Synthesis and evaluation of novel amido-amine cationic gemini surfactants containing flexible and rigid spacers
The invention concerns synthesized amido-amine-based cationic gemini surfactants with flexible and rigid spacers and different hydrophobic. These gemini surfactants were prepared by modified procedure through amidation of long chain carboxylic acids using 3-(dimethylamino)-1-propylamine followed by treatment with halohydrocarbons and showed excellent thermal stability and surface properties useful for various oilfield applications such as enhanced oil recovery.
1. A gemini surfactant, comprising:
an anion part having a combined charge of −2; and
a cation part having a struture (I);
wherein
R1 and R2 are C 8 -C 30 alkyl or C 10 -C 30 alkenyl,
S is a linear C 9 alkyl spacer, C 4 alkenyl spacer, C 6 alkenyl spacer, or C 8 alkenyl spacer, and
n and n′ are in a range of from 2 to 5, or
a compound of formula (5) or (6)
2. The surfactant of claim 1 , wherein the cation part is selected from the group consisting of surfactants of structure (1), (2), (3), (4), (5), and (6):
3. The surfactant of claim 1 , wherein S is the linear C 4 , C 6 , or C 8 alkenyl spacer comprising cis-double bond.
4. The surfactant of claim 1 , wherein S is the linear C 4 , C 6 , or C 8 alkenyl spacer comprising trans-double bond.
5. The surfactant of claim 2 , wherein the cation part has the formula (1).
6. The surfactant of claim 2 , wherein the cation part has the formula (2).
7. The surfactant of claim 2 wherein the cation part has the formula (3).
8. The surfactant of claim 2 , wherein the cation part has the formula (4).
9. The surfactant of claim 2 wherein the cation part has the formula (5).
10. The surfactant of claim 2 , wherein the cation part has the formula (6).
11. A composition, comprising: the gemini surfactant of claim 1 ; and water.
12. The composition of claim 11 , further comprising:
a monomeric surfactant;
a demulsifier; and/or
a coupling agent.
13. A method for increasing a recovery of crude oil or another hydrocarbon from a subterranean hydrocarbon-containing formation or during hydraulic fracturing, the method comprising:
contacting a composition comprising the gemini surfactant of claim 1 with a subterranean hydrocarbon-containing formation.
14. The method of claim 13 , wherein the subterranean hydrocarbon-containing formation comprises a carbonate.
15. The method of claim 13 , wherein the subterranean hydrocarbon-containing formation is a sandstone reservoir.
16. The method of claim 13 , wherein the subterranean hydrocarbon-containing formation is a tight shale reservoir.
17. A method of increasing recovery of hydrocarbons from a hydrocarbon-containing subterranean fractured rock formation, the method comprising:
forming a composition comprising the gemini surfactant of claim 1 and water, and optionally a cationic monomer surfactant, a demulsifier, a coupling agent, or a mixture of two or more of any of these
injecting the composition into the hydrocarbon-containing subterranean fractured rock formation; and
collecting a hydrocarbon from the hydrocarbon-containing subterranean fractured rock formation.
18. The method of claim 17 , where the gemini surfactant is present in the composition at a concentration in a range of from 0.001 to 1 wt. %, based on total composition weight.
19. The method of claim 17 , wherein the water source is produced water or flowback water.
20. The method of claim 17 , wherein the injecting is into a first wellbore connected to the subterranean hydrocarbon-containing fractured rock formation, and
wherein the collecting is from a second wellbore that is connected to the subterranean hydrocarbon-containing fractured rock formation; or
wherein the injecting is into a wellbore connected to the subterranean hydrocarbon-containing fractured rock formation, and the collecting is from the same wellbore.