Process for preparing guanidino acetic acid

Patent metadata

Field	Value
Publication number	US-10844009-B2
Application number	US-201916731551-A
Country	US
Kind code	B2
Filing date	Dec 31, 2019
Priority date	Jan 2, 2019
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

The present invention pertains to a process for preparing guanidino acetic acid (GAA) from cyanamide and glycine in alkaline process solution, in which anionic impurities are removed from the process solution by electrodialysis.

First claim

What is claimed is:

1. A process for preparing guanidino acetic acid (GAA), comprising:
(a) preparing an alkaline process solution comprising glycine;
(b) reacting cyanamide with the excess glycine in the alkaline process solution;
(c) separating off the guanidino acetic acid product; and
(d) recirculating the alkaline process solution comprising glycine;
wherein anionic impurities are removed from the process solution by electrodialysis conducted in a cell comprising at least one feed compartment comprising the alkaline process solution and at least one concentrate compartment, and wherein the pH of the alkaline process solution is between 8.5 and 11.

2. The process of claim 1 , wherein the at least one feed compartment is interconnected with the at least one concentrate compartment by an ion-selective anion exchange membrane (AEM).

3. The process of claim 2 , wherein the at least one feed compartment and the at least one concentrate compartment are each independently connected with another compartment by an ion-selective cation exchange membrane (CEM).

4. The process of claim 1 , wherein the electrodialysis cell comprises a stack of alternating feed compartments and concentrate compartments, the compartments being formed by alternating ion-selective anion exchange membranes and ion-selective cation exchange membranes.

5. The process of claim 1 , wherein the electrodialysis cell is configured as a four compartment cell, the compartments being interconnected by three ion-selective exchange membranes.

6. The process of claim 1 , wherein the electrodialysis cell comprises two outer compartments comprising a solution of sulfuric acid, each compartment being located between an electrode an outer ion-selective cation exchange membrane.

7. The process of claim 1 , wherein the pH of the alkaline process solution is between 9 and 10.

8. The process according of claim 1 , wherein the cyanamide is introduced into the process as an aqueous solution comprising at least one stabilizing agent.

9. The process of claim 8 , wherein the at least one stabilizing agent is present in an amount of between 0.005 wt. % and 3 wt. %, based on the cyanamide solution.

10. The process of claim 8 , wherein the at least one stabilizing agent is selected from the group consisting of: phosphoric acid, formic acid; esters of formic acid; magnesium chloride; magnesium sulfate; and mixtures thereof.

11. The process of claim 1 , wherein, for process step (a), the ratio of cyanamide to glycine is in the range of between 1.1:1 and 10:1.

12. The process of claim 1 , wherein, for process step (a), the ratio of cyanamide to glycine is in the range of between 1.5:1 and 2.5:1.

13. The process of claim 1 , wherein the current density in the electrodialysis cell is in the range of 1 to 750 A/m 2 .

14. The process of claim 1 , wherein the anionic impurities removed from the process solution by electrodialysis are chloride, phosphate, sulfate, sulfide, or sulfite.

15. The process of claim 1 , wherein the process is carried out in a continuous or semi-continuous manner.

16. The process of claim 2 , wherein the at least one feed compartment and the at least one concentrate compartment are each independently connected with another compartment by an ion-selective cation exchange membrane and wherein the electrodialysis cell comprises a stack of alternating feed compartments and concentrate compartments, the compartments being formed by alternating ion-selective anion exchange membranes and ion-selective cation exchange membranes.

17. The process of claim 16 , wherein the electrodialysis cell is configured as a four compartment cell, the compartments being interconnected by three ion-selective exchange membranes.

18. The process of claim 17 , wherein the electrodialysis cell comprises two outer compartments comprising a solution of sulfuric acid, each compartment being located between an electrode and an outer ion-selective cation exchange membrane.

19. The process of claim 10 , wherein, for process step (a), the ratio of cyanamide to glycine is in the range of between 1.1:1 and 10:1.

20. The process of claim 19 , wherein the process is carried out in a continuous or semi-continuous manner.

Assignees

• Evonik Operations Gmbh

Inventors

• Stahl Timo
• Stenner Patrik
• Borgmann Cornelia
• Renner Christian
• Ronneburg Axel

Classifications

• C07C279/14

  being further substituted by carboxyl groups · CPC title

• C07C277/02 Primary

  of guanidine from cyanamide, calcium cyanamide or dicyandiamides · CPC title

• C07C227/40

  Separation; Purification · CPC title

• B01D2311/263

  Chemical reaction · CPC title

• B01D61/44

  Ion-selective electrodialysis · CPC title