Preparative microdroplet synthesis of carboxylic acids from aerobic oxidation of aldehydes

Chemical Science
Xin YanRichard N Zare

Abstract

Single liquid-phase and liquid-liquid phase reactions in microdroplets have shown much faster kinetics than that in the bulk phase. This work extends the scope of microdroplet reactions to gas-liquid reactions and achieves preparative synthesis. We report highly efficient aerobic oxidation of aldehydes to carboxylic acids in microdroplets. Molecular oxygen plays two roles: (1) as the sheath gas to shear the aldehyde solution into microdroplets, and (2) as the sole oxidant. The dramatic increase of the surface-area-to-volume ratio of microdroplets compared to bulk solution, and the efficient mixing of gas and liquid phases using spray nozzles allow effective mass transfer between aldehydes and molecular oxygen. The addition of catalytic nickel(ii) acetate is shown to accelerate further microdroplet reactions of this kind. We show that aliphatic, aromatic, and heterocyclic aldehydes can be oxidized to the corresponding carboxylic acids in a mixture of water and ethanol using the nickel(ii) acetate catalyst, in moderate to excellent yields (62-91%). The microdroplet synthesis is scaled up to make it preparative. For example, aerobic oxidation of 4-tert-butylbenzaldehyde to 4-tert-butylbenzoic acid was achieved at a rate of 10.5 mg...Continue Reading

References

Dec 20, 2011·Journal of the American Chemical Society·Wei LiEugenia Kumacheva
Feb 24, 2012·Chemical Society Reviews·Zhuangzhi ShiNing Jiao
Jul 25, 2012·Journal of the American Society for Mass Spectrometry·Abraham K Badu-TawiahR Graham Cooks
Oct 9, 2012·Angewandte Chemie·Thomas MüllerR Graham Cooks
Nov 26, 2013·Organic Letters·Laurent VanoyeClaude de Bellefon
Oct 10, 2015·Angewandte Chemie·Shibdas Banerjee, Richard N Zare
Jul 15, 2016·The Journal of Physical Chemistry. a·Shinichi EnamiA J Colussi
Jul 28, 2016·Chemical Society Reviews·M MovsisyanC V Stevens
Jan 21, 2017·Chemical Society Reviews·Joshua Britton, Colin L Raston
Feb 23, 2017·Angewandte Chemie·Xin YanRichard N Zare
Mar 24, 2017·The Analyst·Shibdas BanerjeeRichard N Zare
Jun 24, 2017·Physical Chemistry Chemical Physics : PCCP·Shinichi Enami, A J Colussi

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Citations

Dec 15, 2019·Angewandte Chemie·Elumalai GnanamaniRichard N Zare
Feb 28, 2020·Nature Communications·Xiaoqin ZhongRichard N Zare
Apr 22, 2020·Annual Review of Physical Chemistry·Zhenwei WeiXin Yan
Feb 29, 2020·Chemical Science·Chengyuan LiuRichard N Zare
Apr 21, 2021·Chemical Communications : Chem Comm·Dacheng KuaiXin Yan
Jun 9, 2021·Journal of the American Society for Mass Spectrometry·Tobias RainerThomas Müller
Aug 15, 2019·Journal of the American Society for Mass Spectrometry·Brett M MarshR Graham Cooks
Jun 25, 2021·Analytical Chemistry·Zhengzhou LiZongxiu Nie
Aug 23, 2019·The Journal of Physical Chemistry. a·Shibdas Banerjee, Richard N Zare
Dec 26, 2018·The Journal of Organic Chemistry·Wenwen ZhangJinhua Liu
Sep 2, 2020·Analytical Chemistry·Yuze LiZongxiu Nie
Dec 18, 2021·Scientific Reports·Hilary M BrownPatrick W Fedick

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