SELECTIVITY TO CYCLOHEXENES IN THE LIQUID-PHASE HYDROGENATION OF BENZENE AND TOLUENE OVER RUTHENIUM CATALYSTS, AS INFLUENCED BY REACTION MODIFIERS

被引:86
作者
STRUIJK, J [1 ]
SCHOLTEN, JJF [1 ]
机构
[1] DELFT UNIV TECHNOL,FAC CHEM TECHNOL & MAT SCI,POB 5045,2600 GA DELFT,NETHERLANDS
关键词
BENZENE; HYDROGEN BOND; HYDROGENATION; LIQUID PHASE; METHYLCYCLOHEXENE; MODIFIER; RUTHENIUM; SELECTIVITY (METHYLCYCLOHEXENE); TOLUENE;
D O I
10.1016/0926-860X(92)85010-9
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
A study has been made of the selective liquid-phase hydrogenation of benzene and toluene to cyclohexene and methyl-substituted cyclohexenes, respectively, at ambient temperature and pressure. Just as in gas-phase hydrogenation, the selectivities to cyclohexene or to substituted cyclohexenes strongly increase when reaction modifiers are added. Compounds exhibiting a reaction modifying action contain a hydroxyl or an amine group. The action of modifiers in the liquid phase is explained along the same lines of reasoning as advanced for the case of gas-phase hydrogenation (P.J. van der Steen and J.J.F. Scholten, Appl. Catal., 58 (1990) 291 and J. Struijk and J.J.F. Scholten, Appl. Catal., 62 (1990) 151), and is based on the formation of a hydrogen bond between cyclohexene and the modifier. In the hydrogenation of toluene a large difference in the selectivity to 1-methylcyclohexene and 3- and 4-methylcyclohexene is observed. An interpretation of this effect is presented.
引用
收藏
页码:277 / 287
页数:11
相关论文
共 18 条
  • [1] [Anonymous], 1979, CATALYTIC HYDROGENAT
  • [2] AUGUSTINE RL, 1984, J ORG CHEM, V49, P1865, DOI 10.1021/jo00185a004
  • [3] COMPETITIVE CATALYTIC-HYDROGENATION IN THE LIQUID-PHASE ON SOLID CATALYSTS
    CERVENY, L
    RUZICKA, V
    [J]. CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 1982, 24 (04): : 503 - 566
  • [4] PREPARATION AND SURFACE CHARACTERIZATION OF NONSUPPORTED RUTHENIUM CATALYSTS
    DON, JA
    PIJPERS, AP
    SCHOLTEN, JJF
    [J]. JOURNAL OF CATALYSIS, 1983, 80 (02) : 296 - 306
  • [5] DON JA, 1981, THESIS DELFT U TECHN
  • [6] HARTOG F, 1963, J CATAL, V2, P79
  • [7] HARTOG F, 1965, 3 P INT C CATALYSIS, V2, P1210
  • [8] Hartog F, 1968, Patent, Patent No. [US3391206(A), 3391206]
  • [9] KOOPMAN PGJ, 1980, THESIS DELFT U TECHN
  • [10] THE CATALYTIC-HYDROGENATION OF BENZENE OVER SUPPORTED METAL-CATALYSTS .1. GAS-PHASE HYDROGENATION OF BENZENE OVER RUTHENIUM-ON-SILICA
    SCHOENMAKERSTOLK, MC
    VERWIJS, JW
    DON, JA
    SCHOLTEN, JJF
    [J]. APPLIED CATALYSIS, 1987, 29 (01): : 73 - 90