Furan-2,5-dicarboxylic acid purge process

Patent metadata

Field	Value
Publication number	US-9943834-B2
Application number	US-201414317692-A
Country	US
Kind code	B2
Filing date	Jun 27, 2014
Priority date	May 8, 2014
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

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.

First claim

We 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
(ii) after said oxidizing routing said crude carboxylic acid slurry to a solid liquid separation zone that is operated at a temperature between about 100°C. to about 220°C. to produce a mother liquor stream comprising the catalyst and impurities;
(iii) routing at least a portion of the mother liquor stream to a mother liquor purge zone comprising a mixing zone and a liquid-liquid extraction zone;
(iv) mixing at least a portion of the mother liquid stream with a catalyst solvent in the mixing zone to generate an extraction feed stream; and
(v) contacting the extraction feed stream with an extraction solvent stream in the liquid-liquid extraction zone to generate an extract stream comprising the impurities and the extraction solvent, and a raffinate stream comprising the catalyst and the catalyst solvent; wherein said oxidizable raw material stream comprises greater than 20% by weight of 5-HMF.

2. 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.

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

4. 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.

5. 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.

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

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

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

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

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

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

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

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

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

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

16. The process according to claim 11 wherein the weight ratio of cobalt to bromine is about 0.75 to about 3.5.

Assignees

• Eastman Chem Co

Inventors

• Janka Mesfin
• Parker Kenny
• Shaikh Ashfaq
• Partin Lee

Classifications

• B01D11/04

  of solutions which are liquid · CPC title

• B01J23/8892

  Manganese · CPC title

• C07D307/68 Primary

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• Y02P20/584

  Recycling of catalysts · CPC title

• B01J27/128

  with iron group metals or platinum group metals · CPC title