TY - JOUR
T1 - Beckmann rearrangement of 15N-cyclohexanone oxime on zeolites silicalite-1, H-ZSM-5, and H-[B]ZSM-5 studied by solid-state NMR spectroscopy
AU - Marthala, V. R Reddy
AU - Jiang, Yijiao
AU - Huang, Jun
AU - Wang, Wei
AU - Gläser, Roger
AU - Hunger, Michael
PY - 2006/11/22
Y1 - 2006/11/22
N2 - By means of solid-state 15N NMR spectroscopy, evidence for the formation of nitrilium ions as intermediates of the Beckmann rearrangement of 15N-cyclohexanone oxime to ε-caprolactam on silicalite-1, H-ZSM-5, and H-[B]ZSM-5 is reported. The zeolites under study are characterized by different acid strengths (silicalite-1 < H-[B]ZSM-5 < H-ZSM-5). Depending on the nature of catalytically active surface OH groups, reactant and product molecules exist in the nonprotonated or protonated state. In addition, formation of byproducts such as 5-cyano-1-pentene and ε-aminocapric acid as a result of dehydration and hydrolysis of the reactant and product molecules, respectively, were observed.
AB - By means of solid-state 15N NMR spectroscopy, evidence for the formation of nitrilium ions as intermediates of the Beckmann rearrangement of 15N-cyclohexanone oxime to ε-caprolactam on silicalite-1, H-ZSM-5, and H-[B]ZSM-5 is reported. The zeolites under study are characterized by different acid strengths (silicalite-1 < H-[B]ZSM-5 < H-ZSM-5). Depending on the nature of catalytically active surface OH groups, reactant and product molecules exist in the nonprotonated or protonated state. In addition, formation of byproducts such as 5-cyano-1-pentene and ε-aminocapric acid as a result of dehydration and hydrolysis of the reactant and product molecules, respectively, were observed.
UR - http://www.scopus.com/inward/record.url?scp=33845222980&partnerID=8YFLogxK
U2 - 10.1021/ja066392c
DO - 10.1021/ja066392c
M3 - Article
C2 - 17105284
AN - SCOPUS:33845222980
SN - 0002-7863
VL - 128
SP - 14812
EP - 14813
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 46
ER -