Large hydrophobe surfactants

Patent metadata

Field	Value
Publication number	US-9988346-B2
Application number	US-201214237805-A
Country	US
Kind code	B2
Filing date	Apr 17, 2012
Priority date	Apr 22, 2011
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

Provided herein are inter alia novel compositions and methods having application in the field of enhanced oil recovery. In particular, the large hydrophobe compounds and mixtures thereof presented herein can be used, inter alia, for the recovery of a large range of crude oil compositions from challenging reservoirs.

First claim

What is claimed is:

1. A compound having the formula:

wherein
R 1 is branched unsubstituted C 14 -C 30 alkyl;
R 2 is R 10a -substituted or unsubstituted C 8 -C 50 alkyl, R 4a -substituted or unsubstituted heteroalkyl, R 4a -substituted or unsubstituted aryl or R 4a -substituted or unsubstituted cycloalkyl;
R 4a is R 5a -substituted or unsubstituted C 1 -C 50 alkyl, R 5a -substituted or unsubstituted heteroalkyl, R 5a -substituted or unsubstituted aryl or R 5a -substituted or unsubstituted cycloalkyl;
R 5a is R 6a -substituted or unsubstituted C 1 -C 50 alkyl, R 6a -substituted or unsubstituted heteroalkyl, R 6a -substituted or unsubstituted aryl or R 6a -substituted or unsubstituted cycloalkyl;
R 6a is R 7a -substituted or unsubstituted C 1 -C 50 alkyl, R 7a -substituted or unsubstituted heteroalkyl, R 7a -substituted or unsubstituted aryl or R 7a -substituted or unsubstituted cycloalkyl;
R 7a is R 8a -substituted or unsubstituted C 1 -C 50 alkyl, R 8a -substituted or unsubstituted heteroalkyl, R 8a -substituted or unsubstituted heteroalkyl, R 8a -substituted or unsubstituted aryl or R 8a -substituted or unsubstituted cycloalkyl;
R 8a is R 9a -substituted or unsubstituted C 1 -C 50 alkyl, R 9a -substituted or unsubstituted heteroalkyl, R 9a -substituted or unsubstituted aryl or R 9a -substituted or unsubstituted cycloalkyl;
R 9a is unsubstituted C 1 -C 50 alkyl, unsubstituted heteroalkyl, unsubstituted aryl or unsubstituted cycloalkyl;
R 10a is unsubstituted heteroalkyl, unsubstituted aryl or unsubstituted cycloalkyl;
R 3 is independently hydrogen or unsubstituted C 1 -C 6 alkyl;
z is an integer from 2 to 100;

 and
M is a monovalent, divalent or trivalent cation.

2. The compound of claim 1 , wherein R 1 is branched or linear unsubstituted C 8 -C 50 alkyl.

3. The compound of claim 1 , wherein R 1 is branched unsubstituted C 10 -C 50 alkyl.

4. The compound of claim 1 , wherein R 2 is branched or linear unsubstituted C 10 -C 50 alkyl, R 4a -substituted C 10 -C 50 heteroalkyl, or R 4a -substituted phenyl.

5. The compound of claim 1 , wherein R 2 is branched unsubstituted C 20 -C 50 alkyl or linear unsubstituted C 16 -C 40 alkyl.

6. The compound of claim 1 , wherein R 2 is branched R 4a -substituted C 14 -C 50 heteroalkyl.

7. The compound of claim 1 , wherein R 3 is independently hydrogen or unsubstituted C 1 -C 2 alkyl.

8. The compound of claim 1 , wherein z is 10 to 100.

9. The compound of claim 1 , wherein M is Na + , K + , NH 4 + , Ca +2 , Mg +2 or Ba +2 .

10. The compound of claim 1 having the formula:

wherein
R 3 is independently unsubstitued C 1 -C 4 alkyl;
y is an integer from 1 to 50; and
w is an integer from 0 to 60.

11. The compound of claim 10 , wherein R 2 is unsubstituted tristyrylphenyl.

12. The compound of claim 10 , wherein R 3 is independently methyl or ethyl.

13. The compound of claim 1 having the formula:

wherein
R 3 is ethyl;
y is an integer from 1 to 30;
w is an integer from 0 to 30; and
v is an integer from 0 to 30.

