Use of immobilized organic base catalysts for continuous-flow fine chemical synthesis

被引：44

作者：

Soldi, L. ^{[1
]}

Ferstl, W. ^{[2
]}

Loebbecke, S. ^{[2
]}

Maggi, R. ^{[1
]}

Malmassari, C. ^{[1
]}

Sartori, G. ^{[1
]}

Yada, S. ^{[2
]}

机构：

[1] Univ & Consorzio Interuniv Chim Ambiente INCA, Dipartimento Chim Organ & Ind, Clean Synthet Methodol Grp, I-43100 Parma, Italy

[2] Fraunhofer Inst Chem Technol ICT, D-76327 Pfinztal, Germany

来源：

JOURNAL OF CATALYSIS | 2008年 / 258卷 / 02期

关键词：

nitroaldol condensation; Michael addition; heterogeneous catalysis; organic-inorganic hybrid composites; supported catalysts; continuous-flow processes;

D O I：

10.1016/j.jcat.2008.07.005

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 continuous-flow two-step process for the production of multifunctional intermediate compounds was performed with a combination of two column reactors packed with different organic immobilized catalysts. The first step of the reaction, nitroaldol condensation between aromatic aldehydes and nitromethane, is promoted by a silica gel-supported primary amine; the second step, Michael addition of beta-dicarbonyl compounds to the nitrostyrenes obtained in the first step, is catalyzed by a silica gel-supported guanidine TBD. In both cases, the catalysts can be directly reused for several runs with no significant changes in activity. (C) 2008 Elsevier Inc. All rights reserved.

引用

页码：289 / 295

页数：7

共 47 条

[1] AMINO-GROUPS IMMOBILIZED ON SILICA-GEL - AN EFFICIENT AND REUSABLE HETEROGENEOUS CATALYST FOR THE KNOEVENAGEL CONDENSATION [J].

ANGELETTI, E ;

CANEPA, C ;

MARTINETTI, G ;

VENTURELLO, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01) :105-107

[2]

Baer H. H., 1970, CHEM NITRO NITROSO 2, P117

[3] Use of heterogeneous catalyst KG-60-NEt2 in Michael and Henry reactions involving nitroalkanes [J].

Ballini, R ;

Bosica, G ;

Livi, D ;

Palmieri, A ;

Maggi, R ;

Sartori, G .

TETRAHEDRON LETTERS, 2003, 44 (11) :2271-2273

[4] Recent developments on the chemistry of aliphatic nitro compounds under aqueous medium [J].

Ballini, Roberto ;

Barboni, Luciano ;

Fringuelli, Francesco ;

Palmieri, Alessandro ;

Pizzo, Ferdinando ;

Vaccaro, Luigi .

GREEN CHEMISTRY, 2007, 9 (08) :823-838

[5] CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].

BARRETT, AGM ;

GRABOSKI, GG .

CHEMICAL REVIEWS, 1986, 86 (05) :751-762

[6]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[7] Improving solid-supported catalyst productivity by using simplified packed-bed microreactors [J].

Bogdan, Andrew R. ;

Mason, Brian P. ;

Sylvester, Kevin T. ;

McQuade, D. Tyler .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1698-1701

[8]

Buchmeiser M. R., 2003, POLYM MAT ORGANIC SY

[9] Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents [J].

Caldarelli, M ;

Habermann, J ;

Ley, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02) :107-110

[10] Catalytic activity of MCM-41-TBD in the selective preparation of carbamates and unsymmetrical alkyl carbonates from diethyl carbonate [J].

Carloni, S ;

De Vos, DE ;

Jacobs, PA ;

Maggi, R ;

Sartori, G ;

Sartorio, R .

JOURNAL OF CATALYSIS, 2002, 205 (01) :199-204

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