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Catalysis of Organic Reactions

Twenty-first Conference

Edited by Stephen R. Schmidt

Series Editor: Heinz Heinemann

Contributors: Jacob A. Moulijn, Robert L. Augustine, S. David Jackson, Angelo Vaccari, Venu Arunajatesan, Bert Chandler, R.S. Disselkamp, John F. Knifton, Fabrizio Cavani, Peter Johnston, Susannah Scott, Baoshu Chen, Konrad Mobus, Steve S.Y. Wang, Daniel J. Ostgard, James F. White, William K. O'Keefe, Kimberly B. Humphries, Andrew J. Smith, R Pietropaolo, Charles L Liotta, Mark White, Anton A. Kiss, Jason P. Hallett, Thomas A. Puckette, Carlos R. Apesteguia, Jianli Hu, Rahul Singh, Setrak K. Tanielyan, Isamu Yamauchi, Tapio O. Salmi, Marc Thommen, Stephen N. Falling, Aaron Sanders, Joseph R. Zoeller, Mathias Snare, Simona Marincean, Joseph A. Kocal, Hyun-Jin Lee, John Tarabocchia, Tim Pohlmann, Jamie Morrow, Tracy Dunn, Marisa Cruz, Dorit Wolf, Jaime B. Woods, Laura Duran Pachon, Charles A. Eckert, Daryle H. Busch, Noel W. Cant, Sandor Gobolos, Garry L. Rempel, Yong Wang, Dennis J. Miller, Gadi Rothenberg, Flora T.T. Ng, Christopher W. Jones, Dmitry Yu. Murzin, Luca Dal Pozzo, Steven S.C. Chuang, Kenneth G. Griffin, Emilia Talas, Jurgen G.E. Krauter, Steffen Seebald, Gennadii V. Demidenko, Jean Lessard, Jozsef L. Margitfalvi, Freek Kapteijn, Felix Spindler, F. Tzompantzi, Jaime Sanchez Valente, M. Cantu, R. Gomez, A. Mantilla, M. Torres, E. J. Angueira, Ron R. Spence, E. Sulman, L. Nikoshvili, L. Duran-Pachon, J. A. Hageman, F. Clerc, H. W. Fruhauf, J. A. Westerhuis, A. C. Ditlian, Pamela Pollet, M. G. Musolino, G. Apa, A. Donato, Anthony W. Moses, Heather D. Leifeste, Naseem A. Ramshhye, Juergen Eckert, W. Merkl, H. Chung, W. Doubleday, S. Kiang, K. M. de Lathouder, Ferruccio Trifiro, Michael Holbach, John Richardson, William Sommer, Marcus Weck, Kunquan Yu, Xiaolai Zheng, Zoltan Banka, Zoltan Toth, Janos Szammer, Arran S. Canning, Jonathan J. Gamman, Strath Urquart, Mattia Ardizzi, Nicola Ballarini, Luca Maselli, Tiziana Monti, Sara Rovinetti, Massimo Cimini, Patrizia Mangifesta, Diana Scagliarini, Guanguang Xia, Thomas H. Peterson, Mirko Bacchini, Carlotta Cortelli, Stefano Cortesi, Carlo Fumagalli, Gianluca Mazzoni, Francesca Pierelli, Clementina Reyes, Nagendranath Mahata, Michael Korell, Oliver Meyer, Dongsheng S. Liu, Indra Prakash, Kenneth E. Furlong, Handley E. Jackson, Duane D. Miller, Elaine A. Gelder, C. Martin Lok, Valentina G. Matveeva, Mikhail G. Sulman, Ludmila M. Bronstein, Petr M. Valetskiy, Irina B. Tsvetkova, Johan P. Warna, Jyri-Pekka Mikkola, Jeanette E. B. Aumo, Jyrki I. Kuusisto, Virginie Duprez, Monika Berweiler, Stefan Roder, Thomas Tacke, Sarah M. Chajkowski, Kelly R. Boyles, Todd R. Hart, Charles H. F. Peden, Felix Roessler, Reinhard Karge, Simon Robitaille, Genevieve Clement, Jean Marc Chapuzet, Chunshe (James) Cao, John G. Frye, Benoit Pugin, Heidi Landert, Martin Kesselgruber, Hans Meier, Richard Sachleben, Andras Tompos, Mihaly Hegedus, Bethany J. Auten, Christina J. Crump, Anil R. Singh, John R. Monnier, Gerald W. Phillips, Jeffrey S. Kanel, Stephen A. Godleski, Alessandra O. Bianchi, Valerio Borzatta, Elisa Poluzzi, Roger Pretot, Paul A. van der Schaaf, Veronica K. Diez, Juana I. Di Cosimo, Ming Jiang, David Babb, Robbyn Prange, Mark Sonnenschein, Van Delk, Chris Derstine, Kurt Olson, Theresa Barnette, Alexandre C. Dimian, Iva Kubickova, Paivi Maki-Arvela, Kari Eranen, Lars Peereboom, Yaoyan Xi, James E. Jackson, Tie-Pan Shi, Bala Subramaniam, Thomas H. Riermeier, Axel Monsees, Jens Holz, Armin Borner, Norman Marin, Gabriela Alvez, John R. Sanderson, Robin Spears, Tim McCarthy, Micheal Murphy, Lee Hord, Peter Doorley

