Control of the selectivity in multi-functional group molecules using supported gold–palladium nanoparticles

The oxidation of 2-hexen-1-ol and 1-hexen-3-ol with air has been studied using supported gold, palladium and gold–palladium catalysts. The main aim was to determine if either the alcohol or alkene functional group can be oxidised selectively. However, based on the reaction products observed (2-hexen-1-ol forms 2-hexene, hexanal, (E)-2-hexenal, (E)-3-hexen-1-ol, 4-hexen-1-ol and (E)-2-hexanoic acid. 1-Hexen-3-ol forms 1-hexene, 3-hexanone, 1-hexen-3-one and 3-hexenol), the main pathway in these reactions is isomerisation and, in addition, significant yields of the products are due to a disproportionation reaction. Controlling the selectivity in molecules with multiple function groups by manipulating the catalyst composition and reaction conditions can promote or hinder the various reaction pathways, thereby increasing the selectivity to the desired oxidation products.

[1]  Peter J. Miedziak,et al.  Selective Oxidation of Glycerol by Highly Active Bimetallic Catalysts at Ambient Temperature under Base-Free Conditions , 2011, Angewandte Chemie.

[2]  G. Hutchings,et al.  Selective oxidation of alkenes using graphite-supported gold-palladium catalysts , 2011 .

[3]  G. Hutchings,et al.  Controlling the duality of the mechanism in liquid-phase oxidation of benzyl alcohol catalysed by supported Au-Pd nanoparticles. , 2011, Chemistry.

[4]  Peter J. Miedziak,et al.  Oxidation of benzyl alcohol using supported gold-palladium nanoparticles , 2011 .

[5]  F. Rominger,et al.  Gold catalysis: tandem reactions of diyne-diols and external nucleophiles as an easy access to tricyclic cage-like structures. , 2010, Chemistry.

[6]  Frank Rominger,et al.  Gold catalysis: in situ EXAFS study of homogeneous oxidative esterification. , 2010, Chemistry.

[7]  G. Hutchings,et al.  Direct synthesis of hydrogen peroxide and benzyl alcohol oxidation using Au-Pd catalysts prepared by sol immobilization. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[8]  G. Hutchings,et al.  Solvent-free selective epoxidation of cyclooctene using supported gold catalysts , 2009 .

[9]  Kangnian Fan,et al.  A green and efficient oxidation of alcohols by supported gold catalysts using aqueous H2O2 under organic solvent-free conditions , 2009 .

[10]  Xueguang Wang,et al.  Selective oxidation of alcohols to aldehydes and ketones over TiO2-supported gold nanoparticles in supercritical carbon dioxide with molecular oxygen , 2008 .

[11]  Kangnian Fan,et al.  Solvent-free selective oxidation of alcohols by molecular oxygen over gold nanoparticles supported on β-MnO2 nanorods , 2008 .

[12]  Kangnian Fan,et al.  MnO2 Nanorod Supported Gold Nanoparticles with Enhanced Activity for Solvent-free Aerobic Alcohol Oxidation , 2008 .

[13]  Peter J. Miedziak,et al.  Au-Pd supported nanocrystals prepared by a sol immobilisation technique as catalysts for selective chemical synthesis. , 2008, Physical chemistry chemical physics : PCCP.

[14]  A. Villa,et al.  Effect of gold addition on Pt and Pd catalysts in liquid phase oxidations , 2007 .

[15]  A. Corma,et al.  Supported gold nanoparticles for aerobic, solventless oxidation of allylic alcohols , 2007 .

[16]  A. Corma,et al.  Unique gold chemoselectivity for the aerobic oxidation of allylic alcohols. , 2006, Chemical communications.

[17]  A. Corma,et al.  Efficient chemoselective alcohol oxidation using oxygen as oxidant. Superior performance of gold over palladium catalysts , 2006 .

[18]  A. Corma,et al.  A collaborative effect between gold and a support induces the selective oxidation of alcohols. , 2005, Angewandte Chemie.

[19]  H. Sakurai,et al.  Size-specific catalytic activity of polymer-stabilized gold nanoclusters for aerobic alcohol oxidation in water. , 2005, Journal of the American Chemical Society.

[20]  V. Choudhary,et al.  Epoxidation of styrene by anhydrous t-butyl hydroperoxide over gold supported on Al2O3, Ga2O3, In2O3 and Tl2O3 , 2004 .

[21]  R. Sonawane,et al.  Epoxidation of Styrene by Anhydrous t-Butyl Hydroperoxide over Au/TiO2 Catalysts , 2004 .

[22]  C. Pham‐Huu,et al.  Carbon nanofiber supported palladium catalyst for liquid-phase reactions: An active and selective catalyst for hydrogenation of cinnamaldehyde into hydrocinnamaldehyde , 2001 .

[23]  P. Gallezot.  Selective oxidation with air on metal catalysts , 1997 .

[24]  Peter J. Miedziak,et al.  Oxidation of alcohols using supported gold and gold–palladium nanoparticles , 2010 .

[25]  R. Sheldon.  Heterogeneous Catalytic Oxidation and Fine Chemicals , 1991 .