NDLI: One step C–N bond formation from alkylbenzene and ammonia over Cu-modified TS-1 zeolite catalyst

Content Provider	Royal Society of Chemistry (RSC)
Author	Hu, Changwei Xia, Sheng Liu, Huihui Yu, Tianhua Li, Guiying
Copyright Year	2014
Abstract	A Cu doped TS-1 zeolite sample was applied to catalyze the formation of C–N bonds on both the ring and the side chain of toluene, as well as other alkylbenzenes. A yield of 3.4% of toluidine was obtained for the amination of toluene, with a 1.0% yield of nitrobenzene. Cyanobenzene was also obtained as the C–N bond product on the side chain with a yield of 1.0%. The selectivity for C–N bond formation was 52.4%. The catalyst promoted the formation of a hydroxylamine intermediate from ammonia and hydrogen peroxide, and then the instantaneously generated amino cation reacted with the substrate to form C–N bonds on both the ring and side chain. Cyanobenzene was produced from the dehydration of benzylamine, formed via the reaction of ammonia and toluene. The formation of C–N bonds on the ring had an ortho-orientation advantage for mono-substituted-benzenes. With the increase in the number of methyl substituents, the yield of the ring products decreased, which might be caused by steric hindrance.
Starting Page	3108
Ending Page	3119
Page Count	12
File Format	HTM / HTML PDF
ISSN	20444753
Volume Number	4
Issue Number	9
Journal	Catalysis Science & Technology
DOI	10.1039/c4cy00472h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Hydroxylamine Nitrobenzene Toluene Ion Zeolite Steric effects Ammonia Cu Toluidine Peroxide Covalent bond Cyanobenzene Benzylamine Dehydration reaction
Content Type	Text
Resource Type	Article
Subject	Catalysis

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