Issue 6, 2014

Boronate microparticle-supported nano-palladium and nano-gold catalysts for chemoselective hydrogenation of cinnamaldehyde in environmentally preferable solvents

Abstract

Dispersible self-assembled boronate polymers can serve as support materials for metal nanoparticle catalysts. As a proof-of-concept, catalytic systems for the chemoselective hydrogenation of cinnamaldehyde (CA) were prepared by the NaBH4 reduction of PdCl42− and AuCl4 in methanol, in the presence of polyethyleneimine (PEI)-coated boronate particles (BPs) composed of polymeric 3-benzo-2,4,8,10-tetraoxa-3,9-diboraspiro[5.5]undecane. The Pd-deposited BP (Pd/BP) showed highly selective catalytic activity for the hydrogenation of CA to hydrocinnamaldehyde (HCA) under 0.1 MPa of H2 at 25 °C in environmentally preferable solvents such as water and methanol. Of particular note is the recyclability of the hydrogenation catalyst in methanol; repeated 4 h reactions afforded HCA in >90% selectivity with a reaction conversion of 100%. On another front, when the corresponding Au catalyst (Au/BP) was used in the hydrogenation in water, a favorable selective reduction of C[double bond, length as m-dash]O to cinnamyl alcohol (CAL) (selectivity ≈ 80%) was obtained with 78% reaction conversion under 0.8 MPa of H2 at 80 °C for 12 h. The potential use of BP-supported metal nanoparticles as green catalysts is discussed.

Graphical abstract: Boronate microparticle-supported nano-palladium and nano-gold catalysts for chemoselective hydrogenation of cinnamaldehyde in environmentally preferable solvents

Supplementary files

Article information

Article type
Paper
Submitted
04 Mac 2014
Accepted
12 Apr 2014
First published
17 Apr 2014

Green Chem., 2014,16, 3230-3236

Boronate microparticle-supported nano-palladium and nano-gold catalysts for chemoselective hydrogenation of cinnamaldehyde in environmentally preferable solvents

S. Fujiwara, N. Takanashi, R. Nishiyabu and Y. Kubo, Green Chem., 2014, 16, 3230 DOI: 10.1039/C4GC00383G

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