Optimization of continuous-flow diphenyldiazomethane synthesis: an integrated undergraduate chemistry experiment
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Optimization of continuous-flow diphenyldiazomethane synthesis: an integrated undergraduate chemistry experiment Luuk T. C. G. van Summeren 1 & Jan Gerretzen 2 & Floris P. J. T. Rutjes 1,3 & Tom G. Bloemberg 1,3 Received: 30 May 2020 / Accepted: 5 August 2020 # The Author(s) 2020
Abstract We present a challenging flow-chemistry experiment concerning the synthesis of diphenyldiazomethane using the OmuraSharma-Swern oxidation, that we have developed and used in our second-year undergraduate lab classes over the past seven years. The experiment integrates a number of different aspects and concepts of chemistry that are traditionally taught as separate subjects in undergraduate chemical education: organic synthesis, quantitative chemical analysis, design of experiments, optimization, statistical modelling, computer programming and continuous-flow processes. Keywords Diphenyldiazomethane . Chemical education . Flow chemistry . Experimental design . DoE
Introduction Although continuous-flow processes are a mainstay of industrial bulk chemistry, the advent of microreactors has constituted a paradigm change in laboratory-scale synthetic chemistry. As such, it is important that this is also reflected in chemical education programmes [1]. At the same time, by its nature, flow chemistry also offers opportunities for integrating parts of chemical education in lab courses that are otherwise hard to incorporate. Highlights • A challenging undergraduate flow chemistry experiment is presented • A new manner of producing diazo compounds in flow chemistry is presented • Ideas for extension of the experiment are provided Electronic supplementary material The online version of this article (https://doi.org/10.1007/s41981-020-00107-4) contains supplementary material, which is available to authorized users. * Tom G. Bloemberg [email protected] 1
Educational Institute for Molecular Sciences, Radboud University, Heyendaalsweg 135, 6525, AJ Nijmegen, The Netherlands
2
Nouryon Chemicals B.V., Integrated Supply Chain, Advanced Analytics and Control, Zutphenseweg 10, 7418, AJ Deventer, The Netherlands
3
Institute for Molecules and Materials, Radboud University, Heyendaalsweg 135, 6525, AJ Nijmegen, The Netherlands
We have been teaching flow chemistry in our lab courses since 2011, when we acquired two b330 flow start education setups from FutureChemistry, a spin-off company from our university specializing in flow chemistry. From the start, the Omura-Sharma-Swern oxidation has been the reaction that we use to make students acquainted with flow chemistry. The first two years, we provided students with an application note provided by FutureChemistry, based on [2] and describing the straightforward synthesis of cinnamyl aldehyde by oxidation of cinnamyl alcohol. In 2013, we realized that this same reaction could also be used to convert benzophenone hydrazone (1, Fig. 1) to diphenyldiazomethane (2) [3, 4], This reaction is more appealing from a didactic viewpoint, for several reasons: &
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