Preparation and synergetic catalytic effects of amino-functionalized MCM-41 catalysts

Science China Chemistry

Volumn 55, Issue 6, 2012, Pages 1167-1174

  Lang, Wanzhong ^a   Su, Bo ^a   Guo, Yajun ^a   Chu, Lianfeng ^a  

^a SHANGHAI NORMAL UNIVERSITY   (China)

Author keywords

acid base synergism; MCM 41; n butanal; organoamine

Indexed keywords

ACID BASE; CATALYTIC EFFECTS; CATALYTIC PERFORMANCE; CHANNEL WALL; FUNCTIONALIZED; FUNCTIONALIZED MCM-41; HENRY REACTIONS; KNOEVENAGEL CONDENSATION; LOADING AMOUNT; MCM-41; MESOPOROUS CATALYSTS; MESOPOROUS SILICA; N-BUTANAL; ORGANOAMINE; SECONDARY AMINES; SELF-CONDENSATION; SILANOLS;

CATALYSTS; CONDENSATION REACTIONS; MESOPOROUS MATERIALS; ORGANIC COMPOUNDS;

LOADING;

EID: 84862509714     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-012-4594-x     Document Type: Conference Paper

References (43)

1. C.T. Kresge M.E. Leonowicz W.G. Roth J.C. Vartuli J.S. Beck 1992 Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism Nature 359 710 712 10.1038/359710a0 1:CAS:528:DyaK38Xms1entrs%3D (Pubitemid 23589384)
2. Y.V. Subba Rao D.E. De Vos P.A. Jacobs 1997 1,5,7-Triazabicyclo [4.4.0] dec-5-ene immobilized in MCM-41: A strongly basic porous catalyst Angew Chem Int Ed 36 2661 2663 10.1002/anie.199726611
3. Shimizu K, Suzuki H, Hayashi E, Kodama T, Tsuchiya Y, Hagiwara H, Kitayama Y. Catalytic direct 1,4-conjugate addition of aldehydes to vinylketones on secondary-amines immobilised in FSM-16 silica. Chem Commun, 2002, 1068-1069 (Pubitemid 34579486)
4. Inaki Y, Kajita Y, Yoshida H, Ito K, Hattori T. New basic mesoporous silica catalyst obtained by ammonia grafting. Chem Commun, 2001, 2358-2359 (Pubitemid 33078317)
5. Q. Yang M.P. Kapoor N. Shirokura M. Ohashi S. Inagaki J.N. Kondo K. Domen 2005 Ethane-bridged hybrid mesoporous functionalized organosilicas with terminal sulfonic groups and their catalytic applications J Mater Chem 15 666 673 10.1039/b413773f 1:CAS:528:DC%2BD2MXpt1WmsA%3D%3D (Pubitemid 40299073)
6. R.V. Crieken J.A. Melero G. Morales 2006 Etherification of benzyl alcohols with 1-hexanol over organosulfonic acid mesostructured materials J Mol Catal A 256 29 36 10.1016/j.molcata.2006.04.040 (Pubitemid 44247838)
7. 40 immobilized in hydrophobic nanospaces of organomodified mesoporous silica Angew Chem Int Ed 46 7625 7628 10.1002/anie.200702478 1:CAS:528:DC%2BD2sXhtF2rs7vM (Pubitemid 47557012)
8. B.M. Choudary M. Lakshmi Kantam P. Sreekanth T. Bandopadhyay 1999 Knoevenagel and aldol condensations catalysed by a new diamino-functionalised mesoporous material J Mol Catal A 142 361 365 10.1016/S1381-1169(98)00301-X 1:CAS:528:DyaK1MXivVSlsL4%3D
9. A.P. Wight M.E. Davis 2002 Design and preparation of organic-inorganic hybrid catalysts Chem Rev 102 3589 3614 10.1021/cr010334m 1:CAS:528: DC%2BD38Xms1Wntr0%3D (Pubitemid 35350660)
