Sustainable Aldehyde Oxidations in Continuous Flow Using in Situ-Generated Performic Acid,ACS Sustainable Chemistry & Engineering

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Sustainable Aldehyde Oxidations in Continuous Flow Using in Situ-Generated Performic Acid
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2021-04-14 , DOI: 10.1021/acssuschemeng.1c01668
Michael Prieschl _{1,

2} , Sándor B. Ötvös _{1,

2} , C. Oliver Kappe _{1,

2}

Affiliation

The oxidation of aldehydes is one of the most prevalent methods for the synthesis of a diverse range of carboxylic acids. We herein present a performic acid generator and its application for aldehyde oxidations under continuous flow conditions. Low molecular weight performic acid, an environmentally benign and inexpensive oxidant, was readily formed in situ from formic acid and hydrogen peroxide. The safety hazards typically encountered when manipulating this potentially explosive reagent were eliminated, while at the same time a clean and efficient access to valuable carboxylic acids was ensured. By taking advantage of concentrated or even neat aldehyde streams, the amount of organic solvents utilized, and thus waste formation, was successfully minimized as demonstrated by E-factors in the range of 5–18. The process proved applicable for a wide range of aromatic as well as aliphatic aldehydes, while its synthetic utility and stability were corroborated by scale-out experiments leading to multigram-scale syntheses.

中文翻译：

使用原位生成的过甲酸连续流进行可持续的醛氧化

醛的氧化是合成各种羧酸的最普遍方法之一。我们在此提出了一种过甲酸产生剂及其在连续流动条件下用于醛氧化的应用。低分子量过甲酸是一种环境友好且廉价的氧化剂，很容易从甲酸和过氧化氢中就地形成。消除了操作这种潜在爆炸性试剂时通常遇到的安全隐患，同时确保了清洁，有效地获取有价值的羧酸。通过利用浓缩或什至纯净的醛流，成功地将有机溶剂的使用量以及由此形成的废物最小化，如E所示。-因子在5到18之间。事实证明该方法适用于各种芳族醛和脂族醛，而其合成效用和稳定性得到了扩大规模实验的证实，从而导致了数克规模的合成。

更新日期：2021-04-27

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