# US 2019/0245243 A1 · Nonaqueous electrolyte compositions comprising silyl oxalates

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- Number: US 2019/0245243 A1
- Document ID: US20190245243A1
- Status: Published application
- Kind: A1
- Application number: 16/326,466
- Filed: 2017-07-27
- Published: 2019-08-08
- Earliest claimed: 2016-08-19
- Assignees: Solvay SA
- Applicants: Solvay SA
- Inventors: Kenneth Gene MOLOY; Stephen E. BURKHARDT; Kostantinos KOURTAKIS; Brian LEVY-POLIS
- Web page: https://patentgrep.com/patent/US20190245243A1

## CPC

- H01M 10/0567: characterised by the additives
- C07F 7/1896: {Compounds having one or more Si-O-acyl linkages}
- H01M 10/0568: characterised by the solutes
- H01M 10/0569: characterised by the solvents
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 2300/0034: Fluorinated solvents
- Y02E 60/10: Energy storage using batteries
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Disclosed herein are electrolyte compositions comprising a fluorinated solvent, at least one silyl oxalate represented by the formulas RR′Si(C2O4), wherein R and R′ are each the same or different from each other and independently selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or C6-C10 aryl radical, optionally comprising at least one substituent selected from halogen, hydroxyl, alkoxy, carbonyl, and carboxyl groups; and LiPF6. Also disclosed herein are electrolyte compositions comprising a fluorinated solvent and a lithium oxalato phosphate salt represented by the formula LiPF(6-2q)(C2O4)q, wherein q is 1, 2 or 3; wherein the oxalato phosphate salt comprises at least a portion that is derived from at least one silyl oxalate as defined herein. The electrolyte compositions are useful in electrochemical cells, such as lithium ion batteries.

## Claims

### Claim 1

An electrolyte composition comprising:
a) a fluorinated solvent;
b) at least one silyl oxalate represented by Formula I:
RR′Si(C2O4) (I),
wherein R and R′ are each the same or different from each other and independently selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or C6-C10 aryl radical, optionally comprising at least one substituent selected from halogen, hydroxyl, alkoxy, carbonyl, and carboxyl groups; and
c) LiPF6.

### Claim 2

(canceled)

### Claim 3 (depends on 1)

The electrolyte composition of claim 1, wherein the silyl oxalate comprises dimethylsilyl oxalate, vinylphenylsilyl oxalate, methylvinylsilyl oxalate, or diphenylsilyl oxalate.

### Claim 4 (depends on 1)

The electrolyte composition of claim 1, wherein the fluorinated solvent comprises:
a) a fluorinated acyclic carboxylic acid ester represented by the formula:
R1—COO—R2,
b) a fluorinated acyclic carbonate represented by the formula:
R3—OCOO—R4,
c) a fluorinated acyclic ether represented by the formula:
R5—O—R6,
or mixtures thereof;
wherein
i) R1 is H, an alkyl group, or a fluoroalkyl group;
ii) R3 and R5 is each independently a fluoroalkyl group and can be either the same as or different from each other;
iii) R2, R4, and R6 is each independently an alkyl group or a fluoroalkyl group and can be either the same as or different from each other;
iv) either or both of R1 and R2 comprises fluorine; and
v) R1 and R2, R3 and R4, and R5 and R6, each taken as a pair, comprise at least two carbon atoms but not more than seven carbon atoms.

### Claim 5

(canceled)

### Claim 6 (depends on 4)

The electrolyte composition of claim 4, wherein the fluorinated acyclic carboxylic acid ester comprises CH3—COO—CH2CF2H, CH3CH2—COO—CH2CF2H, F2CHCH2—COO—CH3, F2CHCH2—COO—CH2CH3, CH3—COO—CH2CH2CF2H, CH3CH2—COO—CH2CH2CF2H, F2CHCH2CH2—COO—CH2CH3, CH3—COO—CH2CF3, CH3CH2—COO—CH2CF2H, CH3—COO—CH2CF3, H.COO—CH2CF2H, H—COO—CH2CF3, or mixtures thereof.

### Claim 7 (depends on 6)

The electrolyte composition of claim 6, wherein the fluorinated acyclic carboxylic acid ester comprises CH3—COO—CH2CF2H.

