PHOSPHORIC ACID DIESTER SALT, PRODUCTION METHOD THEREFOR, NON-AQUEOUS ELECTROLYTIC SOLUTION FOR POWER STORAGE ELEMENT, AND POWER STORAGE ELEMENT

• US 20180237461A1
• Filed: 08/09/2016
• Published: 08/23/2018
• Est. Priority Date: 08/10/2015
• Status: Active Grant

• Current Assignee: Stella Chemifa Corporation
• Original Assignee: Stella Chemifa Corporation
• Inventors: SAKAGUCHI, Toshitaka, KON, Sojiro, KATSURA, Yoshifumi, YAMAMOTO, Masashi, NISHIDA, Tetsuo
• Granted Patent: US 10,793,585 B2
• Time in Patent Office: Days
• CPC Class Codes: C07F 9/09 Esters of phosphoric acids
• CPC Class Codes: C07F 9/091 with hydroxyalkyl compounds with further substituents on alkyl
• CPC Class Codes: C07F 9/092 substituted by B, Si or a metal
• CPC Class Codes: C07F 9/11 with hydroxyalkyl compounds without further substituents on alkyl
• CPC Class Codes: C07F 9/12 with hydroxyaryl compounds
• CPC Class Codes: C07H 15/252 Naphthacene radicals, e.g. daunomycins, adriamycins
• CPC Class Codes: H01G 11/64 characterised by additives
• CPC Class Codes: H01M 10/052 Li-accumulators
• CPC Class Codes: H01M 10/0525 Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
• CPC Class Codes: H01M 10/054 Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
• CPC Class Codes: H01M 10/0567 characterised by the additives
• CPC Class Codes: H01M 10/0568 characterised by the solutes
• CPC Class Codes: H01M 10/0569 characterised by the solvents
• CPC Class Codes: H01M 4/587 for inserting or intercalating light metals
• CPC Class Codes: Y02E 60/10 Energy storage using batteries
• CPC Class Codes: Y02E 60/13 Energy storage using capacitors

Abstract

Disclosed is a phosphoric acid diester salt which can suppress deterioration of charge-discharge characteristics of a power storage element, and can suppress the rise in internal resistance after storage at high temperature, a production method therefor, a non-aqueous electrolytic solution for a power storage element, and a power storage element. Disclosed is a phosphoric acid diester salt represented by the following chemical formula (1):

wherein Mⁿ⁺ represents a hydrogen ion, an alkali metal ion, an alkali earth metal ion, an aluminum ion, a transition metal ion, or an onium ion; R¹ and R² are different from each other and represent a hydrocarbon group having 1 to 10 carbon atoms, or a hydrocarbon group having 1 to 10 carbon atoms and having at least one of a halogen atom, a heteroatom, and an unsaturated bond; and n represents a valence.

Claims

1. A phosphoric acid diester salt represented by the following chemical formula (1):

2. The phosphoric acid diester salt according to claim 1, wherein either one of R¹ and R² is an alkyl group having 1 to 10 carbon atoms and having a halogen atom, and other one is an alkyl group having 1 to 10 carbon atoms and having no halogen atom.

3. The phosphoric acid diester salt according to claim 1, wherein either one of R¹ and R² is a 2,2,2-trifluoroethyl group, and other one is an ethyl group.

4. The phosphoric acid diester salt according to claim 1, wherein M is at least one selected from the group consisting of lithium, sodium, magnesium, and calcium.

5. The phosphoric acid diester salt according to claim 1, wherein M is triethylmethylammonium, tetraethylammonium, 1-ethyl-3-methylimidazolium, or 1-ethyl-2methylpyrrolidinium.

6. A method for producing a phosphoric acid diester salt, which comprises:

producing a phosphoric acid diester by hydrolyzing a phosphoric acid triester represented by the chemical formula (2) mentioned below; and

producing a phosphoric acid diester salt represented by the chemical formula (1) mentioned below by reacting the phosphoric acid diester with Mⁿ⁺(OH)n (in which Mⁿ⁺ represents a hydrogen ion, an alkali metal ion, an alkali earth metal ion, an aluminum ion, a transition metal ion, or an onium ion, and n represents a valence);

wherein a —

OR¹ group and a —

OR² group in the phosphoric acid triester are leaving groups, and leaving ability of the —

OR¹ group is larger than leaving ability of the —

OR² group;

7. The method for producing a phosphoric acid diester salt according to claim 6, wherein either one of R¹ and R² is an alkyl group having 1 to 10 carbon atoms and having a halogen atom, and other one is an alkyl group having 1 to 10 carbon atoms and having no halogen atom.

8. The method for producing a phosphoric acid diester salt according to claim 6, wherein either one of R¹ and R² is a 2,2,2-trifluoroethyl group, and other one is an ethyl group.

9. A non-aqueous electrolytic solution for a power storage element, comprising, as an additive, a phosphoric acid diester salt represented by the following chemical formula (1):

10. The non-aqueous electrolytic solution for a power storage element according to claim 9, wherein either one of R¹ and R² is an alkyl group having 1 to 10 carbon atoms and having a halogen atom, and other one is an alkyl group having 1 to 10 carbon atoms and having no halogen atom.

11. The non-aqueous electrolytic solution for a power storage element according to claim 9, wherein either one of R¹ and R² is a 2,2,2-trifluoroethyl group, and other one is an ethyl group.

12. The non-aqueous electrolytic solution for a power storage element according to claim 9, wherein M is at least one selected from the group consisting of lithium, sodium, magnesium, and calcium.

13. The non-aqueous electrolytic solution for a power storage element according to claim 9, wherein M is triethylmethylammonium, tetraethylammonium, 1-ethyl-3-methylimidazolium, or 1-ethyl-2methylpyrrolidinium

14. A non-aqueous electrolytic solution for a power storage element, comprising, as an electrolyte, a phosphoric acid diester salt represented by the following chemical formula (1):

15. The non-aqueous electrolytic solution for a power storage element according to claim 14, wherein either one of R¹ and R² is an alkyl group having 1 to 10 carbon atoms and having a halogen atom, and other one is an alkyl group having 1 to 10 carbon atoms and having no halogen atom.

16. The non-aqueous electrolytic solution for a power storage element according to claim 14, wherein either one of R¹ and R² is a 2,2,2-trifluoroethyl group, and the other one is an ethyl group.

17. The non-aqueous electrolytic solution for a power storage element according to claim 14, wherein M is at least one selected from the group consisting of lithium, sodium, magnesium, and calcium.

18. The non-aqueous electrolytic solution for a power storage element according to claim 14, wherein M is triethylmethylammonium, tetraethylammonium, 1-ethyl-3-methylimidazolium, or 1-ethyl-2methylpyrrolidinium.

19. A power storage element using a non-aqueous electrolytic solution comprising, as an additive, a phosphoric acid diester salt represented by the following chemical formula (1):

20. A power storage element using a non-aqueous electrolytic solution comprising, as an electrolyte, a phosphoric acid diester salt represented by the following chemical formula (1):