IP Library Granted Patent US 9,926,486
Granted Patent B2
US 9,926,486 · App. 14/231,307 · Granted Mar 27, 2018

Surfactant assisted oil recovery using alcohol ether sulfonates and cationic surfactants

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,926,486
App. No.
14/231,307
Granted
Mar 27, 2018
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 (62)

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

injecting a composition into a well which is in contact with the subterranean hydrocarbon-containing formation in an amount effective for lowering the interfacial tension between fracturing fluid and oil trapped within the formation and changing the wettability of the subterranean hydrocarbon-containing formation to recover the crude oil from the 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 method 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 method of claim 1 , 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.

4. The method of claim 3 , wherein a is 2 to 25, b is 2 to 25, and a+b equals 4 to 50.

5. The method of claim 3 , wherein a is 3 to 20, b is 6 to 20, and a+b equals 9 to 40.

6. The method of claim 3 , wherein a is 5 to 18, b is 10 to 12, and a+b equals 15 to 30.

7. The method of claim 1 , further comprising injecting a viscosifying agent, a solvent, an alkali, a flow back aid, a non-emulsifier, a friction reducer, a breaker, a crosslinking agent, a biocide, or a proppant into the well.

8. The method of claim 1 , wherein the subterranean hydrocarbon-containing formation comprises a sandstone reservoir or a carbonate reservoir.

9. The method of claim 1 , wherein R 10 and R 11 are independently C 8 to C 18 alkyl and R 12 and R 13 are independently methyl or ethyl.

10. The method 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.

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

12. The method of claim 1 , wherein the injecting step occurs after hydraulic fracturing of the well.

13. The method of claim 1 , wherein the injecting step occurs during hydraulic fracturing of the well.

14. A method of increasing recovery of crude oil from a subterranean hydrocarbon-containing formation, the method comprising:

injecting an alcohol ether sulfonate and a quaternary ammonium salt into a well which is in contact with the subterranean hydrocarbon-containing formation in an amount effective for lowering the interfacial tension between fracturing fluid and oil trapped within the formation and changing the wettability of the subterranean hydrocarbon-containing formation to recover the crude oil from the subterranean hydrocarbon-containing formation,

wherein the alcohol ether sulfonate has the 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;

the quaternary ammonium salt has 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; and

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

15. The method of claim 14 , wherein R 10 and R 11 are independently C 8 to C 18 alkyl and R 12 and R 13 are independently methyl or ethyl.

16. The method of claim 15 , wherein X − is a halide, a sulfate, a nitrate, a nitrite, a carbonate, or a carboxylate.

17. The method of claim 14 , wherein the weight ratio of the alcohol ether sulfonate to quaternary ammonium salt ranging from about 20:1 to about 1:1.

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

19. The method of claim 14 , wherein the alcohol ether sulfonate and the quaternary ammonium salt are injected sequentially into the well.

20. The method of claim 14 , 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.

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 Mar 17, 2015
From: NGUYEN, DUY T.; MUELLER, BRIAN L.
To: ECOLAB USA INC.
Reel/Frame 035179/0338 →