Method of preparing a high purity imidazolium salt

Patent metadata

Field	Value
Publication number	US-9840473-B1
Application number	US-201715619567-A
Country	US
Kind code	B1
Filing date	Jun 12, 2017
Priority date	Jun 14, 2016
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

The present invention encompasses a novel method for synthesizing highly pure salts of the general formula Q + A − , wherein Q + is:

and wherein A − is

First claim

What is claimed is:

1. A process for preparing a high purity compound of formula (I): Q + A − ,
wherein Q + is:

and wherein A − is:

the process comprising:
a) reacting a compound of formula (II) with a compound of formula (III), wherein (II) and (III) are:

to give a crude product comprising a compound of formula (I);

b) adding water to the crude product of formula (I) from step a), to give a diluted crude product comprising a compound of formula (I);
c) at least partial removal of the water added in step b) from the diluted crude product by distillation of the diluted crude product at a temperature T 1 in the range of 30-180° C. and at a pressure p 1 which is lower than the saturated vapour pressure of compound (III) at the temperature T 1 , giving a high purity compound of formula (I);
wherein:
each of R 1 , R 2 , R 3 are independently a hydrogen or alkyl of 1 to 4 carbon atoms;
each of R 4 , R 5 , R 6 , R 7 are independently alkyl of 1 to 4 carbon atoms.

2. The process of claim 1 , wherein R 1 ═R 2 ═R 3 =hydrogen and wherein each of R 4 , R 5 , R 6 , R 7 are independently methyl or ethyl.

3. The process of claim 2 , wherein R 1 ═R 2 ═R 3 =hydrogen, R 5 =methyl and wherein each of R 4 , R 6 , R 7 are independently methyl or ethyl.

4. The process of claim 1 , wherein step a) is carried out in the absence of a solvent.

5. The process of claim 1 , wherein step a) is carried out in the presence of a solvent.

6. The process of claim 5 , wherein the solvent is at least partially removed between steps a) and b).

7. The process of claim 1 , wherein, in step b), water is added in an amount of at least 1 weight-% based on the amount of compounds (II) and (III) used in step a).

8. The process of claim 1 , wherein “partial removal” in step c) means removal of at least 50% of the water added in step b).

9. The process of claim 1 , wherein pressure p 1 is lower than the saturated vapour pressure of compound (III) at the temperature T 1 and higher than the saturated vapour pressure of (I) at the temperature T 1 .

10. The process of claim 1 , wherein steps b) and c) are carried out at least twice, and wherein step b) is carried out with the high purity compound of formula (I) obtained in directly antecedent step c).

11. The process of claim 2 , wherein said process is carried out in the absence of an organic solvent.

12. The process of claim 11 , wherein in step b) water is added in an amount of at least 1 weight-% based on the amount of compounds (II) and (III) used in step a).

13. The process of claim 12 , wherein “partial removal” in step c) means removal of at least 50% of the water added in step b).

14. The process of claim 13 , wherein pressure p 1 is lower than the saturated vapour pressure of compound (III) at the temperature T 1 and higher than the saturated vapour pressure of (I) at the temperature T 1 .

15. The process of claim 14 , wherein steps b) and c) are carried out at least twice, and wherein step b) is carried out with the high purity compound of formula (I) obtained in directly antecedent step c).

16. The process of claim 3 , wherein said process is carried out in the absence of an organic solvent.

17. The process of claim 16 , wherein in step b) water is added in an amount of at least 1 weight-% based on the amount of compounds (II) and (III) used in step a).

18. The process of claim 17 , wherein “partial removal” in step c) means removal of at least 50% of the water added in step b).

19. The process of claim 18 , wherein pressure p 1 is lower than the saturated vapour pressure of compound (III) at the temperature T 1 and higher than the saturated vapour pressure of (I) at the temperature T 1 .

20. The process of claim 19 , wherein steps b) and c) are carried out at least twice, and wherein step b) is carried out with the high purity compound of formula (I) obtained in directly antecedent step c).

Assignees

• Evonik Degussa Gmbh

Inventors

• Wang Xinming
• Zehnacker Olivier
• Willy Benjamin
• Schneider Rolf

Classifications

• C07D233/56 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms · CPC title

• C07F9/141

  Esters of phosphorous acids · CPC title

• C07F9/11

  with hydroxyalkyl compounds without further substituents on alkyl · CPC title

• C07D233/58 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms · CPC title

• C07D239/20

  having two double bonds between ring members or between ring members and non-ring members · CPC title