Premium
Hybrid Inorganic‐Organic Materials Carrying Tertiary Amine and Thiourea Residues Tethered on Mesoporous Silica Nanoparticles: Synthesis, Characterization, and Co‐Operative Catalysis
Author(s) -
Puglisi Alessandra,
Annunziata Rita,
Benaglia Maurizio,
Cozzi Franco,
Gervasini Antonella,
Bertacche Vittorio,
Sala Maria Chiara
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800635
Subject(s) - bifunctional , chemistry , thiourea , acetylacetone , catalysis , amine gas treating , mesoporous silica , imine , mesoporous material , tertiary amine , organic chemistry , polymer chemistry
Mesoporous silica nanoparticles carrying different loadings of tertiary amine and thiourea residues (residues ratios 53/47, 68/32, and 22/78, respectively) were synthesized by the co‐condensation method and fully characterized by CP MAS NMR, powder XRD, SEM, BET, BJH and FT‐IR techniques. These materials were tested as bifunctional catalysts in the conjugate addition of acetylacetone to 2‐nitrostyrene, a reaction that under solvent‐free conditions occurred in quantitative yield. By carrying out several experiments with the bifunctional catalysts featuring different molar ratios of active sites, and with different combinations of monofunctional supported and non‐supported catalyst, the co‐operativity of the tertiary amine and thiourea residues in catalyzing the reaction was demonstrated. The use of the bifunctional catalyst was extended to the addition of acetylacetone to an activated imine. Catalyst recycling for a total of three reaction cycles was demonstrated without significant erosion of activity.