Biomass Waste-Derived Pd–PiNe Catalyst for the Continuous-Flow Copper-Free Sonogashira Reaction in a CPME–Water Azeotropic Mixture,ACS Sustainable Chemistry & Engineering

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Biomass Waste-Derived Pd–PiNe Catalyst for the Continuous-Flow Copper-Free Sonogashira Reaction in a CPME–Water Azeotropic Mixture
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2021-09-01 , DOI: 10.1021/acssuschemeng.1c03634
Francesco Ferlin ₁ , Federica Valentini ₁ , Daniele Sciosci ₁ , Massimo Calamante _{2,

3} , Elena Petricci ₄ , Luigi Vaccaro ₁

Affiliation

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.

中文翻译：

生物质废物衍生的 Pd-PiNe 催化剂，用于 CPME-水共沸混合物中的连续流动无铜 Sonogashira 反应

在此，我们报告了一种废物最小化/价值化方法的开发，该方法适用于在连续流动反应器中进行的代表性基准 Sonogashira 交叉偶联反应，该反应器具有连续流动下游膜有机/水分离器，以最少的回收介质和产品浪费。该协议基于使用生物质废物衍生的异质 Pd 基催化剂，该催化剂是从城市废物松针 (PiNe) 的增值中获得的。在循环经济方法中，PiNe 生物质已被证明能够为 Pd 纳米颗粒的固定提供有效的活性炭载体。此外，该催化剂已用于由工业废物衍生的环戊基甲基醚 (CPME) 和水形成的共沸混合物。由于这种组合和采用流动条件，最终目标产品的高产率可以通过催化剂的高稳定性和耐久性获得。通过在流动中设置在线液液分离器，实现了产品的最终分离，这也使得 CPME 回收并显着减少了产生的废物。该协议已应用于葛兰素史克 API 恩尿嘧啶的代表性制备。

更新日期：2021-09-13

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