An efficient heterogeneous catalytic system for chemoselective hydrogenation of unsaturated ketones in aqueous medium

被引：9

作者：

Deshmukh, Amit ^{[1
,2
]}

Kinage, Anil ^{[1
]}

Kumar, Rajiv ^{[3
]}

Meijboom, Reinout ^{[2
]}

机构：

[1] Natl Chem Lab, Catalysis Div, Pune 411008, Maharashtra, India

[2] Univ Johannesburg, Dept Chem, Johannesburg, South Africa

[3] Tata Chem Ltd, Pune, Maharashtra, India

来源：

POLYHEDRON | 2010年 / 29卷 / 17期

关键词：

Ruthenium; 1; 10; Phenanthroline; Mesoporous materials; alpha beta Unsaturated ketone; Chemoselective hydrogenation; ALPHA; BETA-UNSATURATED KETONE; SELECTIVE HYDROGENATION; DIAMINE(ETHER-PHOSPHINE)RUTHENIUM(II) COMPLEXES; ELECTROCHEMICAL PROPERTIES; MESOPOROUS MATERIALS; ALLYLIC ALCOHOLS; RUTHENIUM(II); ALDEHYDES; PHENANTHROLINE;

D O I：

10.1016/j.poly.2010.09.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A highly chemoselective and green heterogeneous catalytic system of immobilized Ru(II)-phenanthroline complexes on amino functionalised MCM-41 material for the chemoselective hydrogenation of unsaturated ketones to unsaturated alcohols is demonstrated using water as a solvent The XRD and FTIR spectra show the highly ordered hexagonal nature of the MCM-41 even after encapsulation of the ruthenium complex The complex retains its configuration after anchoring as was confirmed by FTIR and UV-Vis analysis The detailed reaction parametric effect was studied for the hydrogenation of 3 methylpent-3-en-2-one to achieve complete conversion up to >99% chemoselectivity of 3-methylpent-3-en-2 ol The anchored heterogeneous catalysts were recycled effectively and reused five times with marginal changes in activity and selectivity The use of water as a solvent not only afforded high activity for the hydroge nation reaction compared to organic solvents but also afforded a green process Crown Copyright (C) 2010 Published by Elsevier Ltd All rights reserved

引用

页码：3262 / 3268

页数：7

共 33 条

[1]

ALMEIDA MR, 1990, J APPL PHYS, V68, P4225

[2] STUDIES ON MESOPOROUS MATERIALS .1. SYNTHESIS AND CHARACTERIZATION OF MCM-41 [J].

CHEN, CY ;

LI, HX ;

DAVIS, ME .

MICROPOROUS MATERIALS, 1993, 2 (01) :17-26

[3] Highly chemoselective catalytic hydrogenation of unsaturated ketones and aldehydes to unsaturated alcohols using phosphine-stabilized copper(I) hydride complexes [J].

Chen, JX ;

Daeuble, JF ;

Brestensky, DM ;

Stryker, JFM .

TETRAHEDRON, 2000, 56 (15) :2153-2166

[4] Heterogeneously catalysed hydrogenation using gold catalysts [J].

Claus, P .

APPLIED CATALYSIS A-GENERAL, 2005, 291 (1-2) :222-229

[5] SOLUBILITY OF HYDROGEN IN WATER, SEAWATER, AND NACL SOLUTIONS [J].

CROZIER, TE ;

YAMAMOTO, S .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1974, 19 (03) :242-244

[6] Mesoporous Zr and Hf catalysts for chemoselective MPV reductions of unsaturated ketones [J].

De Bruyn, M ;

Limbourg, M ;

Denayer, J ;

Baron, GV ;

Parvulescu, V ;

Grobet, PJ ;

De Vos, DE ;

Jacobs, PA .

APPLIED CATALYSIS A-GENERAL, 2003, 254 (02) :189-201

[7] Chemoselective reduction of complex α,β-unsaturated ketones to allylic alcohols over Ir-metal particles on β zeolites [J].

De Bruyn, M ;

Coman, S ;

Bota, R ;

Parvulescu, VI ;

De Vos, DE ;

Jacobs, PA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (43) :5333-5336

[8] High catalytic efficiency of transition metal complexes encapsulated in a cubic mesoporous phase [J].

Eswaramoorthy, M ;

Neeraj ;

Rao, CNR .

CHEMICAL COMMUNICATIONS, 1998, (05) :615-616

[9] Enantio selective hydrogenation of exocyclic α,β-unsaturated ketones -: Part III.: Hydrogenation with Pd in the presence of cinchonidine [J].

Fogassy, G ;

Tungler, A ;

Lévai, A .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 192 (1-2) :189-194

[10] INFRARED-REFLECTANCE SPECTRA OF HEAT-TREATED, SOL-GEL-DERIVED SILICA [J].

KAMITSOS, EI ;

PATSIS, AP ;

KORDAS, G .

PHYSICAL REVIEW B, 1993, 48 (17) :12499-12505

← 1 2 3 4 →