Catalysis of Organic Reactions: Twenty-first Conference

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Edition: 1st
Format: Hardcover
Pub. Date: 2006-12-07
Publisher(s): CRC Press
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Summary

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.

Table of Contents

Board of Editors xxi
Chronology of Organic Reactions Catalysis Society Conferences xxiii
Preface xxv
I. Symposium on Catalysis in Organic Synthesis 1
1. On the Use of Immobilized Metal Complex Catalysts in Organic Synthesis
3
Christopher W. Jones,¹,² Michael Holbach,² John Richardson,¹ William Sommer,² Marcus Weck,² Kunquan Yu,¹ and Xiaolai Zheng¹,²
¹Georgia Institute of Technology, School of Chemical & Biomolecular Engineering and ²School of Chemistry and Biochemistry, Atlanta, GA 30332
2. Supported Re Catalysts for Metathesis of Functionalized Olefins
13
Anthony W. Moses, Heather D. Leifeste, Naseem A. Ramsahye, Juergen Eckert and Susannah L. Scott
Department of Chemical Engineering, University of California, Santa Barbara CA 93106-5080
3. Catalytic Hydrogenation of a Schiff's Base over Pd/Carbon Catalysts: Kinetic Prediction of Impurity Fate and Byproduct Formation
23
Steve S.Y.Wang, William F. Merkl, Hyei-Jha Chung, Wendel Doubleday and San Kiang
Process Research and Development, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191
4. Halophosphite Ligands for the Rhodium Catalyzed Low-Pressure Hydroformylation Reaction
31
Thomas A. Puckette
Eastman Chemical Company, Texas Eastman Division, P.O. Box 7444, Longview TX 75607-7444
5. Development of a Monolithic Bioreactor: Tailor-Made Functionalized Carriers
39
Karen M. de Lathouder, Freek Kapteijn and Jacob A. Moulijn
Delft University of Technology, Faculty of Applied Sciences, DelftChemTech, Section R&CE, Julianalaan 136, 2628 BL Delft, The Netherlands
6. Highly Selective Preparation of trans-4-Aminocyclohexane Carboxylic Acid from cis-Isomer over Raney® Nickel Catalyst
45
Sándor Göbölös, Zoltán Banka, Zoltán Tóth, János Szammer, and József L. Margitfalvi
Chemical Research Center, Institute of Surface Chemistry and Catalysis, 1025 Budapest, Pusztaszeri ut 59-67, Hungary
7. Gas-Phase Acetone Condensation over Hydrotalcite-like Catalysts
55
Francisco Tzompantzi¹, Jaime S. Valente², Manuel S. Cantú² and Ricardo Gómez¹,²
¹Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco No 152, México 09340, D.F.
²Instituto Mexicano del Petróleo, Eje Central Lazaro Cardenas #152, México, D.F. 07730.
8. Gas Phase Trimerization of Isobutene Using Green Catalysts
61
Angeles Mantilla,¹ Francisco Tzompantzi,² Miguel Torres¹ and Ricardo Gómez²
¹Universidad Autónoma Metropolitana Azcapotzalco. Av. San Pablo 180, Reynosa Tamaulipas, Azcapotzalco, México, 02200, D.F.
²Universidad Autónoma Metropolitana, Iztapalapa, Depto. de Quimica, Av. San Rafael Atlixco 152, México 09340 D.F.
9. Synthesis of Methyl Isobutyl Ketone over a Multifunctional Heterogeneous Catalyst: Effect of Metal and Base Components on Selectivity and Activity
67
Arran S. Canning, Jonathan J. Gamman, S. David Jackson and Strath Urquart
WestCHEM, Dept. of Chemistry, The University, Glasgow G12 8QQ, Scotland, UK.
10. The Control of Regio- and Chemo-Selectivity in the Gas-phase, Acid-Catalyzed Methylation of 1,2-Diphenol (Catechol)
77
Mattia Ardizzi, Nicola Ballarini, Fabrizio Cavani, Luca Dal Pozzo, Luca Maselli, Tiziana Monti and Sara Rovinetti
University of Bologna, Dipartimento di Chimica Industriale e dei Materiali, Viale Risorgimento 4, 40136 Bologna, Italy.
11. The Environmentally Benign, Liquid-phase Benzoylation of Phenol Catalyzed by H-β Zeolite. An Analysis of the Reaction Scheme.
83
Mattia Ardizzi, Nicola Ballarini, Fabrizio Cavani, Massimo Cimini, Luca Dal Pozzo, Patrizia Mangifesta and Diana Scagliarini
University of Bologna, Dipartimento di Chimica Industriale e dei Materiali, Viale Risorgimento 4, 40136 Bologna, Italy.
