Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 9, Issue 36, Pages 12196-12204Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.1c03634
Keywords
waste valorization; waste minimization; waste-derived heterogeneous catalyst; circular economy; copper-free Sonogashira; continuous flow; CPME/water azeotrope
Categories
Funding
- Universita degli Studi di Perugia
- MIUR
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This study presents a waste minimization/valorization methodology for the Sonogashira cross-coupling reaction using a Pd-based catalyst derived from urban waste pine needles. By utilizing flow conditions and an in-line liquid-liquid separator, high yields of final products were achieved with reduced waste generation. The catalyst showed high stability and durability, and CPME recovery was significantly improved during the process.
Herein, we report on the development of a waste minimization/valorization methodology applied to the representative benchmark Sonogashira cross-coupling reaction performed in a continuous-flow reactor, featuring a continuous-flow downstream membrane organic/aqueous separator to recover medium and products with minimal waste. The protocol is based on the use of a biomass waste-derived heterogeneous Pd-based catalyst, which is obtained from the valorization of urban-waste pine needles (PiNe). In a circular economy approach, the PiNe biomass has been proven to be capable of producing an effective active carbon support for Pd nanoparticle immobilization. In addition, the catalyst has been utilized in an azeotropic mixture formed by industrial waste-derived cyclopentyl methyl ether (CPME) and water. Thanks to this combination and with the adoption of flow conditions, high yields of final target products could be accessed with high stability and durability of the catalyst. Final isolation of the products has been realized by setting an in-line liquid-liquid separator in flow, which has also allowed CPME recovery with a significant reduction of the waste generated. The protocol has been applied to the representative preparation of eniluracil, a GSK API.
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