# US 11,440,895 B2 · Oxidation process to produce 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC)

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- Number: US 11,440,895 B2
- Document ID: US11440895B2
- Status: Granted
- Kind: B2
- Application number: 16/430,694
- Filed: 2019-06-04
- Published: 2019-12-26
- Granted: 2022-09-13
- Earliest claimed: 2018-06-25
- Assignees: Eastman Chemical Company
- Applicants: Eastman Chemical Company
- Inventors: Mesfin Ejerssa Janka
- Web page: https://patentgrep.com/patent/US11440895B2

## CPC

- C07D 307/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- B01J 10/002: {carried out in foam, aerosol or bubbles}
- B01J 23/8892: {Manganese}
- B01J 27/08: Halides
- B01J 27/128: with iron group metals or platinum group metals
- B01J 31/04: containing carboxylic acids or their salts {(B01J31/0277 - B01J31/0298 take precedence; multi-metal carboxylate complexes like Pd (II) acetate, i.e. Pd3 (OAc) 6 or Cr(II)acetate, i.e. Cr2(OAc)4 B01J31/2226)}
- B01J 35/27: in a liquid or molten state
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

Disclosed herein is a very efficient method to make 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC) from feedstocks comprised of furoates. When a feedstock comprised of methyl 5-methylfuran-2-carboxylate (MMFC) is used a product comprised of (5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC) is obtained in high yield.

## Claims

### Claim 1

A process to produce a carboxylic acid composition said process comprising:
oxidizing in a oxidation zone at least one oxidizable compound in the presence of an oxidizing gas comprising oxygen and a solvent stream and a catalyst system at a temperature to produce a reaction medium comprising ACFC; wherein said oxidation zone comprises at least one oxidation reactor; wherein said oxidable compound comprises -methyl 5-methylfuran-2-carboxylate (MMFC), methyl 5-(hydroxymethyl)furan-2-carboxylate, methyl 5-(methoxymethyl)furan-2-carboxylate, methyl 5-(ethoxymethyl)furan-2-carboxylate, or combination thereof to generate a carboxylic acid composition comprising ACFC; wherein said ACFC is produced at a yield greater than 90%; wherein said catalyst system comprises cobalt in a range from about 100 ppm by weight to about 4500 ppm by weight with respect to the weight of the liquid in the reaction medium, manganese in an amount ranging from about 100 ppm by weight to about 4500 ppm by weight with respect to the weight of the liquid in the reaction medium, and bromine in an amount ranging from about 100 ppm by weight to about 4500 ppm by weight with respect to the weight of the liquid in the reaction medium; wherein said oxidizing is conducted at a temperature from about 110° C. to about 180° C.; wherein said oxidation zone comprises at least once oxidation reactor that has been previously been used in an industrial TPA or IPA process; and wherein said initial oxidation state of cobalt is 2+ and/or 3+, and wherein said initial oxidation state of manganese is 2+ and/or 3+.

### Claim 2 (depends on 1)

A process according to claim 1 wherein said ACFC is produced at a yield greater than 99.5%.

### Claim 3 (depends on 1)

A process according to claim 1 wherein said carboxylic acid composition has a b* value less than 20.

### Claim 4 (depends on 1)

A process according to claim 1 wherein said carboxylic acid composition has a b* value less than 10.

### Claim 5 (depends on 1)

A process according to claim 1 wherein said carboxylic acid composition has a b* value less than 5.

### Claim 6 (depends on 1)

A process according to claim 1 wherein said carboxylic acid composition has a b* value less than 3.

### Claim 7 (depends on 1)

A process according to claim 1 wherein said carboxylic acid composition has a b* value less than 1.

### Claim 8 (depends on 1)

A process according to claim 1 wherein said oxidation reactor comprises a bubble column.

### Claim 9 (depends on 1)

A process according to claim 1 wherein said carboxylic acid composition comprises ACFC and FDCA.

### Claim 10 (depends on 1)

A process according to claim 1 wherein said oxidizing is conducted at a temperature from about 130° C. to 180° C.

### Claim 11 (depends on 1)

A process according to claim 1 wherein said oxidizing is conducted at a temperature from about 130° C. to 160° C.

### Claim 12 (depends on 1)

A process according to claim 1 wherein said oxidizing is conducted at a temperature from about 110° C. to about 160° C.

### Claim 13 (depends on 1)

A process according to claim 1 wherein said oxidizing is conducted at a pressure from about 50 psig to about 1000 psig.