CRC Press – 2006 – 552 pages

Series: Chemical Industries

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    978-0-8493-7557-6
    December 6th 2006

Description

Bringing together academic, industrial, and governmental researchers and developers, Catalysis of Organic Reactions comprises 57 peer-reviewed papers on the latest scientific developments in applied catalysis for organic reactions. The volume describes the use of both heterogeneous and homogeneous catalyst systems and includes original research articles on processes with potential industrial applications.

The contributors, renowned leaders in the field, discuss noteworthy findings that include the award-winning studies by Isamu Yamauchi on metastable precursors to Raney® catalysts and by Gadi Rothenberg on methods for finding the best homogeneous catalysts. The book covers the synthesis of fine chemicals and pharmaceutical intermediates, solid acid catalysis, selective oxidation, chiral synthesis, combinatorial methods, nanotechnology, and “green” processes. These topics are organized by broad groupings based on major process types, such as hydrogenations and oxidations, or themes, such as novel methods and environmental consciousness.

Covering the most recent significant developments in catalysis, this compilation is ideal for chemists and chemical engineers who apply homogeneous and heterogeneous catalysis in the synthesis of pharmaceutical, fine, or commodity chemicals.

Reviews

“… applied catalysis for organic reactions, with sections on organic synthesis, oxidation, hydrogenation, new methods, acid and base catalysis, “green” catalysis, and other topics. These include chiral synthesis, combinatorial methods, nanotechnology, and agriculturally-derived feedstocks. … the book is intended for readers in those fields who apply homogeneus and heterogeneous catalysis in the synthesis of pharmaceutical, fine, or commodity chemicals. …”

— In Book News Inc., June 2007

Contents

Board of Editors

Chronology of Organic Reactions Catalysis Society Conferences

Preface

Symposium on Catalysis in Organic Synthesis

On the Use of Immobilized Metal Complex Catalysts in Organic Synthesis

Christopher W. Jones, Michael Holbach, John Richardson, William Sommer, Marcus Weck, Kunquan Yu, and Xiaolai Zheng

Supported Re Catalysts for Metathesis of Functionalized Olefins

Anthony W. Moses, Heather D. Leifeste, Naseem A. Ramsahye, Juergen Eckert, and Susannah L. Scott

Catalytic Hydrogenation of a Schiff’s Base over Pd/Carbon Catalysts: Kinetic Prediction of Impurity Fate and Byproduct Formation

Steve S.Y. Wang, William F. Merkl, Hyei-Jha Chung, Wendel Doubleday, and San Kiang

Halophosphite Ligands for the Rhodium Catalyzed Low-Pressure Hydroformylation Reaction

Thomas A. Puckette

Development of a Monolithic Bioreactor: Tailor-Made Functionalized Carriers

Karen M. de Lathouder, Freek Kapteijn, and Jacob A. Moulijn

Highly Selective Preparation of trans-4-Aminocyclohexane Carboxylic Acid from cis-Isomer over Raney® Nickel Catalyst

Sándor Gőbölös, Zoltán Banka, Zoltán Tóth, János Szammer, and József L. Margitfalvi

