Process for the separation of organic compounds

Patent metadata

Field	Value
Publication number	US-10730022-B2
Application number	US-201616062615-A
Country	US
Kind code	B2
Filing date	Dec 16, 2016
Priority date	Dec 17, 2015
Publication date	Aug 4, 2020
Grant date	Aug 4, 2020

Abstract

A membrane based process separates amines or organic acids from a solution containing at least one amine or at least one organic acid according to their hydrophobic properties. The more hydrophobic amine or organic acid passes the hydrophobic membrane into an acidic aqueous solution, thus selectively removing the amine or organic acid from the first solution. The process is particularly suitable to obtain chiral amines in high yield. A transaminase-catalyzed transamination of an amino donor and amino acceptor is combined with a hydrophobic membrane separation of the produced chiral amine. The selective removal of the chiral amine from the reaction mixture promotes the further transformation of the amino acceptor into the product chiral amine.

First claim

What is claimed is:

1. A method for a separation of an amine or an organic acid from a first solution comprising at least one amine or at least one organic acid, comprising:
(i) contacting said first solution comprising at least one amine or at least one organic acid with a non-liquid hydrophobic membrane; and
(ii) extracting the amine or the organic acid, from said first solution comprising at least one amine or at least one organic acid into a second solution across said non-liquid hydrophobic membrane, wherein said non-liquid hydrophobic membrane separates said first solution and said second solution, and wherein said non-liquid hydrophobic membrane is a porous inorganic membrane functionalized with an organic functional group.

2. The method according to claim 1 , wherein said porous inorganic membrane comprises an oxide or hydroxide of an element M1, and wherein said organic functional group is linked to said inorganic membrane via a M1-carbon bond, a M1-O—P-carbon bond or a M1-O—Si-carbon bond.

3. The method according to claim 1 , wherein said organic functional group is selected from the group consisting of (a) haloalkyl, preferably fluoroalkyl or perfluoroalkyl, more preferably fluoroC 1 -C 16 alkyl or perfluoroC 1 -C 16 alkyl, more preferably fluoroC 1 -C 8 alkyl or (per)fluoroC 1 -C 8 alkyl; (b) aryl, preferably C 6 -C 16 aryl, more preferably C 6 -C 10 aryl; and (c) haloaryl, preferably fluoroaryl or perfluoroaryl, more preferably fluoroC 6 -C 16 aryl or perfluoroC 6 -C 16 aryl, more preferably fluoroC 6 -C 10 aryl or perfluoroC 6 -C 10 aryl.

4. The method according to claim 1 , wherein said second solution is an aqueous solution, and wherein a pH value of said second solution is adapted so that said amine or said organic acid extracted across said non-liquid hydrophobic membrane is essentially in its charged state to prevent a back extraction of said amine or said organic acid across said non-liquid hydrophobic membrane.

5. The method according to claim 4 , wherein
(a) said aqueous solution of the second solution has a pH at least 2 or at least 3 units below a pKa value of the amine which has been extracted from the first solution to obtain said amine in its dissociated (charged) form; or
(b) said aqueous solution of the second solution has a pH at least 2 or at least 3 units above a pKa value of the organic acid, which has been extracted from the first solution to obtain the organic acid in its dissociated (charged) form.

6. The method according to claim 1 , wherein said first solution is an aqueous solution, preferably with a pH value differing from a pKa value of the amine or organic acid by about 2.0 units or less, preferably by 1.0 unit or less.

7. The method according to claim 1 , further comprising:
(iii) recovering the amine or organic acid extracted across said non-liquid hydrophobic membrane in said step (ii) from said second solution.

8. The method according to claim 1 , wherein said first solution comprises at least one first amine and at least one second amine, with the first and second amine differing in hydrophobicity, expressed as a difference in Log P value, and wherein in said step (ii) the amine with the highest Log P value is extracted from said first solution across said non-liquid hydrophobic membrane.

9. The method according to claim 1 , wherein said first solution comprises at least one chiral amine.

10. The method according to claim 9 , further comprising:
Forming the chiral amine by contacting an amino donor and a prochiral amino acceptor with a transaminase to obtain the chiral amine in said first solution prior to said steps (i) and (ii).

11. The method according to claim 10 , wherein the amino donor is 2-propyl amine.

12. The method according to claim 9 , wherein said first solution is an aqueous alkaline solution.

13. The method according to claim 9 , wherein said first solution is an organic solvent solution.

14. The method according to claim 1 , wherein the first solution is fed to a first compartment of a membrane contactor module, and wherein said step (ii) transfers said organic amine to a second compartment of the membrane contactor module comprising said second solution.

15. The method according to claim 1 , wherein the porous inorganic membrane has a pore size ranging from about 0.5 nm to about 100 nm.

16. The method according to claim 2 , wherein the element M1 is a metal or silicon.

Assignees

• Vito Nv

Inventors

• Satyawali Yamini
• Ormerod Dominic
• Vanbroekhoven Karolien
• Buekenhoudt Anita

Classifications

• B01D71/0213

  Silicon · CPC title

• B01D61/246

  Membrane extraction · CPC title

• C12P7/28

  Acetone-containing products · CPC title

• C07C209/86

  Separation · CPC title

• C12P13/001

  Amines; Imines · CPC title