### Claim 8 (depends on 1)

The electrolyte composition of claim 1, further comprising an organic carbonate.

### Claim 9 (depends on 8)

The electrolyte composition of claim 8, wherein the organic carbonate comprises 4-fluoroethylene carbonate, ethylene carbonate, propylene carbonate, ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate, vinylene carbonate, or mixtures thereof.

### Claim 10 (depends on 9)

The electrolyte composition of claim 9, wherein the organic carbonate comprises 4-fluoroethylene carbonate.

### Claim 11

An electrolyte composition comprising:
a) a fluorinated solvent; and
b) a lithium oxalato phosphate salt represented by Formula III:
LiPF(6-2q)(C2O4)q (III)
wherein q is 1, 2 or 3;
wherein the oxalato phosphate salt comprises at least a portion that is derived from at least one silyl oxalate represented by Formula I:
RR′Si(C2O4) (I),
wherein R and R′ are each the same or different from each other and independently selected from C1-C5 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or C6-C10 aryl radical, optionally comprising at least one substituent selected from halogen, hydroxyl, alkoxy, carbonyl, and carboxyl groups.

### Claim 12

(canceled)

### Claim 13 (depends on 11)

The electrolyte composition of claim 11, wherein the silyl oxalate comprises dimethylsilyl oxalate, vinylphenylsilyl oxalate, methylvinylsilyl oxalate, or diphenylsilyl oxalate.

### Claim 14

(canceled)

### Claim 15

(canceled)

### Claim 16 (depends on 11)

The electrolyte composition of claim 11, wherein the fluorinated solvent comprises a fluorinated acyclic carboxylic acid ester comprising CH3—COO—CH2CF2H, CH3CH2—COO—CH2CF2H, F2CHCH2—COO—CH3, F2CHCH2—COO—CH2CH3, CH3—COO—CH2CH2CF2H, CH3CH2—COO—CH2CH2CF2H, F2CHCH2CH2—COO—CH2CH3, CH3—COO—CH2CF3, CH3CH2—COO—CH2CF2H, CH3—COO—CH2CF3, H.COO—CH2CF2H, H—COO—CH2CF3, or mixtures thereof.

### Claim 17 (depends on 16)

The electrolyte composition of claim 16, wherein the fluorinated acyclic carboxylic acid ester comprises CH3—COO—CH2CF2H.

### Claim 18 (depends on 11)

The electrolyte composition of claim 11, wherein the oxalato phosphate salt comprises lithium tris(oxalato)phosphate.

### Claim 19

A method comprising:
a step of combining:
a) a fluorinated solvent;
b) at least one silyl oxalate represented by Formula I:
RR′Si(C2O4) (I),
wherein R and R′ are each the same or different from each other and independently selected from C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or C6-C10 aryl radical, optionally comprising at least one substituent selected from halogen, hydroxyl, alkoxy, carbonyl, and carboxyl groups; and
c) LiPF6;
to form an electrolyte composition.

### Claim 20 (depends on 11)

An electrochemical cell comprising:
(a) a housing;
(b) an anode and a cathode disposed in the housing and in ionically conductive contact with one another;
(c) the electrolyte composition of claim 11 disposed in the housing and providing an ionically conductive pathway between the anode and the cathode; and
(d) a porous separator between the anode and the cathode.

### Claim 21 (depends on 20)

The electrochemical cell of claim 20, wherein the electrochemical cell is a lithium ion battery.

### Claim at position 22

-25. (canceled)

### Claim 26 (depends on 20)

An electronic device, transportation device, or telecommunications device, comprising an electrochemical cell according to claim 20.

### Claim 27

A dialkylsilyl oxalate of the formula:
RR′Si(C2O4)
wherein R and R are each independently methyl, ethyl, n-propyl, iso-propyl, vinyl, or phenyl.

### Claim 28 (depends on 27)

The dialkylsilyl oxalate of claim 27, wherein R and R′ are each methyl.

### Claim 29 (depends on 27)

The dialkylsilyl oxalate of claim 27, wherein R is methyl and R′ is ethyl, vinyl, or phenyl.