Gas-Phase Acetone Condensation over Hydrotalcite-like Catalysts

Francisco Tzompantzi, Jaime S. Valente, Manuel S. Cantú, and Ricardo Gómez

Gas Phase Trimerization of Isobutene Using Green Catalysts  Angeles Mantilla, Francisco Tzompantzi, Miguel Torres, and Ricardo Gómez

Synthesis of Methyl Isobutyl Ketone over a Multifunctional Heterogeneous Catalyst: Effect of Metal and Base Components on Selectivity and Activity

Arran S. Canning, Jonathan J. Gamman, S. David Jackson, and Strath Urquart

The Control of Regio- and Chemo-Selectivity in the Gas-Phase, Acid-Catalyzed Methylation of 1,2-Diphenol (Catechol)

Mattia Ardizzi, Nicola Ballarini, Fabrizio Cavani, Luca Dal Pozzo, Luca Maselli, Tiziana Monti, and Sara Rovinetti

The Environmentally Benign, Liquid-Phase Benzoylation of Phenol Catalyzed by H-β Zeolite. An Analysis of the Reaction Scheme

Mattia Ardizzi, Nicola Ballarini, Fabrizio Cavani, Massimo Cimini, Luca Dal Pozzo, Patrizia Mangifesta, and Diana Scagliarini

Symposium on Catalytic Oxidation

Biphasic Catalytic Oxidation of Hydrocarbons Using Immobilized Homogeneous Catalyst in a Microchannel Reactor

Jianli Hu, Guanguang Xia, James F. White, Thomas H. Peterson, and Yong Wang

Reaction Pathways for Propylene Partial Oxidation on Au/TiO2

Rahul Singh and Steven S.C. Chuang

The Transformation of Light Alkanes to Chemicals: Mechanistic Aspects of the Gas-Phase Oxidation of n-Pentane to Maleic Anhydride and Phthalic Anhydride

Mirko Bacchini, Nicola Ballarini, Fabrizio Cavani, Carlotta Cortelli, Stefano Cortesi, Carlo Fumagalli, Gianluca Mazzoni, Tiziana Monti, Francesca Pierelli, and Ferruccio Trifirò

Transition Metal Free Catalytic Aerobic Oxidation of Alcohols under Mild Conditions Using Stable Nitroxyl Free Radicals

Setrak K. Tanielyan, Robert L. Augustine, Clementina Reyes, Nagendranath Mahata, Michael Korell, and Oliver Meyer

The Conversion of Aminoalcohols to Aminocarboxylic Acid Salts over Chromia-Promoted Skeletal Copper Catalysts

Dongsheng S. Liu, Noel W. Cant, and Andrew J. Smith

Bromine-Free TEMPO-Based Catalyst System for the Oxidation of Primary and Secondary Alcohols Using NaOCl as the Oxidant

Setrak K. Tanielyan, Robert L. Augustine, Indra Prakash, Kenneth E. Furlong, and Handley E. Jackson

In situ Infrared Study of Catalytic Oxidation over Au/TiO2 Catalysis

Duane D. Miller and Steven S.C. Chuang

Symposium on Catalytic Hydrogenation

2006 Murray Raney Award Lecture: Synthesis and Features of New Raney® Catalysts from Metastable Precursors

Isamu Yamauchi

Competitive Hydrogenation of Nitrobenzene, Nitrosobenzene and Azobenzene

Elaine A. Gelder, S. David Jackson, and C. Martin Lok

Selective Hydrogenation of Dehydrolinalool to Linalool Using Nanostructured Pd-Polymeric Composite Catalysts

Linda Z. Nikoshvili , Ester M. Sulman , Galine N. Demidenko, Valentina G. Matveeva , Mikhail G. Sulman, Ludmila M. Bronstein, Petr M. Valetskiy, and Irina B. Tsvetkova

Modeling and Optimization of Complex Three-Phase Hydrogenations under Mass-Transfer Limitation and Catalyst Deactivation

Tapio O.Salmi, Dmitry Yu.Murzin, Johan P.Wärnå, Jyri-Pekka Mikkola, Jeanette E.B. Aumo, and Jyrki I. Kuusisto

The Effects of Various Catalyst Modifiers on the Hydrogenation of Fructose to Sorbitol and Mannitol

