Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination

Autor: Giulia Brufani, Federica Valentini, Gabriele Rossini, Lucia Rosignoli, Yanlong Gu, Ping Liu, Luigi Vaccaro
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Green Synthesis and Catalysis, Vol 4, Iss 2, Pp 154-159 (2023)
Druh dokumentu: article
ISSN: 2666-5549
DOI: 10.1016/j.gresc.2023.01.004
Popis: Metal contamination is a waste-generating and serious issue in the synthesis of chemicals, in particular in the case of products with biological activity. The appropriate selection of operating conditions plays a crucial role in the abatement of metal leaching in solution and associated wastes. Herein we report a waste-minimized continuous flow process for the synthesis of 1,4-disubstituted β-keto 1,2,3-triazoles exploiting the use of a copper tube flow reactor (CTFR). The selection of the proper azeotropic mixture allowed an almost quantitative recovery of the reaction medium greatly influencing the E-factor of the protocol. A thorough understanding of the main parameters affecting the waste generation was given by calculation of the E-factor distribution for different work-up tested under batch and flow conditions. Furthermore, the measurement of different green metrics (AE: Atom Economy, SF: Stoichiometric Factor, RME: Reaction Mass Efficiency, and MRP: Mass Recover Parameter) clearly demonstrated the benefits of the flow scale-up that allowed to perform a low environmental footprint CuAAC reaction.
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