Purification of cadaverine using high boiling point solvent

Patent metadata

Field	Value
Publication number	US-10464880-B2
Application number	US-201815901475-A
Country	US
Kind code	B2
Filing date	Feb 21, 2018
Priority date	Jan 27, 2017
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

The present invention relates to a method for the purification of cadaverine from an aqueous cadaverine salt composition comprising one or more involatile impurities, the method comprising: (1) mixing the aqueous cadaverine salt composition with one or more bases to provide an aqueous cadaverine composition having a pH of at least about 12; (2) distilling or evaporating the aqueous cadaverine composition to produce an aqueous cadaverine solution, wherein one or more solvents are added to the evaporation/distillation system before the evaporation/distillation stops, and the one or more solvents comprise at least one or more high boiling point (HBP) solvents having a boiling point of at least 185° C. (1 atm); and (3) subjecting the aqueous cadaverine solution to one or more rectification steps to provide a cadaverine product.

First claim

The invention claimed is:

1. A method for the purification of cadaverine from an aqueous cadaverine salt composition comprising one or more involatile impurities, the method comprising:
(1) mixing the aqueous cadaverine salt composition with one or more bases to provide an aqueous cadaverine composition having a pH of at least about 12;
(2) distilling or evaporating the aqueous cadaverine composition to produce an aqueous cadaverine solution, wherein one or more solvents are added to the evaporation/distillation system before the evaporation/distillation stops, and the one or more solvents comprise at least one or more high boiling point (HBP) solvents having a boiling point of at least 185° C. (1 atm); and
(3) subjecting the aqueous cadaverine solution to one or more rectification steps to provide a cadaverine product.

2. The method of claim 1 , wherein the aqueous cadaverine solution is subjected to two or three rectification steps.

3. The method of claim 1 , wherein the one or more HBP solvents are selected from the group consisting of alkanes, chloroalkanes, benzene derivatives, alcohols, ethers, amines, esters, nitriles, and any combinations thereof.

4. The method of claim 3 , wherein the one or more HBP solvents are selected from the group consisting of C 12 alkanes, C 13 alkanes, C 14 alkanes, a C 11 -C 22 alkane mixture such as a C 11 -C 14 alkane mixture, diphenyl ether, glycerol and dodecanol.

5. The method of claim 1 , wherein the one or more HBP solvents do not comprise alcohol.

6. The method of claim 1 , wherein the one or more HBP solvents are added (i) before, during and/or after mixing the aqueous cadaverine salt composition with the one or more bases in step (1), and/or (ii) before and/or during the evaporation/distillation in step (2).

7. The method of claim 1 , wherein the one or more organic bases are added at a temperature of from about room temperature to about 95° C.

8. The method of claim 1 , further comprising concentrating the aqueous cadaverine salt composition before mixing it with the one or more bases, and/or concentrating the mixture of the aqueous cadaverine salt composition and the one or more bases during and/or after mixing them.

9. The method of claim 1 , further comprising steps (1a), (1b) and (1c) after step (1), and comprising step (2′) instead of step (2):
(1a) subjecting the aqueous cadaverine composition to solid-liquid separation to provide a solid and a solution;
(1b) rinsing the solid with water one or more times to provide one or more solutions;
(1c) combining the solution from step (1a) with the one or more solutions from step (1b); and
(2′) distilling or evaporating the combined solutions from step (1c) to produce an aqueous cadaverine solution.

10. The method of claim 9 , wherein steps (1a) and (1b) each comprise centrifugation and/or filtration for solid-liquid separation, and the solid is rinsed in step (1b) until it comprises substantially no cadaverine.

11. The method of claim 1 , wherein the aqueous cadaverine salt composition comprises one or more of sulfates, chlorides, carbonates and phosphates of cadaverine.

12. The method of claim 1 , wherein the aqueous cadaverine salt composition has a pH of 12 or lower.

13. The method of claim 1 , wherein the one or more bases are selected from the group consisting of NaOH, KOH, sodium phosphate, potassium phosphate, sodium carbonate, potassium carbonate, Ca(OH) 2 , Mg(OH) 2 , CaO and MgO.

14. The method of claim 9 , wherein the one or more bases are selected from the group consisting of NaOH, KOH, sodium phosphate, potassium phosphate, sodium carbonate, potassium carbonate, Ca(OH) 2 , Mg(OH) 2 , CaO and MgO.

Assignees

• Cathay R&D Center Co Ltd
• Cibt America Inc
• Cathay Biotech Inc

Inventors

• Liu Xiucai
• Liu Charlie
• Qin Bingbing
• Li Naiqiang
• Chen Yang

Classifications

• C07C211/09

  Diamines · CPC title

• B01D3/34

  with one or more auxiliary substances · CPC title

• B01D21/262

  by using a centrifuge · CPC title

• B01D3/40

  Extractive distillation · CPC title

• B01D1/00

  Evaporating ({evaporation in general, e.g. of liquids for gas phase reactions B01B1/005} ; removal of incrustation B08B; preparation of starch C08B30/00; sugar industry C13; prevention of incrustation C23F; drying solid materials or objects by evaporating liquids therefrom F26) · CPC title