Electrochemical Cyclobutane Synthesis in Flow: Scale-Up of a Promising Melt-Castable Energetic Intermediate,Organic Process Research & Development

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Electrochemical Cyclobutane Synthesis in Flow: Scale-Up of a Promising Melt-Castable Energetic Intermediate
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2020-07-27 , DOI: 10.1021/acs.oprd.0c00270
Longrui Chen ₁ , Lisa M. Barton ₁ , Julien C. Vantourout ₁ , Yinghua Xu ₂ , Chengpu Chu ₂ , Eric C. Johnson ₃ , Jesse J. Sabatini ₃ , Phil S. Baran ₁

Affiliation

The design of a scalable, safe, and robust route to a promising energetic material containing a cyclobutane and four nitric ester groups is described. This route includes a streamlined preparation of a linear cyclobutane precursor, the use of safe methods for tetraester reduction and nitration, and the translation of a small-scale batch electrochemical oxidative cyclization to forge the cyclobutane to a continuous flow setup capable of producing quantities of more than 100 g in a single run. In principle, this scale was limited only by the space considerations of an academic lab, as a larger reservoir would enable kilogram-scale preparations. Lessons learned from an engineering and reaction optimization standpoint in this electrochemical scale-up are also discussed.

中文翻译：

流动中的电化学环丁烷合成：一种有前景的可熔浇注高能中间体的放大

描述了一种可扩展的、安全的和稳健的路线设计，用于获得含有环丁烷和四个硝酸酯基团的有前途的含能材料。该路线包括线性环丁烷前体的流线型制备，使用安全的四酯还原和硝化方法，以及将小规模批量电化学氧化环化转化为能够生产更多数量的环丁烷的连续流动装置。单次运行超过 100 克。原则上，这个规模仅受学术实验室空间考虑的限制，因为更大的水库可以实现公斤级的制备。还讨论了在这种电化学放大过程中从工程和反应优化的角度学到的经验教训。

更新日期：2020-07-27

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