Aminopyridinium ionic liquids
View Patent ↗Disclosed herein are aminopyridinium cations and compositions containing these cations. Piperidino pyridinium cations and compositions containing these cations are also described. Ionic compositions, particularly liquid ionic compositions that contain the aminopyridinium cation or piperidino pyridinium cation are also described. Methods of enhancing the thermal stability of a compound, particularly an ionic compound, using the aminopyridinium or piperidino pyridinium cations, are also presented. Compositions having an expanded liquidus range of from about −73° C. to about 444° C. are also described. Solvents, heat transfer fluids, and lubricants having improved thermal stability characteristics and an expanded and improved liquidus range are also disclosed.
1. A composition comprising an aminopyridinium cation, said cation comprising a structure having the following formula:
wherein: R 1 is butyl or hexyl, R 3 is C n H 2n+1 , and n is 1 to 16, and R 2 , R 5 , R 6 , R 7, and R 8 are each C p H 2p+1 , and wherein p is 0 to 16.
2. The composition of claim 1 , wherein R 1 is butyl.
3. The composition of claim 2 , wherein R 3 is methyl.
4. The composition of claim 3 , wherein R 7 , and R 8 are each methyl.
5. The composition of claim 4 , wherein said cation comprises 1-butyl-3-methyl-4-(dimethylamino)pyridinium.
6. The composition of claim 1 , wherein R 1 is hexyl.
7. The composition of claim 6 , wherein R 3 is methyl.
8. The composition of claim 7 , wherein R 7 , and R 8 are each methyl.
9. The composition of claim 8 , wherein said cation comprises 1-hexyl-3 -methyl-4-(dimethylamino)pyridinium.
10. A composition comprising a pyridinium cation, said cation comprising a structure having the following formula:
wherein: R 1 is hexyl, R 3 and R 5 are each C n H 2n+1 , and n is 1 to 16, R 2 and R 6 are each C p H 2p+1 , and wherein p is 0 to 16, and R 4 is cyclohexyl.
11. The composition of claim 10 , wherein R 3 , and R 5 are each methyl.
12. The composition of claim 11 , wherein said cation comprises 1-hexyl-3,5-dimethylpyridinium.
13. The composition of claim 11 , wherein R 2 is ethyl.
14. The composition of claim 13 wherein said cation comprises 1-hexyl-2-ethyl-3,5-dimethylpyridinium.
15. The composition of claim 10 , wherein R 3 , and R 5 are each ethyl.
16. The composition of claim 15 , wherein R 2 is propyl.
17. The composition of claim 16 , wherein said cation comprises 1-hexyl-2-propyl-3,5-diethylpyridinium.
18. A composition comprising a pyridinium cation, said cation comprising a structure having the following formula:
wherein: R 1 is hexyl or octyl, R 3 is C n H 2n+1 , and n is 1 to 16, and R 2 , R 5 , and R 6 are each C p H 2p+1 , and wherein p is 0 to 16, and R 4 is cyclohexyl.
19. The composition of claim 18 , wherein R 3 is methyl.
20. The composition of claim 19 , wherein said cation comprises 1-octyl-3-methylpyridinium.
21. The composition of claim 19 , wherein said cation comprises 1-hexyl-3-methylpyridinium.
22. A composition comprising an ionic compound, wherein said ionic compound comprises a structure having the following formula:
wherein: R 1 is butyl or hexyl, R 3 is C n H 2n+1 , and n is 1 to 16, R 2 , R 5 , R 6 , R 7 , and R 8 are each C p H 2p+1 , and wherein p is 0 to 16, and X is an anion.
23. The composition of claim 22 wherein the anion is other than chloride.
24. The composition of claim 23 , wherein X is one or more members of the group consisting of: (CF 3 SO 2 ) 2 N, (CN) 2 N, bis(trifluoromethylsulfonyl) imide, ethylsulfate, ester ethyl sulfate, bromide, chloride, Tf 2 N, BF 4 or bromide.
25. The composition of claim 22 wherein the ionic compound is a liquid.
26. The composition of claim 22 , wherein R 1 is butyl.
27. The composition of claim 26 , wherein R 3 is methyl.
28. The composition of claim 27 , wherein R 7 , and R 8 are each methyl.
29. The composition of claim 28 , wherein said ionic compound comprises a 1-butyl-3-methyl-4-(dimethylamino)pyridinium cation.
