# US 11,027,263 B2 · Furan-2,5-dicarboxylic acid purge process

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- Number: US 11,027,263 B2
- Document ID: US11027263B2
- Status: Granted
- Kind: B2
- Application number: 16/914,723
- Filed: 2020-06-29
- Published: 2020-10-15
- Granted: 2021-06-08
- Earliest claimed: 2014-05-08
- Assignees: Eastman Chemical Company
- Applicants: Eastman Chemical Company
- Inventors: Mesfin Ejerssa Janka; Kenny Randolph Parker; Ashfaq Shahanawaz Shaikh; Lee Reynolds Partin
- Web page: https://patentgrep.com/patent/US11027263B2

## CPC

- B01J 27/32: of catalysts comprising compounds of halogens
- B01D 11/04: of solutions which are liquid
- B01D 11/0446: {Juxtaposition of mixers-settlers}
- B01D 17/00: Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion (devices for separating or removing fatty or oily substances or similar floating material from water, waste water, or sewage C02F1/40; cleaning or keeping clear the surface of open water from oil or like materials E02B15/04; arrangements for separating lubricants from refrigerants F25B43/02)
- B01J 10/002: {carried out in foam, aerosol or bubbles}
- B01J 23/8892: {Manganese}
- B01J 27/128: with iron group metals or platinum group metals
- C07B 41/08: of carboxyl groups or salts, halides or anhydrides thereof
- C07B 63/00: Purification; Separation (separation of optically-active compounds C07B57/00); Stabilisation; Use of additives
- C07D 307/48: Furfural
- C07D 307/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- B01D 3/06: Flash distillation
- B01D 3/14: Fractional distillation {or use of a fractionation or rectification column}
- B01J 35/27: in a liquid or molten state
- B01J 38/12: Treating with free oxygen-containing gas
- Y02P 20/584: Recycling of catalysts
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Disclosed is an oxidation process to produce a crude carboxylic acid product carboxylic acid product. The process comprises oxidizing a feed stream comprising at least one oxidizable compound to generate a crude carboxylic acid slurry comprising furan-2,5-dicarboxylic acid (FDCA) and compositions thereof. Also disclosed is a process to produce a dry purified carboxylic acid product by utilizing various purification methods on the crude carboxylic acid.

## Claims

### Claim 1

A process to produce a raffinate stream in a method for making a carboxylic acid, said process comprising:
(i) oxidizing in an oxidation zone an oxidizable raw material stream comprising 5-(hydroxymethyl) furfural (5-HMF) in the presence of an oxidation solvent stream comprising a saturated organic acid having from 2-4 carbon atoms and a catalyst at a temperature of 100° C. to 220° C. to produce a crude carboxylic acid slurry; wherein said oxidation zone comprises at least one oxidation reactor; wherein said crude carboxylic acid slurry comprises furandicarboxylic acid; wherein said catalyst comprises cobalt, manganese and bromine; and wherein the yield of furandicarboxylic acid is greater than 90%;
(ii) routing said crude carboxylic acid slurry to a solid liquid separation zone to produce a mother liquor stream comprising said catalyst and impurities; wherein said solid liquid separation zone comprises at least one pressure drum filter;
(iii) routing at least a portion of said mother liquor stream to a mother liquor purge zone comprising a liquid-liquid extraction zone to produce an extract stream comprising impurities and an extract solvent, and a raffinate stream comprising catalyst solvent and oxidation catalyst; wherein at least a portion of said oxidation catalyst and/or catalyst solvent is optionally recycled to the oxidation zone; and wherein said oxidizable raw material stream comprises greater than 40% by weight of 5-HMF.

### Claim 2 (depends on 1)

The process according to claim 1 wherein said catalyst comprises cobalt in a range from about 500 ppm by weight to about 6000 ppm by weight with respect to the weight of the liquid in the reaction medium, manganese in an amount ranging from about 2 ppm by weight to about 600 ppm by weight with respect to the weight of the liquid in the reaction medium, and bromine in an amount ranging from about 300 ppm by weight to about 4500 ppm by weight with respect to the weight of the liquid in the reaction medium.

### Claim 3 (depends on 1)

The process according to claim 1 wherein said oxidation reactor is a bubble column.

### Claim 4 (depends on 1)

The process according to claim 1 wherein said catalyst comprises cobalt in a range from about 700 ppm 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 20 ppm by weight to about 400 ppm by weight with respect to the weight of the liquid in the reaction medium, and bromine in an amount ranging from about 700 ppm by weight to about 4000 ppm by weight with respect to the weight of the liquid in the reaction medium.

### Claim 5 (depends on 1)

The process according to claim 1 wherein said catalyst comprises cobalt in a range from about 1000 ppm to about 4000 ppm with respect to the weight of the liquid in the reaction medium, manganese in an amount ranging from about 20 ppm to about 200 ppm by weight with respect to the weight of the liquid in the reaction medium and bromine in an amount ranging from about 1000 ppm to about 4000 ppm by weight with respect to the weight of the liquid in the reaction medium.

### Claim 6 (depends on 1)

The process according claim 1 wherein said crude carboxylic acid slurry further comprises 5-formyl furan-2-carboxylic acid (FFCA).

### Claim 7 (depends on 1)

The process according claim 1 wherein said oxidizing is conducted at a temperature from 105° C. to 180° C.

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

The process according to claim 1 wherein said oxidizable raw material stream comprises greater than 2% by weight of 5-HMF.

### Claim 10 (depends on 1)

The process according to claim 1 wherein said oxidizable raw material stream comprises greater than 50% by weight of 5-HMF.

### Claim 11 (depends on 1)

The process according to claim 1 wherein said oxidizable raw material stream comprises greater than 70% by weight of 5-HMF.

### Claim 12 (depends on 10)

The process according to claim 10 wherein the weight ratio of cobalt to manganese is about 400 to about 1.

### Claim 13 (depends on 10)

The process according to claim 10 wherein the weight ratio of cobalt to manganese is about 40 to about 1.

### Claim 14 (depends on 10)

The process according to claim 10 the weight ratio of cobalt to manganese is about 30 to about 1.

### Claim 15 (depends on 10)

The process according to claim 10 wherein the weight ratio of cobalt to manganese is about 20 to about 1.