Analyses of Reaction Mechanisms among Different Sulfonation Reagents and m-Diphenylamine and Crystal Structures of the Formed Compounds  

作　　者：Dongdong Chen Chundong Mi Menglan Yuan Aiquan Jia Qian-Feng Zhang Dongdong Chen;Chundong Mi;Menglan Yuan;Aiquan Jia;Qian-Feng Zhang(Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’,anshan, China)

机构地区：[1]Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’,anshan, China

出　　处：《Journal of Materials Science and Chemical Engineering》2024年第4期84-97,共14页材料科学与化学工程（英文）

摘　　要：In the traditional process, m-phenylenediamine reacts with fuming sulfuric acid at high temperature to get intermediates, and then after dehydration occurs intramolecular rearrangement to get 2,4-diaminobenzenesulfonic acid. Traditional methods need to consume a lot of fuming sulfuric acid or concentrated sulfuric acid, resulting in high industrial large-scale production cost, more waste, and posing a serious environmental pollution risk. In this thesis, three different sulfonation reagents were used for the sulfonation reaction of m-phenylenediamine, and the reaction mechanisms and crystal structures of the three pathways were investigated. The three routes are: 1) one-step synthesis of monosulfonated compound 1 from raw material and sulfur trioxide (SO₃);2) rapid reaction of raw material and chlorosulfonic acid to synthesize bisulfonated compound 2;3) direct eutectic crystallization of raw material and ordinary sulfuric acid to obtain compound 3. The crystal structure of the compounds synthesized by three paths was analyzed by X-ray single crystal diffraction, and compound 1 was characterized by NMR, Fourier infrared spectra, UV-visible spectrum and Mass spectrometry. The one-step synthesis of SO₃ as a sulfonation reagent has the advantages of mild reaction conditions, simple operation and low cost.In the traditional process, m-phenylenediamine reacts with fuming sulfuric acid at high temperature to get intermediates, and then after dehydration occurs intramolecular rearrangement to get 2,4-diaminobenzenesulfonic acid. Traditional methods need to consume a lot of fuming sulfuric acid or concentrated sulfuric acid, resulting in high industrial large-scale production cost, more waste, and posing a serious environmental pollution risk. In this thesis, three different sulfonation reagents were used for the sulfonation reaction of m-phenylenediamine, and the reaction mechanisms and crystal structures of the three pathways were investigated. The three routes are: 1) one-step synthesis of monosulfonated compound 1 from raw material and sulfur trioxide (SO₃);2) rapid reaction of raw material and chlorosulfonic acid to synthesize bisulfonated compound 2;3) direct eutectic crystallization of raw material and ordinary sulfuric acid to obtain compound 3. The crystal structure of the compounds synthesized by three paths was analyzed by X-ray single crystal diffraction, and compound 1 was characterized by NMR, Fourier infrared spectra, UV-visible spectrum and Mass spectrometry. The one-step synthesis of SO₃ as a sulfonation reagent has the advantages of mild reaction conditions, simple operation and low cost.

关 键 词：2 4-Diaminobenzenesulfonic Acid Sulfur Trioxide (SO₃) Spectrometry Crystal Structure 

分 类 号：O62[理学—有机化学]