The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. * Users are It will enhance any encyclopedic page you visit with the magic of the WIKI 2 technology. You have to login with your ACS ID befor you can login with your Mendeley account. Industrial & Engineering Chemistry Research. E-mail: The core of the setup comprised a 316 stainless‐steel micromixer consisting of 17 split‐and‐recombine units connected to a delay loop, a 316 stainless‐steel microchannel reactor with an internal diameter of 0.250 mm and a length of 0.50 m. At 100 °C, the conversion of cyclohexanone oxime was complete and the selectivity towards ϵ‐caprolactam was approximately 99 %. http://pubs.acs.org/page/copyright/permissions.html. © 2011 American Institute of Chemical Engineers AIChE J, 58: 3156–3160, 2012, American Institute of Chemical Engineers 120 Wall St., 23rd floor New York, NY 10005 1-800-AIChemE (1-800-242-4363) (203) 702-7660 www.aiche.org. But in many processes Beckmann rearrangement and Beckmann fragmentation compete. Authors contributing to RSC publications (journal articles, books or book chapters) As an important green synthesis technology of caprolactam, the Beckmann rearrangement reaction of cyclohexanone oxime using high temperature and pressure water as the reaction media was carefully studied with a microreactor. the Altmetric Attention Score and how the score is calculated. The reaction mechanism for this reaction is based on a catalytic cycle with cyanuric chloride activating the hydroxyl group via a nucleophilic aromatic substitution. Beckmann rearrangement catalysis: a review of recent advances. Based on these results and previous mechanism analysis, an equilibrium relation between protonated caprolactam and caprolactam hydrogen sulfate is proposed and the equilibrium constants at 70, 80, and 90°C are gained. The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is an acid-catalyzed rearrangement of an oxime to an amide. Ammonium sulfate is a common agricultural fertilizer providing nitrogen and sulfur. In the transition state leading to the imidate, the water oxygen atom is coordinated to 4 other atoms. Density, Viscosity, and Surface Tension of Liquid Phase Beckmann Rearrangement Mixtures. For reproduction of material from all other RSC journals and books: For reproduction of material from all other RSC journals. Learn about our remote access options, Dept. If you are the author of this article you do not need to formally request permission The viscosity and reaction enthalpy of the organic reaction system are determined. Caprolactam can be produced by Beckmann rearrangement reaction of cyclohexanone and oxime. Learn about our remote access options, Department of Chemical Engineering and Chemistry, Laboratory of Chemical Reactor Engineering, Eindhoven University of Technology, Eindhoven, The Netherlands, DSM Chemical Technology R&D BV Industrial Chemicals, Geleen, The Netherlands. Toward the Scale-Up of a Bicyclic Homopiperazine via Schmidt Rearrangement and Photochemical Oxaziridine Rearrangement in Continuous-Flow. taowang@tsinghua.edu.cn, kaiwang@tsinghua.edu.cn The oxygen atom in the hydroxyl group is stabilized by three acetic acid molecules. The rearrangement occurs stereospecifically for ketoximes and N-chloro/N-fluoro imines, with the migrating group being anti-periplanar to the leaving group on the nitrogen. Information. Your Mendeley pairing has expired. and you may need to create a new Wiley Online Library account. Would you like Wikipedia to always look as professional and up-to-date? Detailed analysis procedures, reaction performance of the modified catalytic system at high COX concentration, and the trend of byproduct. Beckmann Rearrangement An acid-induced rearrangement of oximes to give amides. article provided that the correct acknowledgement is given with the reproduced material. The Beckmann fragmentation is a reaction that frequently competes with the Beckmann rearrangement. Although specific promoting reagent and solvent can favor one over the other. Certain conditions have been known to racemize the oxime geometry, leading to the formation of both regioisomers. Intensification of fast exothermic reaction by gas agitation in a microchemical system.

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