Efficient and Controllable Synthesis of 1-Aminoanthraquinone via High-Temperature Ammonolysis Using Continuous-Flow Method.

Molecules

National & Local Joint Engineering Research Center for Deep Utilization Technology of Rock-Salt Resource, Faculty of Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, China.

Published: May 2023


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Article 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 (), 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 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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254563PMC
http://dx.doi.org/10.3390/molecules28114314DOI Listing

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