II. Symposium on Catalytic Oxidation 89
12. Biphasic Catalytic Oxidation of Hydrocarbons Using Immobilized Homogeneous Catalyst in a Microchannel Reactor
91
Jianli Hu, Guanguang Xia, James F. White, Thomas H. Peterson and Yong Wang
Pacific Northwest National Laboratory, 902 Battelle Boulevard, Richland, WA 99352
13. Reaction Pathways for Propylene Partial Oxidation on Au/TiO2
99
Rahul Singh and Steven S.C. Chuang
Department of Chemical and Biomolecular Engineering, University of Akron, Akron OH, 44325-3906
14. The Transformation of Light Alkanes to Chemicals: Mechanistic Aspects of the Gas-phase Oxidation of n-Pentane to Maleic Anhydride and Phthalic Anhydride
109
Mirko Bacchini¹, Nicola Ballarini¹, Fabrizio Cavani¹, Carlotta Corte Stefano Cortesi¹, Carlo Fumagalli², Gianluca Mazzoni², Tiziana Monti², Francesca Pierelli¹, Ferruccio Trifirò¹¹
¹Dipartimento di Chimica Industriale e dei Materiali, Viale Risorgimento 4, 40136 Bologna, Italy. INSTM, Research Unit of Bologna A member of the Concorde CA and Idecat NoE (6FP of the EU).
²Lonza SpA, Via E. Fermi 51, 24020 Scanzorosciate (BG), Italy
15. Transition Metal Free Catalytic Aerobic Oxidation of Alcohols Under Mild Conditions Using Stable Nitroxyl Free Radicals
119
Setrak K. Tanielyan¹, Robert L. Augustine¹ , Clementina Reyes¹, Nagendranath Mahata¹, Michael Korell² and Oliver Meyer³
¹Center for Applied Catalysis, Seton Hall University, South Orange, NJ 07079
²DegussaCorp. BU Building Blocks, Parsippany, NJ 07054
³Degussa AG, BU Building Blocks, Marl 45764 Germany
16. The Conversion of Aminoalcohols to Aminocarboxylic Acid Salts over ChromiaPromoted Skeletal Copper Catalysts
131
Dongsheng S. Liu, Noel W. Cant and Andrew J. Smith
School of Chemical Engineering and Industrial Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia
17. Bromine-Free TEMPO-Based Catalyst System for the Oxidation of Primary and Secondary Alcohols Using NaOCl as the Oxidant
141
Setrak K. Tanielyan¹, Robert L. Augustine¹, Indra Prakash², Kenneth E. Furlong² and Handley E. Jackson²
¹Center for Applied Catalysis, Seton Hall University, South Orange, NJ 07079
²The NutraSweet Corporation, Chicago, IL 60654
18. In situ Infrared Study of Catalytic Oxidation over Au/TiO2 Catalysts
147
Duane D. Miller and Steven S.C. Chuang
Dept. of Chemical and Biomolecular Engineering, University of Akron, Akron, OH 44325-3906, USA
III. Symposium on Catalytic Hydrogenation 153
19. 2006 Murray Raney Award Lecture: Synthesis and Features of New Raney® Catalysts from Metastable Precursors
155
Isamu Yamauchi
Osaka University, Yamadaoka 2-1 Suita, Osaka, 565-0871 Japan
20. Competitive Hydrogenation of Nitrobenzene, Nitrosobenzene and Azobenzene
167
Elaine A. Gelder', S. David Jackson¹, C. Martin Lok²
¹WestCHEM, Department of Chemistry, The University, Glasgow, G12 8QQ Scotland
²Johnson Matthey Catalysts, Belasis Avenue, Billingham, Cleveland, TS23 1LB U.K.
