JP-2026075237-A - A method for producing organic compounds, a method for producing polystyrene sulfonic acid, a method for producing conductive composites, and a method for producing conductive polymer dispersions.

JP2026075237AJP 2026075237 AJP2026075237 AJP 2026075237AJP-2026075237-A

Abstract

[Problem] To provide a method for producing organic compounds that allows for easy dehalogenation of halogenated organic compounds. [Solution] A method for producing an organic compound, comprising adding magnesium and water to a mixture containing a first organic compound and a second organic compound which is a halogenated product thereof, and dehalogenating the second organic compound to obtain the first organic compound, wherein the first organic compound may have at least one of a vinyl group, an aromatic ring, and a sulfonic acid group or a salt thereof, and specifically may be styrene sulfonic acid or a salt thereof. [Selection Diagram] None

Inventors

松林総

Assignees

信越ポリマー株式会社

Dates

Publication Date: 20260508
Application Date: 20241022

Claims (10)

A method for producing an organic compound, comprising adding magnesium and water to a mixture containing a first organic compound and a second organic compound which is a halogenated form of the first organic compound, and dehalogenating the second organic compound to obtain the first organic compound.
A method for producing an organic compound according to claim 1, comprising adding the magnesium to a solution obtained by dissolving or dispersing the mixture in a solvent.
The method for producing an organic compound according to claim 2, wherein the solvent is water.
A method for producing an organic compound according to any one of claims 1 to 3, wherein the first organic compound has a vinyl group.
A method for producing an organic compound according to any one of claims 1 to 3, wherein the first organic compound has an aromatic ring.
A method for producing an organic compound according to any one of claims 1 to 3, wherein the first organic compound has a sulfonic acid group or a salt thereof.
A method for producing an organic compound according to any one of claims 1 to 3, wherein the first organic compound is styrene sulfonic acid or a salt thereof.
A step of obtaining styrene sulfonic acid or a salt thereof by a method for producing an organic compound according to claim 7, A step of polymerizing the styrene sulfonic acid or a salt thereof to obtain polystyrene sulfonic acid or a salt thereof, A method for producing polystyrene sulfonic acid, including the method described above.
A step of obtaining the polystyrene sulfonic acid by the method for producing polystyrene sulfonic acid described in claim 8, A step of polymerizing monomers that form a π-conjugated conductive polymer in an aqueous dispersion medium in the presence of polystyrene sulfonic acid to form a conductive composite containing the π-conjugated conductive polymer and the polystyrene sulfonic acid, A method for producing a conductive composite, including [the specified element].
The conductive composite is obtained by the method for producing the conductive composite described in claim 9, A method for producing a conductive polymer dispersion, comprising the step of dispersing the conductive composite in a dispersion medium to obtain a conductive polymer dispersion.

Description

This invention relates to a method for producing a conductive polymer dispersion containing a π-conjugated conductive polymer and a polyanion. π-conjugated conductive polymers, whose main chains are composed of π-conjugated groups, form conductive composites and their conductivity is enhanced by doping with polyanions containing anionic groups. Patent Document 1 discloses a method for producing a conductive composite, comprising the steps of: polymerizing a polymerizable anion using a predetermined polymerization initiator to obtain a polyanion; and polymerizing a monomer that forms a π-conjugated conductive polymer in the reaction solution obtained from the polyanion to obtain a conductive composite. The obtained conductive composite can be dispersed in water and has been shown to have excellent storage stability. Patent Document 2 discloses a method for producing a conductive solid that can precipitate in water by reducing the weight-average molecular weight of the polyanions constituting the conductive composite and the polyanion content ratio to the π-conjugated conductive polymer to 1 or less. This reduces the excess anionic groups that do not participate in doping, thereby suppressing dispersibility in water. Patent Document 3 discloses the use of polyanions having a naphthalene skeleton and sulfonic acid groups in repeating units as polyanions constituting conductive composites, in addition to the commonly used polystyrene sulfonic acid. It has been shown that the use of these naphthalene sulfonic acid compounds improves conductivity. Incidentally, methods for producing styrene sulfonic acids, which are monomers of polystyrene sulfonic acids, have been studied for some time. For example, a method is known in which styrene or β-phenethyl alcohol is used as a starting material, and a sulfonic acid group is introduced using β-bromoethylbenzene as an intermediate to obtain styrene sulfonic acids. In this series of synthesis processes, bromine and chlorine may remain as impurities, and attempts have been made to remove halogen impurities for applications requiring precise chemistry (for example, Patent Documents 4 and 5). Japanese Patent Publication No. 2024-089947Japanese Patent Publication No. 2022-052253Japanese Patent Publication No. 2023-007679International Publication No. 2014/061357Japanese Patent Publication No. 2023-131236 Methods for producing organic compounds A first aspect of the present invention is a method for producing an organic compound, comprising adding magnesium and water to a mixture containing a first organic compound and a second organic compound which is a halogenated product thereof, and dehalogenating the second organic compound to obtain the first organic compound. When R represents the atomic group constituting part or all of an organic compound, X represents the halogen, M represents the metal, and RX represents the halogenated atomic group of the organic compound, the metal-halogen exchange shown in formula (1) below occurs. Furthermore, as shown in formula (2) below, the resulting organometallic compound (RM) is hydrolyzed. (1)...RX+M→RMX (2)...RMX+ H2O →RH+MOH Here, if M is Mg, the dehalogenation reaction is represented by the following reaction equation. (1')...RX+Mg→RMgX (2')...RMgX+ H2O →RH+MgOHX In this embodiment, it is considered that the metallic magnesium undergoes metal-halogen substitution with the second organic compound as shown in formulas (1) and (2) above, and then undergoes hydrolysis with water to produce the first organic compound. However, the reaction mechanism in this embodiment is not limited to the above, and the first organic compound may be produced by other reaction mechanisms. In the above mixture, the upper limit of the mass-based content ratio of the bonded halogen m3 to the sum of the content m1 of the first organic compound and the content m2 of the second organic compound (m1 + m2), expressed as (m3/(m1 + m2)), is preferably 5% by mass or less, more preferably 1% by mass or less, even more preferably 0.5% by mass or less, and most preferably 0.1% by mass or less (1000 ppm or less). The lower limit is greater than 0% by mass, preferably 10 ppm or more, and more preferably 100 ppm or more. Within the preferred content ratio range described above, it becomes easy to obtain a first organic compound with increased purity by removing the halogenated compounds. From the viewpoint of increasing the reaction efficiency between the second organic compound and magnesium, it is preferable to add magnesium to a solution obtained by dissolving or dispersing the mixture in a solvent. In this specification and the claims, when an operation is performed on a mixture in a solution (for example, when magnesium is added), the phrase "an operation is performed on the mixture" may also be used. From the viewpoint of increasing the solubility of the first and second organic compounds in the solvent and enhancing their reactivity with magnesium, the molecular weig