Theoretical study on vapour phase Beckmann rearrangement of cyclohexanone oxime over a high silica MFI zeolite

被引：34
作者：
Ishida, M
Suzuki, T
Ichihashi, H
Shiga, A
机构：
[1] Sumitomo Chem Co Ltd, Tsukuba Res Lab, Tsukuba, Ibaraki 3003294, Japan
[2] Sumitomo Chem Co Ltd, Basic Chem Res Lab, Sobiraki, Niihama 7925821, Japan
来源：
CATALYSIS TODAY | 2003年 / 87卷 / 1-4期
关键词：
cyclohexanone; Beckmann rearrangement; double numerical polarization;
D O I：
10.1016/j.cattod.2003.10.021
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
We have studied an activation mechanism of cyclohexanone oxime in a cavity of high silica MFI zeolite by using PIO analysis proposed by Fujimoto et al. DFT calculation reveals that the bond length of N-OH becomes longer when water coordinates on oxygen of oxime. The PIO clearly shows out-of-phase interaction between N and O. This out-of-phase interaction is also observed in the PIO of oxime/MFI zeolite cluster model and weakens the N-O bond. Hydrogen bond of Si-OH of nest silanols to oxime is a trigger of vapour phase Beckmann rearrangement. (C) 2003 Elsevier B.V. All rights reserved.
引用
收藏
页码：187 / 194
页数：8
相关论文
共 50 条
  • [21] Vapor phase Beckmann rearrangement of cyclohexanone oxime over metal loaded Nb-ilerite
    Kim, SJ
    Jung, KD
    Joo, OS
    RECENT ADVANCES IN THE SCIENCE AND TECHNOLOGY OF ZEOLITES AND RELATED MATERIALS, PTS A - C, 2004, 154 : 2815 - 2822
  • [22] CATALYST DEACTIVATION OF HIGH-SILICA HZSM-5 IN THE BECKMANN REARRANGEMENT REACTION OF CYCLOHEXANONE OXIME
    TAKAHASHI, T
    NISHI, M
    TAGAWA, Y
    KAI, T
    MICROPOROUS MATERIALS, 1995, 3 (4-5): : 467 - 471
  • [23] Vapor-phase Beckmann rearrangement of cyclohexanone oxime over modified titania-zirconia catalyst
    Mao, DS
    Lu, GZ
    Chen, QL
    Xie, ZK
    Zhang, YX
    ACTA CHIMICA SINICA, 2001, 59 (07) : 1139 - 1144
  • [24] DFT-based study of liquid-phase Beckmann rearrangement mechanism of cyclohexanone oxime
    Xian G.
    Chen L.
    Qi Z.
    Huagong Xuebao/CIESC Journal, 2024, 75 (01): : 302 - 311
  • [25] Vapor phase Beckmann rearrangement of cyclohexanone oxime on Hβ-zeolites treated by ammonia
    Zhang, Yongje
    Wang, Yaquan
    Bu, Yifeng
    MICROPOROUS AND MESOPOROUS MATERIALS, 2008, 107 (03) : 247 - 251
  • [26] Beckmann rearrangement of cyclohexanone oxime over Silicalite-1: an FT-IR spectroscopic study
    Flego, C
    Dalloro, L
    MICROPOROUS AND MESOPOROUS MATERIALS, 2003, 60 (1-3) : 263 - 271
  • [27] Vapour-phase Beckmann rearrangement using B-MFI zeolites
    Roseler, J
    Heitmann, G
    Holderich, WF
    APPLIED CATALYSIS A-GENERAL, 1996, 144 (1-2) : 319 - 333
  • [28] Beckmann rearrangement over phosphotungstic acid/SiMCM-41 cyclohexanone oxime to ε-caprolactam
    Maheswari, R
    Shanthi, K
    Sivakumar, T
    Narayanan, S
    APPLIED CATALYSIS A-GENERAL, 2003, 248 (1-2) : 291 - 301
  • [29] Vapor-phase Beckmann rearrangement of cyclohexanone oxime over phosphorus modified Si-MCM-41
    Dongshun Zhang
    Rijie Wang
    Xiaoxia Yang
    Wensheng Yao
    Reaction Kinetics, Mechanisms and Catalysis, 2010, 101 : 455 - 463
  • [30] Catalytic application of mesoporous molecular sieves to vapor‐phase Beckmann rearrangement of cyclohexanone oxime
    Lian‐Xin Dai
    Katsuyuki Koyama
    Takashi Tatsumi
    Catalysis Letters, 1998, 53 : 211 - 214
12345