EP-4741818-A1 - COMPOUND TREATMENT METHOD, METHOD FOR PRODUCING COMPOUND OR REACTION PRODUCT OF SAME, SYSTEM FOR TREATING COMPOUND, AND REPLACEMENT TREATMENT COLUMN

Abstract

Provided is a method of treating a compound, including treating the compound by passing a solution containing the compound as a solute through a treatment column. The treatment column includes a macroporous monolith in a path through which the solution passes. At least part of the solution passes through at least a partial section of the macroporous monolith in a supersaturated state with respect to the compound or a reaction product of the compound. The treatment method is suitable for the treatment of a compound having a low solubility.

Inventors

• KANAMORI KAZUYOSHI
• MIYAMOTO RIICHI
• KAJI HIRONORI
• TANAKA HIROYUKI
• NAKAGAWA HIROMICHI

Assignees

• Flugelz Co., Ltd.

Dates

Publication Date

20260513

Application Date

20240701

Claims (20)

1. A method of treating a compound, comprising treating the compound by passing a solution containing the compound as a solute through a treatment column, wherein the treatment column includes a macroporous monolith in a path through which the solution passes, and wherein at least part of the solution passes through at least a partial section of the macroporous monolith in a supersaturated state with respect to the compound or a reaction product of the compound.
2. The method of treating a compound according to claim 1, wherein at least part of the solution is recovered from the treatment column as a treated solution in a supersaturated state with respect to the compound or the reaction product.
3. The method of treating a compound according to claim 1, wherein the solution is discharged from the treatment column while the compound or the reaction product is substantially prevented from being precipitated from the solution inside the macroporous monolith.
4. The method of treating a compound according to claim 1, further comprising performing solvent displacement on a stock solution, which contains the compound as a solute and is in a saturated or unsaturated state with respect to the compound, to provide the solution in a supersaturated state with respect to the compound, wherein the solution in a supersaturated state thus obtained is supplied to the treatment column.
5. The method of treating a compound according to claim 4, wherein the solution substantially free of a halogenated organic solvent is obtained by performing solvent displacement on the stock solution containing the halogenated organic solvent.
6. The method of treating a compound according to claim 1, wherein a solubility of the compound in a solvent of the solution at 25°C is 100 mg/mL or less.
7. The method of treating a compound according to claim 1, wherein the solution having a pressure of atmospheric pressure ± 0.3 atm is passed through the treatment column.
8. The method of treating a compound according to claim 1, wherein the compound is a liquid crystal compound or a π-conjugated aromatic compound.
9. The method of treating a compound according to claim 1, wherein a solubility of the compound in toluene or ethyl acetate at 25°C is 1/3 or less of a solubility thereof in a halogen-substituted methane at 25°C.
10. The method of treating a compound according to claim 1, wherein at least one kind of treatment selected from the group consisting of: purification; a reaction; and concentration is performed on the compound.
11. A method of producing a compound or a reaction product thereof, comprising treating the compound by the method of treating a compound of claim 1 to provide the compound that has been treated or a reaction product of the compound.
12. The method of producing a compound or a reaction product thereof according to claim 11, further comprising precipitating the treated compound or the reaction product without performing solvent displacement.
13. A system for treating a compound, comprising: a treatment unit including a treatment column through which a solution containing the compound as a solute is passed; and a supply unit configured to supply the solution to the treatment unit, wherein the treatment column includes a macroporous monolith in a path through which the solution passes, and wherein at least part of the solution passes through at least a partial section of the macroporous monolith in a supersaturated state with respect to the compound or a reaction product of the compound.
14. The system for treating a compound according to claim 13, wherein the solution in a supersaturated state is supplied to the treatment column.
15. The system for treating a compound according to claim 14, wherein the supply unit includes a solvent displacement unit configured to perform solvent displacement on a stock solution, which contains the compound as a solute and is in a saturated or unsaturated state with respect to the compound, to provide the solution in a supersaturated state.
16. The system for treating a compound according to claim 15, wherein in the solvent displacement unit, the solution substantially free of a halogenated organic solvent is obtained from the stock solution containing the halogenated organic solvent.
17. The system for treating a compound according to claim 13, wherein the treatment column includes a container configured to accommodate the macroporous monolith, and wherein the container is formed of a resin layer or a glass layer having a thickness of 5 mm or less, and is in contact with the macroporous monolith.
18. The system for treating a compound according to claim 13, wherein the system for treating a compound further comprises a solid-liquid separation unit configured to obtain the compound treated by the treatment column as a solid from a treated solution discharged from the treatment unit.
19. The system for treating a compound according to claim 18, wherein in the solid-liquid separation unit, the compound treated by the treatment column is precipitated from the treated solution without performing solvent displacement.
20. A treatment column for replacement, comprising: a macroporous monolith; and a container configured to accommodate the macroporous monolith, wherein the treatment column includes the macroporous monolith in a path through which a solution containing a compound as a solute passes, and wherein the treatment column is used in at least one selected from the group consisting of: the method of treating a compound of any one of claims 1 to 10; the method of producing a compound or a reaction product thereof of claim 11 or 12; and the system for treating a compound of any one of claims 13 to 19.

