated α-olefin maleic anhydride copolymer functionalized with an amino-hydroxy compound.

13. The method of claim 12 , wherein the amino-hydroxy compound is

selected from the group consisting of 2-aminoethan-1-ol,

3-aminopropan-1-ol, 4-aminobutan-1-ol,

2-aminobutan-1-ol, 1-(aminomethyl)cyclopentan-1-ol,

5-aminopentan-1-ol, 1-aminopropan-2-ol,

4-aminocyclohexan-1-ol, 2-aminopropane-1,3-diol,

2-aminocyclohexan-1-ol,

2-((2-aminoethyl)amino)ethan-1-ol,

2-(2-aminoethoxy)ethan-1-ol,

2-amino-2-(hydroxymethyl)propane-1,3-diol,

2-((3-aminopropyl)amino)ethan-1-ol,

4-aminophenol, 3-aminophenol, 2-aminophenol,

4-(2-aminoethyl)benzene-1,2-diol, 5-(2-aminoethyl)benzene-1,2,3-triol,

4-(aminomethyl phenol, 4-(2-aminoethyl)phenol,

2-amino-1-phenylethan-1-ol, 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol,

(4-aminophenyl)methanol, 3-(2-amino-1-hydroxyethyl)phenol,

2-(4-aminophenyl)ethan-1-ol, (2-amino-3-methylphenyl)methanol,

(3-aminophenyl)methanol, 2-(3-aminophenyl)ethan-1-ol,

4-(aminomethyl)benzene-1,2-diol, 2-(2-aminophenyl)ethan-1-ol,

(2-aminophenyl)methanol, 4-aminobenzene-1,2-diol, and any combination thereof.

14. The method of claim 4 , wherein R is a C 16 to C 36 alkyl group.

15. The method of claim 4 , wherein X is an arylene group, an alkylene group, a —CH 2 CH 2 NHCH 2 CH 2 —group or a —CH 2 CH 2 OCH 2 CH 2 —group.

16. The method of claim 4 , wherein the composition is added to the water, the oil, and/or the emulsion during a refinery desalting operation.

17. The method of claim 4 , wherein the composition excludes an alkylphenol compound or wherein an alkylphenol compound is not added to the oil, the wash water, or the emulsion.

18. The method claim 4 , wherein the emulsion is a water-in-oil emulsion.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2022
From: DHAWAN, ASHISH; JONES, REGAN ANDREW
To: ECOLAB USA INC.
Reel/Frame 059639/0105 →
Continuity (2)
Provisional Application 63177677 · Apr 21, 2021
Related Publication 20220364000A1 · Nov 17, 2022
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