Catalytic transfer hydrogenation of hydrophobic substrates by water-insoluble hydrogen donors in aqueous microemulsions

Charlie Batarseh; Zackaria Nairoukh; Iryna Volovych; Michael Schwarze; Reinhard Schomäcker; Monzer Fanun; Jochanan Blum

doi:10.1016/j.molcata.2012.09.025

Catalytic transfer hydrogenation of hydrophobic substrates by water-insoluble hydrogen donors in aqueous microemulsions

Charlie Batarseh, Zackaria Nairoukh, Iryna Volovych, Michael Schwarze, Reinhard Schomäcker, Monzer Fanun, Jochanan Blum^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

In the course of our attempts to replace harmful organic solvents used in organic processes by environmentally favored media, we investigated the transfer hydrogenation of various, unsaturated substrates by cyclohexene and similar water-insoluble hydrogen donors. The catalyst in these reactions was Pd(0) in form of nanoparticles, stabilized by hydrophobic silica sol-gel which can be reused at least 4-6 times without significant loss of activity. The process was shown to depend on the electronic nature of the surfactants. Marlipal ^® 24/70 gave in most experiments the best results. Except for the hydrolysable 1-chloromethylnaphthalene, where chlorine can be substituted by a hydroxyl group, the aqueous medium does not take part in the catalytic process.

Original language	English
Pages (from-to)	210-214
Number of pages	5
Journal	Journal of Molecular Catalysis A: Chemical
Volume	366
DOIs	https://doi.org/10.1016/j.molcata.2012.09.025
State	Published - Jan 2013

Bibliographical note

Funding Information:
We thank Dr. Inna Popov for performing the TEM measurements and Dr. Vitaly Gutking for the XPS analyses. We also acknowledge the financial support of the Deutsche Forschungsgemeinschaft (DFG) for a trilateral grant No. SCHO687/8-2 .

Keywords

Aqueous microemulsion
Heterogeneous catalysis
Palladium
Sustainable chemistry
Transfer hydrogenation

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10.1016/j.molcata.2012.09.025

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title = "Catalytic transfer hydrogenation of hydrophobic substrates by water-insoluble hydrogen donors in aqueous microemulsions",

abstract = "In the course of our attempts to replace harmful organic solvents used in organic processes by environmentally favored media, we investigated the transfer hydrogenation of various, unsaturated substrates by cyclohexene and similar water-insoluble hydrogen donors. The catalyst in these reactions was Pd(0) in form of nanoparticles, stabilized by hydrophobic silica sol-gel which can be reused at least 4-6 times without significant loss of activity. The process was shown to depend on the electronic nature of the surfactants. Marlipal {\textregistered} 24/70 gave in most experiments the best results. Except for the hydrolysable 1-chloromethylnaphthalene, where chlorine can be substituted by a hydroxyl group, the aqueous medium does not take part in the catalytic process.",

keywords = "Aqueous microemulsion, Heterogeneous catalysis, Palladium, Sustainable chemistry, Transfer hydrogenation",

author = "Charlie Batarseh and Zackaria Nairoukh and Iryna Volovych and Michael Schwarze and Reinhard Schom{\"a}cker and Monzer Fanun and Jochanan Blum",

note = "Funding Information: We thank Dr. Inna Popov for performing the TEM measurements and Dr. Vitaly Gutking for the XPS analyses. We also acknowledge the financial support of the Deutsche Forschungsgemeinschaft (DFG) for a trilateral grant No. SCHO687/8-2 .",

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doi = "10.1016/j.molcata.2012.09.025",

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AU - Batarseh, Charlie

AU - Nairoukh, Zackaria

AU - Volovych, Iryna

AU - Schwarze, Michael

AU - Schomäcker, Reinhard

AU - Fanun, Monzer

AU - Blum, Jochanan

N1 - Funding Information: We thank Dr. Inna Popov for performing the TEM measurements and Dr. Vitaly Gutking for the XPS analyses. We also acknowledge the financial support of the Deutsche Forschungsgemeinschaft (DFG) for a trilateral grant No. SCHO687/8-2 .

PY - 2013/1

Y1 - 2013/1

N2 - In the course of our attempts to replace harmful organic solvents used in organic processes by environmentally favored media, we investigated the transfer hydrogenation of various, unsaturated substrates by cyclohexene and similar water-insoluble hydrogen donors. The catalyst in these reactions was Pd(0) in form of nanoparticles, stabilized by hydrophobic silica sol-gel which can be reused at least 4-6 times without significant loss of activity. The process was shown to depend on the electronic nature of the surfactants. Marlipal ® 24/70 gave in most experiments the best results. Except for the hydrolysable 1-chloromethylnaphthalene, where chlorine can be substituted by a hydroxyl group, the aqueous medium does not take part in the catalytic process.

AB - In the course of our attempts to replace harmful organic solvents used in organic processes by environmentally favored media, we investigated the transfer hydrogenation of various, unsaturated substrates by cyclohexene and similar water-insoluble hydrogen donors. The catalyst in these reactions was Pd(0) in form of nanoparticles, stabilized by hydrophobic silica sol-gel which can be reused at least 4-6 times without significant loss of activity. The process was shown to depend on the electronic nature of the surfactants. Marlipal ® 24/70 gave in most experiments the best results. Except for the hydrolysable 1-chloromethylnaphthalene, where chlorine can be substituted by a hydroxyl group, the aqueous medium does not take part in the catalytic process.

KW - Aqueous microemulsion

KW - Heterogeneous catalysis

KW - Palladium

KW - Sustainable chemistry

KW - Transfer hydrogenation

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SN - 1381-1169

VL - 366

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EP - 214

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

ER -

Catalytic transfer hydrogenation of hydrophobic substrates by water-insoluble hydrogen donors in aqueous microemulsions

Abstract

Bibliographical note

Keywords

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