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

Patent metadata

Field	Value
Publication number	US-10654787-B2
Application number	US-201715722454-A
Country	US
Kind code	B2
Filing date	Oct 2, 2017
Priority date	Sep 29, 2014
Publication date	May 19, 2020
Grant date	May 19, 2020

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 product comprising an aqueous extract and a separation media comprising a resin in contact with the aqueous extract, the aqueous extract comprising:
from about 85 wt. % to about 99 wt. % glucaric acid and any lactones thereof,
gluconic acid and any lactones thereof, wherein the concentration of the gluconic acid and any lactones thereof is less than about 5 wt. %,
from about 0.1 wt. % to about 5 wt. % guluronic acid and any lactones thereof,
less than about 2.5 wt. % of one or more ketogluconic acids and any lactones thereof,
less than about 10 wt. % of one or more C 2 -C 5 di-acids and any lactones thereof, and
less than about 1 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the product.

2. The product of claim 1 comprising from about 0.1 wt. % to about 2.5 wt. % guluronic acid and any lactones thereof based on the dissolved solids content.

3. A product comprising an aqueous extract and a separation media comprising a resin in contact with the aqueous extract, the aqueous extract comprising:
from about 85 wt. % to about 99 wt. % glucaric acid and any lactones thereof,
from about 1 wt. % to about 5 wt. % gluconic acid and any lactones thereof,
from about 0.1 wt. % to about 5 wt. % guluronic acid and any lactones thereof,
less than about 2.5 wt. % of one or more ketogluconic acids and any lactones thereof,
less than about 10 wt. % of one or more C 2 -C 5 di-acids and any lactones thereof, and
less than about 1 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the product.

4. The product of claim 1 wherein the concentration of the ketogluconic acids and any lactones thereof is from about 0.01 wt. % to about 1 wt. % of the dissolved solids content and wherein the ketogluconic acids are a mixture of 2-ketogluconic acid, 3-ketogluconic acid, 4-ketogluconic acid, and 5-ketogluconic acid.

5. A product comprising an aqueous extract and a separation media comprising a resin in contact with the aqueous extract, the aqueous extract comprising:
from about 85 wt. % to about 99 wt. % glucaric acid and any lactones thereof,
gluconic acid and any lactones thereof, wherein the concentration of the gluconic acid and any lactones thereof is less than about 5 wt. %,
from about 0.1 wt. % to about 5 wt. % guluronic acid and any lactones thereof,
less than about 2.5 wt. % of one or more ketogluconic acids and any lactones thereof,
from about 1 wt. % to about 10 wt. % C 2 -C 5 di-acids and any lactones thereof, and
less than about 1 wt. % glucose, wherein each weight percent is based on the dissolved solids content of the product.

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

7. The product of claim 1 wherein the product contains less than about 0.01 wt. % of nitric acid and salts thereof.

8. The product of claim 1 wherein the product is free of nitric acid and salts thereof.

9. The product of claim 1 wherein the concentration of glucaric acid and any lactones thereof is from about 90 wt. % to about 95 wt. % of the dissolved solids content.

10. The product of claim 4 wherein the concentration of glucaric acid and any lactones thereof is from about 90 wt. % to about 95 wt. % of the dissolved solids content.

11. The product of claim 1 wherein the concentration of gluconic acid and any lactones thereof is from about 1 wt. % to about 2.5 wt. % of the dissolved solids content.

12. The product of claim 9 wherein the concentration of the C 2 -C 5 di-acids and any lactones thereof is from about 2.5 wt. % to about 7.5 wt. % of the dissolved solids content.

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

14. The product of claim 1 wherein the glucose concentration is less than about 0.1 wt. % of the dissolved solids content.

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

16. The product of claim 10 wherein the concentration of the one or more C 2 -C 5 di-acids and any lactones thereof is from about 2.5 wt. % to about 7.5 wt. % of the dissolved solids content.

17. The product of claim 16 wherein the C 2 -C 5 di-acids comprise tartaric acid, tartronic acid, and oxalic acid.

18. The product of claim 17 wherein the concentration of guluronic acid and any lactones thereof is from about 0.1 wt. % to about 2.5 wt. % based on the dissolved solids content.

19. The product of claim 5 wherein the concentration of glucaric acid and any lactones thereof is from about 90 wt. % to about 95 wt. % of the dissolved solids content.

20. The product of claim 1 wherein the resin comprises an anion exchange chromatography resin.

21. The product of claim 20 wherein the anion exchange chromatography resin is in glucarate form.

22. The product of claim 20 wherein the anion exchange chromatography resin comprises a weakly basic anion exchange chromatography resin.

23. The product of claim 20 wherein the anion exchange chromatography resin comprises from about 60% to about 100% weak base functionality.

24. The product of claim 20 wherein the anion exchange chromatography resin comprises from about 0% to about 40% strong base functionality.

Assignees

• Archer Daniels Midland Co

Inventors

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

Classifications

• C07C51/16

  by oxidation (C07C51/145 takes precedence) · CPC title

• C07C51/27

  with oxides of nitrogen or nitrogen-containing mineral acids · CPC title

• C07C51/47 Primary

  by solid-liquid treatment; by chemisorption · CPC title

• B01D15/363

  Anion-exchange · CPC title

• B01D15/1821

  Simulated moving beds · CPC title