IP Library Granted Patent US 9,587,168
Granted Patent B2
US 9,587,168 · App. 14/039,377 · Granted Mar 7, 2017

Alkylaromatic sulfonates for enhanced oil recovery process

Inventors: Curt B. Campbell (San Ramon, CA); Andrew Howes (San Ramon, CA); Terri Denslow (San Ramon, CA)
Assignee: Chevron Oronite Company LLC
C09K8/584E21B43/16
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Quick Facts
Patent No.
US 9,587,168
App. No.
14/039,377
Granted
Mar 7, 2017
Kind
B2
Abstract

An alkylaromatic sulfonate is disclosed wherein the alkyl group contains a distribution of alkyl chain lengths which comprise greater than 15 weight percent and up to about 35 weight percent of C 30 to C 58 . Also disclosed is a process for preparing an alkylaromatic sulfonate and its use in recovering crude oil from a subterranean hydrocarbon containing formation.

Claims (33)

1. An alkylaromatic sulfonate wherein the alkyl group contains a distribution of alkyl chain lengths which comprise from 16.5 weight percent and up to about 35 weight percent of C 30 to C 58 .

2. The alkylaromatic sulfonate of claim 1 , wherein the at least one aromatic compound is selected from the group consisting of unsubstituted aromatic compounds, monosubstituted aromatic compounds, and disubstituted aromatic compounds.

3. The alkylaromatic sulfonate of claim 2 , wherein the unsubstituted aromatic compounds, monosubstituted aromatic compounds, and disubstituted aromatic compounds are selected from the group consisting of benzene, toluene, meta-ylene, para-xylene, ortho-xylene, and mixtures thereof.

4. The alkylaromatic sulfonate of claim 1 , wherein the alkyl group is derived from a mixture of linear alpha olefins or isomerized olefins containing from about 10 to about 58 carbon atoms.

5. The alkylaromatic sulfonate of claim 1 , wherein the alkyl chain lengths comprise from about 45 weight percent to about 75 weight percent of C 12 to C 20 and from 16.5 weight percent and up to about 35 weight percent of C 30 to C 58 .

6. The alkylaromatic sulfonate of claim 1 , which is an alkylxylene sulfonate represented by the following formula:

wherein R is an alkyl group containing from about 10 to about 58 carbon atoms, M is a mono-valent cation, and wherein the alkyl group contains a distribution of alkyl chain lengths wherein the alkyl chain lengths comprise from 16.5 weight percent and up to about 35 weight percent of C 30 to C 58 .

7. The alkylaromatic sulfonate of claim 6 , wherein the mono-valent cation is an alkali metal.

8. The alkylaromatic sulfonate of claim 6 , wherein the mono-valent cation is sodium.

9. The alkylaromatic sulfonate of claim 6 , wherein the alkylxylene sulfonate has an optimum salinity in the range of about 0.3 to 0.8 weight percent sodium chloride.

10. A process for preparing an alkylaromatic sulfonate, the process Comprising:

(a) reacting at least one aromatic compound with a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, wherein the mixture of olefins contains a distribution of carbon atoms that comprise from greater than 15 weight percent and up to about 23 weight percent C 30 to C 58 , in the presence of an acidic alkylation catalyst;

(b) sulfonating the product of step (a); and

(c) neutralizing the sulfonated product of step (b) with an alkali or alkaline earth metal hydroxide; wherein the resulting alkylaromatic sulfonate possesses an alkyl group containing a distribution of alkyl chain lengths which comprise from 16.5 weight percent and up to about 35 weight percent of C 30 to C 58 .

11. The process of claim 10 , wherein the aromatic compound is selected from the group consisting of benzene, toluene, meta-ylene, para-xylene, ortho-xylene, and mixtures thereof.

12. The process of claim 10 , wherein the mixture of olefins is a mixture of linear olefins, a mixture of linear isomerized olefins, a mixture of branched olefins, a mixture of partially branched olefins or a mixture thereof.

13. The process of claim 12 , wherein the mixture of linear olefins is a mixture of normal alpha olefins containing from about 10 to about 58 carbon atoms.

14. The process of claim 10 , wherein the step of sulfonating comprises reacting the product of step (a) with sulfur trioxide, which has been diluted with air.

15. A method for recovering crude oil from a subterranean hydrocarbon containing formation, the method comprising:

(a) injecting into the formation an aqueous solution containing an amount of one or more alkylaromatic sulfonates or a mixture of alkylaromatic sulfonates effective for the recovery of crude oil wherein the alkyl group of alkylaromatic sulfonate contains a distribution of alkyl chain lengths which comprise from 16.5 weight percent up to about 35 weight percent of C 30 to C 58 ; and

(b) displacing the crude oil with the aqueous solution injected into the formation to thereby recover hydrocarbons from a production well.

16. The method of claim 15 , wherein in step (a) the alkylaromatic sulfonate is present in an amount of about 0.03 weight percent to about 3.0 weight percent, based on the total weight of the aqueous solution.

17. The method of claim 15 , wherein the alkylaromatic sulfonate is an alkylxylene sulfonate represented by the following formula:

wherein R is an alkyl group containing from about 10 to about 58 carbon atoms, M is a mono-valent cation, and wherein the alkyl group contains a distribution of alkyl chain lengths wherein the alkyl chain lengths comprise from from 16.5 weight percent and up to about 35 weight percent of C 30 to C 58 .

18. The method of claim 15 , wherein the aqueous solution in step (a) further contains a co-solvent or a co-surfactant.

19. The method of claim 15 , wherein the hydrocarbon in the subterranean formation is a waxy crude oil.

20. The method of claim 15 , further comprising, concurrently with or subsequent to the injection of the aqueous solution in step (a), injecting into the formation an amount of water effective for driving the aqueous solution of step (a) into the formation to displace the crude oil to thereby recover hydrocarbons from a production well.

21. The method of claim 15 , further comprising, concurrently with or subsequent to the injection of the aqueous solution in step (a), injecting into the formation an amount of a polymer effective for driving the aqueous solution of step (a) into the formation to displace the crude oil to thereby recover hydrocarbons from a production well.

22. The method of claim 21 , wherein the polymer is a polysaccharide, an acrylamide or a partially hydrolyzed polyacrylamide.

23. The method of claim 15 , further comprising, concurrently with or subsequent to the injection of the or the polymer, injecting into the formation an amount of water effective for driving the aqueous solution of step (a) into the formation to displace the crude oil to thereby recover hydrocarbons from a production well.

24. The alkylaromatic sulfonate of claim 1 , wherein the alkyl group contains a distribution of alkyl chain lengths which comprise from 20.4 weight percent and up to about 35 weight percent of C30 to C 58 .

25. The alkylaromatic sulfonate of claim 6 , wherein the alkyl group contains a distribution of alkyl chain lengths wherein the alkyl chain lengths comprise from 20.4 weight percent and up to about 35 weight percent of C 30 to C 58 .

26. The process of claim 10 , wherein the resulting alkylaromatic sulfonate possesses an alkyl group containing a distribution of alkyl chain lengths which comprise from 20.4 weight percent and up to about 35 weight percent of C 30 to C 58 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2013
From: CAMPBELL, CURTIS B.; HOWES, ANDREW; DENSLOW, THERESA ANN
To: CHEVRON ORONITE COMPANY LLC
Reel/Frame 031732/0065 →
Continuity (2)
Provisional Application 61707116 · Sep 28, 2012
Related Publication 20140090838A1 · Apr 3, 2014