Zwitterionic surfactants suitable for enhanced oil recovery

Patent metadata

Field	Value
Publication number	US-2019153298-A1
Application number	US-201716091227-A
Country	US
Kind code	A1
Filing date	Mar 30, 2017
Priority date	Apr 8, 2016
Publication date	May 23, 2019
Grant date	—

Abstract

The instant invention relates to surfactants having the following formula (I) wherein: each of R a and R b is a a linear or branched, saturated or unsaturated, hydrocarbon chain, each of R c and R d is a alkyl chain having 1 to 10 carbon atoms, each of (E 1 ) and (E 2 ) is a divalent hydrocarbon radical, A is: a group a carboxylate group —COO − (optionally in all or part in the form —COOH); or a sulfonate group —SO 3 − (optionally in all or part in the form —SO 3 H). The invention also relate to the preparation of these surfactants and their use in oil extraction, especially in EOR applications.

First claim

1 . A surfactant having the formula (I):

wherein:
each of R a and R b , which are identical or different, is a linear or branched, saturated or unsaturated, hydrocarbon chain that may be interrupted and/or substituted by at least a monocyclic or polycyclic group,
each of R c and R d , which are identical or different, is a linear or branched, alkyl chain having 1 to 10 carbon atoms,
each of (E 1 ) and (E 2 ) is a divalent hydrocarbon radical linear or branched, not substituted or substituted, optionally carrying a —OH group,
A is:
a carboxylate group —COO − , optionally in all or part in its protonated form —COOH; or
a sulfonate group —SO 3 − , optionally in all or part in its protonated form —SO 3 H.

2 . The surfactant according to claim 1 , which is a betaine of the formula (I-1):

wherein R a , R b , R c , R d , (E 1 ) and (E 2 ) have the meaning given in claim 1 and wherein:
the amino group —NH— between (E 1 ) and CR a R b may be in its protonated form —NH 2 + —; and/or
the COO − group may be in its a protonated form —COOH.

3 . The surfactant according to claim 1 , which is a sultaine of the formula (I-2):

wherein R a , R b , R c , R d , (E 1 ) and (E 2 ) have the meaning given in claim 1 and wherein:
the amino group —NH— between (E 1 ) and CR a R b may be in its protonated form —NH 2 + —; and/or
the SO 3 − group may be in its a protonated form —SO 3 H.

4 . The surfactant according to claim 1 , 2 or 3 , wherein R a and R b are linear groups.

5 . A process for preparing the surfactant according to claim 1 , the process comprising:
STEP 1: reacting two acids Ra—COOH and Rb—COOH, wherein Ra and Rb are identical or different, via a Piria decarboxylating ketonization, whereby an internal ketone is obtained having the formula (II):

wherein R a and R b have the meaning given in claim 1 for formula (I);
STEP 2: reacting the internal ketone (II) obtained in step 1 with a diamine of formula H 2 N-(E1)-NR c R d in a reductive amination reaction

whereby a compound of formula (III) is obtained:

wherein R a , R b , R c , R d and (E 1 ) have the meaning given herein-above for formula (I);
STEP 3: grafting a group -(E2)-A on the amine group —NR c R d of the compound of formula (III) obtained in step (2), wherein (E 2 ) and A have the meaning given herein-above for formula (I), whereby the compound of formula (I) is obtained.

6 . The process of claim 5 , wherein step 3 comprises a reaction of the compound (III) with a compound of formula X-(E 2 )-COOH, optionally deprotonated in all or part in the form of a carboxylate, wherein (E 2 ) is a divalent hydrocarbon radical linear or branched, not substituted or substituted, optionally carrying a —OH group, and X is a leaving group.

7 . The process of claim 5 , wherein step 3 comprises a reaction of the compound (III) with a compound of formula X-(E 2 )-SO 3 H wherein (E 2 ) is a divalent hydrocarbon radical linear or branched, not substituted or substituted, optionally carrying a —OH group.

8 . (canceled)

9 . A method for extracting oil from a subterranean formation, wherein the surfactant of formula (I) according to claim 1 is injected in the subterranean formation.

10 . An EOR formulation, comprising at least one surfactant of formula (I) according to claim 1 in admixture with other hydrophilic surfactants.

11 . The surfactant of claim 1 , wherein each of R c and R d , which are identical or different, is a linear or branched, alkyl chain having 1 to 4 carbon atoms.

12 . The surfactant of claim 1 , wherein each of (E 1 ) and (E 2 ) is an alkanediyl radical of formula —(CH 2 ) n — wherein n=1, 2, 3 or 4, wherein one of the hydrogen may be substituted by a —OH group.

13 . The surfactant of claim 1 , wherein (E 2 ) is a divalent hydrocarbon radical linear or branched, not substituted or substituted, carrying a —OH group.

14 . The surfactant of claim 1 , wherein (E 2 ) is an alkanediyl radical of formula —(CH 2 ) n — wherein n=1, 2, 3 or 4, wherein one of the hydrogen is substituted by a —OH group.

15 . The surfactant according to claim 4 , wherein R a and R b are each:
a linear alkyl chain having 1 to 24 carbon atoms; or a linear alkenyl chain having 1 to 20 carbon atoms and having one or more unsaturations.

16 . The surfactant according to claim 14 , wherein R a and R b are each a linear alkyl chain having at least 4 carbon atoms.

17 . The surfactant according to claim 15 , wherein the sum of the number of carbon in R a and R b is at least 7.

18 . The process of claim 6 , wherein the compound of formula X-(E 2 )-COOH is deprotonated in all or part in the form of a carboxylate.

19 . The process of claim 6 , wherein X is Cl.

20 . The method of claim 9 , wherein the surfactant of formula (I) is injected in the subterranean formation in admixture with other hydrophilic surfactants.

Assignees

• Rhodia Operations

Inventors

• Back Olivier
• Marion Philippe
• Morvan Mikel

Classifications

• C07C229/12

  to carbon atoms of acyclic carbon skeletons · CPC title

• C09K8/584 Primary

  characterised by the use of specific surfactants · CPC title

• C07C309/14

  containing amino groups bound to the carbon skeleton · CPC title

• E21B43/16

  Enhanced recovery methods for obtaining hydrocarbons · CPC title