Continuous‐Flow Synthesis of Adipic Acid from Cyclohexene Using Hydrogen Peroxide in High‐Temperature Explosive Regimes

Damm, Markus; Gutmann, Bernhard; Kappe, C. Oliver

doi:10.1002/cssc.201300197

Cited by 50 publications

(31 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Kappe et al developed another protocol which did not require a phase transfer catalyst and employed 25% aqueous H2O2 in the presence of tungstic acid as a catalyst. 270 The isolated yield of adipic acid reached 63% at 140°C with just 20 min residence time.…”

Section: Oxidation Processes In Flow By Means Of Hydrogen Peroxidementioning

confidence: 99%

Liquid phase oxidation chemistry in continuous-flow microreactors

et al. 2016

View full text Add to dashboard Cite

Continuous-flow liquid phase oxidation chemistry in microreactors receives a lot of attention as the reactor provides enhanced heat and mass transfer characteristics, safe use of hazardous oxidants, high interfacial areas, and scale-up potential. In this review, an up-to-date overview of both technological and chemical aspects of liquid phase oxidation chemistry in continuous-flow microreactors is given. A description of mass and heat transfer phenomena is provided and fundamental principles are deduced which can be used to make a judicious choice for a suitable reactor. In addition, the safety aspects of continuous-flow technology are discussed. Next, oxidation chemistry in flow is discussed, including the use of oxygen, hydrogen peroxide, ozone and other oxidants in flow. Finally, the scale-up potential for continuous-flow reactors is described.

show abstract

Section: Oxidation Processes In Flow By Means Of Hydrogen Peroxidementioning

confidence: 99%

Liquid phase oxidation chemistry in continuous-flow microreactors

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Thereaction was run for 1h to provide 12 g( 84 mmol;7 2%)o fp ure,c rystalline adipic acid after as imple filtration step. [103] An analogous continuous-flow synthesis of adipic acid by the oxidation of neat cyclohexene with aqueous hydrogen peroxide was described by Hessel and co-workers. [104] Thep rocess used Na 2 WO 4 ·2 H 2 Oa sac atalyst and [CH 3 (n-C 8 H 17 ) 3 …”

Section: H 2 O 2 Hoxmentioning

confidence: 99%

“…Continuous-flow synthesis of adipic acid. [103] Flow Chemistry Angewandte ap hase-transfer catalyst. Improved mixing was achieved by using apacked-bed reactor containing glass spheres.…”

Section: N]hso 4 Asmentioning

confidence: 99%

Continuous‐Flow Technology—A Tool for the Safe Manufacturing of Active Pharmaceutical Ingredients

Gutmann¹,

Cantillo²,

Kappe³

2015

Angew Chem Int Ed

Self Cite

1,313

676

View full text Add to dashboard Cite

In the past few years, continuous-flow reactors with channel dimensions in the micro- or millimeter region have found widespread application in organic synthesis. The characteristic properties of these reactors are their exceptionally fast heat and mass transfer. In microstructured devices of this type, virtually instantaneous mixing can be achieved for all but the fastest reactions. Similarly, the accumulation of heat, formation of hot spots, and dangers of thermal runaways can be prevented. As a result of the small reactor volumes, the overall safety of the process is significantly improved, even when harsh reaction conditions are used. Thus, microreactor technology offers a unique way to perform ultrafast, exothermic reactions, and allows the execution of reactions which proceed via highly unstable or even explosive intermediates. This Review discusses recent literature examples of continuous-flow organic synthesis where hazardous reactions or extreme process windows have been employed, with a focus on applications of relevance to the preparation of pharmaceuticals.

show abstract

“…Kontinuierliche Durchflusssynthese von Adipinsäure. [103] Schema 26. Kontinuierliche Durchflussoxidation mit Natriumhypochlorit in einem Zweiphasensystem.…”

Section: Singulett-sauerstoffunclassified

Kontinuierliche Durchflussverfahren: ein Werkzeug für die sichere Synthese von pharmazeutischen Wirkstoffen

2015

Self Cite

View full text Add to dashboard Cite

In den letzten Jahren haben Durchflussreaktoren mit Kanalabmessungen im Mikrometer‐ oder Millimeterbereich weitverbreitete Anwendung in der organischen Synthese gefunden. Diese Reaktoren sind durch ihre außergewöhnlich schnellen Wärme‐ und Stoffübertragung gekennzeichnet. Außer bei den schnellsten Reaktionen kann in mikrostrukturierten Bauelementen dieses Typs eine fast augenblickliche Vermischung der Reaktanten erreicht werden. Ebenso lassen sich Probleme wie Wärmestau, Überhitzungszonen (Hot‐Spots) und thermisches Durchgehen vermeiden. Aufgrund der kleinen Reaktorvolumina ist die Prozesssicherheit erheblich verbessert, selbst wenn harsche Reaktionsbedingungen angewendet werden. Somit bietet die Mikroreaktortechnologie eine einzigartige Möglichkeit, ultraschnelle exotherme Reaktionen durchzuführen, und erlaubt die Realisierung von Reaktionen, die über sehr instabile oder sogar explosive Zwischenprodukte ablaufen. Dieser Aufsatz behandelt aktuelle Literaturbeispiele für die organische Synthese unter kontinuierlichem Durchfluss, in denen eine gefährliche Chemie oder extreme Prozessfenster angewendet wurden, wobei der Schwerpunkt vor allem auf Anwendungen liegt, die für die Herstellung von Pharmazeutika von Bedeutung sind.

show abstract

Continuous‐Flow Synthesis of Adipic Acid from Cyclohexene Using Hydrogen Peroxide in High‐Temperature Explosive Regimes

Cited by 50 publications

References 64 publications

Liquid phase oxidation chemistry in continuous-flow microreactors

Liquid phase oxidation chemistry in continuous-flow microreactors

Continuous‐Flow Technology—A Tool for the Safe Manufacturing of Active Pharmaceutical Ingredients

Kontinuierliche Durchflussverfahren: ein Werkzeug für die sichere Synthese von pharmazeutischen Wirkstoffen

Contact Info

Product

Resources

About