Literature DB >> 29286370

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid.

Alex Aw1, Marshall Fritz2, Jonathan W Napoline1, Pamela Pollet3, Charles L Liotta1.   

Abstract

Continuous flow technology has been identified as instrumental for its environmental and economic advantages leveraging superior mixing, heat transfer and cost savings through the "scaling out" strategy as opposed to the traditional "scaling up". Herein, we report the reaction of diphenyldiazomethane with p-nitrobenzoic acid in both batch and flow modes. To effectively transfer the reaction from batch to flow mode, it is essential to first conduct the reaction in batch. As a consequence, the reaction of diphenyldiazomethane was first studied in batch as a function of temperature, reaction time, and concentration to obtain kinetic information and process parameters. The glass flow reactor set-up is described and combines two types of reaction modules with "mixing" and "linear" microstructures. Finally, the reaction of diphenyldiazomethane with p-nitrobenzoic acid was successfully conducted in the flow reactor, with up to 95% conversion of the diphenyldiazomethane in 11 min. This proof of concept reaction aims to provide insight for scientists to consider flow technology's competitiveness, sustainability, and versatility in their research.

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Year:  2017        PMID: 29286370      PMCID: PMC5755396          DOI: 10.3791/56608

Source DB:  PubMed          Journal:  J Vis Exp        ISSN: 1940-087X            Impact factor:   1.355


  9 in total

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Review 2.  Flow chemistry syntheses of natural products.

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3.  End-to-end continuous manufacturing of pharmaceuticals: integrated synthesis, purification, and final dosage formation.

Authors:  Salvatore Mascia; Patrick L Heider; Haitao Zhang; Richard Lakerveld; Brahim Benyahia; Paul I Barton; Richard D Braatz; Charles L Cooney; James M B Evans; Timothy F Jamison; Klavs F Jensen; Allan S Myerson; Bernhardt L Trout
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

4.  Taming hazardous chemistry by continuous flow technology.

Authors:  M Movsisyan; E I P Delbeke; J K E T Berton; C Battilocchio; S V Ley; C V Stevens
Journal:  Chem Soc Rev       Date:  2016-07-25       Impact factor: 54.564

5.  The Hitchhiker's Guide to Flow Chemistry ∥.

Authors:  Matthew B Plutschack; Bartholomäus Pieber; Kerry Gilmore; Peter H Seeberger
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6.  Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines.

Authors:  Marcus Baumann; Antonio M Rodriguez Garcia; Ian R Baxendale
Journal:  Org Biomol Chem       Date:  2015-03-06       Impact factor: 3.876

7.  Continuous Flow Polymer Synthesis toward Reproducible Large-Scale Production for Efficient Bulk Heterojunction Organic Solar Cells.

Authors:  Geert Pirotte; Jurgen Kesters; Pieter Verstappen; Sanne Govaerts; Jean Manca; Laurence Lutsen; Dirk Vanderzande; Wouter Maes
Journal:  ChemSusChem       Date:  2015-08-21       Impact factor: 8.928

8.  Cross-Coupling between Difluorocarbene and Carbene-Derived Intermediates Generated from Diazocompounds for the Synthesis of gem-Difluoroolefins.

Authors:  Jian Zheng; Jin-Hong Lin; Liu-Ying Yu; Yun Wei; Xing Zheng; Ji-Chang Xiao
Journal:  Org Lett       Date:  2015-12-04       Impact factor: 6.005

Review 9.  The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry.

Authors:  Marcus Baumann; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2015-07-17       Impact factor: 2.883

  9 in total

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