Daniel J. Ostgard, Virginie Duprez, Monika Berweiler, Stefan Röder, and Thomas Tacke

Cavitating Ultrasound Hydrogenation of Water-Soluble Olefins Employing Inert Dopants: Studies of Activity, Selectivity and Reaction Mechanisms

Robert S. Disselkamp, Sarah M. Chajkowski, Kelly R. Boyles, Todd R. Hart, and Charles H.F. Peden

The Treatment of Activated Nickel Catalysts for the Selective Hydrogenation of Pynitrile

Daniel J. Ostgard, Felix Roessler, Reinhard Karge, and Thomas Tacke

Deactivation of Sponge Nickel and Ru/C Catalysts in Lactose and Xylose Hydrogenations

Jyrki Kuusisto, Jyri-Pekka Mikkola, and Tapio Salmi

Selectivity Control in 1-Phenyl-1-Propyne Hydrogenation: Effect of Modifiers

S. David Jackson and Ron R. Spence

Hydrogenation and Isomerization Reactions of Olefinic Alcohols Catalyzed in Homogeneous Phase by Rh(I) Complexes

Maria G. Musolino, Giuseppe Apa, Andrea Donato, and Rosario Pietropaolo

Reductive Amination of Isobutanol to Diisobutylamine on Vanadium Modified Raney® Nickel Catalyst

Sándor Gőbölös and József L. Margitfalvi

Symposium on Novel Methods in Catalysis of Organic Reactions

How to Find the Best Homogeneous Catalyst

Gadi Rothenberg, Jos A. Hageman, Frédéric Clerc, Hans-Werner Frühauf, and Johan A. Westerhuis

Novel Chloroaluminate Ionic Liquids for Arene Carbonylation

Ernesto J. Angueira and Mark G. White

Chemoselective Hydrogenation of Nitro Compounds to the Corresponding Amines on Raney® Copper Catalysts

Simon Robitaille, Genevieve Clément, Jean Marc Chapuzet, and Jean Lessard

Selective Hydrogenolysis of Sugar Alcohols over Structured Catalysts

Chunshe (James) Cao, James F. White, Yong Wang, and John G. Frye

Twinphos: A New Family of Chiral Ferrocene Tetra-Phosphine Ligands for Asymmetric Catalytic Transformations

Benoit Pugin, Heidi Landert, Martin Kesselgruber, Hans Meier, Richard Sachleben, Felix Spindler, and Marc Thommen

Catalyst Library Design for Fine Chemistry Applications

József L. Margitfalvi, András Tompos, Sándor Gőbölös, Emila Tálas, and Mihály Hegedűs

Dendrimer Templates for Pt and Au Catalysts

Bethany J. Auten, Christina J. Crump, Anil R. Singh, and Bert D. Chandler

Symposium on Acid and Base Catalysis

Development of an Industrial Process for the Lewis Acid/Iodide Salt-Catalyzed Rearrangement of 3,4-Epoxy-1-Butene to 2,5-Dihydrofuran

Stephen N. Falling, John R. Monnier, Gerald W. Phillips, Jeffrey S. Kanel, and Stephen A. Godleski

A New Economical and Environmentally Friendly Synthesis of 2,5-Dimethyl-2,4-Hexadiene

Alessandra O. Bianchi, Valerio Borzatta, Elisa Poluzzi, and Angelo Vaccari

Supported Heteropoly Acid Catalysts for Friedel-Crafts Acylation Kenneth G. Griffin, Peter Johnston, Roger Prétôt, and Paul A. van der Schaaf

Synthesis of Pseudoionones by Aldol Condensation of Citral with Acetone on Li-Modified MgO Catalyst

Veronica K. Diez, Juana I. Di Cosimo, and Carlos Apesteguía

The One Step Synthesis of MIBK via Catalytic Distillation: A Preliminary Pilot Scale Study

William K. O’Keefe, Ming Jiang, Flora T.T. Ng, and Garry L. Rempel

Symposium on “Green” Catalysis

Producing Polyurethane Foam from Natural Oil 

Aaron Sanders, David Babb, Robbyn Prange, Mark Sonnenschein, Van Delk, Chris Derstine, and Kurt Olson

