Iharanikkei Chemical Industry for toluene chlorination, photochlorination and chlorine technology

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Conference and Journal Presentations


2025

Journal

Sodium Hypochlorite Pentahydrate as an Environmentally Benign Oxidizing Agent: Effective Synthesis of Carboxylic Acids from Primary Alcohols and Sulfones from Sulfides開く
Kirihara, M; Shimazu, H; Kawai, T; Kinoshita, Y; Sakamoto, Y; Akiyama, T; Osugi, E; Kikkawa, Y; Okada, T; Kimura, Y:
Synthesis, 2025, 57, 1742-54


2024

Journal

Metal-Free Photooxidation of Toluene Derivatives into the Corresponding Carboxylic Acids and Aldehydes by a HBr/NaOCl·5H2O System開く
Masayuki Kirihara, Takuma Kawai, Atsuhito Kitajima, Sho Yamahara, Nena Mori, Yoshikazu Kimura, ChemistrySelect 2024,9

Sustainable synthesis of fine chemicals and polymers using industrial chlorine chemistry開く
Yasuhiro Kohsaka, Daisuke Matsuura, Yoshikazu Kimura, Communications chemistry (2024)7:265

Green and Efficient Protocols for the Synthesis of Sulfonyl Fluorides Using Potassium Fluoride as the Sole Fluorine Source開く
Sho Yamahara, Mohamed S. H. Salem, Takuma Kawai, Mai Watanabe, Yugo Sakamoto, Tomohide Okada, Yoshikazu Kimura, Shinobu Takizawa, Masayuki Kirihara, ACS Sustainable Chemistry & Engineering 2024.12, 12135-12142

Product Selectivity Control under Acidic and Basic Conditions on Oxidative Transformation of 1,3-Dicarbonyls Using Sodium Hypochlorite Pentahydrate
開く
Masayuki Kirihara, Yugo Sakamoto, Takumi Tanaka, Takuma Kawai, Tomohide Okada, Yoshikazu Kimura, Shinobu Takizawa, Synthesis 2024, 56, 1873-1880

Synthesis of itaconyl dichloride with high purity and its application to polycondensation開く
Ryo Kawatani, Yoshino Aoki, Souichi Tezuka, Yoshikazu Kimura, Yasuhiro Kohsaka, Tetrahedron 161 (2024) 134071

Phthaloyl Dichloride: Synthesis, Its applications and the Related Reagents開く
Yoshikazu Kimura, The Society of Synthetic Organis Chemistry (SSOCJ) Journals, Vol.82 No.8 2024


2023

Journal

Practical Synthesis of Pent-4-yn-1-ol and Pent-4-en-1-ol from Tetrahydrofurfuryl Halides開く
Katsuya Saito, Tomoya Sawazakima, Osamu Furusawa, Teruo Kosugi, Yoshikazu Kimura, Masayuki Kirihara, Synthesis 2023, 55, 2670

Conference Presentations

Synthesis of monomer-oriented acid chlorides開く
Yoshikazu Kimura,  Research group for the creation of functional resins governed by monomer-oriented exchange, transformation and cleavage of covalent bonds Invited lecture at Shinshu University;December 14, 2023.

Visible-light oxidation of toluene derivatives via bromination with excellent atom economy開く
Yoshikazu Kimura, Nena Mori, Sho Yamahara, Atsuhito Kitajima, Masayuki Kirihara
The Japanese Society for Process Chemistry, 2022 Summer Symposium 1P-02;Tokyo, August 3-4, 2023.

Chlorination and photobromination of toluenes開く
Yoshikazu Kimura, 2023 Mini-symposium on the use of halogens;Kochi, December 1, 2023

Chlorination of aromatic compounds using sodium hypochlorite pentahydrate開く
Takuma Kawai, Takumi Tanaka, Yoshikazu Kimura, Masayuki Kirihara
Symposium on Advances in Reactions and Synthesis;Gifu, November 2023

2022

Journal

Aerobic photooxidation of toluene derivatives into carboxylic acids with bromine-water under catalyst-free conditions開く
Aerobic photooxidation of toluene derivatives into carboxylic acids with bromine-water under catalyst-free conditions.
Kirihara, M.; Sakamoto, Y.; Yamahara, S.; Kitajima, A.; Kugisaki, N.; Kimura, Y. Synlett, 2022, 33, 1670-1674.A novel method was developed to synthesize the corresponding benzoic acid derivatives in high yields by adding 2 equivalents of bromine to toluene derivatives and irradiating them with visible or ultraviolet light in the presence of air.

