Catalysis in flow: Au-catalysed alkylation of amines by alcohols

Zotova, Natalia; Roberts, Felicity J.; Kelsall, G. H.; Jessiman, Alan S.; Hellgardt, Klaus; Hii, King Kuok

doi:10.1039/c1gc16118k

Cited by 64 publications

(37 citation statements)

References 32 publications

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“…The first dehydrogenation step was presumed to be irreversible [14,23], while for the second and third steps the reverse reactions were also taken into account.…”

Section: Kinetic Modelingmentioning

confidence: 99%

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Demidova

Simakova

Wärnå

et al. 2014

Chemical Engineering Journal

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“…The first dehydrogenation step was presumed to be irreversible [14,23], while for the second and third steps the reverse reactions were also taken into account.…”

Section: Kinetic Modelingmentioning

confidence: 99%

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Demidova

Simakova

Wärnå

et al. 2014

Chemical Engineering Journal

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“…The synthesis of amines from alcohols, catalyzed by Au has been proposed in flow mode [153]. It seems more appropriately a recirculating/mixing system, rather than a continuous flow reactor.…”

Section: Misleading Conceptsmentioning

confidence: 99%

Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry

Rossetti

Compagnoni

2016

Chemical Engineering Journal

200

103

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Flow chemistry has been proposed in modern organic chemistry as a mean for process intensification, to improve the control over reaction performance and to achieve higher yield. However, many open issues can be evidenced regarding the true possibility of scale-up, as well as currently lacking information for process design and economical evaluation. This review proposes some recent examples of flow synthesis deepening in particular the scale-up and engineering issues. Required information is evidenced, as well as some transport and kinetic data required for the practical implementation of the results.

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“…The Gas Module allows using further 13 Scheme 1. Comparison of the atom economy values of an oxidation process with a typical oxidating agent and oxidation with molecular oxygen synthesis gas etc.)…”

Section: Case Study 1: Oxidation With Elemental Oxygen Inmentioning

confidence: 99%

“…In our study, we investigated the selective oxidation of primary and secondary alcohols in flow reactors that apply closed cartridges [13] filled with commercially available catalysts to deliver a practical synthesis of aldehydes and ketones that meets several criteria of green chemistry. As shown, the significant improvement of atom economy with elemental oxygen is an important green factor.…”

Section: Case Study 1: Oxidation With Elemental Oxygen Inmentioning

confidence: 99%

“…The origin of selectivity is attributed to the accessibility of high temperature and short residence time. Adopting nearly equimolar equivalents of the reactants at a higher concentration and lower catalytic loading (0.9 mol%), the reaction proceeded smoothly to completion with very high selectivity for the formation of the secondary amine [31]. A mixture of amine (aniline) and alcohol (benzyl alcohol) in toluene (10 mL) was circulated through a heated cartridge containing 1.5 wt.% Au/TiO 2 , at a flow rate of 1.5 mL/min (residence time=27 s) at 50 bar pressure and 180°C.…”

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confidence: 99%

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Important Industrial Procedures Revisited in Flow: Very Efficient Oxidation and N-Alkylation Reactions with High Atom-Economy

Sipos¹,

Gyóllai²,

Sipőcz³

et al. 2013

J Flow Chem

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The atom economy concept is one of the earliest recognition for green and sustainable aspects of organic synthesis. Over the years, novel technologies emerged that made this important feature of reactions into practice. Continuousflow devices increased the efficiency of the chemical transformations with novel process windows (high T, high p and heterogeneous packed catalysts etc.) and increased safety which turned the attention to reexamine old, industrial processes. Oxidation can be performed under flow catalytic conditions with molecular oxygen; alcohols can be oxidized to carbonyl compounds with high atom economy (AE=87 %). Using O 2 and 1 % Au/TiO 2 , alcohol oxidation in flow was achieved with complete conversion and >90 % yield. N-alkylation is another good example for achieving high atom economy. Under flow catalytic conditions (Raney Ni), amines were successfully reacted with alcohols directly (AE=91 %) with >90 % conversion and selectivity. In both examples, the effective residence time was less than 1 min. These two examples demonstrate the significant contribution of flow technology to the realization of key principles in green and sustainable chemistry.

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Catalysis in flow: Au-catalysed alkylation of amines by alcohols

Cited by 64 publications

References 32 publications

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry

Important Industrial Procedures Revisited in Flow: Very Efficient Oxidation and N-Alkylation Reactions with High Atom-Economy

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