N-functionalized imidazole-containing systems and methods of use
View Patent ↗Systems containing imidazoles or blends of imidazoles and amines are described herein. Methods of their preparation and use are also described herein. The methods of using the systems include the reduction of volatile compounds from gas streams and liquid streams.
1. A method for removing carbon dioxide from a stream, comprising:
contacting the stream with a solvent system comprising an N-functionalized imidazole and an amine to capture the carbon dioxide,
wherein the N-functionalized imidazole is non-ionic under neutral conditions and the N-functionalized imidazole and amine comprises more than 97% by weight of the solvent system.
2. The method of claim 1 , wherein the N-functionalized imidazole is with shorten pendant alkyl chains.
3. The method of claim 1 , wherein the N-functionalized imidazole has the following structure:
wherein
R 1 is 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 thio, substituted or unsubstituted amino, substituted or unsubstituted alkoxyl, substituted or unsubstituted aryloxyl, silyl, siloxyl, cyano, or nitro; and
R 2 , R 3 , and R 4 are each independently selected from hydrogen, halogen, hydroxyl, 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 thio, substituted or unsubstituted alkoxyl, substituted or unsubstituted aryloxyl, substituted or unsubstituted amino, cyano, or nitro.
4. The method of claim 1 , wherein the amine is selected from the group consisting of primary amines, secondary amines, tertiary amines, cyclic amines, monoamine, diamine, polyamine and mixtures thereof.
5. The method of claim 4 , wherein the primary amine is selected from the group consisting of monoethanolamine, diglycolamine, 2-amino-2-methylpropanol, and mixtures thereof, the secondary amine is selected from the group consisting of diethanolamine, diisopropanolamine, and mixtures thereof, the tertiary amine is N-methyldiethanolamine, and the cyclic amine is substituted or unsubstituted piperazine.
6. The method of claim 1 , wherein the amine has the following structure:
wherein
R 1 , R 2 , and R 3 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 thio, substituted or unsubstituted amino, substituted or unsubstituted alkoxyl, substituted or unsubstituted aryloxyl, silyl, siloxyl, cyano, or nitro.
7. The method of claim 1 , wherein the amine is selected from the group consisting of N-methylethanolamine, monoethanolamine, and mixtures thereof.
8. The method of claim 1 , wherein the N-functionalized imidazole comprises at least 10% by weight of the solvent system.
9. The method of claim 1 , wherein the amine comprises at least 10% by weight of the solvent system.
10. The method of claim 1 , wherein the N-functionalized imidazole and the amine are present in a weight ratio from 9:1 to 1:9.
11. The method of claim 1 , wherein the solvent system is substantially free from volatile compounds.
12. The method of claim 1 , wherein the viscosity of the N-functionalized imidazole is less than 10 cP at 24° C.
13. The method of claim 1 , wherein the carbon dioxide is captured through the formation of carbamate-imidazolium salt between the carbon dioxide and the N-functionalized imidazole and amine.
14. The method of claim 13 , wherein the carbamate-imidazolium salt releases carbon dioxide upon heating and forms the regenerated solvent system.
15. A method for removing carbon dioxide, sulfur dioxide, or hydrogen sulfide from a stream, comprising:
contacting the stream with a solvent system comprising an N-functionalized imidazole,
wherein the N-functionalized imidazole is non-ionic under neutral conditions, and the N-functionalized imidazole comprises at least 50% by weight of the solvent system.
16. The method of claim 15 , wherein the N-functionalized imidazole is with shorten pendent alkyl chains.
17. The method of claim 15 , wherein the N-functionalized imidazole has the following structure:
wherein
R 1 is 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 thio, substituted or unsubstituted amino, substituted or unsubstituted alkoxyl, substituted or unsubstituted aryloxyl, silyl, siloxyl, cyano, or nitro; and
R 2 , R 3 , and R 4 are each independently selected from hydrogen, halogen, hydroxyl, 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 thio, substituted or unsubstituted alkoxyl, substituted or unsubstituted aryloxyl, substituted or unsubstituted amino, cyano, or nitro.
