EP-4741371-A1 - METHOD FOR PRODUCING DICARBOXYLIC ACID COMPOUND AND METHOD FOR PRODUCING RECYCLED RESINS

EP4741371A1EP 4741371 A1EP4741371 A1EP 4741371A1EP-4741371-A1

Abstract

The present invention addresses the problem of efficiently recycling waste resin compositions such as synthetic resins, enabling the reuse of a wider variety of resins than before. The problem is solved by a method for producing a dicarboxylic acid compound, said method including a crystallization step for crystallizing at least the dicarboxylic acid compound from a mixed liquid containing a dicarboxylic acid compound represented by general formula (1-1) or general formula (1-2) and a dihydroxy compound represented by general formula (2-1) or general formula (2-2). The substituents and the like in the general formulas are as described in the description of the present application.

Inventors

KATO NORIYUKI
NISHIMORI Katsushi
MOTEGI ATSUSHI
ISHIHARA KENTARO
MATSUMOTO MUTSUMI
TAKAMATSU KAZUTAKA
SATO ATSUHIRO

Assignees

MITSUBISHI GAS CHEMICAL COMPANY, INC.

Dates

Publication Date: 20260513
Application Date: 20240702

Claims (16)

A method for producing a dicarboxylic acid compound represented by general formula (1-1) below or general formula (1-2) below, the method comprising: a crystallization step in which at least the dicarboxylic acid compound is crystallized from a liquid mixture containing the dicarboxylic acid compound and a dihydroxy compound represented by general formula (2-1) below or general formula (2-2) below: in general formula (1-1), R a1 and R b1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, an optionally substituted alkoxyl group with 1-20 carbon atoms, an optionally substituted cycloalkyl group with 5-20 carbon atoms, an optionally substituted cycloalkoxyl group with 5-20 carbon atoms, an optionally substituted aryl group with 6-20 carbon atoms, an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, an optionally substituted aryloxy group with 6-20 carbon atoms, and -C≡C-R h1 , R h1 represents an optionally substituted aryl group with 6-20 carbon atoms or an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, X 1 represents a single bond or an optionally substituted fluorene group, A 1 and B 1 each independently represent an optionally substituted alkylene group with 1-5 carbon atoms, m 1 and n 1 each independently represent an integer from 0 to 6, a 1 and b 1 each independently represent an integer from 0 to 10, and R 1 ' and R 1 " are each independently selected from the group consisting of a hydrogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, and an optionally substituted aryl group with 6-20 carbon atoms; in general formula (1-2), R a2 and R b2 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, an optionally substituted alkoxyl group with 1-20 carbon atoms, an optionally substituted cycloalkyl group with 5-20 carbon atoms, an optionally substituted cycloalkoxyl group with 5-20 carbon atoms, an optionally substituted aryl group with 6-20 carbon atoms, an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, an optionally substituted aryloxy group with 6-20 carbon atoms, and -C≡C-R h2 , R h2 represents an optionally substituted aryl group with 6-20 carbon atoms or an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, X 2 is a single bond, an optionally substituted fluorene group, or any of the structural formulae represented by formulae (8)-(15) below: in formulae (8)-(15), R 61 , R 62 , R 71 , R 72, , R 81 , and R 82 each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, or an optionally substituted aryl group with 6-30 carbon atoms, or R 61 and R 62 or R 71 and R 72 bond to each other to form an optionally substituted carbon or heterocyclic ring with 1-20 carbon atoms, A 2 and B 2 each independently represent an optionally substituted alkylene group with 1-5 carbon atoms, m 2 and n 2 each independently represent an integer from 0 to 6, a 2 and b 2 each independently represent an integer from 0 to 10, and R 2 ' and R 2 " are each independently selected from the group consisting of a hydrogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, and an optionally substituted aryl group with 6-20 carbon atoms; in general formula (2-1), R c and R d are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, an optionally substituted alkoxyl group with 1-20 carbon atoms, an optionally substituted cycloalkyl group with 5-20 carbon atoms, an optionally substituted cycloalkoxyl group with 5-20 carbon atoms, an optionally substituted aryl group with 6-20 carbon atoms, an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, an optionally substituted aryloxy group with 6-20 carbon atoms, and -C≡C-R h3 , R h3 represents an optionally substituted aryl group with 6-20 carbon atoms or an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, Y 1 represents a single bond or an optionally substituted fluorene group, C 1 and D 1 each independently represent an optionally substituted alkylene group with 1-5 carbon atoms, p and q each independently represent an integer from 0 to 6, and c and d each independently represent an integer from 0 to 10; and in general formula (2-2), R e and R f are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, an optionally substituted alkoxyl group with 1-20 carbon atoms, an optionally substituted cycloalkyl group with 5-20 carbon atoms, an optionally substituted cycloalkoxyl group with 5-20 carbon atoms, and an optionally substituted aryl group with 6-20 carbon atoms, Y 2 is a single bond, an optionally substituted fluorene group, or any of the structural formulae represented by formulae (8)-(15) below: in formulae (8)-(15), R 61 , R 62 , R 71 , R 72, , R 81 , and R 82 each independently represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, or an optionally substituted aryl group with 6-30 carbon atoms, or R 61 and R 62 or R 71 and R 72 bond to each other to form an optionally substituted carbon or heterocyclic ring with 1-20 carbon atoms, and r and s each independently represent an integer from 0 to 5,000, E 2 and F 2 each independently represent an optionally substituted alkylene group with 1-5 carbon atoms, t and u each independently represent an integer from 0 to 4, and e and f each independently represent an integer from 0 to 10.
The method for producing a dicarboxylic acid compound according to claim 1, further comprising a first washing step in which the liquid mixture containing the dicarboxylic acid compound is washed with an acidic aqueous solution.
The method for producing a dicarboxylic acid compound according to claim 1, further comprising a first solution forming step in which the dicarboxylic acid compound is dissolved in a polar solvent to obtain the liquid mixture.
