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Synthesis and characterization of a magnetic hybrid catalyst containing lipase and palladium and its application on the dynamic kinetic resolution of amines
Molecular Catalysis ( IF 4.6 ) Pub Date : 2020-07-08 , DOI: 10.1016/j.mcat.2020.111106
Clara A. Ferraz , Marcelo A. do Nascimento , Rhudson F.O. Almeida , Gabriella G. Sergio , Aldo A.T. Junior , Gisele Dalmônico , Richard Caraballo , Priscilla V. Finotelli , Raquel A.C. Leão , Robert Wojcieszak , Rodrigo O.M.A. de Souza , Ivaldo Itabaiana

Recent papers estimates that about 40 % of drugs present chiral amines in their structure and their synthesis in a sustainable and cost-competitive way is still a challenge for the industry. Kinetic resolution is one of the most applied method to produce these desired compounds where the association with lipase as a catalyst is a good alternative. However, the use of separate racemization catalyst and enzymes in the reaction medium still limits recovery, recycling and can occasionally be responsible for decreasing in selectivity for the desired product. In this work we proposed the synthesis and characterization of a hybrid magnetic catalyst composed containing lipase CaL B and Pd immobilized on the same recovered nanometric magnetic support for the application on Dynamic Kinetic Resolution of (rac)-1-phenylethylamine both in batch and continuous flow conditions. As results it was possible to achieve 99 % of conversion, with 95 % of selectivity and 93 % of enantiomeric excess after 12 h in batch. For a continuous flow system, it was possible to achieve 95 % of conversion with 71 % of selectivity and ee > 99 % after 60 min of reaction. The hybrid catalyst had around 50−100 nm with nanoparticulated Pd (5−10 nm) on its surface, presented a superparamagnetic behavior without remaining magnetization and 22 emu/g of saturation magnetization.



中文翻译:

含脂肪酶和钯的磁性杂化催化剂的合成,表征及其在胺动态动力学拆分中的应用

最近的论文估计,约有40%的药物在结构上以手性胺的形式存在,并且以可持续且具有成本竞争力的方式合成手性胺仍然是该行业的挑战。动力学拆分是生产这些所需化合物的最常用方法之一,其中与脂肪酶作为催化剂的缔合是一个很好的选择。然而,在反应介质中使用单独的外消旋化催化剂和酶仍然限制了回收,再循环,并且有时可能导致所需产物选择性的降低。在这项工作中,我们提出了一种包含脂肪酶CaL B和钯的杂化磁性催化剂的合成和表征,该杂化催化剂固定在同一回收的纳米磁性载体上,用于(rac)动态动力学拆分。)-1-苯基乙胺分批和连续流动。结果,在分批处理12小时后,有可能实现99%的转化率,95%的选择性和93%的对映体过量。对于连续流系统,在反应60分钟后,有可能实现95%的转化率和71%的选择性,ee > 99%。杂化催化剂的表面约为50-100 nm,表面具有纳米级Pd(5-10 nm),表现出超顺磁性能而没有剩余磁化强度和22 emu / g饱和磁化强度。

更新日期:2020-07-08
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