10. D.E. De Vos M. Dams B.F. Sels P.A. Jacobs 2002 Ordered mesoporous and microporous molecular sieves functionalized with transition metal complexes as catalysts for selective organic transformations Chem Rev 102 3615 3640 10.1021/cr010368u (Pubitemid 35350661)
11. D.J. Macquarrie R. Maggi A. Mazzacani G. Sartori R. Sartorio 2003 Understanding the influence of the immobilization procedure on the catalytic activity of aminopropylsilicas in C-C forming reactions Appl Catal A-Gen 246 183 188 10.1016/S0926-860X(03)00004-8 1:CAS:528:DC%2BD3sXkvVSnsLk%3D
12. M. Árpád R. Bulcsú 2006 Organic transformations over silica materials modified by covalently bonded surface functional groups Curr Org Chem 10 1697 1726 10.2174/138527206778249649 (Pubitemid 44356005)
13. S. Angloher J. Kecht T. Bein 2008 Mesoporous ordered silica structures modified by metal organic reagents and their application in catalytic Michael additions Micropor Mesopor Mater 115 629 633 10.1016/j.micromeso.2008.02.019 1:CAS:528:DC%2BD1cXhtVOmu7nE
14. E. Angeletti C. Canepa G. Martinetti P. Venturello 1988 Silica gel functionalized with amino groups as a new catalyst for Knoevenagel condensation under heterogeneous catalysis conditions Tetrahedron Lett 29 2261 2264 10.1016/S0040-4039(00)86727-1 1:CAS:528:DyaL1MXnvVSq
15. Macquarrie DJ, Jackson DB. Aminopropylated MCMs as base catalysts: A comparison with aminopropylated silica. Chem Commun, 1997, 1781-1782 (Pubitemid 127495536)
16. Y. Kubota Y. Nishizaki H. Ikeya M. Saeki T. Hida S. Kawazu M. Yoshida H. Fujii Y. Sugi 2004 Organic-silicate hybrid catalysts based on various defined structures for Knoevenagel condensation Micropor Mesopor Mater 70 135 149 10.1016/j.micromeso.2004.02.017 1:CAS:528:DC%2BD2cXjs1ejsb8%3D (Pubitemid 38549790)
17. X.G. Wang K.S.K. Lin J.C.C. Chan S.F. Cheng 2005 Direct synthesis and catalytic applications of ordered large pore aminopropyl-functionalized SBA-15 mesoporous materials J Phys Chem B 109 1763 1769 10.1021/jp045798d 1:CAS:528:DC%2BD2MXjtFKqsQ%3D%3D (Pubitemid 40213178)
18. F. Bigi S. Carloni R. Maggi A. Mazzacani G. Sartori 2000 Nitroaldol condensation promoted by organic bases tethered to amorphous silica and MCM-41-type materials Stud Surf Sci Catal 130 3501 3506 10.1016/S0167-2991(00) 80565-0
19. G. Demicheli R. Maggi A. Mazzacani P. Righi G. Sartori F. Bigi 2001 Supported organic catalysts: Synthesis of (E)-nitrostyrenes from nitroalkanes and aromatic aldehydes over propylamine supported on MCM-41 silica as a reusable catalyst Tetrahedron Lett 42 2401 2403 10.1016/S0040-4039(01)00156-3 1:CAS:528:DC%2BD3MXhslOgs78%3D (Pubitemid 32200455)
20. Y. Kubota K. Goto S. Miyata Y. Goto Y. Fukushima Y. Sugi 2003 Enhanced effect of mesoporous silica on base-catalyzed aldol reaction Chem Lett 32 234 235 10.1246/cl.2003.234 1:CAS:528:DC%2BD3sXitlCltbs%3D (Pubitemid 36702953)
