Surfactant compositions

Patent metadata

Field	Value
Publication number	US-10501677-B2
Application number	US-201715666686-A
Country	US
Kind code	B2
Filing date	Aug 2, 2017
Priority date	Aug 2, 2016
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

Provided herein are novel surfactant compositions and methods having application in a variety of fields including enhanced oil recovery, the cleaning industry as well as groundwater remediation. The surfactant compositions are based on lignin bio-oil with a phenol hydroxyl group as the main functional group. The compositions include carboxylic surfactant s and mixed hydrophilic and hydrophobic surfactant structures, which can be used for the recovery of crude oil compositions from challenging reservoirs.

First claim

What is claimed is:

1. A lignin amphiphile comprising:
a lipophilic portion of the lignin amphiphile comprising a lignin phenol characterized as having an oxygen content of <=7%, a phenolic to carboxylic ratio ranging from 90:10 to 99:1, and an average molecular weight ranging from 150 to 450; and
a hydrophilic portion of the lignin amphiphile comprising the general formula:
O-EO w —(CH 2 —CH(R)—O) x -EO w —PO y -EO z —X(Y) a M b+ ,

wherein EO corresponds to an ethoxy group,
w is an integer from 0 to 25,
wherein —(CH2—CH(R)—O) corresponds to an alkylates group,
R in any alkyl group that independently has a carbon number being an integer of 2-20,
wherein PO corresponds to a propoxy group,
y is an integer from 0 to 50,
z is an integer from 0 to 70,
wherein w+y+z is at least 40,
wherein X is selected from a single bond, an alkylene group with 1 to 10 carbon atoms or an alkenylene group with 2 to 10 carbon atoms,
wherein Y is an anionic group selected from the group of hydroxy groups, sulfate groups, sulfonate groups, carboxylate groups, phosphate groups or phosphonate groups,
wherein M is selected from the group consisting of H + , Na + , K + , Li + , Mg + , Ca 2+ , and NH 4 + ,
wherein a corresponds to an integer from 1 or 3, and
wherein b corresponds to an integer from 1 to 3.

2. A method of producing a lignin amphiphile from lignin, the method comprising:
providing a lignin phenol characterized as having an oxygen content of <=7%, a phenolic to carboxylic ratio ranging from 90:10 to 99:1, and an average molecular weight ranging from 150 to 450, and wherein the lignin phenol is produced in a reduction reaction at a hydrogen partial pressure from about 3.4 MPa (500 psig) to about 15 MPa (2200 psig); and
converting the lignin phenol into the lignin amphiphile in one or more reactions of alkoxylation, alkylation, sulfonation, sulfation, alkoxysulfation, sulfomethylation, sulfoalkylation, carboxylation, carboxymethylation, carboxyalkylation, or combinations thereof, wherein the lignin amphiphile comprises at least 40 and less than 71 alkylene oxide units.

3. The method of claim 2 , wherein the phenolic to carboxylic ratio ranges from 95:2 to 98:2.

4. The method of claim 2 , wherein the phenolic to carboxylic ratio ranges from 90:10 to 98:2.

5. The method of claim 2 , wherein the lignin phenol is produced in a reduction reaction in the presence of a catalyst of iron oxide; iron sulfides; supported iron oxide catalyst; and iron hydroxide mixed with sulfur, inorganic sulfur compound and organic sulfur compounds.

6. The method of claim 2 , wherein the lignin phenol is produced in a reduction reaction in the presence of a reducing agent of carbon monoxide, hydrogen, hydrogen sulfide, or combinations thereof.

7. The method of claim 2 , wherein the lignin amphiphile is a co-solvent.

8. The method of claim 2 , wherein the lignin amphiphile is a surfactant.

9. The method of claim 2 , wherein the alkylene oxide units comprise from 1 to 70 ethylene oxide units.

10. The method of claim 2 , wherein the alkylene oxide units comprise from 1 to 50 propylene oxide units.

11. The method of claim 2 , wherein the alkylene oxide units comprise 1 to 70 ethylene oxide units and 1 to 50 propylene oxide units.

