Water and thermal treatment of purified 2,5-furandicarboxylic acid

Patent metadata

Field	Value
Publication number	US-12371411-B2
Application number	US-202017780080-A
Country	US
Kind code	B2
Filing date	Dec 18, 2020
Priority date	Dec 20, 2019
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

Abstract

Thermal treatment of purified 2,5-furandicarboxylic acid (FDCA) for producing a carboxylic acid composition, the process comprising the steps of providing or producing a thermal treatment composition comprising a purified carboxylic acid composition and a water containing treatment solvent composition; subjecting the thermal treatment composition to an elevated temperature, wherein the FDCA is partially dissolved, and cooling the treated composition and separating at least a portion of the FDCA from the treated composition to obtain a carboxylic acid composition.

First claim

The invention claimed is:

1. A process for producing a carboxylic acid composition comprising 2,5-furandicarboxylic acid, the process comprising the steps:
a) providing or producing a crude carboxylic acid composition comprising 2,5-furandicarboxylic acid and 5-formyl-2-furancarboxylic acid;
b) purifying the crude carboxylic acid composition to produce a purified carboxylic acid composition comprising 2,5-furandicarboxylic acid, wherein the purifying comprises at least one step selected from the group consisting of:
hydrogenating at least a portion of the 5-formyl-2-furancarboxylic acid;
oxidizing at least a portion of the 5-formyl-2-furancarboxylic acid;
recrystallization of at least a portion of the 2,5-furandicarboxylic acid; and
hydrolyzing of dialkyl ester of 2,5-furandicarboxylic acid;

c) providing or producing a treatment solvent composition comprising more than 95% by weight of water, with respect to the weight of the treatment solvent composition;
d) providing or producing a thermal treatment composition comprising the purified carboxylic acid composition and the treatment solvent composition;
e) subjecting the thermal treatment composition to an elevated temperature in the range of 140 to 200° C. for a time in the range of 5 to 240 min, wherein the percentage of dissolved 2,5-furandicarboxylic acid, relative to the total amount of 2,5-furandicarboxylic acid, is in the range of 10 to 80% to obtain a treated composition; and
f) cooling the treated composition to a temperature in the range of 20 to 80° C. and separating at least a portion of the 2,5-furandicarboxylic acid from the treated composition to obtain a carboxylic acid composition and a treatment mother liquor comprising water.

2. The process according to claim 1 , wherein the crude carboxylic acid composition and/or the purified carboxylic acid composition comprise mono methyl ester of 2,5-furandicarboxylic acid.

3. The process according to claim 1 ,
wherein step e) is conducted in a reactor that is pressurized with an inert gas,
and/or
wherein the thermal treatment composition in step e) is agitated for at least a portion of the time to expose the solid 2,5-furandicarboxylic acid to shear forces.

4. The process s according to claim 1 ,
wherein the thermal treatment composition comprises 2,5-furandicarboxylic acid in an amount of 15 to 45% by weight with respect to the weight of the thermal treatment solvent composition,
and/or
wherein the treatment solvent composition comprises acetic acid and water.

5. The process according to claim 1 , wherein the crude carboxylic acid composition comprises 2-furan carboxylic acid in an amount in the range of 1 to 2000 ppm by weight with respect to the weight of the composition and wherein the carboxylic acid composition comprises 2-furan carboxylic acid in an amount of not more than 700 ppm by weight.

6. The process according to claim 1 , wherein the crude carboxylic acid composition comprises mono alkyl ester of 2,5-furandicarboxylic acid in an amount in the range of 0.2 to 5.0% by weight with respect to the weight of the crude carboxylic acid composition.

7. The process according to claim 1 , wherein the purifying in step b) comprises the step of hydrogenating at least a portion of the 5-formyl-2-furancarboxylic acid.

8. The process according to claim 1 , wherein in step e) the percentage of dissolved 2,5-furandicarboxylic acid, relative to the total amount of 2,5-furandicarboxylic acid, is in the range of 20 to 60%.

9. The process according to claim 1 ,
wherein the temperature in step e) is in the range of 150 to 190° C.,
and/or
wherein the thermal treatment composition in step e) is subjected to an elevated temperature for a time in the range of 15 to 120 min.

10. The process according to claim 1 , wherein the treated composition in step f) is cooled to a temperature in the range of 30 to 80° C.

Assignees

• Furanix Technologies Bv

Inventors

• Kolstad Jeffrey John
• De Sousa Dias Ana Sofia Vagueiro
• Sijben Johannes Maria Franciscus
• Almeida Ana Rita Martins Guerreiro Rocha
• Gonzalez Jimenez Ines Dacil

Classifications

• C08G63/672

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07D307/68 Primary

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