Process for producing ionic liquids

1. A process for producing an ionic liquid of the formula [R 1 Q] + R F − , said process comprising:

reacting a compound of the formula Q with a quaternizing agent of the formula R 1 X in the absence of a volatile solvent under conditions sufficient to produce a quaternary salt of the formula:

[R 1 Q] + X −

reacting said quaternary salt with an acidic form of an ionic liquid counter anion compound of the formula HR F under conditions sufficient to produce said ionic liquid of the formula [R 1 Q] + R F − and a volatile acid of the formula HX,

wherein

Q is an amine, phosphine, or arsine;

R 1 is a quaternizing moiety, such that [R 1 Q] + forms an ionic liquid cation;

X is a leaving group;

R F is an ionic liquid anion moiety.

2. The process of claim 1 , wherein Q is an amine heterocycle moiety having three to six carbon atoms in the ring system.

3. The process of claim 2 , wherein Q is selected from the group consisting of pyrrolidine, imidazole, pyridine, and piperidine, each of which is optionally substituted.

4. The process of claim 1 , wherein Q is a tertiary amine, phosphine or arsine.

5. The process of claim 1 , wherein no solid is produced during said process of producing said ionic liquid.

6. The process of claim 1 , wherein the reaction temperature of said step of reacting said compound of formula Q with said quaternizing agent of the formula R 1 X is in the range from about 50° C. to about 200° C.

7. The process of claim 1 further comprising the step of separating said volatile acid from said ionic liquid.

8. The process of claim 1 , wherein said process for producing said ionic liquid is a continuous process.

9. The process of claim 1 , wherein said ionic liquid anion moiety is of the formula [YSO 2 ] 2 N − , wherein each Y is independently F or a fluorohydrocarbon.

10. The process of claim 9 , wherein each of Y is independently F or perfluorohydrocarbon.

11. The process of claim 10 , wherein each of Y is independently F or trifluoromethyl.

12. The process of claim 9 , wherein said ionic liquid anion is bis(trifluoromethylsulfonyl)imide or bis(fluorosulfonyl)imide.

13. The process of claim 1 , wherein said step of reacting said compound of formula Q with said quaternizing agent of the formula R 1 X is conducted in a nonvolatile solvent.

14. The process of claim 13 , wherein said nonvolatile solvent is an ionic liquid solvent.

15. The process of claim 14 , wherein said ionic liquid solvent is of the formula [R 1 Q] + R F − , wherein R 1 , Q and R F are those defined in claim 1 .

16. The process of claim 14 , wherein at least a portion of said ionic liquid solvent is recycled.

17. The process of claim 14 , wherein at least a portion of said ionic liquid that is produced is used as the ionic liquid solvent in said process.

18. The process of claim 1 , wherein said volatile acid is removed by contacting said ionic liquid with an inert gas stream.

19. The process of claim 1 , wherein said volatile acid is removed by subjecting the ionic liquid to a reduced pressure.

20. A process for producing an ionic liquid of the formula [R 1 Q 1 ] + R 1 F − , said process comprising:

reacting a compound of the formula Q 1 with a quaternizing agent of the formula R 1 X in the absence of a volatile solvent under conditions sufficient to produce a quaternary salt of the formula:

[R 1 Q 1 ] + X −

reacting said quaternary salt with a fluorinated acidic form of an ionic liquid counter anion compound of the formula HR 1 F under conditions sufficient to produce said ionic liquid of the formula [R 1 Q] + R 1 F − and a volatile acid of the formula HX,

wherein

Q 1 is a tertiary amine, phosphine or arsine compound;

R 1 is a quaternizing moiety, such that [R 1 Q 1 ] + forms a quaternary ionic liquid cation;

X is a leaving group;

R 1 F is a fluorinated ionic liquid anion moiety.

21. The process of claim 20 , wherein Q 1 is a tertiary amine compound comprising a nitrogen-containing heterocycle with three to six carbon atoms in the ring system.

22. The process of claim 21 , wherein said nitrogen-atom containing heterocycle compound is selected from the group consisting of pyrrolidine, imidazole, pyridine, and piperidine, each of which is optionally substituted.

23. The process of claim 20 , wherein said ionic liquid anion moiety is of the formula [YSO 2 ] 2 N − , wherein each Y is independently F or a fluorohydrocarbon.

24. The process of claim 23 , wherein each of Y is independently F or perfluorohydrocarbon.

25. The process of claim 24 , wherein each of Y is independently F or trifluoromethyl.

26. The process of claim 23 , wherein said ionic liquid anion is bis(trifluoromethylsulfonyl)imide or bis(fluorosulfonyl)imide.