# US 12,006,470 B2 · Sulphonated internal ketone-based formulations for assisted recovery of oil

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- Number: US 12,006,470 B2
- Document ID: US12006470B2
- Status: Granted
- Kind: B2
- Application number: 17/258,523
- Filed: 2019-07-05
- Published: 2021-09-02
- Granted: 2024-06-11
- Earliest claimed: 2018-07-19
- Assignees: Rhodia Operations; Ifp Energies Nouvelles
- Applicants: Ifp Energies Nouvelles; Rhodia Operations
- Inventors: Mikel Morvan; Pascal Pitiot; Loïc Baussaron; Roberto Company
- Web page: https://patentgrep.com/patent/US12006470B2

## CPC

- C09K 8/584: characterised by the use of specific surfactants
- E21B 43/16: Enhanced recovery methods for obtaining hydrocarbons
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- E21B: EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS

## Abstract

The present invention relates to compositions for enhanced oil recovery, comprising: (A) internal ketones sulfonated alpha to the ketone group; and (B) unsulfonated internal ketones, with a molar ratio B/(A+B) greater than or equal to the limiting molar concentration of unsulfonated ketones from which a stabilization is observed in the reduction in mobility when the mixture of said ketones is injected into a porous medium.

## Claims

### Claim 1

A composition suitable for enhanced oil recovery, comprising:
(A) internal ketones sulfonated alpha to the ketone group; and
(B) unsulfonated internal ketones,
with a molar ratio B/(A+B), corresponding to the molar concentration of unsulfonated ketones, ranging between 10% and 50%.

### Claim 2 (depends on 1)

The composition as claimed in claim 1, wherein the compounds A comprise a mixture of at least one monosulfonate and at least one disulfonate, conforming respectively to the formulae (1) and (2) below:
where:
each of R1, R3 and R5, which are identical or different, is independently a hydrogen or a linear or branched alkyl chain having from 1 to 20 carbon atoms;
each of R2 and R4, which are identical or different, is independently a linear alkyl chain or having from 4 to 24 carbon atoms, it being possible for said alkyl chain to comprise cycloaliphatic groups; and
X is H; or else —SO3X is a sulfonate salt formed with 1/n mol of a cation Xn+ in which n is the valence of the cation.

### Claim 3 (depends on 2)

The composition as claimed in claim 2, wherein the compounds B conform to the formula (3) below:
where:
each of R1, R3 and R5, which are identical or different, is independently a hydrogen or a linear or branched alkyl chain having from 1 to 20 carbon atoms;
each of R2 and R4, which are identical or different, is independently a linear alkyl chain or having from 4 to 24 carbon atoms, it being possible for said alkyl chain to comprise cycloaliphatic groups; and
R6 is a hydrogen or else a linear or branched alkyl chain having from 1 to 20 carbon atoms.

### Claim 4 (depends on 3)

The composition as claimed in claim 3, which is prepared by only partial sulfonation of a compound of formula (3) or else a mixture of compounds of formula (3) using a sulfonating agent.

### Claim 5 (depends on 4)

The composition as claimed in claim 4, wherein the sulfonation is performed using gaseous sulfur trioxide SO3 as sulfonating agent.

### Claim 6 (depends on 5)

The composition as claimed in claim 5, wherein the sulfonation is further performed using the falling-film technique.

### Claim 7 (depends on 1)

The composition as claimed in claim 1, further comprising:
an aqueous medium comprising dissolved salts; and/or
an anionic surfactant.

### Claim 8 (depends on 7)

The composition as claimed in claim 7, wherein the anionic surfactant is an AGES or an AAGES.

### Claim 9 (depends on 1)

A method for enhanced oil recovery from an underground formation, the method comprising:
injecting a composition as claimed in claim 1 into said underground formation via at least one injection well; and
recovering a fluid conveying the oil leaving the underground formation via at least one production well.