Analyses of Reaction Mechanisms among Different Sulfonation Reagents and <i>m</i>-Diphenylamine and Crystal Structures of the Formed Compounds
- 1 Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’anshan, China
- 2 Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’anshan, China
- 3 Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’anshan, China
- 4 Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’anshan, China
- 5 Institute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma’anshan, China
Abstract
In the traditional process, <i>m</i>-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 <i>m</i>-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 <b>1</b> from raw material and sulfur trioxide (SO<sub>3</sub>); 2) rapid reaction of raw material and chlorosulfonic acid to synthesize bisulfonated compound <b>2</b>; 3) direct eutectic crystallization of raw material and ordinary sulfuric acid to obtain compound <b>3</b>. The crystal structure of the compounds synthesized by three paths was analyzed by X-ray single crystal diffraction, and compound <b>1</b> was characterized by NMR, Fourier infrared spectra, UV-visible spectrum and Mass spectrometry. The one-step synthesis of SO<sub>3</sub> as a sulfonation reagent has the advantages of mild reaction conditions, simple operation and low cost.
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