Biphasic hydroformylation of monoterpenes employing Rh/TPPTS/CTAC: the role of the substrate in the mass transfer between the phases

被引:50
作者
Barros, HJV
Hanson, BE
Gusevskaya, EV [1 ]
dos Santos, EN
机构
[1] Univ Fed Minas Gerais, Dept Quim, BR-31270901 Belo Horizonte, MG, Brazil
[2] Virginia Polytech Inst & State Univ, Dept Chem, Blacksburg, VA 24061 USA
关键词
terpene; hydroformylation; cationic surfactant; Rh/TPPTS; CTAC;
D O I
10.1016/j.apcata.2004.09.025
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 rhodium catalyzed hydroformylation of myrcene, limonene and camphene is achieved in a toluene/water biphasic system employing tris(3-sulfonatophenyl)phosphine, trisodium salt (TPPTS) as ancillary ligand as a function of the cationic surfactant cetyltrimethylammonium chloride (CTAC-) concentration. In some cases the observed conversion rates were superior to the similar homogeneous systems. The promotion effect of CTAC and its optimal concentration depends on the conformational characteristics of the substrate. For myrcene, a pronounced promotion effect is observed for CTAC concentrations around 2.5 x 10(-2) M, whereas for camphene there is an inhibition effect even at concentrations as low as 2.5 x 10(-3) M. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:57 / 63
页数:7
相关论文
共 32 条
  • [1] HYDROFORMYLATION BY SUPPORTED AQUEOUS-PHASE CATALYSIS - A NEW CLASS OF HETEROGENEOUS CATALYSTS
    ARHANCET, JP
    DAVIS, ME
    MEROLA, JS
    HANSON, BE
    [J]. NATURE, 1989, 339 (6224) : 454 - 455
  • [2] Rhodium catalyzed hydroformylation of β-pinene and camphene:: effect of phosphorous ligands and reaction conditions on diastereoselectivity
    Barros, HJV
    Ospina, ML
    Arguello, E
    Rocha, WR
    Gusevskaya, EV
    dos Santos, EN
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 671 (1-2) : 150 - 157
  • [3] CHATT LM, 1957, J CHEM SOC, P4735
  • [4] Synergistic effect of TPPTS and TPPDS on the regioselectivity of olefin hydroformylation in two-phase catalytic system
    Chen, H
    Li, YZ
    Chen, JR
    Cheng, PM
    Li, XJ
    [J]. CATALYSIS TODAY, 2002, 74 (1-2) : 131 - 135
  • [5] Chen TT, 1999, MAR BIOTECHNOL, V1, P1
  • [6] Convenient one-pot synthesis of 4,8-dimethyl-bicyclo[3.3.1]non-7-en-2-ol via platinum/tin catalyzed hydroformylation/cyclization of limonene
    Dias, AD
    Augusti, R
    dos Santos, EN
    Gusevskaya, EV
    [J]. TETRAHEDRON LETTERS, 1997, 38 (01) : 41 - 44
  • [7] New water soluble chelating phosphines for aqueous phase catalysis
    Ding, H
    Kang, JX
    Hanson, BE
    Kohlpaintner, CW
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 124 (01) : 21 - 28
  • [8] HYDROFORMYLATION OF ALPHA-PINENE AND BETA-PINENE CATALYZED BY RHODIUM AND COBALT CARBONYLS
    DOS SANTOS, EN
    PITTMAN, CU
    TOGHIANI, H
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1993, 83 (1-2): : 51 - 65
  • [9] Hydroformylation of myrcene:: metal and ligand effects in the hydroformylation of conjugated dienes
    Foca, CM
    Barros, HJV
    dos Santos, EN
    Gusevskaya, EV
    Bayón, JC
    [J]. NEW JOURNAL OF CHEMISTRY, 2003, 27 (03) : 533 - 539
  • [10] Diastereoselective hydroformylation of camphene catalyzed by platinum/tin complexes
    Foca, CM
    dos Santos, EN
    Gusevskaya, EV
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 185 (1-2) : 17 - 23