# US 8,772,522 B2 · Salts of 5-sulfoisophthalic acid and method of making same

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- Number: US 8,772,522 B2
- Document ID: US8772522B2
- Status: Granted
- Kind: B2
- Application number: 13/586,024
- Filed: 2012-08-15
- Published: 2013-08-15
- Granted: 2014-07-08
- Earliest claimed: 2011-08-16
- Assignees: FutureFuel Chemical Company
- Applicants: Timothy A. Oster
- Inventors: Timothy A. Oster
- Web page: https://patentgrep.com/patent/US8772522B2

## CPC

- C07C 303/32: of salts of sulfonic acids
- C07C 309/58: Carboxylic acid groups or esters thereof
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

This invention relates to methods for the production of various metal salts of 5-sulfoisophthalic acid including those where the metal cation is selected from the group consisting of silver (I), sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, manganese (II), iron (II), cobalt (II), nickel (II), copper (I), copper (II), zinc, yttrium, and cadmium. The methods utilize a solvent system that comprises acetic acid or water or a mixture of both. The invention also encompasses the various metal salts of 5-sulfoisophthalic acid.

## Claims

### Claim 1

A process for the preparation of metal salts of 5-sulfoisophthalic acid, the process comprising the steps of:
forming a solvent system comprising 5-sulfoisophthalic acid, a metal cation producing compound, and acetic acid and water wherein the acetic acid to water ratio is between and includes 0:1 and 1:0 and wherein said metal cation is selected from the group consisting of silver (I), sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, manganese (II), iron (II), cobalt (II), nickel (II), copper (I), copper (II), zinc, yttrium, and cadmium; and
maintaining said solvent system under conditions sufficient to form a metal salt of 5-sulfoisophthalic acid.

### Claim 2 (depends on 1)

A process according to claim 1 wherein said solvent system comprises acetic acid and water.

### Claim 3 (depends on 1)

A process according to claim 1 wherein said metal cation producing compound comprises a metal salt.

### Claim 4 (depends on 1)

A process according to claim 1 further comprising the prior step of isolating 5-sulfoisophthalic acid from a sulfonation solution and washing said 5-sulfoisophthalic acid prior to forming said solvent system.

### Claim 5 (depends on 1)

A process according to claim 1 further comprising the steps of recovery of said metal salt of 5-sulfoisophthalic acid and recycle of said solvent system.

### Claim 6 (depends on 1)

A process according to claim 1 wherein said metal cation is selected from the group consisting of sodium, potassium, and rubidium.

### Claim 7 (depends on 1)

A process according to claim 1 wherein said metal cation is cesium.

### Claim 8 (depends on 1)

A process according to claim 1 wherein said metal cation is selected from the group consisting of magnesium, calcium, and barium.

### Claim 9 (depends on 1)

A process according to claim 1 wherein said metal cation is selected from the group consisting of manganese (II), cobalt (II), nickel (II); copper (II), and zinc.

### Claim 10 (depends on 1)

A process according to claim 1 wherein said metal cation is selected from the group consisting of silver (I), strontium, iron (II), copper (I), yttrium and cadmium.

### Claim 11

A process for the preparation of a metal salt of 5-sulfoisophthalic acid, the process comprising the step of contacting previously isolated 5-sulfoisophthalic acid with a metal cation producing compound under conditions sufficient to form a metal salt of 5-sulfoisophthalic acid wherein the metal cation is selected from the group consisting of silver (I), sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, manganese (II), iron (II), cobalt (II), nickel (II), copper (I), copper (II), zinc, yttrium, and cadmium.

### Claim 12 (depends on 11)

A process according to claim 11 wherein the step of contacting 5-sulfoisophthalic acid with a metal cation producing compound comprises creating a solvent system comprising said 5-sulfoisophthalic acid; said metal cation producing compound; and acetic acid and water wherein the acetic acid to water ratio is between and includes 0:1 and 1:0 and wherein said metal cation producing compound is a metal salt.

### Claim 13

A composition of matter comprising the reaction product of 5-sulfoisophthalic acid and a metal cation producing compound wherein the metal cation is selected from the group consisting of silver (I), strontium, iron (II), copper (I), yttrium, and cadmium.

### Claim 14

A metal salt of 5-sulfoisophthalic acid wherein the metal is selected from the group consisting of silver (I), strontium, iron (II), copper (I), yttrium, and cadmium.

### Claim 15 (depends on 14)

A metal salt according to claim 14 wherein the metal is silver (I).

### Claim 16 (depends on 14)

A metal salt according to claim 14 wherein the metal is strontium.

### Claim 17 (depends on 14)

A metal salt according to claim 14 wherein the metal is iron (II).

### Claim 18 (depends on 14)

A metal salt according to claim 14 wherein the metal is copper (I).

### Claim 19 (depends on 14)

A metal salt according to claim 14 wherein the metal is yttrium.

### Claim 20 (depends on 14)

A metal salt according to claim 14 wherein the metal is cadmium.

### Claim 21 (depends on 14)

A composition of matter comprising a metal salt of claim 14.