Preparation and separation of a di-carboxylic acid-containing mixture

Patent metadata

Field	Value
Publication number	US-11078149-B2
Application number	US-202016849471-A
Country	US
Kind code	B2
Filing date	Apr 15, 2020
Priority date	Sep 29, 2014
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

Processes for separating a di-carboxylic acid or salt thereof from a mixture containing the di-carboxylic acid or salt thereof and one or more other components are provided. Also separation media useful for these separation processes is provided. In particular, processes for preparing an aldaric acid are described, such as glucaric acid from glucose, which includes separating the aldaric acid from the reaction product. Also, various glucaric acid products are described.

First claim

What is claimed is:

1. A mixture comprising a glucaric acid product and a separation media comprising an anion exchange chromatography resin in contact with the glucaric acid product, wherein the glucaric acid product comprises:
from about 20 wt. % to about 65 wt. % glucaric acid or a salt thereof,
from about 25 wt. % to about 70 wt. % gluconic acid or a salt thereof,
less than about 10 wt. % of one or more ketogluconic acids or salts thereof,
less than about 5 wt. % of one or more C 2 -C 5 di-acids or salts thereof, and
less than about 5 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the glucaric acid product; and
wherein the anion exchange chromatography resin is in di-carboxylate form.

2. A mixture comprising a glucaric acid product and a separation media comprising an anion exchange chromatography resin in contact with the glucaric acid product, wherein the glucaric acid product comprises:
from about 20 wt. % to about 65 wt. % glucaric acid or a salt thereof,
from about 25 wt. % to about 70 wt. % gluconic acid or a salt thereof,
from about 1 wt. % to about 20 wt. % guluronic acid or a salt thereof,
less than about 10 wt. % of one or more ketogluconic acids or salts thereof,
less than about 5 wt. % of one or more C 2 -C 5 di-acids or salts thereof, and
less than about 5 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the glucaric acid product; and
wherein the anion exchange chromatography resin comprises a weakly basic anion exchange chromatography resin.

3. The mixture of claim 2 wherein the anion exchange chromatography resin comprises from about 60% to about 100% weak base functionality.

4. The mixture of claim 1 wherein the anion exchange chromatography resin is in glucarate form.

5. The mixture of claim 1 further comprising from about 1 wt. % to about 20 wt. % guluronic acid or a salt thereof based on the dissolved solids content.

6. The mixture of claim 1 wherein the concentration of glucaric acid or a salt thereof is from about 25 wt. % to about 65 wt. % of the dissolved solids contents.

7. The mixture of claim 1 wherein the concentration of gluconic acid or a salt thereof is from about 25 wt. % to about 65 wt. % of the dissolved solids contents.

8. The mixture of claim 1 wherein the concentration of the ketogluconic acids or salts thereof is from about of 1 wt. % to about 5 wt. % of the dissolved solids contents.

9. The mixture of claim 1 wherein the ketogluconic acids are 2-ketogluconic acid, 3-ketogluconic acid, 4-ketogluconic acid, and 5-ketogluconic acid.

10. The mixture of claim 1 wherein the concentration of the C 2 -C 5 di-acids or salts thereof is from about 1 wt. % to less than about 5 wt. % of the dissolved solids contents.

11. The mixture of claim 1 wherein the glucose concentration is from about 0.001 wt. % to about 2.5 wt. % of the dissolved solids contents.

12. The mixture of claim 1 wherein the C 2 -C 5 di-acids comprise xylaric acid, tartaric acid, tartronic acid, and oxalic acid.

13. The mixture of claim 1 further comprising from about 0.01 wt. % to about 1 wt. % glucuronic acid or a salt thereof based on the dissolved solids content.

14. The mixture of claim 1 wherein the glucaric acid product comprises:
from about 30 wt. % to about 50 wt. % glucaric acid,
from about 25 wt. % to about 45 wt. % gluconic acid,
from about 5 wt. % to about 15 wt. % guluronic acid,
less than about 2 wt. % of glucuronic acid,
less than about 6 wt. % of one or more ketogluconic acids,
less than about 5 wt. % of one or more C 2 -C 5 di-acids, and
less than about 2 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the glucaric acid product.

15. The mixture of claim 1 wherein the glucaric acid product has a metal content of less than about 1 wt. % and contains less than about 0.1 wt. % of nitric acid and salts thereof based on the total weight of the glucaric acid product.

16. The mixture of claim 2 wherein the concentration of the ketogluconic acids or salts thereof is from about of 1 wt. % to about 5 wt. % of the dissolved solids contents.

17. The mixture of claim 2 wherein the ketogluconic acids are 2-ketogluconic acid, 3-ketogluconic acid, 4-ketogluconic acid, and 5-ketogluconic acid.

18. The mixture of claim 2 wherein the concentration of the C 2 -C 5 di-acids or salts thereof is from about 1 wt. % to less than about 5 wt. % of the dissolved solids contents.

19. The mixture of claim 2 wherein the C 2 -C 5 di-acids comprise xylaric acid, tartaric acid, tartronic acid, and oxalic acid.

20. The mixture of claim 2 further comprising from about 0.01 wt. % to about 1 wt. % glucuronic acid or a salt thereof based on the dissolved solids content.

21. The mixture of claim 2 wherein the glucaric acid product comprises:
from about 30 wt. % to about 50 wt. % glucaric acid,
from about 25 wt. % to about 45 wt. % gluconic acid,
from about 5 wt. % to about 15 wt. % guluronic acid,
less than about 2 wt. % of glucuronic acid,
less than about 6 wt. % of one or more ketogluconic acids,
less than about 5 wt. % of one or more C 2 -C 5 di-acids, and
less than about 2 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the glucaric acid product.

Assignees

• Archer Daniels Midland Co

Inventors

• Diamond Gary M
• Dias Eric L
• Archer Raymond
• Murphy Vincent J
• Boussie Thomas R

Classifications

• B01D15/1821

  Simulated moving beds · CPC title

• B01D15/363

  Anion-exchange · CPC title

• C07C59/285

  Polyhydroxy dicarboxylic acids having five or more carbon atoms, e.g. saccharic acids · CPC title

• C07C51/47 Primary

  by solid-liquid treatment; by chemisorption · CPC title

• C07C51/23

  of oxygen-containing groups to carboxyl groups · CPC title