21. Y. Kubota H. Ikeya Y. Sugi T. Yamada T. Tatsumi 2006 Organic-inorganic hybrid catalysts based on ordered porous structures for michael reaction J Mol Catal A 249 181 190 10.1016/j.molcata.2006.01.015 1:CAS:528:DC%2BD28XjslCksbk%3D
22. A.C. Blanc D.J. Macquarrie S. Valle G. Renard C.R. Quinn D. Brunel 2000 The preparation and use of novel immobilised guanidine catalysts in base-catalysed epoxidation and condensation reactions Green Chem 2 283 288 10.1039/b005929n 1:CAS:528:DC%2BD3cXoslWjtrk%3D (Pubitemid 33205959)
23. X.G. Wang Y.H. Tseng J.C.C. Chan S. Cheng 2005 Catalytic applications of aminopropylated mesoporous silica prepared by a template-free route in flavanones synthesis J Catal 233 266 275 10.1016/j.jcat.2005.04.007 1:CAS:528:DC%2BD2MXmtFGitbk%3D (Pubitemid 40972835)
24. T.M. Suzuki T. Nakamura K. Fukumoto M. Yamamoto Y. Akimoto K. Yano 2008 Direct synthesis of amino-functionalized monodispersed mesoporous silica spheres and their catalytic activity for nitroaldol condensation J Mol Catal A: Chem 280 224 232 10.1016/j.molcata.2007.11.012 1:CAS:528:DC%2BD1cXot1Kjuw%3D%3D
25. A. Anan K.K. Sharma T. Asefa 2008 Selective, efficient nanoporous catalysts for nitroaldol condensation: Co-placement of multiple site-isolated functional groups on mesoporous materials J Mol Catal A 288 1 13 10.1016/j.molcata.2008.03.027 1:CAS:528:DC%2BD1cXms1yrtLk%3D
26. B. Su W.Z. Lang Q.Y. Zeng X.W. Liu C.J. Yang Y.J. Guo 2010 Preparation of organic functionalized mesoporous catalysts and their applications to the self-condensation reaction of n-butanal to 2-ethylhexenal Chin J Proc Eng 103 55 360
27. W.Z. Lang X.W. Liu Y.J. Guo B. Su L.F. Chu C.X. Guo 2011 A novel MCM-41-supported bi-functional catalyst by immobilizing organoamine and Rh-P complex for one-pot synthesis of 2-ethylhexenal from propene Micropor Mesopor Mater 142 7 16 10.1016/j.micromeso.2010.07.019 1:CAS:528:DC%2BC3MXjtFOntL8%3D
28. K.I. Shimizu E. Hayashi T. Inokuchi T. Kodama H. Hagiwara Y. Kitayama 2002 Self-aldol condensation of unmodified aldehydes catalysed by secondary-amine immobilised in FSM-16 silica Tetrahedron Lett 43 9073 9075 10.1016/S0040-4039(02)02313-4 1:CAS:528:DC%2BD38Xos1ansLg%3D (Pubitemid 35305072)
29. J.D. Bass A. Solovyov A.J. Pascall A. Katz 2006 Acid-base bifunctional and dielectric outer-sphere effects in heterogeneous catalysis: A comparative investigation of model primary amine catalysts J Am Chem Soc 128 3737 3747 10.1021/ja057395c 1:CAS:528:DC%2BD28Xhs12ltLg%3D
30. K.K. Sharma T. Asefa 2007 Efficient bifunctional nanocatalysts by simple postgrafting of spatially isolated catalytic groups on mesoporous materials Angew Chem Int Ed 119 2879 2882 10.1002/anie.200604570 (Pubitemid 46981289)
31. K.K. Sharma A. Anan R.P. Buckley W. Ouellette T. Asefa 2008 Toward efficient nanoporous catalysts: Controlling site-isolation and concentration of grafted catalytic sites on nanoporous materials with solvents and colorimetric elucidation of their site-isolation J Am Chem Soc 130 218 228 10.1021/ja074128t 1:CAS:528:DC%2BD2sXhsVWgurjF