12. The method of claim 2 , wherein the lignin amphiphile comprises at least one carboxylate group.

13. A method for enhancing oil recovery, comprising:
(a) providing a wellbore in fluid communication with a subsurface reservoir containing hydrocarbons therewithin;
(b) providing a lignin amphiphile, wherein:
the lignin amphiphile was prepared via conversion of a lignin phenol in one or more reactions of alkoxylation, alkylation, sulfonation, sulfation, alkoxysulfation, sulfomethylation, sulfoalkylation, carboxylation, carboxymethylation, carboxyalkylation, or combinations thereof, and the lignin phenol is characterized as having an oxygen content of <=7%, a phenolic to carboxylic ratio ranging from 90:10 to 98:2, and an average molecular weight ranging from 150 to 450, and wherein the lignin phenol is produced in a reduction reaction at a hydrogen partial pressure from about 3.4 MPa (500 psig) to about 15 MPa (2200 psig), wherein the lignin amphiphile comprises at least 40 and less than 71 alkylene oxide units;
(c) forming an injection solution by mixing water with the lignin amphiphile; and
(d) injecting the injection solution through the wellbore into the subsurface reservoir.

14. The method for enhancing oil recovery of claim 13 , wherein one or more surfactants are added to the injection solution prior to injecting the injection solution through the wellbore into the subsurface reservoir.

15. The method for enhancing oil recovery of claim 13 , wherein the lignin amphiphile is a surfactant.

16. The method for enhancing oil recovery of claim 13 , wherein the lignin amphiphile is a co-solvent.

17. The method for enhancing oil recovery of claim 13 , wherein the injection solution further comprises one or more surfactants and one or more co-solvents.

18. The method for enhancing oil recovery of claim 13 , wherein the injection solution further comprises one or more co-solvents.

19. The method for enhancing oil recovery of claim 13 , wherein the hydrophilic portion of the lignin amphiphile comprises the general formula:
O-EO w —(CH 2 —CH(R)—O) x -EO w —PO y -EO z —X(Y) a M b+ ,

wherein EO corresponds to an ethoxy group,
w is an integer from 0 to 25,
wherein —(CH2—CH(R)—O) corresponds to an alkylates group,
R in any alkyl group independently has a carbon number being an integer of 2-20,
wherein PO corresponds to a propoxy group,
y is an integer from 0 to 50,
z is an integer from 0 to 70,
wherein X is selected from a single bond, an alkylene group with 1 to 10 carbon atoms or an alkenylene group with 2 to 10 carbon atoms,
wherein Y is an anionic group selected from the group of hydroxy groups, sulfate groups, sulfonate groups, carboxylate groups, phosphate groups or phosphonate groups,
wherein M is selected from the group consisting of H + , Na + , K + , Li + , Mg + , Ca 2+ , and NH 4 + ,
wherein a corresponds to an integer from 1 or 3, and
wherein b corresponds to an integer from 1 to 3.

20. The method of claim 13 , wherein the alkylene oxide units comprise from 1 to 70 ethylene oxide units.

21. The method of claim 13 , wherein the alkylene oxide units comprise from 1 to 50 propylene oxide units.

22. The method of claim 13 , wherein the alkylene oxide units comprise 1 to 70 ethylene oxide units and 1 to 50 propylene oxide units.

23. The method of claim 13 , wherein the lignin amphiphile comprises at least one carboxylate group.

Assignees

• Chevron Usa Inc

Inventors

• Naae Douglas G
• Winslow Gregory A
• Dwarakanath Varadarajan
• Malik Taimur
• Pinnawala Arachchilage Gayani

Classifications

• C08K5/057

  Metal alcoholates {(metal enolates C08K5/0091)} · CPC title

• C09K8/584

  characterised by the use of specific surfactants · CPC title

• C08G65/2612

  containing aromatic or arylaliphatic hydroxyl groups · CPC title

• C09K8/604

  Polymeric surfactants · CPC title

• C08G65/2606

  containing hydroxyl groups · CPC title