Catalysis of Organic Reactions

by Sowa, Jr.; John R.

• ISBN13: 9780824727291
• ISBN10: 0824727290
• Edition: 1st
• Format: Hardcover
• Copyright: 2005-03-30
• Publisher: CRC Press

Summary

This volume compiles 63 peer-reviewed scientific papers documenting the latest developments in the study and applications of homogeneous and heterogeneous catalysts to organic synthesis. Emphasizing processes with actual applications in industry, each paper represents current and outstanding research by recognized leaders in the field. They are organized into five major symposia: Catalytic Hydrogenation; Novel Approaches and Concepts in Catalysis of Organic Reactions; Acid-Base Catalysis; Catalytic Oxidation; and Catalysis in Organic Synthesis. These proceedings are of interest to the chemical scientists and engineers whose special interest is to apply homogenous and heterogeneous catalysts in organic synthesis to pharmaceutical, fine, and commodity chemicals.

Table of Contents

Board of Editors	xiii
Chronology of Organic Reactions Catalysis Society (ORCS) Conferences	xiv
Preface	xv
I. Symposium on Catalytic Hydrogenation	1	(174)
Hydrogenation on Raney-Type Catalysts
2004 Murray Raney Award: Electrocatalytic Hydrogenation of Organic Compounds at Raney Metal Electrodes: Scope and Limitations	3	(16)
Jean Lessard
Low Pressure Slurry Hydrogenation Process for the Production of Dimethylaminopropylamine Using Sponge Nickel Catalyst	19	(8)
Gregory J. Ward
Bryan C. Blanchard
The Conversion of Ethanolamine to Glycine Salt Over Skeletal Copper Catalysts	27	(10)
Dongsheng Liu
Noel W. Cant
Liyan Ma
Mark S. Wainwright
Hydrogenation Catalysis in a Nylon Recycle Process	37	(8)
Alan M. Allgeier
Theodore A. Koch
Sourav K. Sengupta
Hydrogenation of Dodecanenitrile Over Raney Type and Supported Group VIII Metal Catalysts and Effect of Metal on Selectivity	45	(8)
Sandor Gobolos
Jozsef L. Margitfalvi
Anchored and Supported Hydrogenation Catalysts	51	(2)
Highly Efficient Metal Catalysts Supported on Activated Carbon Cloths	53	(6)
Alain Perrard
Pierre Gallezot
Anchored Wilkinson's Catalyst	59	(6)
Clementina Reyes
Setrak Tanielyan
Robert Augustine
Carbon Supported Anchored Homogeneous Catalysts	65	(6)
Pradeep Goel
Clementina Reyes
Setrak Tanielyan
Robert Augustine
Catalytic Hydrogenation of Cinnamaldehyde on Pt/Carbon Catalysts: The Effects of Metal Location, and Dispersion on Activity and Selectivity	71	(6)
Nabin K. Nag
Para-substituted Aniline Hydrogenation Over Rhodium Catalysts: Metal Crystallite Size and Catalyst Pore Size Effects	77	(8)
Kenneth J. Hindle
S. David Jackson
Geoff Webb
Reductive Alkylation During Nitrobenzene Hydrogenation Over Copper/Silica	85	(6)
David S. Anderson
S. David Jackson
David Lennon
Geoff Webb
Hydrogenolysis of Butyl Acetate to Butanol Over Naphtha Reforming Type Catalysts in Conventional and High Throughput Slurry Phase Reactors	91	(10)
Sandor Gobolos
M. Hegedus
I. Borbath
J. L. Margitfalvi
New Ways for the Full Hydrogenation of Quinoline in Mild Conditions	101	(10)
M. Campanati
S. Franceschini
O. Piccolo
A. Vaccari
Some Recent Developments in Heterogeneous Hydrogenation Catalysts for Organic Synthesis	111	(14)
Jianping J.P. Chen
Charles R. Penquite
Hydrogenation of Interesting Substrates and Renewable Sources	123	(2)
Hydrogenation of Nitrile Butadiene Rubber Catalyzed by [Ir(COD)py(PCy3)]PF6	125	(10)
Jianzhong Hu
Neil T. McManus
Garry L. Rempel
Catalytic Hydrogenation and Hydrogenolysis of Lignin Model Compounds Using In-Situ, Water-Soluble Ru/P(CH2OH)3 Systems	135	(10)
Maria B. Ezhova
Andy Z. Lu
Brian R. James
Thomas Q. Hu
Catalytic Preparation of Pyrrolidones from Renewable Resources	145	(10)
John G. Frye, Jr.
Alan H. Zacher
Todd A. Werpy
Yong Wang
Hydrogenation of Glutamic Acid to Value Added Products	155	(10)
Johnathan E. Holladay
Todd A. Werpy
Catalytic Hydrogenolysis of 5-Carbon Sugar Alcohols	165	(10)
Alan H. Zacher