Synthesis of sulfonyl halides from disulfides or thiols using sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals開く
Synthesis of sulfonyl halides from disulfides or thiols using sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals
Kirihara, M.; Yamahara, S.; Okada, T.; Matsumuro, H.; Kinoshita, Y.; Titajima, A.;Takamura, Y.; Odagiri, T.; Asawa, T. Sugiyama, Y.; Kimura, Y. Synthesis 2022, 54, 4120-4128.
Sulfonyl chlorides were synthesized by the reaction of disulfides or thiols with sodium hypochlorite pentahydrate in acetic acid, and sulfonyl bromides were obtained in the presence of NaBr. A simple synthetic method was developed to obtain sulfonyl chlorides by blowing carbon dioxide gas through benzotrifluoride solvent instead of acetic acid.

Conference Presentations

Sulfonyl fluoride using potassium fluoride with sodium hypochlorite pentahydrate開く
Watanabe, M.; Yamahara, S.; Okada, T.; Kimura, Y.; Takizawa, S.; Kirihara. M.  45th Fluorine Conference of Japan, P-19, Kyoto, November 1, 2022.

Aerobic photo oxidation of toluenes to benzoic acids by HBr-NaOCl •5H2O開く
Kitajima, A.; Tanaka, T.; Takamura, Y.; Kugisaki, N.; Kimura, Y.; Kirihara, M. The Japanese Society for Process Chemistry, 2022 Summer Symposium, 1P-21;Toyama, June 30, 2022.

Catalysts free aerobic photo-oxidation of aromatic aldehydes to benzoic acids開く
Takamura, Y.; Kitajima, A.;Yamahara, S.; Kugisaki, N.; Kimura, Y.; Kirihara, M. The Japanese Society for Process Chemistry  2022 Summer Symposium 1P-22;Toyama, June 30, 2022.

Practical synthesis of sulfonyl fluoride using potassium fluoride開く
Yamahara, S.; Watanabe, M; Kimura, Y.; Kirihara, M.  The Japanese Society for Process Chemistry  2022 Summer Symposium 1P-23;Toyama, June 30, 2022.

Itaconyl dichloride for the synthesis of polyesters/polyamides開く
Aoki, Y.; Kawatani, R.; Kousaka, Y.; Matsuura, D.; Onogawa, Y,; Kimura, Y. 31th Polymer Materials Forum,  2PA17, Tokyo, November 15, 2022,



2021

Journal

Chloroamidation of alkenes using sodium hypochlorite pentahydrate and its application to synthesis of aziridines開く
Chloroamidation of alkenes using sodium hypochlorite pentahydrate and its application to synthesis of aziridines
Kirihara, M.; Adachu, K.; Sakamoto, Y.; Tujimoto, K.; Yamahara, S.; Matsushima, R.; Namba, Y.; Sato, K.; Kamada, T.; Kimura, Y.; Takizawa, S. Heterocycles 2021, 103, 699-706.
The reaction of sodium hypochlorite pentahydrate and nitrile compounds with alkenes in the absence of a catalyst gave chloroamidation products, and a novel route was developed to synthesize aziridine derivatives by treatment with alkali.

Synthesis of polyarylate and aliphatic polyesters by divalent acyl-1,2,4-triazole: A route to metal-free synthesis at low temperature開く
Synthesis of polyarylate and aliphatic polyesters by divalent acyl-1,2,4-triazole: a route to metal-free synthesis at low temperature
Kohsaka, Y.; Mori, I.; Homma, K.; Akae, Y.; Matuura, D.; Kimura, Y. Polymer J. 2021, 53, 887-893.
A new method was developed to synthesize various polyesters from bifunctional acyltriazoles and alcohols under halogen-free conditions without using metal catalysts.