Carbonylation of Chloropinacolone: A Greener Path to Commercially Useful Methyl Pivaloylacetate

Joseph R. Zoeller and Theresa Barnette

Recycling Homogeneous Catalysts for Sustainable Technology Jason P. Hallett, Pamela Pollet, Charles A. Eckert, and Charles L. Liotta

“Green” Catalysts for Enhanced Biodiesel Technology

Anton A. Kiss, Gadi Rothenberg, and Alexandre C. Dimian

Continuous Deoxygenation of Ethyl Stearate: A Model Reaction for Production of Diesel Fuel Hydrocarbons

Mathias Snåre, Iva Kubičková, Päivi Mäki-Arvela, Kari Eränen, and Dmitry Yu. Murzin

Glycerol Hydrogenolysis to Propylene Glycol under Heterogeneous Conditions

Simona Marincean, Lars Peereboom, Yaoyan Xi, Dennis J. Miller, and James E. Jackson

Developing Sustainable Process Technology

Joseph A. Kocal

Selective Oxidation of Propylene to Propylene Oxide in CO2 Expanded Liquid System

Hyun-Jin Lee, Tie-Pan Shi, Bala Subramaniam, and Daryle H. Busch

Symposium on Other Topics in Catalysis

catASium® M: A New Family of Chiral Bisphospholanes and their Application in Enantioselective Hydrogenations

Thomas H. Riermeier, Axel Monsees, Jens Holz, Armin Börner, and John Tarabocchia

Synthesis of Chiral 2-Amino-1-Phenylethanol

Robert Augustine, Setrak Tanielyan, Norman Marin, and Gabriela Alvez

Selective Tertiary-Butanol Dehydration to Isobutylene via Reactive Distillation and Solid Acid Catalysis

John F. Knifton and John R. Sanderson

Leaching Resistance of Precious Metal Powder Catalysts—Part 2

Tim Pohlmann, Kimberly Humphries, Jaime Morrow, Tracy Dunn, Marisa Cruz, Konrad Möbus, and Baoshu Chen

Optimization of Reductive Alkylation Catalysts by Experimental Design

Venu Arunajatesan, Marisa Cruz, Konrad Möbus, and Baoshu Chen

Accelerated Identification of the Preferred Precious Metal Powder Catalysts for Selective Hydrogenation of Multi-Functional Substrates

Dorit Wolf, Steffen Seebald, and Thomas Tacke

Transition Metal Removal from Organic Media by Deloxan® Metal Scavengers

Jaime B. Woods, Robin Spears, Jürgen Krauter, Tim McCarthy, Micheal Murphy, Lee Hord, Peter Doorley, and Baoshu Chen

