# US 2020/0399527 A1 · Formulations for enhanced oil recovery comprising sulfonates

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- Number: US 2020/0399527 A1
- Document ID: US20200399527A1
- Status: Published application
- Kind: A1
- Application number: 17/013,964
- Filed: 2020-09-08
- Published: 2020-12-24
- Earliest claimed: 2015-05-07
- Assignees: Rhodia Operations
- Applicants: Rhodia Operations
- Inventors: Olivier BACK; Remy LEROY; Mikel MORVAN; Patrick MOREAU; Philippe MARION
- Web page: https://patentgrep.com/patent/US20200399527A1

## CPC

- C09K 8/584: characterised by the use of specific surfactants
- C07C 309/07: containing oxygen atoms bound to the carbon skeleton
- E21B 43/16: Enhanced recovery methods for obtaining hydrocarbons
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- E21B: EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS

## Abstract

Compositions suitable for enhanced oil recovery comprising a) a mixture of α-sulfocarbonyl compounds of formulae (1) and (2) in a mixture ratio (1) to (2) of from 1:99 to 99:1 wherein R1, R3 and R5, which may be the same or different at each occurrence, are hydrogen or a linear or branched alkyl chain having 1 to 20 carbon atoms, R2 and R4, which may be the same or different at each occurrence, may be a linear or branched alkyl group having 4 to 24 carbon atoms and in which the alkyl chain may comprise one or more cycloaliphatic groups, and X is H or a metal forming a salt with the sulfonate group, and b) a salt containing aqueous solution.

## Claims

### Claim 1

A composition suitable for enhanced oil recovery comprising
a) a mixture of α-sulfocarbonyl compounds of formulae (1) and (2) in a mixture ratio (1) to (2) of from 1:99 to 99:1
wherein
R1, R3 and R5, which may be the same or different at each occurrence, are hydrogen or a linear or branched alkyl chain having 1 to 20 carbon atoms,
R2 and R4, which may be the same or different at each occurrence, are a linear or branched alkyl group having 4 to 24 carbon atoms and in which the alkyl chain may comprise one or more cycloaliphatic groups, and
X is H or a cation forming a salt with the sulfonate group, and
b) a salt containing aqueous solution.

### Claim 2 (depends on 1)

The composition in accordance with claim 1 comprising component a) in an amount of from 0.5 to 50 g/L.

### Claim 3 (depends on 1)

The composition in accordance with claim 1 comprising component a) in an amount of from 1 to 25 g/L.

### Claim 4 (depends on 1)

The composition in accordance with claim 1 wherein X is an ammonium cation or a metal cation selected from the group consisting of sodium, potassium, calcium and magnesium.

### Claim 5 (depends on 1)

The composition in accordance with claim 1 wherein R1, R3 and R5, which may be the same or different, are hydrogen or an alkyl group with 1 to 6 carbon atoms.

### Claim 6 (depends on 1)

The composition in accordance with claim 1 wherein R2 and R4, which may be the same or different, comprise 6 to 18 carbon atoms.

### Claim 7 (depends on 1)

The composition in accordance with claim 1 wherein component a) is a mixture of 12-tricosanone monosulfonate and 12-tricosanondisulfonate.

### Claim 8 (depends on 1)

The composition in accordance with claim 1 wherein component a) is a mixture of mono- and disulfonates of internal ketones obtained through ketonization of a coconut or palm kernel oil derived fatty acids cut.

### Claim 9 (depends on 1)

The composition in accordance with claim 1 wherein component a) is a mixture of mono- and disulfonates of ketones obtained through ketonization of fatty acids selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, naphthenic acids, isostearic acids, arachidic acid, behenic acid, lignoceric acid, cerotic acid, and mixtures thereof.

### Claim 10 (depends on 1)

The composition in accordance with claim 1 wherein component a) is a mixture of mono- and disulfonates of ketones obtained through ketonization of fatty acids selected from the group consisting of 10-undecenoic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid erucic acid, and mixtures thereof.

