1. Efficient and Controllable Synthesis of 1-Aminoanthraquinone via High-Temperature Ammonolysis Using Continuous-Flow Method
- Author
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Feng Zhou, Lei Cai, Wenjie Ye, Kai Zhu, Jin Li, Yanxing Li, Weichuan Xu, Pan Wang, and Chuansong Duanmu
- Subjects
Chemistry (miscellaneous) ,Organic Chemistry ,Drug Discovery ,Molecular Medicine ,Pharmaceutical Science ,Physical and Theoretical Chemistry ,ammonolysis ,continuous-flow ,1-aminoanthraquinone ,optimization ,kinetic ,Analytical Chemistry - Abstract
Anthraquinone dyes are the second most important type of dyes after azo dyes. In particular, 1-aminoanthraquinone has been extensively utilized in the preparation of diverse anthraquinone dyes. This study employed a continuous-flow method to synthesize 1-aminoanthraquinone safely and efficiently through the ammonolysis of 1-nitroanthraquinone at high temperatures. Various conditions (reaction temperature, residence time, molar ratio of ammonia to 1-nitroanthraquinone (M-ratio), and water content) were investigated to explore the details of the ammonolysis reaction behavior. Operation conditions for the continuous-flow ammonolysis were optimized using Box–Behnken design in the response surface methodology, and ~88% yield of 1-aminoanthraquinone could be achieved with an M-ratio of 4.5 at 213 °C and 4.3 min. The developed process’s reliability was evaluated by performing a 4 h process stability test. The kinetic behavior for the preparation of 1-aminoanthraquinone was investigated under continuous-flow mode to guide the reactor design and to gain a deeper understanding of the ammonolysis process.
- Published
- 2023
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