Trifluoroacetic Acid Hydroxylamine System as Organocatalyst Reagent in a One-Pot Salt Free Process for the Synthesis of Caprolactam and Amides of Industrial Interest

In this work we studied the reactivity of the Trifluoroacetic acid hydroxylamine system in the one step salt free synthesis of amides from ketones. A particular regards was paid to the caprolactam synthesis because of its industrial relevance. Synthesis, reactivity and characterization of the hydrox...

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Bibliographic Details
Published in:Catalysis letters 2021-12, Vol.151 (12), p.3543-3549
Main Authors: Manente, F., Pietrobon, L., Ronchin, L., Vavasori, A.
Format: Article
Language:English
Subjects:
Acids
Amides
Caprolactam
Catalysis
Chemistry
Chemistry and Materials Science
Distillation
Hydroxides
Industrial Chemistry/Chemical Engineering
Ketones
Nitric acid
Organometallic Chemistry
Oximes
Physical Chemistry
Reagents
Room temperature
Synthesis
Trifluoroacetates
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Summary:In this work we studied the reactivity of the Trifluoroacetic acid hydroxylamine system in the one step salt free synthesis of amides from ketones. A particular regards was paid to the caprolactam synthesis because of its industrial relevance. Synthesis, reactivity and characterization of the hydroxylamine trifluoroacetate is given. Fast oximation reaction of several ketones was gained at room temperature (1 h of reaction quantitative conversion for several ketones). In the same reactor, by raising the temperature at 383 K, the Beckmann rearrangement of the so obtained oximes is easily accomplished in the presence of three equivalent of TFA. The possibility of obtaining the trifluoroacetate of the hydroxylamine with a modified nitric acid hydrogenation reactions was verified, too. Reuse of solvent and trifluoroacetic acid is easily achieved by distillation. Graphical abstract Salt free one-pot caprolactam and amides process catalyzed by CF 3 COOH, in the presence of NH 2 OH TFA as the oximation agent.
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-021-03590-z