Beckmann Rearrangement of Cyclohexanone Oxime to ϵ‐Caprolactam in a Microreactor

Zuidhof, N. T.; Croon, M.H.J.M. de; Schouten, J.C.; Tinge, J.T.

doi:10.1002/ceat.201100550

Cited by 24 publications

(16 citation statements)

References 10 publications

(13 reference statements)

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“…This kind of reactor can also provide more accurate residence time by controlling the tube length and the flow rate . In recent years, a lot of chemical reactions have been enhanced in yield, selectivity and conversion by microreactors, such as the partial oxidation of DME for production of hydrogen, Claisen rearrangement and Sonogashira coupling, the sulfuric acid‐catalyzed Beckmann rearrangement of cyclohexanone oxime, and so on. However, the working system with high viscous fluid and extreme flow rate ratio is still a challenge for the development of microreactor today for the very weak mixing performance in microchannel device .…”

Section: Introductionmentioning

confidence: 99%

Synthesizing bromobutyl rubber by a microreactor system

Xie

Wang

et al. 2016

AIChE Journal

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Bromobutyl rubber (BIIR) is an important synthetic rubber with better vulcanizing behavior than traditional butyl rubber (IIR). It is hard to synthesize for the high reactant viscosity and strong corrosion caused by Br2 and HBr. A microreactor platform was developed to solve the corrosion problem with cheap materials and obtain high quality BIIR based on microscaled mixing. The results showed that low reaction temperature and quickly eliminating HBr from the reacting solution were crucial to obtain high selectivity of demanded molecule structure and prevent polymer from decomposition. Owing to the corrosion resistance ability, a water assistant technology was successfully implemented in the microreactor system, which produced high quality BIIR with almost 100% selectivity and less reduced molecule weight. © 2016 American Institute of Chemical Engineers AIChE J, 63: 1002–1009, 2017

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Section: Introductionmentioning

confidence: 99%

Synthesizing bromobutyl rubber by a microreactor system

Xie

Wang

et al. 2016

AIChE Journal

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“…Curved geometries of each elements oriented perpendicularly to the flow direction have been designed and organic reactions or emulsions, crystallizations and extraction processes performed inside (Zuidhof et al 2012;Okubo et al 2004). In the design of each mixing element, several parameters to improve mixing efficiency have to be taken into consideration.…”

Section: ð8:8þmentioning

confidence: 99%

Microfluidics in Planar Microchannels: Synthesis of Chemical Compounds On-Chip

Arima

Watts

Pascali

2014

Lab-on-a-Chip Devices and Micro-Total Analysis Systems

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Microreactors are a wide class of devices that are currently playing a prominent role in several research fields such as biology, medicine, food chemistry, environmental analysis, up to the production of compounds in organic chemistry. Several typologies of microreactors have been produced with tubular or planar shapes, of different materials and designs. In this chapter, an overview of planar microchannel-based microreactors and their application to organic chemistry is given. Initially, after recalling the main theoretical parameters of microfluidics, an introduction of the proposed technology and the main requirements to perform mixing, which is essential to perform chemical synthesis on-chip, is presented. Silicon and glass microreactors, the most common planar systems for organic chemistry, are described with the aim of pointing out the most important parameters to be taken into consideration in the planning of a specific microreactor to be used for mixing, purification or crystallization of chemicals at the microscale. Then, several applications of initially described microreactors to organic chemistry for research applications are given. In the next section, the use of planar microchannel microreactors in the field of radiochemistry is reported. The radiopharmaceutical application is not casual, being a sector in which the microreactor technology is very promising, due to the need of quickly producing small and fresh amounts of products in a controlled environment. Finally, for completeness, other approaches beyond planar microchannels are mentioned: mesoreactors towards industrial level synthesis and micro-vessels for radiochemistry.

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“…The development of microreaction technology provides a promising method to study the organocatalyzed rearrangement kinetics. First of all, enhanced mixing of the reactants is easily achieved by the microreaction technology, and the reaction conditions are well controlled in the limited space . Second, higher pressure is easily operated and then the reaction can be proceeded at higher temperature, decreasing the evaporation of TFA.…”

Section: Introductionmentioning

confidence: 99%

Organocatalyzed Beckmann rearrangement of cyclohexanone oxime in a microreactor: Kinetic model and product inhibition

Zhang

2017

AIChE Journal

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The kinetic study of Beckmann rearrangement of cyclohexanone oxime catalyzed by trifluoroacetic acid and acetonitrile in a microreactor is presented in this article. Parametric studies are conducted varying temperature, ratio of trifluoroacetic acid to acetonitrile, and concentration of cyclohexanone oxime. The inhibition effect of E-caprolactam in this reaction system is firstly reported. A comprehensive mathematic kinetic model considering the product inhibition effect of caprolactam has been developed in the temperature range of 368-391 K, which agrees well with the experimental results across a broad experimental parameter space. In addition, kinetic study indicates that the esterification of cyclohexanone oxime and transposition reaction of the intermediate are both supposed to be the rate-determining steps, and in this catalyst system, the ratio of trifluoroacetic acid and acetonitrile mainly influences the reaction rate and the activation energy of the transposition step. The developed model could provide much reliable knowledge for industrial application.

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Beckmann Rearrangement of Cyclohexanone Oxime to ϵ‐Caprolactam in a Microreactor

Cited by 24 publications

References 10 publications

Synthesizing bromobutyl rubber by a microreactor system

Synthesizing bromobutyl rubber by a microreactor system

Microfluidics in Planar Microchannels: Synthesis of Chemical Compounds On-Chip

Organocatalyzed Beckmann rearrangement of cyclohexanone oxime in a microreactor: Kinetic model and product inhibition

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