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Ammoximation Reaction in Gas and Liquid Phase
Published in Mike G. Scaros, Michael L. Prunier, Catalysis of Organic Reactions, 2017
M. A. Mantegazza, G. Paparatto, G. Petrini, G. Fornasati, F. Trifirò
Cyclohexanone oxime, intermediate for the production of Σ-caprolactam (starting material for nylon-6), is produced with different processes all having similar drawbacks.1 As an example, the BASF process is described by the following equations: NH3+O2→NONO+H2→NH2OHcyclohexanone+NH2OH⋅H2SO4→cyclohexanoneoxime+(NH4)2SO4+H2O
Chemical Analysis
Published in Rudolf Puffr, Vladimír Kubánek, Lactam-Based Polyamides, 2019
Božena Lánská, Jaroslav Stehlíček
Cyclohexanone oxime appears in caprolactam as a production intermediate. Linear amines are formed from the respective linear alcohols, impurities which are present in cyclohexa-none, during oximation. Cyclohexyl amine may arise under the conditions of the Beckmann rearrangement from oxime; under the same conditions, it may be dehydrogenated to aniline, and further oxidized to nitrobenzene. Oxidation of cyclohexyl amine may give rise to nitrocyclohexane. In the reaction medium of rearrangement, octahydrophenazine may be formed from oxime, and toluidines may arise from methylcyclohexanones.1
Task-Specific Ionic Liquids
Published in Pedro Lozano, Sustainable Catalysis in Ionic Liquids, 2018
The Beckmann rearrangement is the acidic reagent promoted rearrangement of a different kind of ketoximes to corresponding amides. It is used in industry preparation of ε-caprolactam from cyclohexanone oxime. Sun et al. have reported a novel task-specific ionic liquid consisting of sulfonyl chloride specifically designed to promote Beckmann rearrangement, Figure 1.8 [30].
Synthesis of six- and seven-membered and larger heterocylces using Au and Ag catalysts
Published in Inorganic and Nano-Metal Chemistry, 2018
This method was applicable to nonaromatic unsaturated nitro compounds like 1-nitro-1-cyclohexene. The industrially important cyclohexanone oxime was obtained by gold/titanium(IV) oxide catalyzed reaction. The cyclohexanone oxime served as intermediate to afford ε-caprolactame in excellent yields (Scheme 18). This Au-catalyzed protocol avoided the use of hydroxylamine, which is an unstable and toxic product.[24]