21. Selective Hydrogenation of Dehydrolinalool to Linalool Using Nanostructured Pd-Polymeric Composite Catalysts
177
Linda Z. Nikoshvilia , Ester M. Sulmana , Galine N. Demidenkoa, Valentina G. Matveevaa , Mikhail G. Sulmana, Ludmila M. Bronsteinb Petr M. Valetskiyc and Irina B. Tsvetkovaa
a Dept. of Biotechnology and Chemistry, Tver Technical University, A. Nikitina str., 22, 170026, Tver, Russia
b Chemistry Department, Indiana University, Bloomington, IN 47405, USA Wesmeyanov Institute of Organoelement Compounds of RAS, Vavilov str., 28, Moscow, Russia
22. Modeling and Optimization of Complex Three-Phase Hydrogenations and Isomerizations under Mass-Transfer Limitation and Catalyst Deactivation
187
Tapio O. Salmi, Dmitry Yu. Murzin, Johan P. Wärnå, Jyri-Pekka Mikkola, Jeanette E.B. Aumo, and Jyrki I. Kuusisto
Åbo Akademi, Process Chemistry Centre, FI-20500 Turku/Åbo, Finland
23. The Effects of Various Catalyst Modifiers on the Hydrogenation of Fructose to Sorbitol and Mannitol
197
Daniel J. Ostgard, Virginie Duprez, Monika Berweiler, Stefan Röder and Thomas Tacke
Degussa AG, Rodenbacher Chaussee 4, 63457 Hanau, Germany
24. Cavitating Ultrasound Hydrogenation of Water-Soluble Olefins Employing Inert Dopants: Studies of Activity, Selectivity and Reaction Mechanisms
213
Robert S. Disselkamp, Sarah M. Chajkowski, Kelly R. Boyles, Todd R. Hart, Charles H.F. Peden
Institute for Interfacial Catalysis, Pacific Northwest National Laboratory, Richland, WA 99352 USA
25. The Treatment of Activated Nickel Catalysts for the Selective Hydrogenation of Pynitrile
227
Daniel J. Ostgard¹, Felix Roessler, Reinhard Karge² and Thomas Tacke¹
¹Degussa AG, Exclusive Synthesis and Catalysts, Rodenbacher Chaussee 4, D-63457 Hanau, Germany
²DSM Nutritional Products Ltd, Postfach 3255, CH-4002 Basel, Switzerland
26. Deactivation of Sponge Nickel and Ru/C Catalysts in Lactose and Xylose Hydrogenations
235
Jyrki Kuusisto, Jyri-Pekka Mikkola and Tapio Salmi
Laboratory of Industrial Chemistry, Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, FIN-20500 Turku, Finland
27. Selectivity Control in 1-Phenyl-1-Propyne Hydrogenation: Effect of Modifiers
241
S. David Jackson and Ron R. Spence
WestCHEM, Department of Chemistry, The University, Glasgow, G12 8QQ, Scotland
28. Hydrogenation and Isomerization Reactions of Olefinic Alcohols Catalyzed in Homogeneous Phase by Rh(I) Complexes
247
Maria G. Musolino, Giuseppe Apa, Andrea Donato and Rosario Pietropaolo
Department of Mechanics and Materials, Faculty of Engineering, University of Reggio Calabria, Loc. Feo di Vito, 1-89060 Reggio Calabria, Italy
29. Reductive Amination of Isobutanol to Diisobutylamine on Vanadium Modified Raney® Nickel Catalyst
253
Sándor Gobölös and József L. Margitfalvi
Chemical Research Center, Institute of Surface Chemistry and Catalysis, H-1025 Budapest, Pusztaszeri zit 59-67, Hungary
IV. Symposium on Novel Methods in Catalysis of Organic Reactions 259
30. How to Find the Best Homogeneous Catalyst
261
Gadi Rothenberg¹, Jos A. Hageman², Frederic Clerc³, Hans-Werner Frühauf¹ and Johan A. Westerhuis²
¹Van't Hoff Institute for Molecular Sciences and ²Swammerdam Institute of Life Sciences, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands. ³Institut de Recherches sur la Catalyse, 2 avenue Albert Einstein, 69626 Villeurbanne Cedex, France
31. Novel Chloroaluminate Ionic Liquids for Arene Carbonylation
271
Ernesto J. Angueira and Mark G. White
School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, GA 30332-0100
32. Chemoselective Hydrogenation of Nitro Compounds to the Corresponding Amines on Raney® Copper Catalysts
281
Simon Robitaille, Genevieve Clément, Jean Marc Chapuzet and Jean Lessard
Laboratoire de Chimie et Electrochimie Organiques, Département de Chimie, Université de Sherbrooke, Sherbrooke, Québec J1K 2R1, Canada
33. Selective Hydrogenolysis of Sugar Alcohols over Structured Catalysts
289
Chunshe (James) Cao, James F. White, Yong Wang and John G. Frye
Pacific Northwest National Laboratory
902 Battelle Blvd, MS K8-93, Richland, WA 99352
34. Twinphos: A New Family of Chiral Ferrocene Tetra-Phosphine Ligands for Asymmetric Catalytic Transformations
293
Benoit Pugin, Heidi Landert, Martin Kesselgruber, Hans Meier, Richard Sachleben, Felix Spindler and Marc Thommen