30. The composition of claim 29 , wherein said composition comprises 1-butyl-3-methyl-4-dimethylaminopyridinium (CN) 2 N.
31. The composition of claim 29 , wherein said composition comprises 1-butyl-3-methyl-4-dimethylaminopyridinium CF 3 CO 2 .
32. The composition of claim 29 , wherein said composition comprises 1-butyl-3-methyl-dimethylaminopyridinium BF 4 .
33. The composition of claim 29 , wherein said composition comprises 1-butyl-3-methyl-dimethylaminopyridinium NO 3 .
34. The composition of claim 29 , wherein said composition comprises 1-butyl-3-methyl-4-dimethylaminopyridinium bromide.
35. The composition of claim 22 , wherein R 1 is hexyl.
36. The composition of claim 35 , wherein R 3 is methyl.
37. The composition of claim 36 , wherein R 7 , and R 8 are each methyl.
38. The composition of claim 37 , wherein said ionic compound comprises a 1-hexyl-3-methyl-4-(dimethylamino)pyridinium cation.
39. The composition of claim 38 , wherein said composition comprises 1-hexyl-3-methyl-dimethylaminopyridinium bromide.
40. The composition of claim 38 , wherein said composition comprises 1-hexyl-3-methyl-dimethylaminopyridinium (CF 3 SO 2 ) 2 N.
41. A composition comprising an ionic compound, wherein said ionic compound comprises a structure having the following formula:
wherein: R 1 is hexyl, R 3 and R 5 are each C n H 2n+1 , and n is 1 to 16, and R 2 and R 6 are each C p H 2p+1 , and wherein p is 0 to 16, and R 4 is cyclohexyl.
42. The composition of claim 41 wherein the anion is other than chloride.
43. The composition of claim 42 , wherein X is one or more members of the group consisting of: (CF 3 SO 2 ) 2 N, (CN) 2 N, bis(trifluoromethylsulfonyl) imide, ethylsulfate, ester ethyl sulfate, bromide, chloride, Tf 2 N, BF 4 or bromide.
44. The composition of claim 41 wherein the ionic compound is a liquid.
45. The composition of claim 41 , wherein R 3 , and R 5 are each methyl.
46. The composition of claim 45 , wherein said ionic compound comprises a 1-hexyl-3,5-dimethylpyridinium cation.
47. The composition of claim 45 , wherein R 2 is ethyl.
48. The composition of claim 47 , wherein said ionic compound comprises a 1-hexyl-2-ethyl-3,5-dimethylpyridinium cation.
49. The composition of claim 47 , wherein R 3 is methyl.
50. A composition comprising an ionic compound, wherein said ionic compound comprises a structure having the following formula:
wherein: R 1 is hexyl or octyl, R 3 is C n H 2n+1 , and n is 1 to 16, and R 2 , R 5 , and R 6 are each C p H 2p+1 , and wherein p is 0 to 16, and R 4 is cyclohexyl.
51. The composition of claim 50 wherein the anion is other than chloride.
52. The composition of claim 51 , wherein X is one or more members of the group consisting of: (CF 3 SO 2 ) 2 N, (CN) 2 N, bis(trifluoromethylsulfonyl) imide, ethylsulfate, ester ethyl sulfate, bromide, chloride, Tf 2 N, BF 4 or bromide.
53. The composition of claim 50 , wherein the ionic compound is a liquid.
54. The composition of claim 52 , wherein R 2 is propyl.
55. The composition of claim 54 , wherein said cation comprises a 1-hexyl-2-propyl-3,5-diethylpyridinium compound.
56. The composition of claim 55 , wherein R 3 , and R 5 are each ethyl.
57. The composition of claim 50 , wherein said ionic compound comprises a 1-octyl-3-methylpyridinium compound.
58. The composition of claim 50 , wherein said ionic compound comprises a 1-hexyl-3-methylpyridinium compound.
59. A composition comprising an ionic compound including a 1-ethyl nicotinic acid ethyl ester cation.
60. The composition of claim 59 , wherein the ionic compound includes an anion other than chloride.
61. The composition of claim 60 , wherein the anion is one or more members of the group consisting of: (CF 3 SO 2 ) 2 N, (CN) 2 N, bis(trifluoromethylsulfonyl) imide, ethylsulfate, ester ethyl sulfate, bromide, chloride, Tf 2 N, BF 4 or bromide.
62. The composition of claim 59 , wherein the ionic compound is a liquid.