IP Library Granted Patent US 10,400,157
Granted Patent B2
US 10,400,157 · App. 15/839,523 · Granted Sep 3, 2019

Surfactant assisted oil recovery using alcohol ether sulfonates and cationic surfactants

Inventors: Duy T. Nguyen (Sugar Land, TX); Brian L. Mueller (Missouri City, TX)
Assignee: Ecolab USA Inc.
C09K8/584C09K8/602C09K8/62C09K8/605C09K2208/26C09K2208/28
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Quick Facts
Patent No.
US 10,400,157
App. No.
15/839,523
Granted
Sep 3, 2019
Kind
B2
Abstract

A composition comprising an alcohol ether sulfonate and a quaternary ammonium salt is provided for use in methods of increasing recovery of crude oil from a subterranean hydrocarbon-containing formation.

Claims (44)

1. A composition for increasing recovery of crude oil from a subterranean hydrocarbon-containing formation, the composition comprising:

an alcohol ether sulfonate having formula I:

wherein:

R 1 is alkyl;

R 2 is alkylene;

R 3 and R 4 are each independently ethylene or propylene;

R 5 is hydroxyl and R 6 is —SO 3 M, or R 5 is —SO 3 M and R 6 is hydroxyl;

M is independently an alkali metal, an alkaline earth metal, hydronium, NH 3 or NH 2 ; and

a and b are each independently an integer from 0 to 30, and a+b equals 1 to 60; and

a quaternary ammonium salt having the formula II:

wherein:

R 10 and R 11 are independently C 8 to C 30 alkyl;

R 12 and R 13 are independently lower alkyl; and

X − is an anion;

the weight ratio of the alcohol ether sulfonate to quaternary ammonium salt ranging from about 40:1 to about 1:1.

2. The composition of claim 1 , wherein the alcohol ether sulfonate has the formula III

wherein:

R 3 is isopropylene and R 4 is ethylene, or R 3 is ethylene and R 4 is isopropylene;

R 5 is hydroxyl and R 6 is —SO 3 M, or R 5 is —SO 3 M and R 6 is hydroxyl;

M is independently Na, K, Ca, Mg, hydronium, NH 3 or NH 2 ;

x and y are each independently an integer from 0 to 27, and x+y equals 5 to 27; and

a and b are each independently an integer from 0 to 30, and a+b equals 1 to 60.

3. The composition of claim 1 , wherein R 3 is isopropylene and R 4 is ethylene.

4. The composition of claim 1 , wherein R 5 is hydroxyl and R 6 is —SO 3 M.

5. The composition of claim 1 , wherein R 5 is —SO 3 M and R 6 is hydroxyl.

6. The composition of claim 2 , wherein the alcohol ether sulfonate has the formula III, x and y are each independently an integer from 0 to 15, and x+y equals 5 to 15.

7. The composition of claim 2 , wherein a is 2 to 25, b is 2 to 25, and a+b equals 4 to 50.

8. The composition of claim 2 , wherein a is 3 to 20, b is 6 to 20, and a+b equals 9 to 40.

9. The composition of claim 2 , wherein a is 5 to 18, b is 10 to 12, and a+b equals 15 to 30.

10. The composition of claim 1 , wherein R 10 and R 11 are independently C 8 to C 18 alkyl.

11. The composition of claim 1 , wherein R 12 and R 13 are independently methyl or ethyl.

12. The composition of claim 1 , wherein X − is a halide, a sulfate, a nitrate, a nitrite, a carbonate, or a carboxylate.

13. The composition of claim 1 , wherein the weight ratio of the alcohol ether sulfonate to quaternary ammonium salt ranging from about 20:1 to about 1:1.

14. The composition of claim 1 , further comprising a carrier which comprises water, an alcohol, an ether, a glycol, or a combination thereof.

15. The composition of claim 2 , wherein R 3 is isopropylene and R 4 is ethylene.

16. The composition of claim 15 , wherein the alcohol ether sulfonate has the formula III, x and y are each independently an integer from 0 to 15, and x+y equals 5 to 15.

17. The composition of claim 16 , wherein a is 2 to 25, b is 2 to 25, and a+b equals 4 to 50.

18. The composition of claim 17 , wherein a is 3 to 20, b is 6 to 20, and a+b equals 9 to 40.

19. The composition of claim 18 , wherein a is 5 to 18, b is 10 to 12, and a+b equals 15 to 30.

20. The composition of claim 17 , wherein:

R 10 and R 11 are independently C 8 to C 18 alkyl; or

R 12 and R 13 are independently methyl or ethyl; or

X − is a halide, a sulfate, a nitrate, a nitrite, a carbonate, or a carboxylate; or

the weight ratio of the alcohol ether sulfonate to quaternary ammonium salt ranging from about 20:1 to about 1:1.

Assignments (6)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 17, 2025
From: JPMORGAN CHASE BANK, N.A.
To: CHAMPIONX LLC; APERGY ESP SYSTEMS, LLC; APERGY BMCS ACQUISITION CORP; HARBISON-FISCHER, INC.; NORRIS RODS, INC.,; NORRIS RODS, INC.,; NORRISEAL-WELLMARK, INC.; PCS FERGUSON, INC.; QUARTZDYNE, INC.; US SYNTHETIC CORPORATION
Reel/Frame 072004/0019 →
RELEASE OF SECURITY INTEREST Recorded Jun 7, 2022
From: BANK OF AMERICA, N.A.
To: CHAMPIONX USA INC.
Reel/Frame 060304/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: ECOLAB USA INC.
To: CHAMPIONX USA INC.
Reel/Frame 053849/0537 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 052848/0368 →
SECURITY INTEREST Recorded Jun 5, 2020
From: CHAMPIONX USA INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 053250/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 13, 2017
From: NGUYEN, DUY T.; MUELLER, BRIAN L.
To: ECOLAB USA INC.
Reel/Frame 044384/0755 →
Continuity (2)
Division 14231307 · Mar 31, 2014
Related Publication 20180100097A1 · Apr 12, 2018