Ionic liquid, nonaqueous electrolyte, and power storage device

Patent metadata

Field	Value
Publication number	US-10991984-B2
Application number	US-201615008487-A
Country	US
Kind code	B2
Filing date	Jan 28, 2016
Priority date	Dec 23, 2011
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

A nonaqueous electrolyte of the present invention includes an ionic liquid including a first alicyclic quaternary ammonium cation having one or more substituents, a second alicyclic quaternary ammonium cation having an alicyclic skeleton that is the same as an alicyclic skeleton of the first alicyclic quaternary ammonium cation, and a counter anion to the first alicyclic quaternary ammonium cation and the second alicyclic quaternary ammonium cation and an alkali metal salt. In the second alicyclic quaternary ammonium cation, one of substituents bonded to a nitrogen atom in the alicyclic skeleton is a substituent including a halogen element. In the ionic liquid, the amount of a salt including the second alicyclic quaternary ammonium cation is less than or equal to 1 wt % per unit weight of the ionic liquid, or is less than or equal to 0.8 wt % per unit weight of the nonaqueous electrolyte.

First claim

What is claimed is:

1. A method of synthesizing an ionic liquid, comprising the steps of:
reacting a tertiary amine compound and an alkyl halide compound in a first solution to obtain a first product; and
exchanging an ion between the first product and a metal salt to obtain the ionic liquid,
wherein the first solution comprises a first organic solvent which does not include a halogen element in the structural formula,
wherein the tertiary amine compound comprises a six membered ring,
wherein the first product comprises a cation represented by Formula (G1):

wherein R 1 to R 5 each represent any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, a methoxymethyl group and a methoxyethyl group,
wherein a concentration of a compound represented by Formula (G2) in the ionic liquid is lower than 0.67 wt %:

and
wherein reacting the tertiary amine compound and the alkyl halide compound is performed under reflux.

2. The method according to claim 1 , further comprising the step of:
reacting an amine compound and a carbonyl compound in a second solution to obtain the tertiary amine compound.

3. The method according to claim 2 , wherein the second solution comprises a hydride.

4. The method according to claim 2 , wherein the second solution comprises formic acid.

5. The method according to claim 1 , wherein the alkyl halide compound is a propane halide.

6. The method according to claim 1 , wherein the alkyl halide compound is bromopropane.

7. The method according to claim 1 , wherein the metal salt comprises an anion selected from any of a monovalent imide-based anion, a monovalent methide-based anion, a perfluoroalkyl sulfonic acid anion, tetrafluoroborate and hexafluorophosphate.

8. The method according to claim 7 , wherein the metal salt comprises potassium.

9. The method according to claim 8 , wherein the ionic liquid comprises an alicyclic quaternary ammonium cation.

10. The method according to claim 1 , wherein the first organic solvent is tetrahydrofuran.

11. The method according to claim 1 , wherein the ionic liquid is obtained by distilling off the first organic solvent.

12. A method of synthesizing an ionic liquid, comprising the step of:
reacting a tertiary amine compound and an alkyl halide compound in a first solution to obtain a first product; and
wherein the first solution comprises a first organic solvent which does not include a halogen element in the structural formula,
wherein the first product comprises a cation represented by Formula (G1):

wherein R 1 to R 5 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, a methoxymethyl group and a methoxyethyl group,
wherein a concentration of a compound represented by Formula (G2) in the ionic liquid is lower than 0.67 wt %:

and
wherein reacting the tertiary amine compound and the alkyl halide compound is performed under reflux.

13. The method according to claim 12 ,
wherein the tertiary amine compound is represented by Formula (13-2):

14. The method according to claim 13 ,
wherein the tertiary amine compound is represented by Formula (β-9):

15. The method according to claim 12 , further comprising the step of:
exchanging an ion between the first product and a metal salt to obtain the ionic liquid.

16. The method according to claim 15 ,
wherein the ionic liquid comprises a cation represented by Formula (G1) and an anion selected from the group consisting of a monovalent imide-based anion, a monovalent methide-based anion, a perfluoroalkyl sulfonic acid anion, tetrafluoroborate, and hexafluorophosphate.

17. The method according to claim 12 , wherein the first organic solvent is one of tetrahydrofuran and toluene.

18. A method of synthesizing an ionic liquid, comprising the step of:
reacting a tertiary amine compound and an alkyl halide compound in a first solution to obtain a first product; and
wherein the first solution comprises a first organic solvent which does not include a halogen element in the structural formula,
wherein the first product comprises a cation represented by Formula (G7):

wherein R 1 to R 4 each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, a methoxymethyl group and a methoxyethyl group,
wherein a concentration of a compound represented by Formula (G8) in the ionic liquid is lower than 0.67 wt %:

and
wherein reacting the tertiary amine compound and the alkyl halide compound is performed under reflux.

19. The method according to claim 18 ,
wherein the tertiary amine compound is represented by Formula (β-6):

20. The method according to claim 18 , further comprising the step of:
exchanging an ion between the first product and a metal salt to obtain the ionic liquid.

21. The method according to claim 20 ,
wherein the ionic liquid comprises a cation represented by Formula (G7) and an anion selected from the group consisting of a monovalent imide-based anion, a monovalent methide-based anion, a perfluoroalkyl sulfonic acid anion, tetrafluoroborate, and hexafluorophosphate.

22. The method according to claim 18 , wherein the first organic solvent is tetrahydrofuran.

Assignees

• Semiconductor Energy Lab

Inventors

• Itakura Toru
• Ito Kyosuke
• Yokoi Rie
• Ishikawa Jun

Classifications

• Y02E60/10

  Energy storage using batteries · CPC title

• H01M2300/0045

  Room temperature molten salts comprising at least one organic ion · CPC title

• H01M10/0569 Primary

  characterised by the solvents · CPC title

• H01M10/0566 Primary

  Liquid materials · CPC title

• C25D3/665

  from ionic liquids · CPC title