John G. Frye, Jr.
Todd A. Werpy
Dennis J. Miller
II. Symposium on Novel Concepts and Approaches to Catalysis of Organic Reactions	175	(151)
Featured Technology Area: Combinatorial and Parallel Methods in Catalyst Design, Optimization and Utilization
Combinatorial Approaches for New Catalyst Discovery: The First Homogeneous Catalysts Derived from Combinatorial Technologies for a Variety of Cross-Coupling Reactions	177	(8)
George Y. Li
High Throughput Experiments in Design and Optimization of Catalytic Package for Direct Synthesis of Diphenylcarbonate	185	(10)
Grigorii L. Soloveichik
Kirill V. Shalyaev
Ben P. Patel
Yan Gao
Eric J. Pressman
Rapid Optimization of Hydrogenation Process Variables by Combining Experimental Design and Parallel Reactors	195	(6)
Venu Arunajatesan
ShaRee L. McIntosh
Marisa Cruz
Roman F. Renneke
Baoshu Chen
Design and Parallel Synthesis of New Oxidative Dehydrogenation Catalysts	201	(10)
Gadi Rothenberg
E. A. (Bart) de Graaf
Jurriaan Beckers
Alfred Bliek
Nanocluster-based Cross-coupling Catalysts: A High-Throughput Approach	211	(6)
Mehul B. Thathagar
Jurriaan Beckers
Gadi Rothenberg
General Papers	216	(1)
Do You Need A Transition Metal for Biaryl Synthesis?	217	(10)
A. S. Kotnis
K. Zhu
B. L. Lotz
K. J. Natalie
J. H. Simpson
D. Kacusr
D. Thurston
J. S. Prasad
S. Mathew
A. K. Singh
Enzyme-like Acceleration in Catalytic Anti-Markovnikov Hydration of Alkynes to Aldehydes	227	(10)
Douglas B. Grotjahn
Daniel A. Lev
An Enzyme-like Mechanism Involving Bifunctional Ru Catalysts	237	(6)
Daniel A. Lev
Douglas B. Grotjahn
Activation of Dendrimer Encapsulated Pt Nanoparticles for Heterogeneous Catalysts	243	(8)
HuiFang Lang
R. Alan May
Brianna L. Iversen
Bert D. Chandler
Avada---a New Green Process for the Production of Ethyl Acetate	251	(10)
Flora T. T. Ng
Te Mure
Ming Jiang
Manzoor Sultan
Jin-hai Xie
Pierre Gayraud
Warren J. Smith
Matthew Hague
Robert Watt
Steve Hodge
A Catalytic Distillation Process for the One Step Synthesis of Methyl Isobutyl Ketone from Acetone: Liquid Phase Kinetics of the Hydrogenation of Mesityl Oxide	261	(6)
W. K. O'Keefe
M. Jiang
F. T. T. Ng
G. L. Rempel
A Strategy for the Preparation of Isolated Organometallic Catalysts on Silica Supports -- Towards Single-Site Solid Catalysts	267	(12)
Michael W. McKittrick
Shara D. McClendon
Christopher W. Jones
Ring Opening of Naphthenes for Clean Diesel Fuel Production	279	(14)
David Kubicka
Narendra Kumar
Paivi Maki-Arvela
Marja Tiitta
Tapio Salmi
Dmitry Yu. Murzin
The Use of Copper Catalysts in the Hydrogen Transfer Reduction of 4-Tert-butylcyclohexanone	293	(10)
Federica Zaccheria
Achille Fusi
Rinaldo Psaro
Nicoletta Ravasio
The Effect of Ultrasound on the Isomerization versus Reduction Reaction Pathways in the Hydrogenation of 3-Buten-2-ol and 1,4-Pentadien-3-ol on Pd-Black	303	(10)
R.S. Disselkamp
C.H.F. Peden
Lessons Learned: Batch Processing, Scaleup from Laboratory to Plant	313	(13)
John D. Super
III. Symposium on Acid-Base Catalysis	326	(66)
Improved Solid-Acid Catalysis for Sustainable, High 2-Phenyl, LAB Production	327	(10)
John F. Knifton
Prakasa Rao Anantaneni
Melvin E. Stockton
Recent Advances in Thermally Stable Resins for Olefin Hydration	337	(10)
Ajit Pujari
Setrak Tanielyan
Robert L. Augustine
Dorai Ramprasad
Pat Crawford
Enhancement of Regioselectivity in the Gas-phase Methylation of m-Cresol with Multifunctional Heterogeneous Catalysts	347	(10)
F. Cavani
L. Dal Pozzo
C. Felloni
L. Maselli
D. Scagliarini
C. Flego
C. Perego
Hydroxymethylation of 2-Methoxyphenol with Formaldehyde to Yield Vanillic Alcohols: A Comparison Between Homogeneous and Heterogeneous Acid Catalysis	357	(6)
M. Ardizzi
F. Cavani
L. Dal Pozzo
L. Maselli
The Aldol Condensation of Acetone Over a CsOH/SiO2 Solid Base Catalyst	363	(10)
Arran S. Canning
S. David Jackson
Eilidh McLeod
Elaine M. Vass
Solid Acid Catalysed Esterification of Amino Acids and Other Bio-based Acids	373	(6)
