Amine separation method

Patent metadata

Field	Value
Publication number	US-2026062375-A1
Application number	US-202319105984-A
Country	US
Kind code	A1
Filing date	Aug 24, 2023
Priority date	Aug 25, 2022
Publication date	Mar 5, 2026
Grant date	—

Abstract

Provided is an amine separation method that includes separating an amine through chromatography using a stationary phase including a ligand having a crown ether-like cyclic structure and being supported on a carrier; and a mobile phase containing a salt of a cation and an acid anion at a concentration of 0.2 mM or more and 50.0 mM or less and containing a solvent having a water content of 50 vol. % or less.

First claim

1 . An amine separation method comprising separating an amine through chromatography using:
a stationary phase comprising a ligand having a crown ether-like cyclic structure and being supported on a carrier; and a mobile phase comprising a salt of a cation and an acid anion at a concentration of 0.2 mM or more and 50.0 mM or less and comprising a solvent having a water content of 50 vol. % or less.

2 . The amine separation method according to claim 1 , wherein the mobile phase comprises an acid at a concentration of more than 0 mM and 50.0 mM or less.

3 . The amine separation method according to claim 1 , wherein the solvent has a water content of 20 vol. % or less.

4 . The amine separation method according to claim 1 , wherein a liquid other than water in the solvent is one or more selected from the group consisting of an organic solvent and subcritical or supercritical carbon dioxide.

5 . The amine separation method according to claim 4 , wherein the organic solvent is one or more selected from the group consisting of acetonitrile, acetone, methanol, ethanol, 2-propanol, hexane, tetrahydrofuran, and tert-butyl methyl ether.

6 . The amine separation method according to claim 1 , wherein the solvent comprises acetonitrile in an amount of 70 vol. % or more.

7 . The amine separation method according to claim 1 , wherein an acid from which the acid anion is derived has a pKa n of −2.0 or more and 6.5 or less in water at 25° C.:
wherein, n is a valence of the acid anion.

8 . The amine separation method according to claim 1 , wherein the acid anion is one or more selected from the group consisting of a nitrate ion, a trifluoroacetate ion, an oxalate ion, a hydrogen oxalate ion, a dihydrogen phosphate ion, a glycolate ion, a formate ion, an acetate ion, and a hydrogen carbonate ion.

9 . The amine separation method according to claim 1 , wherein the acid anion is one or more selected from the group consisting of an oxalate ion, a formate ion, and an acetate ion.

10 . The amine separation method according to claim 1 , wherein the cation is one or more selected from the group consisting of a tetrahydroammonium ion, a secondary ammonium ion, and a tertiary ammonium ion.

11 . The amine separation method according to claim 2 , wherein a value calculated by Formula (1) for the mobile phase is 0.01 or more and 0.90 or less:

[

Math
.

1

]



qY

X
+
qY

(
1
)

wherein,
X is a concentration (mM) of the acid in the mobile phase;
Y is a concentration (mM) of the salt in the mobile phase; and
q is the number of acid anions per molecule of the salt.

12 . The amine separation method according to claim 1 , wherein the chromatography is carried out by liquid chromatography-mass spectrometry.

Assignees

• Daicel Corp

Inventors

• Shibata Toru
• Shinkura Satoshi
• Kawahara Nobuhiro
• Fujioka Yuichi
• Terada Miyu

Classifications

• G01N2030/027

  Liquid chromatography · CPC title

• G01N30/72

  Mass spectrometers {(mass spectrometers per se H01J49/00)} · CPC title

• C07D209/20 Primary

  substituted additionally by nitrogen atoms, e.g. tryptophane · CPC title

• C07B57/00

  Separation of optically-active compounds · CPC title

• B01J20/29

  Chiral phases · CPC title