18. The method of claim 15 , wherein the solvent system further comprises an amine.
19. The method of claim 18 , wherein the amine is selected from the group consisting of primary amines, secondary amines, tertiary amines, cyclic amines, monoamine, diamine, polyamine and mixtures thereof.
20. The method of claim 19 , wherein the primary amine is selected from the group consisting of monoethanolamine, diglycolamine, 2-amino-2-methylpropanol, and mixtures thereof, the secondary amine is selected from the group consisting of diethanolamine, diisopropanolamine, and mixtures thereof, the tertiary amine is N-methyldiethanolamine, and the cyclic amine is substituted or unsubstituted piperazine.
21. The method of claim 19 , wherein the amine is selected from the group consisting of N methylethanolamine, monoethanolamine, and mixtures thereof.
22. The method of claim 18 , wherein the amine has the following structure:
wherein
R 1 , R 2 , and R 3 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 thio, substituted or unsubstituted amino, substituted or unsubstituted alkoxyl, substituted or unsubstituted aryloxyl, silyl, siloxyl, cyano, or nitro.
23. The method of claim 18 , wherein the amine comprises at least 10% by weight of the solvent system.
24. The method of claim 15 , wherein the N-functionalized imidazole and the amine are present in a weight ratio from 9:1 to 1:1.
25. The method of claim 15 , wherein the solvent system is substantially free from volatile compounds.
26. The method of claim 15 , wherein the viscosity of the N-functionalized imidazole is less than 10 cP at 24° C.
27. The method of claim 15 , wherein the stream is a gas stream or a liquid stream.
28. The method of claim 27 , wherein the gas stream is a natural gas stream or a flue gas stream.
29. A method for sweetening a natural gas feed stream, comprising:
contacting the natural gas feed stream with a solvent system comprising an N-functionalized imidazole, wherein the N-functionalized imidazole is non-ionic under neutral conditions and comprises at least 50% by weight of the solvent system, to form a purified natural gas feed stream and a gas-rich system; and
separating the purified natural gas feed stream from the gas-rich system.
30. The method of claim 29 , wherein the solvent system further comprises an amine.
31. The method of claim 29 , further comprising contacting the natural gas feed stream with a second solvent system comprising an N-functionalized imidazole, wherein the N-functionalized imidazole is non-ionic under neutral conditions.
32. The method of claim 31 , wherein the second solvent system further comprises an amine.
33. The method of claim 29 , further comprising regenerating the solvent system.
34. The method of claim 33 , wherein the solvent system is regenerated by heating or depressurizing the gas-rich system.
35. A solvent system for capturing volatile compounds, comprising:
at least 50% by weight of an N-functionalized imidazole, wherein the N-functionalized imidazole is non-ionic under neutral conditions; and
the volatile compound is selected from the group consisting of carbon dioxide, hydrogen sulfide, sulfur dioxide, nitrogen oxide, nitrogen dioxide, carbonyl sulfide, carbon disulfide, and mixtures thereof.
36. The solvent system of claim 35 , further comprising an amine.
37. The solvent system of claim 36 , wherein the N-functionalized imidazole and the amine are present in a weight ratio from 9:1 to 1:1.
38. The solvent system of claim 36 , wherein the N-functionalized imidazole and amine comprises more than 97% by weight of the solvent system.
39. The solvent system of claim 36 , wherein the N-functionalized imidazole is 1-butylimidazole and the amine is N-methylethanolamine (NMEA).
40. The solvent system of claim 35 , wherein the viscosity of the system is less than 20 cP at 24° C.
41. The solvent system of claim 35 , wherein the N-functionalized imidazole is with shorten pendent alkyl chains.
42. The solvent system of claim 35 , wherein the N-functionalized imidazole is selected from a group consisting of 1,2-dimethyl, 1-n-methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl imidazole, and a combination thereof.
43. The solvent system of claim 35 , wherein the N-functionalized imidazole is 1,2-dimethyl imidazole.