Oxidation of fluoroalkyl alcohols using sodium hypochorite pentahydrate開く
Oxidation of fluoroalkyl alcohols using sodium hypochorite pentahydrate
Kirihara, M.; Suzuki, K.; Nakakura, K.; Saito, K.; Nakamura, R.; Tujimoto, K.; Sakamoto, Y.; Kikkawa, Y.; Shimazu, H.; Kimura, Y. J. Fluorine Chem. 2021, 243, 109719
It is known that alcohols with fluoro chains such as CF3 and CHF2 are not easily oxidized. Oxidation of fluorochain-containing secondary alcohols to the ketones and primary alcohols to the aldehydes with sodium hypochlorite pentahydrate in the presence of TEMPO were found to occur in high yields.


2020

Journal

Organic syntheses using sodium hypochlorite pentahydrate (NaOCl • 5H2O) crystals開く
Kirihara, M.; Okada, T.; Asawa, T.; Sugiyama, Y.; Kimura,Y.  Journal of Synthetic Oraganic Chemistry, Japan, Vol. 78, pp 11–27, 2020.
2017 Synthetic Organic Chemistry Award, Japan



2019

Journal

Sodium hypochlorite pentahydrate as a reagent for the cleavage of trans-cyclic glycols 開く
Sodium hypochlorite pentahydrate as a reagent for the cleavage of trans-cyclic Glycols
trans-cyclic
Kirihara, M.; Osugi, R.; Saito, K.; Adachi, K.; Yamazaki, K.; Matsushima, R.; Kimura, Y. J. Org. Chem. 2019, 84, 8330-8336.
Trans-1,2-glycols, which are not easily oxidized, were efficiently cleaved by sodium hypochlorite pentahydrate to give dicarbonyl compounds.

Direct Formylation of fluorine-containing aromatics with dichloromethyl alkyl ethers開く
Direct Formylation of florine-containing aromatics with dichloromethyl alkyl ethers
Warashina, T.; Matsuura, D.; Kimura, Y. Chem. Pharm. Bull. 2019, 67, 587-593.
Highlighted paper selected by editor-in-chief

Formylations of fluorine-containing aromatic compounds with dichloromethyl alkyl ethers were investigated. Dichloromethyl propyl ether and dichloromethyl butyl ether applied to  the formylation of fluorine-containing aromatics to give the corresponding aldehydes in good yields.

Regioselective formylation of pyrrole-2-carboxylate: Crystalline Vilsmeier reagent vs dichloromethyl alkyl ether開く
Regioselective formylation of pyrrole-2-carboxylate: crysatalline Vilsmeier reagent vs dichloromethyl alkyl ether
Warashina, T.; Matsuura, D.; Sengoku, T.; Takahashi, M.; Yoda, H; Kimura, Y. Org. Process Res. Dev. 2019, 23, 614-618.

A novel synthetic method for solid Vilsmeier reagents and dichloromethyl alkyl ethers was developed. Formylation of pyrroles with an ester group at the 2-position were investigated with the reagents above, and were found to be formylated with high selectivity at different positions. Those products are useful medicinal raw materials.

A novel synthetic method for solid Vilsmeier reagents and dichloromethyl alkyl ethers was developed. Formylation of pyrroles with an ester group at the 2-position were investigated with the reagents above, and were found to be formylated with high selectivity at different positions. Those products are useful medicinal raw materials.開く
A concise, catalyst-free synthesis of Davis’ oxaziridines using sodium hypochlorite
Kitagawa, S.; Mori, H.; Odagiri, T.; Suzuki, K.; Kikkawa, Y.: Osugi.; R.; Takizawa, S.; Kimura, Y.; Kirihara, M. SynOpen 2019, 3, 21-25.

A highly selective synthesis of N-sulfonyloxaziridine (Davis' oxaziridine) was developed by reaction of N-sulfonylimine with sodium hypochlorite pentahydrate without any catalyst which is a less dangerous oxidation method.

Efficient preparation of dichloromethyl alkyl ethers and their application in the formylation of aromatic compounds: Scope and limitations開く
Efficient preparation of dichloromethyl alkyl ethers and their application in the formylation of aromatic compounds: scope and limitations
Warashina, T.; Matsuura, D.; Kimura, Y. Tetrahedron 2019, 75, 608-616.

A new synthetic method for dichloromethyl alkyl ethers using alkyl formate and oxalyl chloride in the presence of N-methylformanilide was developed, and their formylating abilities were examined. There was a correlation between the length of the alkyl group and the reaction substrate.



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