Journal of Flow Chemistry
Volume/Issue:
Volume 2: Issue 1
Safe Generation and Synthetic Utilization of Hydrazoic Acid in a Continuous Flow Reactor
Authors:
Bernhard Gutmann Christian Doppler Laboratory for Microwave Chemistry and Institute of Chemistry, Karl-Franzens-University Graz, A-8010, Heinrichstrasse 28, Graz, Austria

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David Obermayer Christian Doppler Laboratory for Microwave Chemistry and Institute of Chemistry, Karl-Franzens-University Graz, A-8010, Heinrichstrasse 28, Graz, Austria

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Jean-Paul Roduit Microreactor Technology, Lonza AG, CH-3930, Visp, Switzerland

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Dominique M. Roberge Microreactor Technology, Lonza AG, CH-3930, Visp, Switzerland

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C. Oliver Kappe Microreactor Technology, Lonza AG, CH-3930, Visp, Switzerland

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Pages:
8–19
Online Publication Date:
21 Mar 2012
Publication Date:
21 Mar 2012
Article Category:
Research Article
DOI:
https://doi.org/10.1556/jfchem.2012.00021
Keywords:
flow chemistry; hydrazoic acid; microreactor; process intensification; tetrazoles
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Abstract

Hydrazoic acid (HN3) was used in a safe and reliable way for the synthesis of 5-substitued-1H-tetrazoles and for the preparation of N-(2-azidoethyl)acylamides in a continuous flow format. Hydrazoic acid was generated in situ either from an aqueous feed of sodium azide upon mixing with acetic acid, or from neat trimethylsilyl azide upon mixing with methanol. For both processes, subsequent reaction of the in situ generated hydrazoic acid with either organic nitriles (tetrazole formation) or 2-oxazolines (ring opening to β-azido-carboxamides) was performed in a coil reactor in an elevated temperature/pressure regime. Despite the explosive properties of HN3, the reactions could be performed safely at very high temperatures to yield the desired products in short reaction times and in excellent product yields. The scalability of both protocols was demonstrated for selected examples. Employing a commercially available benchtop flow reactor, productivities of 18.9 g/h of 5-phenyltetrazole and 23.0 g/h of N-(1-azido-2-methylpropan- 2-yl)acetamide were achieved.

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Cover Journal of Flow Chemistry
Journal of Flow Chemistry A Journal of the Flow Chemistry Society
Print ISSN:
2062-249X
Online ISSN:
2063-0212

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Journal of Flow Chemistry
Language English
Size A4
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Foundation		 2011
Volumes
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Issues
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Founder Áramlásos Kémiai Tudományos Társaság
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Springer Nature Switzerland AG
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ISSN 2062-249X (Print)
ISSN 2063-0212 (Online)

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