The method for producing a dicarboxylic acid compound according to claim 3, wherein in the first solution forming step, the dicarboxylic acid compound and the dihydroxy compound are dissolved in a polar solvent to obtain the liquid mixture, and in the crystallization step, a crystal of only the dicarboxylic acid compound is crystallized from the liquid mixture.
The method for producing a dicarboxylic acid compound according to claim 1, further comprising a second washing step in which the liquid mixture containing the dicarboxylic acid compound is washed with an organic solvent.
The method for producing a dicarboxylic acid compound according to claim 1, further comprising a second solution forming step in which the dicarboxylic acid compound is dissolved in an organic solvent to obtain the liquid mixture.
The method for producing a dicarboxylic acid compound according to claim 6, wherein in the second solution forming step, the dicarboxylic acid compound and the dihydroxy compound are dissolved in an organic solvent to obtain the liquid mixture, and in the crystallization step, a co-crystal of the dicarboxylic acid compound and the dihydroxy compound is crystallized from the liquid mixture.
The method for producing a dicarboxylic acid compound according to claim 1, further comprising a decomposition step in which a polyester carbonate resin and/or a polyester resin, which has at least a structural unit derived from a dicarboxylic acid compound represented by general formula (1-1') below or general formula (1-2') below, is decomposed to obtain the dicarboxylic acid compound represented by general formula (1-1) above or general formula (1-2) above: each symbol in general formula (1-1') is synonymous with the one in general formula (1-1) above, and each symbol in general formula (1-2') is synonymous with the one in general formula (1-2) above.
The method for producing a dicarboxylic acid compound according to claim 8, wherein in the decomposition step, the polyester carbonate resin and/or the polyester resin is dissolved in a first solvent and treated with an alkaline solution to obtain a reaction solution containing the first solvent and the dicarboxylic acid compound represented by formula (1-1) or formula (1-2) above, in the crystallization step, the dicarboxylic acid compound is crystallized from a liquid mixture subjected to crystallization which is obtained by adding a second solvent to the reaction solution, and the difference between the solubility of the dicarboxylic acid compound in the first solvent at 25°C and the solubility of the dicarboxylic acid compound in the second solvent at 25°C is 0.1 g/10 mL or more.
The method according to claim 9, wherein the content of the first solvent in the liquid mixture subjected to crystallization is 0.1-10 g/g relative to the total amount of the mixture of the dicarboxylic acid compound.
The method according to claim 9, wherein the content of the second solvent in the liquid mixture subjected to crystallization is 0.3-3 g/g relative to the total amount of the mixture of the dicarboxylic acid compound.
The method according to claim 9, wherein the total content of the first and second solvents in the liquid mixture subjected to crystallization is 1-10 g/g relative to the total amount of the dicarboxylic acid compound.
The method according to claim 9, wherein the ratio of the content of the first solvent (g/g) to the content of the second solvent (g/g) (first solvent/second solvent) in the liquid mixture subjected to crystallization is 0.8-10.
The method according to claim 1, wherein, in the crystallization step, a seed crystal of the dicarboxylic acid compound or the dihydroxy compound is added to the liquid mixture to crystallize a co-crystal of the dicarboxylic acid compound and the dihydroxy compound.
A method for producing a dicarboxylic acid compound represented by general formula (1-1) below or general formula (1-2) below, the method comprising: a crystallization step in which at least the dicarboxylic acid compound is crystallized from a liquid mixture containing the dicarboxylic acid compound, in general formula (1-1), R a1 and R b1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, an optionally substituted alkoxyl group with 1-20 carbon atoms, an optionally substituted cycloalkyl group with 5-20 carbon atoms, an optionally substituted cycloalkoxyl group with 5-20 carbon atoms, an optionally substituted aryl group with 6-20 carbon atoms, an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, an optionally substituted aryloxy group with 6-20 carbon atoms, and -C≡C-R h1 , R h1 represents an optionally substituted aryl group with 6-20 carbon atoms or an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, X 1 represents a single bond or an optionally substituted fluorene group, A 1 and B 1 each independently represent an optionally substituted alkylene group with 1-5 carbon atoms, m 1 and n 1 each independently represent an integer from 0 to 6, a 1 and b 1 each independently represent an integer from 0 to 10, and R 1 ' and R 1 " are each independently selected from the group consisting of a hydrogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, and an optionally substituted aryl group with 6-20 carbon atoms; and in general formula (1-2), R a2 and R b2 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, an optionally substituted alkoxyl group with 1-20 carbon atoms, an optionally substituted cycloalkyl group with 5-20 carbon atoms, an optionally substituted cycloalkoxyl group with 5-20 carbon atoms, an optionally substituted aryl group with 6-20 carbon atoms, an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, an optionally substituted aryloxy group with 6-20 carbon atoms, and -C≡C-R h2 , R h2 represents an optionally substituted aryl group with 6-20 carbon atoms or an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, X 2 is a single bond or an optionally substituted fluorene group, A 2 and B 2 each independently represent an optionally substituted alkylene group with 1-5 carbon atoms, m 2 and n 2 each independently represent an integer from 0 to 6, a 2 and b 2 each independently represent an integer from 0 to 10, and R 2 ' and R 2 " are each independently selected from the group consisting of a hydrogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, and an optionally substituted aryl group with 6-20 carbon atoms.
A method for producing a recycled resin, comprising a polymerization step in which a dicarboxylic acid compound produced by the method according to any one of claims 1-15 is polymerized.

