Multicarboxylate compositions and method of making the same

Patent metadata

Field	Value
Publication number	US-9976072-B2
Application number	US-201514668147-A
Country	US
Kind code	B2
Filing date	Mar 25, 2015
Priority date	Mar 26, 2014
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

The present disclosure generally relates to a multicarboxylate, such as an alkyl alkoxy dicarboxylate a method of making the multicarboxylate, and methods to use the multicarboxylate. A specific embodiment of the disclosure is a compound comprising the chemical formula: R 1 -R 2 -R 3 , wherein R 1 comprises a branched or unbranched, saturated or unsaturated, cyclic or non-cyclic, hydrophobic carbon chain having 7-150 carbon atoms; an oxygen atom linking R 1 and R 2 ; R 2 comprises an alkoxylated chain comprising ethylene oxide, propylene oxide, butylene oxide, or a combination thereof; and R 3 comprises a branched or unbranched hydrocarbon chain comprising 2-12 carbon atoms and 2-5 —COOH or —COOM groups wherein M is a monovalent, divalent, or trivalent cation. The composition has a variety of uses but in some embodiments may be used in enhanced oil recovery processes.

First claim

What is claimed is:

1. An additive compound for use in enhanced oil recovery applications, comprising the chemical formula:
R 1 -R 2 -R 3 , wherein
R 1 comprises a branched or unbranched, saturated or unsaturated, cyclic or non-cyclic, hydrophobic carbon chain having 7-150 carbon atoms and an oxygen atom linking R 1 and R 2 ;
R 2 comprises an alkoxylated chain comprising at least one oxide group selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and combinations thereof wherein R 2 is selected from the group consisting of —(BO) m —(PO) n -(EO) o -, —(BO) p —(PO) q —(BO) 1 -(EO) s -, and —(BO) t -(EO) u -, wherein m through u≠0, m+n+o=8-190, p+r+s=8-190, and t+u=8-190;

and
R 3 comprises a branched or unbranched hydrocarbon chain comprising 2-12 carbon atoms and 2-5 —COOH or 2-5 —COOM groups wherein M is a monovalent, divalent, or trivalent cation.

2. The compound of claim 1 , wherein R 1 comprises 12-36 carbon atoms.

3. The compound of claim 1 , wherein R 2 comprises between 2-80 ethylene oxide groups, 2-80 propylene oxide groups, and 2-80 butylene oxide groups.

4. The compound of claim 1 , wherein R 3 comprises 2 —COOH or —COOM groups.

5. The compound of claim 1 , wherein R 3 comprises 3 —COOH or —COOM groups.

6. The compound of claim 1 , wherein R 3 comprises 4 —COOH or —COOM groups.

7. The compound of claim 1 , wherein M comprises Na, K, NH 4 , Ca, Mg, or Ba.

8. The compound of claim 1 , wherein R 2 comprises an aryl group.

9. The compound of claim 8 , wherein the aryl group is a phenyl group having in a range from 0 to 3 alkyl substitutions selected from the group consisting of methyl and ethyl.

10. The compound of claim 1 , wherein the compound functions as a stabilizer when added to an aqueous solution at a temperature of >70° C. in a concentration ranging from 200 ppm (0.02%) to 1500 ppm (0.15%), for the aqueous solution to have an NTU of less than 20, wherein the aqueous solution comprises at least 750 ppm of associative polymer, unhydrolyzed polyacrylamide, or partially hydrolyzed polyacrylamide (PHPA) and at least 500 ppm of divalent cations.

11. An aqueous stream for injecting into reservoir for enhanced oil recovery applications, the aqueous stream having a composition comprising:
0.01-20% by weight of the additive compound of claim 1 ;
250 to 5000 ppm of a polymer selected from the group consisting of xanthan gum, scleroglucan, water soluble unhydrolyzed or partially hydrolyzed polyacrylamides, hydrophobically-modified associative polymers, co-polymers of polyacrylamide, 2-acrylamido 2-methylpropane sulfonic acid and its sodium salt, and N-vinyl pyrrolidone;
0.3 to 20 weight percent of a basic salt of a Group IA alkali metal; and
0.5 to about 6.0 weight percent of a lower carbon chain alcohol co-solvent.

