TY - JOUR T1 - Activation and reactivity of epoxides on solid acid catalysts JF - Journal of Catalysis Y1 - 2007 A1 - Saikia, Lakshi A1 - Satyarthi, J. K. A1 - Srinivas, Darbha A1 - Ratnasamy, P. KW - aminolysis and alcoholysis of epoxides KW - beta-Amino alcohols KW - ring opening of epoxides KW - SBA-15 functionalized with propylsulfortic acid KW - Solid acids KW - Ti-MCM-41 AB -

The aminolysis of epoxides over novel solid catalysts (Bronsted-acidic SBA-15 functionalized with propylsulfonic acid and Lewis-acidic Ti-MCM-41) is reported. The acidic properties of these catalysts were determined by FTIR spectroscopy and temperature-programmed desorption of pyridine and NH3, respectively. The mesoporous solid acids of the present study are reusable and exhibit significantly higher catalytic activities than known catalysts for opening of the oxirane ring with nitrogen (aromatic and aliphatic amines)-containing and oxygen (alcohols)-containing nucleophiles. A range of beta-amino, alcohols with high regioselectivity and stereoselectivity were synthesized. Adsorption studies as well as the sigmoid shape of the conversion- versus-time plots show that the epoxide and amine compete for adsorption on the acidic sites (-SO3H or Ti4+) on the catalyst surface. Epoxide adsorption and activation on acid sites are the more critical processes. Catalytic activity decreases with increasing basicity of the amines and/or the alcohol, as well as the dielectric constant of the solvent. (C) 2007 Elsevier Inc. All rights reserved.

PB - ACADEMIC PRESS INC ELSEVIER SCIENCE CY - 525 B ST, STE 1900, SAN DIEGO, CA 92101-4495 USA VL - 252 IS - 2 U3 -

Foreign

U4 - 7.354 ER -