# US 10,479,804 B2 · Preparation of ammonium or phosphonium borate salts

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- Number: US 10,479,804 B2
- Document ID: US10479804B2
- Status: Granted
- Kind: B2
- Application number: 16/075,547
- Filed: 2017-01-27
- Published: 2019-02-07
- Granted: 2019-11-19
- Earliest claimed: 2016-02-05
- Assignees: Gotion Inc.
- Applicants: Gotion Inc.
- Inventors: Nicole Holub; Juergen Herbel
- Web page: https://patentgrep.com/patent/US10479804B2

## CPC

- C07F 5/022: {without C-boron linkages}
- C07C 211/63: having quaternised nitrogen atoms bound to acyclic carbon atoms
- C07D 295/088: to an acyclic saturated chain
- H01G 11/62: characterised by the solute, e.g. salts, anions or cations therein
- H01M 10/0525: Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
- H01M 10/0568: characterised by the solutes
- Y02E 60/10: Energy storage using batteries
- Y02E 60/13: Energy storage using capacitors
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H01G: CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE (selection of specified materials as dielectric H01B3/00; capacitors having potential barriers H10D1/62, H10K10/10)
- H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A process for preparing an ammonium or phosphonium borate salt KA containing a cation K and an anion A. The process includes providing a melt of a borate salt K1A, and adding a solution of an ammonium or phosphonium salt KA1 in a solvent or solvent mixture (i), wherein K is an organic ammonium or phosphonium cation, and A is a borate anion of formula (Ia) or (Ib).

## Claims

### Claim 1

A process for preparing an ammonium or phosphonium borate salt KA containing a cation K and an anion A, comprising the steps:
(a) providing a melt of a borate salt K1A; and
(b) adding a solution of an ammonium or phosphonium salt KA1 in a solvent or solvent mixture (i),
wherein
K is an organic ammonium or phosphonium cation;
A is a borate anion of formula (Ia) or (Ib)
wherein Hal is halogen, and
is a bidentate radical derived from a 1,2-, 1,3- or 1,4-diol, from a 1,2-, 1,3- or 1,4-dicarboxylic acid or from a 1,2-, 1,3- or 1,4-hydroxycarboxylic acid by abstracting the two H atoms of pairs of adjacent OH groups of the respective diol, hydroxycarboxylic acid or dicarboxylic acid in 1,2-, 1,3- or 1,4-position;
A1 is an organic or inorganic anion; and
K1 is an ammonium cation different from K.

### Claim 2 (depends on 1)

The process according to claim 1 wherein compound KA is precipitated during or after step (b) and is separated from the mixture containing the solvent or solvent mixture (i) and K1A1 in dissolved form.

### Claim 3 (depends on 1)

The process according to claim 1, wherein during step (b) cooling is applied.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the temperature of the solution of the ammonium or phosphonium salt KA1 added in step (b) is lower than the temperature of the melt of the borate salt K1A provided in step (a).

### Claim 5 (depends on 1)

The process according to claim 1, wherein the temperature of the solution of the ammonium or phosphonium salt KA1 added in step (b) is below 25° C.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the mixture obtained in step (b) is cooled.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the solvent or solvent mixture (i) contains at least one protic solvent.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the solvent or solvent mixture (i) contains at least one solvent selected from water and C1 to C6 alcohols.

### Claim 9 (depends on 1)

The process according to claim 1, wherein the molar ratio of K1A to KA1 used in step (b) is above 1:1.

### Claim 10 (depends on 1)

The process according to claim 1, wherein A is a borate anion of formula (Ia) and Hal is F.

### Claim 11 (depends on 1)

The process according to claim 1, wherein
is a bidentate radical derived from oxalic acid, salicylic acid, or phthalic acid.

### Claim 12 (depends on 1)

The process according to claim 1, wherein the ammonium or phosphonium cation K is selected from [XR1R2R3R4]+
wherein X is selected from P and N;
R1, R2, R3, and R4 are selected independently from each other from optionally substituted C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C5-C12 (hetero)aryl, and C6-C30 (hetero)aralkyl, wherein one or more CH2 groups of alkyl, alkenyl, alkynyl and (hetero)aralkyl which are not directly bound to the X-atom may be replaced by O, 1,2-epoxyethylene, cyclopropylene, OSO2, SO2O, OC(O), C(O)O, OC(O)O, or OC(O)C(O)O;
or wherein R1 and R2 are linked and jointly selected from a 4- to 5-membered hydrocarbon group forming together with the central X-atom a five- or six-membered heterocycle which may be substituted by one or more substituents selected from C1-C10 alkyl, and wherein one or more members of the 4- to 5-membered hydrocarbon group may be replaced by one or more O, S or NR′;
R′ is selected from H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C5-C12 (hetero)aryl, and C6-C24 (hetero)aralkyl, which may be substituted by one or more groups selected from F, cyclopropyl, 1,2-epoxyethyl, and sulfonate, and wherein one or more CH2 groups of alkyl, alkenyl, alkynyl and (hetero)aralkyl which are not directly bound to the N-atom may be replaced by O, 1,2-epoxyethylene, cyclopropylene, OSO2 or SO2O.

### Claim 13 (depends on 1)

The process according to claim 1, wherein cation K1 is selected ammonium cations of formula [NR5R6R7R8]+
wherein R5, R6, R7, and R8 are selected independently from each other from H and C1-C20 alkyl or wherein R5 and R6 are linked and jointly selected from a 4- to 5-membered hydrocarbon group forming together with the central N-atom a five- or six-membered heterocycle which may substituted by one or more substituents selected from C1-C10 alkyl, and wherein one or more member of the 4- to 5-membered hydrocarbon group may be replaced by one or more O, S or NR″, and
R″ is selected from H and C1-C10 alkyl.

### Claim 14 (depends on 1)

The process according to claim 1, wherein K1 is isopropyl ammonium.

### Claim 15 (depends on 1)

The process according to claim 1, wherein anion A1 is selected from [R9—SO3]−, Cl−, Br−, and I−,
wherein R9 is selected from C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C5-C12 (hetero)aryl, and C6-C24 (hetero)aralkyl, which may be substituted by one or more groups selected from F, cyclopropyl, 1,2-epoxyethyl, and sulfonate, and wherein one or more CH2 groups of alkyl, alkenyl, alkynyl and (hetero)aralkyl which are not directly bound to the SO3− group may be replaced by O, 1,2-epoxyethylene, cyclopropylene, OSO2 or SO2O.