Electrochemical Cyclobutane Synthesis in Flow: Scale-Up of a Promising Melt-Castable Energetic Intermediate

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...

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Bibliographic Details
Published in:Organic process research & development 2021-12, Vol.25 (12), p.2639-2645
Main Authors: Chen, Longrui, Barton, Lisa M, Vantourout, Julien C, Xu, Yinghua, Chu, Chengpu, Johnson, Eric C, Sabatini, Jesse J, Baran, Phil S
Format: Article
Language:English
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Summary: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.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.0c00270