32. K.K. Sharma R.P. Buckley T. Asefa 2008 Optimizing acid-base bifunctional mesoporous catalysts for the henry reaction: Effects of the surface density and site isolation of functional groups Langmuir 24 14306 14320 10.1021/la8030107 1:CAS:528:DC%2BD1cXhtlGrsr%2FM
33. S.L. Hruby B.H. Shanks 2009 Acid-base cooperativity in condensation reactions with functionalized mesoporous silica catalysts J Catal 263 181 188 10.1016/j.jcat.2009.02.011 1:CAS:528:DC%2BD1MXjt1Khsrc%3D
34. Y.W. Xie K.K. Sharma A. Anan G. Wang A.V. Biradar T. Asefa 2009 Efficient solid-base catalysts for aldol reaction by optimizing the density and type of organoamine groups on nanoporous silica J Catal 265 131 140 10.1016/j.jcat.2009. 04.018 1:CAS:528:DC%2BD1MXnvVClt7k%3D
35. J.D. Bass A. Katz 2006 Bifunctional surface imprinting of silica: Thermolytic synthesis and characterization of discrete thiol-amine functional group pairs Chem Mater 18 1611 1620 10.1021/cm052382j 1:CAS:528: DC%2BD28Xhs12ltro%3D
36. J.M. Notestein A. Katz 2006 Enhancing heterogeneous catalysis through cooperative hybrid organic-inorganic interfaces Chem Eur J 12 3954 3965 10.1002/chem.200501152 1:CAS:528:DC%2BD28XlsV2qsb8%3D (Pubitemid 43759719)
37. R.K. Zeidan S.J. Hwang M.E. Davis 2006 Multifunctional heterogeneous catalysts: SBA-15-containing primary amines and sulfonic acids Angew Chem Int Ed 45 6332 6335 10.1002/anie.200602243 1:CAS:528:DC%2BD28XhtVKmsb%2FO (Pubitemid 44483857)
38. R.K. Zeidan M.E. Davis 2007 The effect of acid-base pairing on catalysis: An efficient acid-base functionalized catalyst for aldol condensation J Catal 247 379 382 10.1016/j.jcat.2007.02.005 1:CAS:528:DC%2BD2sXjvVans7s%3D (Pubitemid 46497126)
39. K. Motokura M. Tada Y. Iwasawa 2007 Heterogeneous organic base-catalyzed reactions enhanced by acid supports J Am Chem Soc 129 9540 9541 10.1021/ja0704333 1:CAS:528:DC%2BD2sXns1CntLc%3D (Pubitemid 47237436)
40. S. Shylesh A. Wagner A. Seifert S. Ernst W.R. Thiel 2009 Cooperative acid-base effects with functionalized mesoporous silica nanoparticles: Applications in carbon-carbon bond-formation reactions Chem Eur J 15 7052 7062 10.1002/chem.200900851 1:CAS:528:DC%2BD1MXoslyjsL4%3D
41. Y.Q. Shao J.Q. Guan S.J. Wu H. Liu B. Liu Q.B. Kan 2010 Synthesis, characterization and catalytic activity of acid-base bifunctional materials by controlling steric hindrance Micropor Mesopor Mater 128 120 125 10.1016/j.micromeso.2009.08.013 1:CAS:528:DC%2BD1MXhsVWmsL7N
42. S. Cousinié M. Gressier P. Alphonse M.J. Menu 2007 Silica-based nanohybrids containing dipyridine, urethan, or urea derivatives Chem Mater 19 6492 6503 10.1021/cm7019075
43. J.Y. Kim P. Seidler L.S. Wan C. Fil 2009 Formation, structure, and reactivity of amino-terminated organic films on silicon substrates Colloid Interf Sci 329 114 119 10.1016/j.jcis.2008.09.031 1:CAS:528:DC%2BD1cXhtlCkt7rK