Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination
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. Here...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2023-05-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666554923000042 |
| _version_ | 1797809755362689024 |
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| author | Giulia Brufani Federica Valentini Gabriele Rossini Lucia Rosignoli Yanlong Gu Ping Liu Luigi Vaccaro |
| author_facet | Giulia Brufani Federica Valentini Gabriele Rossini Lucia Rosignoli Yanlong Gu Ping Liu Luigi Vaccaro |
| author_sort | Giulia Brufani |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-13T06:57:33Z |
| format | Article |
| id | doaj.art-0aa7372809b94a46b08760fd8d46724e |
| institution | Directory Open Access Journal |
| issn | 2666-5549 |
| language | English |
| last_indexed | 2024-03-13T06:57:33Z |
| publishDate | 2023-05-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj.art-0aa7372809b94a46b08760fd8d46724e2023-06-07T04:49:56ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492023-05-0142154159Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contaminationGiulia Brufani0Federica Valentini1Gabriele Rossini2Lucia Rosignoli3Yanlong Gu4Ping Liu5Luigi Vaccaro6Laboratory of Green S.O.C. – Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, Perugia 06123, ItalyLaboratory of Green S.O.C. – Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, Perugia 06123, ItalyLaboratory of Green S.O.C. – Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, Perugia 06123, ItalyLaboratory of Green S.O.C. – Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, Perugia 06123, ItalyKey Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, ChinaSchool of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832003, ChinaLaboratory of Green S.O.C. – Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, Perugia 06123, Italy; Peoples Friendship University of Russia (RUDN University), Moscow 117198, Russian Federation; Corresponding author. Laboratory of Green S.O.C.– Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123, Perugia, Italy.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.http://www.sciencedirect.com/science/article/pii/S2666554923000042Flow chemistryCuAACAzeotropeWaste-minimizationCopper tube flow reactor |
| spellingShingle | Giulia Brufani Federica Valentini Gabriele Rossini Lucia Rosignoli Yanlong Gu Ping Liu Luigi Vaccaro Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination Green Synthesis and Catalysis Flow chemistry CuAAC Azeotrope Waste-minimization Copper tube flow reactor |
| title | Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination |
| title_full | Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination |
| title_fullStr | Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination |
| title_full_unstemmed | Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination |
| title_short | Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination |
| title_sort | waste minimized continuous flow copper catalyzed azide alkyne cycloaddition with low metal contamination |
| topic | Flow chemistry CuAAC Azeotrope Waste-minimization Copper tube flow reactor |
| url | http://www.sciencedirect.com/science/article/pii/S2666554923000042 |
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