14. The compound of claim 1 having the formula:

wherein
R 2′ is linear unsubstituted C 10 -C 60 alkyl;
R 3 is independently hydrogen or unsubstitued C 1 -C 4 alkyl;
n is an integer from 0 to 50; and
z is an integer from 5 to 25.

15. The compound of claim 1 having the formula:

wherein
R 3 is independently methyl or ethyl;
n is an integer from 0 to 50;
t is an integer from 0 to 30; and
u is an integer from 5 to 30.

16. An aqueous composition comprising a co-surfactant and the compound of claim 1 .

17. The aqueous composition of claim 16 , further comprising an alkali agent.

18. The aqueous composition of claim 16 having a pH of less than 13.

19. The aqueous composition of claim 16 having a pH of less than 8.

20. The aqueous composition of claim 16 having a salinity of at least 10,000 ppm.

21. The aqueous composition of claim 16 , wherein the temperature of said aqueous composition is at least 40° C.

22. An emulsion composition comprising an unrefined petroleum phase and an aqueous, wherein said aqueous phase comprises the compound of claim 1 .

23. The emulsion composition of claim 22 , further comprising a co-surfactant.

24. The biphasic composition of claim 22 , wherein the oil and water solubilization ratios of the aqueous phase are insensitive to the combined concentration of Ca +2 and Mg +2 combined within in the aqueous phase.

25. The biphasic composition of claim 22 , wherein the oil and water solubilization ratios of the aqueous phase are insensitive to the salinity of the water within the aqueous phase.

26. A method of displacing a hydrocarbon material in contact with a solid material, said method comprising:
(i) contacting a hydrocarbon material with the compound of claim 1 , wherein said hydrocarbon material is in contact with a solid material;
(ii) allowing said hydrocarbon material to separate from said solid material thereby displacing said hydrocarbon material in contact with said solid material.

27. The method of claim 26 , further comprising contacting the solid material with the compound.

28. The method of claim 27 , wherein said method is an enhanced oil recovery method.

29. A method of converting an unrefined petroleum acid into a surfactant, said method comprising:
(i) contacting a petroleum material with an aqueous composition thereby forming an emulsion in contact with said petroleum material, wherein said aqueous composition comprises the compound of claim 1 and a co-surfactant;
(ii) allowing an unrefined petroleum acid within said unrefined petroleum material to enter into said emulsion, thereby converting said unrefined petroleum acid into a surfactant.

30. A compound having the formula:

wherein
R 1 is R 10 -substituted or unsubstituted C 8 -C 50 alkyl, R 4 -substituted or unsubstituted heteroalkyl, R 4 -substituted or unsubstituted aryl or R 4 -substituted or unsubstituted cycloalkyl;
R 4 is R 5 -substituted or unsubstituted C 1 -C 50 alkyl, R 5 -substituted or unsubstituted heteroalkyl, R 5 -substituted or unsubstituted aryl or R 5 -substituted or unsubstituted cycloalkyl;
R 5 is R 6 -substituted or unsubstituted C 1 -C 50 alkyl, R 6 -substituted or unsubstituted heteroalkyl, R 6 -substituted or unsubstituted aryl or R 6 -substituted or unsubstituted cycloalkyl;
R 6 is R 7 -substituted or unsubstituted C 1 -C 50 alkyl, R 7 -substituted or unsubstituted he

Assignees

• Weerasooriya Upali P
• Pope Gary A
• Radford Peter
• Stevenson Howard
• Univ Texas
• Harcros Chemicals Inc

Inventors

• Weerasooriya Upali P
• Pope Gary A
• Radford Peter
• Stevenson Howard

Classifications

• C07C69/003

  Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom · CPC title

• C07C69/708

  Ethers · CPC title

• C07C309/10 Primary

  with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom · CPC title

• C07C305/10

  being further substituted by singly-bound oxygen atoms · CPC title

• C09K8/584

  characterised by the use of specific surfactants · CPC title