N. S. Asthana
Z. Zhang
Dennis J. Miller
One Pot Transformation of Geraniol into Citronellol and Menthol Over Cu/Al2O3	379	(6)
Nicoletta Ravasio
Achille Fusi
Rinaldo Psaro
Federica Zaccheria
Investigation of Chlorine Substitution Effects in the Claisen-Schmidt Condensation of 2'-hydroxyacetophenone with Chlorobenzaldehydes Over MgO	385	(7)
Sirena C. Hargrove-Leak
Janine Lichtenberger
Michael D. Amiridis
IV. Symposium on Catalytic Oxidation	392	(42)
The Effect of Single Metal Variation in Mo-V-Nb-W/Al2O3 System on Propane Selective Oxidation	393	(10)
Giacomo Grasso
Julian R.H. Ross
Partial Oxidation of Propylene Over Supported Rhodium Catalysts	403	(10)
Rajesh A. Khatri
Rahul Singh
Steven S. C. Chuang
Robert W. Stevens, Jr.
The Effect of Bismuth Promotion on the Selective Oxidation of Alcohols Using Platinum Catalysts	413	(10)
J. R. Anderson
G. A. Attard
K. G. Griffin
P. Johnston
Preparation and Activity of a V-Ti/Silica Catalyst for Olefin Epoxidation	423	(6)
Susannah L. Scott
Azfar Hassan
Aerobic Formaldehyde Oxidation Under Mild Conditions Mediated by Ce-Containing Polyoxometalates	429	(5)
Oxana A. Kholdeeva
Maria N. Timofeeva
Gennadii M. Maksimov
Raisa I. Maksimovskaya
Anastasia A. Rodionova
Craig L. Hill
V. Symposium on Catalysis in Organic Synthesis	434	(127)
General Papers
2004 Paul N. Rylander Award: Palladium-Catalyzed Annulation and Migration Reactions	435	(14)
Richard C. Larock
New Palladium-Catalysed Processes for the Synthesis of Selectively Substituted Aromatics	449	(10)
Marta Catellani
Elena Motti
Sara Deledda
Fiorenza Faccini
O-Acylphosphites: New and Promising Ligands for Isomerizing Hydroformylation	459	(12)
Detlef Selent
Klaus-Diether Wiese
Armin Borner
The Synthesis of Carbamate from the Reductive Carbonylation of Nitrobenzene Over Pd-based Catalysts	471	(14)
Bei Chen
Steven S. C. Chuang
Microwave Synthesis in the Suzuki-Miyaura Cross Coupling Reaction with Pd/C Catalysts
John R. Sowa, Jr.
Thomas Carrell
Megha Kandhari
Joanna Manansala
Nicole Heuschkel
Katharine Hodock
Amanda Thiel
Lubabalo T. Bululu
Deprotection	484	(1)
Improved Catalyst for the Removal of Carbobenzyloxy Protective Groups	485	(8)
Kimberly B. Humphries
Konrad Mobus
Tracy D. Dunn
Baoshu Chen
The Effect of N-containing Modifiers on the Deprotection of a Carbobenzyloxy Protected Amino Acid	493	(6)
Kimberly B. Humphries
Tracy D. Dunn
Konrad Mobus
Baoshu Chen
Selective Debenzylation in the Presence of Aromatic Chlorine on Pd/C Catalysts: Effects of Catalyst Types and Reaction Kinetics	499	(14)
Steve S. Y. Wang
Jun Li
Karen TenHuisen
Jale Muslehiddinoglu
Srinivas Tummala
San Kiang
Jianping J. P. Chen
Asymmetric Catalysis	511	(2)
A Comparison Between the Homogeneous and the Anchored Rhodium Skewphos Catalyst	513	(6)
Nagendranath Mahata
Setrak Tanielyan
Robert Augustine
Asymmetric Heck Reactions Using Dipeptido Phosphinite Metal Complexes	519	(6)
Dushmanthi Jayasinghe
Heinz-Bernhard Kraatz
Enantioselective Hydrogenations of Exo- and Endocyclic C=C Double Bond with Highly Mesoporous Carbon Supported Pd	525	(10)
E. Sipos
G. Fogassy
P.V. Samant
J. L. Figueiredo
A. Tungler
Influence of Achiral Tertiary Amines on the Enantioselective Hydrogenation of α,β-diketones Over Cinchonidine-Pt/Al2O3 Catalyst	535	(6)
J. L. Margitfalvi
E. Talas
N. Marin-Astorga
T. Marzialetti
Enantioselective Hydrogenation of Diketones on Pt Supported Catalysts	541	(6)
N. Marin-Astorga
G. Pecchi
P. Reyes
J. L. Margitfalvi
E. Talas
O. Egyed
Enantioselective Hydrogenation of α,β-Unsaturated Acids or Esters	547	(6)
S. Franceschini
A. Vaccari
The Effects of Pt/Al2O3 Structure and Stability on the O-Methyl-10,11-dihydrocinchonidine Modified Enantioselective Hydrogenation of Activated Ketones	553	(8)
Daniel J. Ostgard
Rolf Hartung
Jurgen G. E. Krauter
Steffen Seebald
Pavel Kukula
Ukrike Nettekoven
Martin Struderb
Hans-Ulrich Blaser
Author Index	561	(6)
Keyword Index	567