The Mechanochemical Beckmann Rearrangement over Solid Acids: From the Ball Mill to the Extruder

IF 6.1 Q1 CHEMISTRY, MULTIDISCIPLINARY
Daniel M. Baier, Tilo Rensch, Desislava Dobreva, Carolina Spula, Stephen Fanenstich, Marisol Rappen, Konrad Bergheim, Dr. Sven Grätz, Prof. Dr. Lars Borchardt
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引用次数: 2

Abstract

Beckmann rearrangement was carried out in the solid state in a ball mill using metal oxides as solid acids. After a comprehensive investigation of different reaction parameters, acids as well as further additives, a combination of aluminosilicate materials, phosphorus pentoxide, and para-toluenesulfonic acid was identified as the optimal system. This allowed the model compounds ϵ-caprolactam and acetanilide to be obtained in yields of 46 % and 94 %, respectively, while the robustness of the method was demonstrated by applying it to additional substrates. Finally, we scaled up our optimized reaction into a continuous process using a twin screw extruder. With this, yields beyond 90 % could be achieved in a residence time as low as seven minutes.

Abstract Image

固体酸的机械化学贝克曼重排:从球磨机到挤出机
贝克曼重排是在固体状态下在球磨机中使用金属氧化物作为固体酸进行的。在综合考察了不同的反应参数、酸以及其他添加剂后,确定了铝硅酸盐材料、五氧化二磷和对甲苯磺酸的组合为最佳体系。这使得模型化合物ϵ-caprolactam和乙酰苯胺的产率分别为46%和94%,而将该方法应用于其他底物则证明了该方法的稳健性。最后,我们扩大了我们的优化反应成一个连续过程使用双螺杆挤出机。这样,在低至7分钟的停留时间内,收率可以达到90%以上。
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CiteScore
7.30
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