Benzylation of benzene by benzyl chloride over iron mesoporous molecular sieves materials

被引:100
作者
Bachari, K
Millet, JMM
Benaïchouba, B
Cherifi, O
Figueras, F
机构
[1] Inst Rech Catalyse, CNRS, F-69626 Villeurbanne, France
[2] Fac Chim, Lab Chim Gaz Nat, Bab Ezzouar, Algeria
[3] CRAPC, Algiers 16004, Algeria
[4] Univ Mostaganem, Lab Valorisat Mat, Mostaganem 27000, Algeria
关键词
catalytic benzylation; Friedel-Crafts alkylation; Hammett relationship; HMS; iron-containing mesoporous materials;
D O I
10.1016/S0021-9517(03)00295-1
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The alkylation of benzene with benzyl chloride has been investigated over a series of iron-containing mesoporous silicas with different Fe contents. These materials (Fe-HMS-n) have been prepared at room temperature using a route based on hydrogen bonding and self-assembly between neutral primary amine micelles (S-0) and neutral inorganic precursors (I-0). They have been characterized by chemical analysis, BET, XRD, and UV-vis spectroscopy. The mesoporous Fe-containing materials were very active benzylation catalysts with almost 100% selectivity to monoalkylated product and showed excellent stability. The kinetics of the benzene benzylation over this catalyst have been thoroughly investigated. A mechanism in which the reaction could be initiated by an oxidation of benzyl chloride with formation of a charge transfer complex is proposed. (C) 2003 Elsevier Inc. All rights reserved.
引用
收藏
页码:55 / 61
页数:7
相关论文
共 27 条
  • [1] [Anonymous], 1985, ADV ORG CHEM
  • [2] HIGH CATALYTIC ACTIVITY OF IRON SULFATES FOR FRIEDEL-CRAFTS TYPE BENZYLATION OF TOLUENE WITH BENZYL CHLORIDE
    ARATA, K
    TOYOSHIM.I
    [J]. CHEMISTRY LETTERS, 1974, (08) : 929 - 930
  • [3] FRIEDEL-CRAFTS REACTION IN HETEROGENEOUS SYSTEM .5. FRIEDEL-CRAFTS BENZYLATION AND BENZOYLATION OF TOLUENE CATALYZED BY CALCINED IRON SULFATES
    ARATA, K
    YABE, K
    TOYOSHIMA, I
    [J]. JOURNAL OF CATALYSIS, 1976, 44 (03) : 385 - 391
  • [4] A NEW FAMILY OF MESOPOROUS MOLECULAR-SIEVES PREPARED WITH LIQUID-CRYSTAL TEMPLATES
    BECK, JS
    VARTULI, JC
    ROTH, WJ
    LEONOWICZ, ME
    KRESGE, CT
    SCHMITT, KD
    CHU, CTW
    OLSON, DH
    SHEPPARD, EW
    MCCULLEN, SB
    HIGGINS, JB
    SCHLENKER, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) : 10834 - 10843
  • [5] BELTRAME P, 1957, CHIM IND-MILAN, V39, P270
  • [6] Cao JM, 1998, STUD SURF SCI CATAL, V117, P461
  • [7] STERIC EFFECTS .1. ESTERIFICATION AND ACID-CATALYZED HYDROLYSIS OF ESTERS
    CHARTON, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) : 1552 - 1556
  • [8] Benzylation of benzene and substituted, benzenes by benzyl chloride over InCl3, GaCl3, FeCl3 and ZnCl2 supported on clays and Si-MCM-41
    Choudhary, VR
    Jana, SK
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 180 (1-2) : 267 - 276
  • [9] Acylation of aromatic compounds using moisture insensitive InCl3 impregnated mesoporous Si-MCM-41 catalyst
    Choudhary, VR
    Jana, SK
    Patil, NS
    [J]. TETRAHEDRON LETTERS, 2002, 43 (06) : 1105 - 1107
  • [10] Highly active and low moisture sensitive supported thallium oxide catalysts for Friedel-crafts-type benzylation and acylation reactions: Strong thallium oxide-support interactions
    Choudhary, VR
    Jana, SK
    [J]. JOURNAL OF CATALYSIS, 2001, 201 (02) : 225 - 235