Surface active ionic liquid with activity in aqueous and non-aqueous media
Disclosed herein are surfactant compounds, that are surface active, liquid, chiral, and micelle forming. Also disclose herein are ionic liquids and compsitions comprising the surfactant compounds.
1. A salt of formula (I)
wherein
X— has formula (II)
R 1 and R 2 are each independently hydrogen, C 1-4 alkyl, C 3-4 cycloalkyl, or —CH 2 -cyclopropyl; or R 1 and R 2 , taken together with the nitrogen to which they attach form a 4- to 7-membered saturated heterocycle;
R 3 is hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, C 3-4 cycloalkyl, —CH 2 -cyclopropyl, or —CH 2 —OH;
R 4 is halogen, cyano, C 1-4 alkyl, C 1-4 haloalkyl, OH, —OC 1-4 alkyl, or —OC 1-4 haloalkyl; wherein optionally two alkyl groups, taken together with the carbon atoms to which they attach form a 5- to 7-membered carbocyclic ring;
n is 0, 1, 2, 3, 4, or 5;
R 5 and R 6 are each independently hydrogen, —C(O)C 1-4 alkyl, —C(O)C 3-4 cycloalkyl, —C(O)—CH 2 -cyclopropyl, C 1-4 alkyl, or C 1-4 haloalkyl; and
R 7 is C 6-18 alkyl optionally substituted with 1-6 halogen.
2. The salt of claim 1 , wherein R 1 is hydrogen.
3. The salt of claim 2 , wherein R 2 is hydrogen.
4. The salt of claim 3 , wherein R 3 is C 1-4 alkyl.
5. The salt of claim 4 , wherein R 3 is CH 3 .
6. The salt of claim 3 , wherein n is 0.
7. The salt of claim 3 , wherein R 5 is —C(O)C 1-4 alkyl.
8. The salt of claim 7 , wherein R 5 is —C(O)CH 3 .
9. The salt of claim 7 , wherein R 6 is —C(O)C 1-4 alkyl.
10. The salt of claim 9 , wherein R 6 is —C(O)CH 3 .
11. The salt of claim 3 , wherein R 7 is C 12 alkyl.
12. The salt of claim 11 , wherein R 7 is straight chain C 12 alkyl.
13. The salt of claim 1 , wherein the salt of formula (I) has formula (I-a)
14. The salt of claim 1 , wherein the salt of formula (I) has formula (I-b)
15. The salt of claim 1 , wherein formula (II) is formula (II-a)
16. An ionic liquid comprising the salt of claim 1 .
17. A composition comprising the salt of claim 1 .
18. The composition of claim 17 further comprising an aqueous medium, wherein the salt has a critical micelle concentration of about 0.0001-0.0005 M in the aqueous medium.
19. The composition of claim 17 further comprising a micellar aggregate, the micellar aggregate comprising the salt.
20. The composition of claim 19 , wherein the micellar aggregate comprises a spherical micelle, a rod-like micelle, and/or a lamellar structure.
21. The composition of claim 17 further comprising an organic medium, wherein the salt has a critical micelle concentration of about 0.003-0.1 M in the organic medium.
22. The composition of claim 17 further comprising a reverse micellar aggregate, the reverse micellar aggregate comprising the salt.
23. The composition of claim 19 , wherein the micellar aggregate contains an aggregation number of salt greater than 50.
24. The salt of claim 1 of the following formula
25. The ionic liquid of claim 16 , wherein the monoalkylester from tartaric acid formula (II) is the monoalkylester from D-tartaric.