Description

TECHNICAL FIELD The present invention relates to a method for producing a dicarboxylic acid compound, a method for producing a recycled resin, and the like. BACKGROUND ART In recent years, there have been growing concerns about the deterioration of the natural environment and the increase in discharged wastes, and the movement to reuse and recycle plastic products has been further fueled in an effort to realize a recycling-oriented society. Synthetic resins, such as polycarbonate resins, are major components of plastic products and have been widely used in various applications, including home appliances, electronic and electrical equipment, office automation equipment, optical media, automotive parts, and construction components. Since large amounts of waste materials from the synthetic resins are discharged during the manufacture of the plastic products and after the use of the plastic products, these waste materials are reused. In particular, when a synthetic resin is molded to manufacture a plastic product, the portions originating from the mold passages, such as the sprue, runner, and gate, are removed to form the plastic product. Efforts have been made to recycle, rather than dispose, such an unwanted synthetic resin removed from the plastic product, as well as other waste resins such as defective molded products, to reuse them in products. For example, Patent literature 1 describes a method for recovering a polycarbonate resin, the method comprising a step of comminuting waste optical discs and/or recovered optical discs having a polycarbonate resin substrate and chemically treating the resulting comminuted material. In such a recovery method, the chemically treated product obtained in the chemical treatment step undergoes the steps of: removing magnetic metallic foreign matter using a magnet, removing colored foreign matter using an optical camera, and removing a resin containing metallic foreign matter using a metallic foreign matter detector. There are also known methods for recycling waste resin compositions and reusing compounds that have been used as resin feedstocks (e.g. Patent literature 2). PRIOR ART DOCUMENTS PATENT DOCUMENTS Patent literature 1: Japanese Patent Publication No. 2011-131507Patent literature 2: International Publication WO2023/058599 SUMMARY OF THE INVENTION PROBLEMS TO BE SOLVED BY THE INVENTION Among the conventional methods for recovering synthetic resins, for example, in the method described in Patent literature 1, the synthetic resin is recovered, for example, based on the metal contained or the appearance of the coloration. However, if there is no significant difference in the presence or absence of metal content, degree of coloration, etc. between the desired synthetic resin and other unwanted organic impurities, efficient recovery of the desired synthetic resin may be difficult. Additionally, the types of resins that can be recovered and reused are limited in the conventional methods for recycling waste resin compositions. Under such circumstances, there is a need for a new method for efficiently recycling a waste resin composition and reusing a wider variety of resins than before. Therefore, the main purpose of the present invention is to provide a method for recycling a waste resin composition containing a synthetic resin to enable the reuse of a wider variety of resins than before. MEANS FOR SOLVING THE PROBLEMS The present invention has, for example, the following aspects. [1] A method for producing a dicarboxylic acid compound represented by general formula (1-1) below or general formula (1-2) below, the method comprising: a crystallization step in which at least the dicarboxylic acid compound is crystallized from a liquid mixture containing the dicarboxylic acid compound and a dihydroxy compound represented by general formula (2-1) below or general formula (2-2) below: in general formula (1-1),Ra1 and Rb1 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl group with 1-20 carbon atoms, an optionally substituted alkoxyl group with 1-20 carbon atoms, an optionally substituted cycloalkyl group with 5-20 carbon atoms, an optionally substituted cycloalkoxyl group with 5-20 carbon atoms, an optionally substituted aryl group with 6-20 carbon atoms, an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S, an optionally substituted aryloxy group with 6-20 carbon atoms, and -C≡C-Rh1,Rh1 represents an optionally substituted aryl group with 6-20 carbon atoms or an optionally substituted heteroaryl group with 6-20 carbon atoms containing one or more heteroatoms selected from O, N, and S,X1 represents a single bond or an optionally substituted fluorene group,A1 and B1 each independently represent an optionally substituted alkylene group with 1-5 carbon atoms,m1 and n1 each independently represent an integer from 0 to 6,a1 and b1 each