12. The aqueous stream composition of claim 11 , wherein
R 1 comprises 12-36 carbon atoms;
R 2 comprises between 0-80 ethylene oxide groups, 0-80 propylene oxide groups, and 0-80 butylene oxide groups;
R 3 comprises any of 2, 3, or 4 —COOH or —COOM groups;
M comprises Na, K, NH 4 , Ca, Mg, or Ba.

13. The aqueous stream composition of claim 11 , wherein
R 1 comprises 12-36 carbon atoms;
R 2 comprises an aryl group;
R 3 comprises any of 2, 3, or 4 —COOH or —COOM groups;
M comprises Na, K, NH 4 , Ca, Mg, or Ba.

14. The aqueous stream for injecting into reservoir for enhanced oil recovery applications, wherein:
the polymer is selected from the group consisting of associative polymers, water soluble unhydrolyzed polyacrylamides, and partially hydrolyzed polyacrylamides;
the aqueous stream is injected into the reservoir at a temperature of at least 70° C.;
the aqueous stream has a concentration of divalent cations of at least 500 ppm; and the additive compound of claim 1 is present in an amount ranging from 200 ppm (0.02%) to 1500 ppm (0.15%) for the aqueous stream to have an NTU of <20.

15. The aqueous stream of claim 12 , wherein the polymer is partially hydrolyzed polyacrylamide.

16. A method of enhancing oil recovery in a subterranean reservoir, comprising:
a) forming at least one injection/production well pair in a subterranean reservoir;
b) providing an aqueous stream comprising: 0.01-20% by weight of the additive compound of claim 1 ; 250 to 5000 ppm of a polymer selected from the group consisting of xanthan gum, scleroglucan, water soluble unhydrolyzed or partially hydrolyzed polyacrylamides, hydrophobically-modified associative polymers, co-polymers of polyacrylamide, 2-acrylamido 2-methylpropane sulfonic acid and its sodium salt, and N-vinyl pyrrolidone; 0.3 to 5 weight percent of a basic salt of a Group IA alkali metal; and 0.5 to about 6.0 weight percent of a lower carbon chain alcohol co-solvent;
c) injecting the aqueous stream via the injection well into the reservoir; and
d) recovering oil via the production well from the subterranean reservoir.

17. The method of claim 16 , wherein the additive compound of claim 1 is present in the aqueous stream in an amount ranging from 200 ppm (0.02%) to 1500 ppm (0.15%).

18. The method of claim 16 , wherein
R 1 comprises 12-36 carbon atoms;
R 2 comprises between 0-80 ethylene oxide groups, 0-80 propylene oxide groups, and 0-80 butylene oxide groups;
R 3 comprises any of 2, 3, or 4 —COOH or —COOM groups;
M comprises Na, K, NH 4 , Ca, Mg, or Ba.

19. The method of claim 16 , wherein
R 1 comprises 12-36 carbon atoms;
R 2 comprises an aryl group;
R 3 comprises any of 2, 3, or 4 —COOH or —COOM groups;
M comprises Na, K, NH 4 , Ca, Mg, or Ba.

Assignees

• Chevron Usa Inc

Inventors

• Shong Robert George
• Dwarakanath Varadarajan
• Winslow Gregory A
• Thach Sophany

Classifications

• C09K8/588

  characterised by the use of specific polymers {(polymeric surfactants C09K8/584)} · CPC title

• E21B43/16

  Enhanced recovery methods for obtaining hydrocarbons · CPC title

• C07C59/305

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C09K8/584 Primary

  characterised by the use of specific surfactants · CPC title