### Claim 11 (depends on 1)

The composition in accordance with claim 1 wherein mono- and disulfonates in component a) are present in a molar ratio of 5:95 to 95:5.

### Claim 12 (depends on 1)

The composition in accordance with claim 1, further comprising an alkyl glyceryl ether sulfonate of general formula (3)
R6—O—[—CH2—CH(OH)—CH2—O—]m—CH2CH(OH)—CH2—SO3Y (3)
or an alkoxylated alkyl glyceryl ether of formula 4
R6—O—[—CH2—CH(OH)—CH2—O—]m[—CH2—CH(CH3)—O—]n—[—CH2—CH2—O]p—CH2CH(OH)—CH2—SO3Y (4)
wherein R6 represents a linear or branched alkyl or alkenyl chain having of from 3 to 32 carbon atoms, m is 0 or an integer in the range of from 1 to 20, n and p are integers of from 0 to 20, and Y is a cation of the sulfonate group selected from the group consisting of sodium, potassium, ammonium, calcium and magnesium.

### Claim 13

A composition comprising
c) a mixture of α-sulfocarbonyl compounds of formulae (1) and (2) in a mixture ratio (1) to (2) of from 1:99 to 99:1
wherein
R1, R3 and R5, which may be the same or different at each occurrence, are hydrogen or a linear or branched alkyl chain having 1 to 20 carbon atoms,
R2 and R4, which may be the same or different at each occurrence, are a linear or branched alkyl group having 4 to 24 carbon atoms and in which the alkyl chain may comprise one or more cycloaliphatic groups, and
X is H or a cation forming a salt with the sulfonic acid group, and
d) an alkyl glyceryl ether sulfonate of general formula (3)
R6—O—[—CH2—CH(OH)—CH2—O—]mOCH2CH(OH)—CH2—SO3Y (3)
or an alkoxylated alkyl glyceryl ether of formula (4)
R6—O—[—CH2—CH(OH)—CH2—O—]m[CH2CH(CH3)—O]n—[—CH2—CH2—O]p—CH2CH(OH)—CH2—SO3Y (4)
or a mixture thereof wherein R6 represents a linear or branched alkyl or alkenyl chain having of from 3 to 18 carbon atoms, m is 0 or an integer in the range of from 1 to 20, n and p are integers of from 0 to 20, and Y is a cation of the sulfonate group selected from the group consisting of sodium, potassium, ammonium, calcium and magnesium.

### Claim 14 (depends on 1)

A process for enhanced oil recovery, the process comprising a first step of determining the salinity of the injection water and thereafter preparing a blend of internal ketone monosulfonates and disulfonates as defined in claim 1 having a mixing ratio of mono- and disulfonates providing the lowest interfacial tension with the crude oil for the given salinity, mixing the internal ketone sulfonate mixture with the injection water and optionally further ingredients and pumping the final composition into the reservoir to recover oil from the reservoir.

### Claim 15

(canceled)

### Claim 16 (depends on 12)

The composition in accordance with claim 12, wherein R6 represents a linear or branched alkyl or alkenyl chain having of from 5 to 18 carbon atoms.

### Claim 17 (depends on 12)

The composition in accordance with claim 12, wherein m is an integer in the range of from 2 to 15.

### Claim 18 (depends on 12)

The composition in accordance with claim 12, wherein n and p are integers of from 2 to 15 and n and p cannot be both equal to 0.

### Claim 19 (depends on 13)

The composition in accordance with claim 13, wherein R6 represents a linear or branched alkyl or alkenyl chain having of from 5 to 18 carbon atoms.

### Claim 20 (depends on 13)

The composition in accordance with claim 13, wherein m is an integer in the range of from 2 to 15.

### Claim 21 (depends on 13)

The composition in accordance with claim 13, wherein n and p are integers of from 2 to 15 and n and p cannot be both equal to 0.