N-SUBSTITUTED GLYCINIUM BIS(FLUOROSULFONYL)IMIDE IONIC LIQUID
The present invention provides N-substituted glycinium bis(fluorosulfonyl)imide compounds and methods for producing and using the same. In particular, the N-substituted glycinium bis(fluorosulfonyl)imide compound is of the formula: wherein each of R 1 , R 2 and R 3 is independently selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, (cycloalkyl)alkyl, heteroaryl, (heteroaryl)alkyl, heterocyclyl, and (heterocyclyl)alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached to form a nitrogen-heterocyclyl, or a nitrogen-heteroaryl.
1 . An ionic liquid compound of the formula:
wherein
each of R 1 , R 2 and R 3 is independently selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, (cycloalkyl)alkyl, heteroaryl, (heteroaryl)alkyl, heterocyclyl, and (heterocyclyl)alkyl; or
R 1 and R 2 together with the nitrogen atom to which they are attached to form a nitrogen-heterocyclyl, or a nitrogen-heteroaryl.
2 . The ionic liquid compound according to claim 1 , wherein each of R 1 , R 2 and R 3 is independently alkyl.
3 . The ionic liquid compound according to claim 1 , wherein R 1 and R 2 together with the nitrogen atom to which they are attached to form a nitrogen-heterocyclyl or a nitrogen-heteroaryl.
4 . The ionic liquid compound according to claim 3 , wherein R 1 and R 2 together with the nitrogen atom to which they are attached to form a nitrogen-heterocyclyl or a nitrogen-heteroaryl selected from the group consisting of 3,4-dihydro-2H-pyrrolidinium, 2,3,4,5-tetrahydropyridinium, imidazolium, pyridinium, pyrrolidinium, piperidinium, and morpholinium.
5 . A method for producing an ionic liquid compound of the formula:
said method comprising:
(a) contacting a zwitter-ion of the formula:
with bis(fluorosulfonyl)imide under conditions sufficient to produce said ionic liquid compound of Formula I; or
(b) contacting a salt of the formula:
with a metal salt of bis(fluorosulfonyl)imide under conditions sufficient to produce said ionic liquid compound of Formula I;
wherein
each of R 1 , R 2 and R 3 is independently selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, (cycloalkyl)alkyl, heteroaryl, (heteroaryl)alkyl, heterocyclyl, and (heterocyclyl)alkyl; or
R 1 and R 2 together with the nitrogen atom to which they are attached to form a nitrogen-heterocyclyl, or a nitrogen-heteroaryl.
6 . The method of claim 5 , wherein said method comprises anhydrous conditions.
7 . The method of claim 5 , wherein each of R 1 , R 2 and R 3 is independently C 1 -C 10 alkyl.
8 . The method of claim 7 , wherein R 1 , R 2 and R 3 are methyl.
9 . The method of claim 5 , wherein said method comprises adding bis(fluorosulfonyl)imide to said zwitter-ion of Formula II while maintaining the reaction temperature below 65° C.
10 . The method of claim 9 , wherein bis(fluorosulfonyl)imide is added to said zwitter-ion of Formula II at a temperature of at least 50° C.
11 . The method of claim 9 further comprising the step of increasing the reaction temperature to above 65° C. after complete addition of bis(fluorosulfonyl)imide.
12 . The method of claim 9 , wherein said method is conducted in the absence of any solvent.
13 . The method of claim 9 , wherein said zwitter-ion of Formula II is in an aqueous solution.
14 . The method of claim 13 , wherein bis(fluorosulfonyl)imide is added to said aqueous solution of zwitter-ion of Formula II at a temperature of 40° C. or less.
15 . The method of claim 13 , wherein the reaction temperature is maintained at 40° C. or less.
16 . The method of claim 15 further comprising the step of removing water while maintaining the temperature at 50° C. or below to obtain said ionic liquid compound of Formula I with a yield of at least 95% having at least 95% purity.
17 . The method of claim 5 , wherein said salt of Formula III comprises a hydro-halogen salt of Formula III.
18 . The method of claim 5 , wherein said metal salt of bis(fluorosulfonyl)imide is of the formula: M[N(SO 2 F) 2 ] y , wherein
M is an alkali metal, an alkaline earth metal, or a transition metal; and
y is an oxidation state of M.
19 . The method of claim 18 , wherein said the reaction between said salt of Formula III and said salt of bis(fluorosulfonyl)imide is conducted in the presence of a solvent.
20 . The method of claim 19 further comprising the step of removing M(X) y from the reaction mixture, wherein y is as defined in claim 18 .
21 . A method for dissolving a metal oxide, a metal hydroxide, a metal salt or a combination thereof from a sample, said method comprising contacting a sample that comprises a metal hydroxide, a metal salt or a combination thereof with a compound of claim 1 under conditions sufficient to dissolve a metal oxide, a metal hydroxide, a metal salt or a combination thereof from said sample to produce a solution of dissolved metal comprising said compound of claim 1 and a processed sample.
22 . The method of claim 21 , wherein said processed sample comprises decontaminated soil.
23 . The method of claim 21 , wherein said processed sample comprises a polished metal surface.
24 . The method of claim 21 , wherein said processed sample comprises a process ore.
25 . The method of claim 24 further comprising the step of recovering a precious metal from said solution of dissolved metal.