Chemo-, regio- and stereo-selective aerial oxidation of limonene to the endo-1,2-epoxide over Mn(Salen)-sulfonated SBA-15

被引：89

作者：

Saikia, Lakshi ^{[1
]}

Srinivas, D. ^{[1
]}

Ratnasamy, Paul ^{[1
]}

机构：

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

来源：

APPLIED CATALYSIS A-GENERAL | 2006年 / 309卷 / 01期

关键词：

aerial oxidation of limonene; chemo-; regio- and stereo-selective epoxidation; catalysis by Mn(Salen) complexes; sulfonic acid-functionalized SBA-15; immobilized Mn Schiff base complexes; mesoporous molecular sieves; Mukaiyama-type oxidation; MESOPOROUS SILICA; SELECTIVE OXIDATION; EPOXIDATION; COMPLEXES; CATALYSTS; THIOL; EPR; ADSORPTION; OLEFINS; COPPER;

D O I：

10.1016/j.apcata.2006.05.011

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：

Mn(Salen) complexes immobilized on sulfonic acid-functionalized SBA-15 molecular sieves (SBA-15-pr-SO3-Mn(Salen)) catalyze the Mukaiyama-type oxidation of R-(+)-limonene selectively to the 1,2-epoxide with molecular oxygen at 298 K (Salen = N,N-ethylenebis(salicylidenaminato)). The endo-diastereomer is formed with a diasteromeric excess of 39.8%. This catalyst exhibited higher catalytic activity than "neat" Mn(Salen) complexes directly supported on SBA-15 or zeolite-Y. A change in the oxidation state of Mn from +3 in the "neat" complex to +2 when immobilized on the sulfonated surface is a probable cause for the observed enhancement of catalytic activity. A part of the Mn complexes was leached out of the solid phase during the reaction. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：144 / 154

页数：11

共 54 条

[1] Epoxidation of limonene over hydrotalcite-like compounds with hydrogen peroxide in the presence of nitriles
Aramendía, MA
Borau, V
Jiménez, C
Luque, JM
Marinas, JM
Ruiz, JR
Urbano, FJ
[J]. APPLIED CATALYSIS A-GENERAL, 2001, 216 (1-2) : 257 - 265
[2] Comparison of liquid-phase olefin epoxidation over MoOx inserted within mesoporous silica (MCM-41, SBA-15) and grafted onto silica
Bakala, PC
Briot, E
Salles, L
Brégeault, JM
[J]. APPLIED CATALYSIS A-GENERAL, 2006, 300 (02) : 91 - 99
[3] EPR spectroscopy of copper and manganese complexes encapsulated in zeolites
Bennur, TH
Srinivas, D
Ratnasamy, P
[J]. MICROPOROUS AND MESOPOROUS MATERIALS, 2001, 48 (1-3) : 111 - 118
[4] EFFECTS ON MOLECULAR ASSOCIATION, CHELATE CONFORMATION, AND REACTIVITY TOWARD SUBSTITUTION IN CU(5-X-SALEN) COMPLEXES, SALEN2- = N,N'-ETHYLENEBIS(SALICYLIDENAMINATO), X = H, CH3O, AND CL - SYNTHESIS, X-RAY STRUCTURES, AND EPR INVESTIGATIONS
BHADBHADE, MM
SRINIVAS, D
[J]. INORGANIC CHEMISTRY, 1993, 32 (24) : 5458 - 5466
[5] Synthesis and application of layered double hydroxide-hosted catalysts for stereoselective epoxidation using molecular oxygen or air
Bhattacharjee, S
Dines, TJ
Anderson, JA
[J]. JOURNAL OF CATALYSIS, 2004, 225 (02) : 398 - 407
[6] Selectivity in the oxidation of limonene by amphiphilized metalloporphyrins in micellar media
Borocci, S
Marotti, F
Mancini, G
Monti, D
Pastorini, A
[J]. LANGMUIR, 2001, 17 (23) : 7198 - 7203
[7] Liquid phase oxidation of limonene catalyzed by palladium supported on hydrotalcites
Bussi, J
López, A
Peña, F
Timbal, P
Paz, D
Lorenzo, D
Dellacasa, E
[J]. APPLIED CATALYSIS A-GENERAL, 2003, 253 (01) : 177 - 189
[8] Ti-MCM-41 silylation:: Development of a simple methodology for its estimation -: Silylation effect on the activity and selectivity in the limonene oxidation with H2O2
Cagnoli, MV
Casuscelli, SG
Alvarez, AM
Bengoa, JF
Gallegos, NG
Crivello, ME
Herrero, ER
Marchetti, SG
[J]. CATALYSIS TODAY, 2005, 107-08 : 397 - 403
[9] Clean limonene epoxidation using Ti-MCM-41 catalyst
Cagnoli, MV
Casuscelli, SG
Alvarez, AM
Bengoa, JF
Gallegos, NG
Samaniego, NM
Crivello, ME
Ghione, GE
Pérez, CF
Herrero, ER
Marchetti, SG
[J]. APPLIED CATALYSIS A-GENERAL, 2005, 287 (02) : 227 - 235
[10] Sulfonic acid-functionalized silica through quantitative oxidation of thiol groups
Cano-Serrano, E
Campos-Martin, JM
Fierro, JLG
[J]. CHEMICAL COMMUNICATIONS, 2003, (02) : 246 - 247

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