Description

TECHNICAL FIELD The present invention relates to a method of treating a compound, a method of producing a compound or a reaction product thereof, a system for treating a compound, and a treatment column for replacement. BACKGROUND ART The separation and purification of a compound by liquid chromatography (hereinafter referred to as "LC") are each an indispensable technique in various fields typified by chemistry and pharmacy. The LC can achieve substance selectivity higher than that of each of the other separation and purification techniques, such as recrystallization and nanofiltration. A column packed with particles such as silica gel as a separation medium has heretofore been widely used as a treatment column in LC. As a treatment column different from the particle-packed column, in Patent Literature 1, there is a disclosure of a column including a macroporous monolith, which has through-holes each having a pore diameter of 500 nm or more and pores each having a pore diameter of from 5 nm to 100 nm, the pores being formed on the inner wall surfaces of the through-holes, and in which the through-holes and a skeleton have a three-dimensional network-like co-continuous structure. CITATION LIST Patent Literature Patent Literature 1: JP 06-265534 A SUMMARY OF INVENTION Technical Problem In the LC, while substance selectivity higher than that of each of the other separation and purification techniques can be achieved, the amount of solvent used increases. In addition, a compound serving as an organic electroluminescence (organic EL) material or a raw material for a pharmaceutical product often has a planar structure in which an aromatic ring is expanded by a π-conjugated system. A highly planar π-conjugated aromatic compound is liable to form an associated state based on so-called π-π stacking, and hence tends to have a low solubility in a solvent. To perform treatment based on the LC on a compound having a low solubility, a further large amount of a solvent is required. However, to cope with a demand for environmental protection, a reduction in the amount of a solvent to be used in the treatment of a compound has been desired. An object of the present invention is to provide a method of treating a compound and a system for treating a compound that are suitable for the treatment of a compound having a low solubility. Solution to Problem The inventors of the present invention have found that a solution present in a macropore of a macroporous monolith can take a stable state, in which the precipitation of its solute is suppressed, while being in a supersaturated state. Thus, the inventors have completed the present invention. The present invention provides a method of treating a compound, including treating the compound by passing a solution containing the compound as a solute through a treatment column, wherein the treatment column includes a macroporous monolith in a path through which the solution passes, and wherein at least part of the solution passes through at least a partial section of the macroporous monolith in a supersaturated state with respect to the compound or a reaction product of the compound. The present invention further provides a method of producing a compound or a reaction product thereof, including treating the compound by the treatment method of the present invention described above to provide the compound that has been treated or a reaction product of the compound. The present invention further provides a system for treating a compound, including: a treatment unit including a treatment column through which a solution containing the compound as a solute is passed; and a supply unit configured to supply the solution to the treatment unit, wherein the treatment column includes a macroporous monolith in a path through which the solution passes, and wherein at least part of the solution passes through at least a partial section of the macroporous monolith in a supersaturated state with respect to the compound or a reaction product of the compound. The present invention further provides a treatment column for replacement, including: a macroporous monolith; and a container configured to accommodate the macroporous monolith, wherein the treatment column includes the macroporous monolith in a path through which a solution containing a compound as a solute passes, and wherein the treatment column is used in at least one selected from the group consisting of: the method of treating a compound of the present invention described above; the method of producing a compound or a reaction product thereof of the present invention described above; and the system for treating a compound of the present invention described above. Advantageous Effects of Invention The present invention can provide the method of treating a compound and the system for treating a compound that are suitable for the treatment of a compound having a low solubility. BRIEF DESCRIPTION OF DRAWINGS FIG. 1A is a cross-sectional view for s