Electroreductive Pd-Catalyzed Ullmann Reactions in Ionic Liquids

Laura Durán Pachón and Gadi Rothenberg

Author Index

Keyword Index

Name: Catalysis of Organic Reactions: Twenty-first Conference (Hardback)CRC Press 
Description: Edited by Stephen R. SchmidtSeries Editor: Heinz HeinemannContributors: Jacob A. Moulijn, Robert L. Augustine, S. David Jackson, Angelo Vaccari, Venu Arunajatesan, Bert Chandler, R.S. Disselkamp, John F. Knifton, Fabrizio Cavani, Peter Johnston, Susannah Scott, Baoshu Chen, Konrad Mobus, Steve S.Y. Wang, Daniel J. Ostgard, James F. White, William K. O'Keefe, Kimberly B. Humphries, Andrew J. Smith, R Pietropaolo, Charles L Liotta, Mark White, Anton A. Kiss, Jason P. Hallett, Thomas A. Puckette, Carlos R. Apesteguia, Jianli Hu, Rahul Singh, Setrak K. Tanielyan, Isamu Yamauchi, Tapio O. Salmi, Marc Thommen, Stephen N. Falling, Aaron Sanders, Joseph R. Zoeller, Mathias Snare, Simona Marincean, Joseph A. Kocal, Hyun-Jin Lee, John Tarabocchia, Tim Pohlmann, Jamie Morrow, Tracy Dunn, Marisa Cruz, Dorit Wolf, Jaime B. Woods, Laura Duran Pachon, Charles A. Eckert, Daryle H. Busch, Noel W. Cant, Sandor Gobolos, Garry L. Rempel, Yong Wang, Dennis J. Miller, Gadi Rothenberg, Flora T.T. Ng, Christopher W. Jones, Dmitry Yu. Murzin, Luca Dal Pozzo, Steven S.C. Chuang, Kenneth G. Griffin, Emilia Talas, Jurgen G.E. Krauter, Steffen Seebald, Gennadii V. Demidenko, Jean Lessard, Jozsef L. Margitfalvi, Freek Kapteijn, Felix Spindler, F. Tzompantzi, Jaime Sanchez Valente, M. Cantu, R. Gomez, A. Mantilla, M. Torres, E. J. Angueira, Ron R. Spence, E. Sulman, L. Nikoshvili, L. Duran-Pachon, J. A. Hageman, F. Clerc, H. W. Fruhauf, J. A. Westerhuis, A. C. Ditlian, Pamela Pollet, M. G. Musolino, G. Apa, A. Donato, Anthony W. Moses, Heather D. Leifeste, Naseem A. Ramshhye, Juergen Eckert, W. Merkl, H. Chung, W. Doubleday, S. Kiang, K. M. de Lathouder, Ferruccio Trifiro, Michael Holbach, John Richardson, William Sommer, Marcus Weck, Kunquan Yu, Xiaolai Zheng, Zoltan Banka, Zoltan Toth, Janos Szammer, Arran S. Canning, Jonathan J. Gamman, Strath Urquart, Mattia Ardizzi, Nicola Ballarini, Luca Maselli, Tiziana Monti, Sara Rovinetti, Massimo Cimini, Patrizia Mangifesta, Diana Scagliarini, Guanguang Xia, Thomas H. Peterson, Mirko Bacchini, Carlotta Cortelli, Stefano Cortesi, Carlo Fumagalli, Gianluca Mazzoni, Francesca Pierelli, Clementina Reyes, Nagendranath Mahata, Michael Korell, Oliver Meyer, Dongsheng S. Liu, Indra Prakash, Kenneth E. Furlong, Handley E. Jackson, Duane D. Miller, Elaine A. Gelder, C. Martin Lok, Valentina G. Matveeva, Mikhail G. Sulman, Ludmila M. Bronstein, Petr M. Valetskiy, Irina B. Tsvetkova, Johan P. Warna, Jyri-Pekka Mikkola, Jeanette E. B. Aumo, Jyrki I. Kuusisto, Virginie Duprez, Monika Berweiler, Stefan Roder, Thomas Tacke, Sarah M. Chajkowski, Kelly R. Boyles, Todd R. Hart, Charles H. F. Peden, Felix Roessler, Reinhard Karge, Simon Robitaille, Genevieve Clement, Jean Marc Chapuzet, Chunshe (James) Cao, John G. Frye, Benoit Pugin, Heidi Landert, Martin Kesselgruber, Hans Meier, Richard Sachleben, Andras Tompos, Mihaly Hegedus, Bethany J. Auten, Christina J. Crump, Anil R. Singh, John R. Monnier, Gerald W. Phillips, Jeffrey S. Kanel, Stephen A. Godleski, Alessandra O. Bianchi, Valerio Borzatta, Elisa Poluzzi, Roger Pretot, Paul A. van der Schaaf, Veronica K. Diez, Juana I. Di Cosimo, Ming Jiang, David Babb, Robbyn Prange, Mark Sonnenschein, Van Delk, Chris Derstine, Kurt Olson, Theresa Barnette, Alexandre C. Dimian, Iva Kubickova, Paivi Maki-Arvela, Kari Eranen, Lars Peereboom, Yaoyan Xi, James E. Jackson, Tie-Pan Shi, Bala Subramaniam, Thomas H. Riermeier, Axel Monsees, Jens Holz, Armin Borner, Norman Marin, Gabriela Alvez, John R. Sanderson, Robin Spears, Tim McCarthy, Micheal Murphy, Lee Hord, Peter Doorley. Bringing together academic, industrial, and governmental researchers and developers, Catalysis of Organic Reactions comprises 57 peer-reviewed papers on the latest scientific developments in applied catalysis for organic reactions. The volume describes...
Categories: Catalysis, Organic Chemistry