Imido-acid salts and methods of use
View Patent ↗Imido-acid salts and compositions containing imido-acid salts are described herein. Methods of their preparation and use are also described herein. The methods of using the imido-acid salts include the reduction of volatile compounds from gas and liquid streams and the delivery of pharmaceutical agents to subjects.
1. A compound of the following formula:
wherein:
L is substituted or unsubstituted C 1-20 alkyl;
M + is substituted or unsubstituted imidazolium;
R 1 , R 2 , and R 3 are each hydrogen; and
X − is a carboxylate.
2. The compound of claim 1 , wherein L is substituted or unsubstituted C 1-6 alkyl.
3. A composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.
4. An ionic liquid, comprising:
a substituted or unsubstituted imidazolium cation; and
an anion, wherein the anion includes a compound of the following formula:
wherein:
L is substituted or unsubstituted C 1-20 alkyl;
R 1 , R 2 , and R 3 are each hydrogen; and
X − is carboxylate.
5. A method for reducing a volatile compound from a stream, comprising contacting the stream with a system comprising:
water; and
a compound of the following formula:
wherein:
L is substituted or unsubstituted C 1-20 alkyl;
M + is substituted or unsubstituted imidazolium;
R 1 , R 2 , and R 3 are each hydrogen; and
X − is carboxylate.
6. The method of claim 5 , wherein the volatile compound is carbon dioxide, sulfur dioxide, or hydrogen sulfide.
7. The method of claim 5 , wherein the system further comprises an ionic liquid.
8. The method of claim 5 , wherein the stream is a gas stream or a liquid stream.
9. The method of claim 8 , wherein the gas stream is a natural gas stream or a flue gas stream.
10. The method of claim 5 , wherein the system further comprises a substituted or unsubstituted imidazole.
11. The method of claim 10 , wherein the imidazole is an N-functionalized imidazole.
12. The method of claim 11 , wherein the N-functionalized imidazole is an N-alkyl imidazole, an N-alkenyl imidazole, an N-alkynyl imidazole, or an N-aryl imidazole.
13. The method of claim 5 , wherein the system further comprises an amine.
14. The method of claim 13 , wherein the amine is a monoamine, a diamine, or a polyamine.
15. The method of claim 13 , wherein the amine is selected from the group consisting of primary amines, secondary amines, tertiary amines, and cyclic amines.
16. The method of claim 13 , wherein the amine has the following structure:
wherein
R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted C 1-20 alkyl, substituted or unsubstituted C 2-20 alkenyl, substituted or unsubstituted C 2-20 alkynyl, substituted or unsubstituted C 1-20 heteroalkyl, substituted or unsubstituted C 2-20 heteroalkenyl, substituted or unsubstituted C 2-20 heteroalkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted amino, substituted or unsubstituted alkoxyl, substituted or unsubstituted aryloxyl, silyl, siloxyl, cyano, thio, and nitro.
17. The method of claim 16 , wherein the primary amine is selected from the group consisting of monoethanolamine, diglycolamine, and 2-amino-2-methylpropanol.
18. The method of claim 16 , wherein the secondary amine is selected from the group consisting of diethanolamine, and diisopropanolamine.
19. The method of claim 16 , wherein the tertiary amine is N-methyldiethanolamine.
20. The method of claim 16 , wherein the cyclic amine is substituted or unsubstituted piperazine.
21. A method for sweetening a natural gas feed stream, comprising:
(a) contacting the natural gas feed stream with a system comprising water and a compound of the following formula:
wherein:
L is substituted or unsubstituted C 1-20 alkyl;
M + is substituted or unsubstituted imidazolium;
R 1 , R 2 , and R 3 are each hydrogen; and
X − is carboxylate, to form a purified natural gas feed stream and a gas-rich system; and
(b) separating the purified natural gas feed stream from the gas-rich system.
22. The method of claim 21 , wherein the system further comprises an amine, a substituted or unsubstituted imidazole, an ionic liquid, or a mixture of these.
23. A system, comprising:
water; and
a compound of the following formula:
wherein:
L is substituted or unsubstituted C 1-20 alkyl;
M + is substituted or unsubstituted imidazolium;
R 1 , R 2 , and R 3 are each hydrogen; and
X − is carboxylate.
24. The system of claim 23 , further comprising an amine, a substituted or unsubstituted imidazole, an ionic liquid, or a mixture of these.