NDLI: The Catalysis of Vapor-Phase Beckmann Rearrangement for the Production of ε-Caprolactam

Content Provider	Springer Nature Link
Author	Ichihashi, Hiroshi Ishida, Masaya Shiga, Akibu Kitamura, Masaru Suzuki, Tatsuya Suebu, Katsuhiro Sugita, Keisuke
Copyright Year	2003
Abstract	Recently, Sumitomo Chemical Co., Ltd. developed the vapor-phase Beckmann rearrangement process for the production of ε-caprolactam. In the process, cyclohexanone oxime is rearranged into ε-caprolactam using a zeolite as a catalyst instead of sulfuric acid. EniChem in Italy developed the ammoximation process that involves the direct production of cyclohexanone oxime without producing any ammonium sulfate. Sumitomo Chemical Co., Ltd. has commercialized the combined process of vapor-phase Beckmann rearrangement and ammoximation in 2003.In this paper, the authors focus on some aspects of the vapor-phase Beckmann rearrangement catalysis. A solid catalyst that is mainly composed of a high-silica MFI zeolite (Silicalite-1) has been developed for the vapor-phase Beckmann rearrangement. This catalyst does not possess acidity that can be detected by ammonia TPD. Methanol fed into the reactor with cyclohexanone oxime improves the yield of caprolactam. Methanol reacts with terminal silanols on the zeolite surface and converts them to methoxyl groups. The modification of the catalyst by methanol has an important role for the Beckmann rearrangement reaction.Nest silanols located just inside the pore mouth of the MFI zeolite are supposed to be the active sites of the catalyst. We propose that the coordination between the NOH group of cyclohexanone oxime molecule and the nest silanols through hydrogen bonding is responsible for the reaction. The reaction mechanism of Beckmann rearrangement under vapor-phase conditions is the same as in the liquid phase, namely, the alkyl group in anti-position against the hydroxyl group of the oxime migrates to the nitrogen atom's position.
Starting Page	261
Ending Page	270
Page Count	10
File Format	PDF
ISSN	15711013
Journal	Catalysis Surveys from Asia
Volume Number	7
Issue Number	4
e-ISSN	15749266
Language	English
Publisher	Kluwer Academic Publishers-Plenum Publishers
Publisher Date	2003-01-01
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Physical Chemistry Industrial Chemistry/Chemical Engineering Catalysis Characterization and Evaluation Materials
Content Type	Text
Resource Type	Article
Subject	Chemistry Catalysis

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