Reductive aminations using a 3D printed supported metal(0) catalyst system
- 23 Downloads
Additively manufactured catalytic static mixers were used for the intensified reductive amination of aldehydes and ketones inside a continuous flow reactor. This efficient synthesis method is enabled by the use of tubular reactors fitted with 3D printed metal static mixers which are coated with a catalytically active layer, either Pd or Ni. The 3D printing process allows for maximum design flexibility for the mixer scaffold and is compatible with a range of deposition methods including electroplating and metal cold spraying. Single- and multi-stage continuous flow processing yielded high to full conversion and has the potential to scale-up these operations without the need for manual handling of reactive imine intermediates.
KeywordsHeterogeneous catalysis Flow chemistry Hydrogenation Amines Palladium Nickel
The authors thank Winston Liew for ICP-OES measurements, Andrew Urban for cold-spraying of the nickel catalyst, Darren Fraser for 3D printing of the mixer substrates, John Tsanaktsidis, Oliver Hutt and Dayalan Gunasegaram for many helpful discussions and the Active Integrated Matter (AIM) Future Science Platform for financial support for Charlotte Genet.
- 4.Kato H, Shibata I, Yasaka Y et al (2006) The reductive amination of aldehydes and ketones by catalytic use of dibutylchlorotin hydride complex. Chem Commun :4189–4191. https://doi.org/10.1039/B610614E
- 12.Brechtelsbauer C, Hii KK (Mimi) (2014) 1. Catalysis in flow. In: Applications fundamentals and applications. De Gruyter, Berlin. https://doi.org/10.1515/9783110367508.3
- 13.de Bellefon C (2014) 2. Catalytic engineering aspects of flow chemistry. In: Applications fundamentals and applications. De Gruyter, Berlin. https://doi.org/10.1515/9783110367508.31
- 19.Nguyen X, Carafa A, Hornung CH (2017) Hydrogenation of vinyl acetate using a continuous flow tubular reactor with catalytic static mixers. Chem Eng Process Process Intensif. https://doi.org/10.1016/j.cep.2017.12.007
- 21.Von Angerer E, Egginger G, Kranzfelder G et al (1982) N,N’-Dialkyl-1,2-bis(hydroxyphenyl)ethylenediamines and N,N’-dialkyl-4,5-bis(4-hydroxyphenyl)imidazolidines. Syntheses and evaluation of their mammary tumor inhibiting activity. J Med Chem 25:832–837. https://doi.org/10.1021/jm00349a013 CrossRefGoogle Scholar
- 27.Hollmann D, Bähn S, Tillack A, Beller M (2008) N -Dealkylation of aliphatic amines and selective synthesis of monoalkylated aryl amines. Chem Commun :3199–3201. https://doi.org/10.1039/B803114B
- 29.Fujita K, Enoki Y, Yamaguchi R (2003) Iridium-catalyzed N-Heterocyclization of primary amines with diols: N-Benzylpiperidine. In: Organic syntheses. John Wiley & Sons, Inc. https://doi.org/10.1002/0471264229.os083.28
- 32.Vapourtec Flow Chemistry Equipment. http://www.vapourtec.co.uk/. Accessed 23 Oct 2015