アミン類の連続生産をより安価に、より高速に行う方法を開発(Researchers Devise Cheaper, Faster Way to Continuously Produce Amines)

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2022-05-04 ノースカロライナ州立大学(NCState)

ノースカロライナ州立大学の研究者らは、医薬品や農薬から洗剤や有機発光ダイオードに至るまで、さまざまな製品の構成要素として使用されている化学物質の一種であるヒンダードアミンを、より速く、より安価に製造する技術を開発しました。

<関連情報>

ヒンダードアミン類のヒドロアミノメチル化反応を促進するリサイクル型協同触媒の連続分割フロー反応器への適用 Recyclable cooperative catalyst for accelerated hydroaminomethylation of hindered amines in a continuous segmented flow reactor

Malek Y. S. Ibrahim & Milad Abolhasani
Nature Communications  Published: 04 May 2022
DOI:https://doi.org/10.1038/s41467-022-30175-0

figure 1

Abstract

Synthesis of hindered amines using the atom-efficient hydroaminomethylation (HAM) route remains a challenge. Here, we report a general and accelerated HAM in segmented flow, achieved via a cooperative effect between rhodium (Rh)/N-Xantphos and a co-catalyst (2-Fluoro-4-methylbenzoic acid) to increase the reactivity by 70 fold when compared to Rh/Xantphos in batch reactors. The cooperation between Rh and the co-catalyst facilitates the cleavage of the H–H bond and drives the equilibrium-limited condensation step forward. Online reaction optimization expands the scope to include alkyl, aryl, and primary amines. In-flow solvent tuning enables selectivity switching from amine to enamine without the need for changing the ligand. Furthermore, leveraging the ionic nature of the catalyst, we present a robust Rh recovery strategy up to 4 recycles without loss of activity.

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有機化学・薬学
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