Solvias AG, Klybeckstrasse 19, Postfach CH 4002, Basel, Switzerland
35. Catalyst Library Design for Fine Chemistry Applications
303
József L. Margitfalvi, András Tompos, Sándor Gobölös, Emila Tálas and Mihály Hegedus
Chemical Research Center, Institute of Surface Chemistry and Catalysis, Department of Organic Catalysis, 1025 Budapest, Pusztaszeri ut 59-67Hungary
36. Dendrimer Templates for Pt and Au Catalysts
315
Bethany J. Auten, Christina J. Crump, Anil R. Singh and Bert D. Chandler Department of Chemistry, Trinity University, 1 Trinity Place, San Antonio, TX 78212-7200
V. Symposium on Acid and Base Catalysis 325
37. Development of an Industrial Process for the Lewis Acid/Iodide Salt-Catalyzed Rearrangement of 3,4-Epoxy-l-Butene to 2,5-Dihydrofuran
327
Stephen N. Falling¹, John R. Monnier,¹,² Gerald W. Phillips¹, Jeffrey S. Kanel¹, and Stephen A. Godleski³
¹Eastman Chemical Company Research Laboratories, Bldg. 150B, P.O. Box 1972 Kingsport, TN 37662-5150
²Department of Chemical Engineering, University of South Carolina, Columbia, SC, 29208
³Eastman Kodak Company, Rochester, New York, 14650
38. A New Economical and Environmentally Friendly Synthesis of 2,5-Dimethyl-2,4-Hexadiene
337
Alessandra O. Bianchia, Valerio Borzattaa, Elisa Poluzzia and Angelo Vaccarib
a Endura SpA, Viale Pietramellara 5, 40012 Bologna (Italy)
b Dipartimento di Chiinica Industriale e dei Materials, Alma Mater Studiorum University di Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy
39. Supported Heteropoly Acid Catalysts for Friedel-Crafts Acylation
347
Kenneth G. Griffin¹, Peter Johnston¹, Roger Prétôt², Paul A. van der Schaaf²
¹Johnson Matthey plc, Catalyst Development, Royston, SG8 5HE, UK
²Ciba Specialty Chemicals Inc., CH-4002 Basel, Switzerland
40. Synthesis of Pseudoionones by Aldol Condensation of Citral with Acetone on Li-Modified MgO Catalysts
355
Veronica K. Diez, Juana Di Cosimo and Carlos Apesteguia
Catalysis Science and Engineering Research Group (GICIC), Institute de Investigaciones en Catalisis y Petroquimica (UNL-CONICET), Santiago del Estero 2654(3000) Santa Fe, Argentina
41. The One Step Synthesis of MIBK via Catalytic Distillation: A Preliminary Pilot Scale Study
365
William K. O'Keefe, Ming Jiang, Flora T.T. Ng and Garry L. Rempel
The University of Waterloo, Department of Chemical Engineering, 200 University Avenue West, Waterloo, Ontario, Canada N2L 3G1
VI. Symposium on "Green" Catalysis 375
42. Producing Polyurethane Foam from Natural Oil
377
Aaron Sanders, David Babb, Robbyn Prange, Mark Sonnenschein, Van Delk, Chris Derstine and Kurt Olson
The Dow Chemical Company, 2301 N Brazosport Blvd., Freeport, TX 77541
43. Carbonylation of Chloropinacolone: A Greener Path to Commercially Useful Methyl Pivaloylacetate
385
Joseph R. Zoeller and Theresa Barnette
Eastman Chemical Company, P.O. Box 1972, Kingsport, TN 37662
44. Recycling Homogeneous Catalysts for Sustainable Technology
395
Jason P. Hallett, Pamela Pollet, Charles A. Eckert and Charles L. Liotta
School of Chemistry and Biochemistry, School of Chemical & Biomolecular Engineering, and Specialty Separations Center, Georgia Institute of Technology, Atlanta, Georgia 30332-0325
45. "Green" Catalysts for Enhanced Biodiesel Technology
405
Anton A. Kiss, Gadi Rothenberg and Alexandre C. Dimian
University of Amsterdam, van 't Hoff Institute for Molecular Sciences, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands
46. Continuous Deoxygenation of Ethyl Stearate: A Model Reaction for Production of Diesel Fuel Hydrocarbons
415
Mathias Snåre, Iva Kubicková, Päivi Mäki-Arvela, Kari Eränen and Dmitry Yu. Murzin
Laboratory of Industrial Chemistry, Process Chemistry Centre, Åbo Akademi University Biskopsgatan 8, FIN-20500 Turku/Åbo, Finland
47. Glycerol Hydrogenolysis to Propylene Glycol under Heterogeneous Conditions
427
Simona Marincean, Lars Peereboom, Yaoyan Xi, Dennis J. Miller and James E. Jackson
Department of Chemistry, Department of Chemical Engineering and Materials Science, Michigan State University, East Lansing MI 48824-1322
48. Developing Sustainable Process Technology
437
Joseph A. Kocal
UOP LLC, 25 East Algonquin Road, Des Plaines, IL 60017-5017
49. Selective Oxidation of Propylene to Propylene Oxide in CO2 Expanded Liquid System
447
Hyun-Jin Lee, Tie-Pan Shi, Bala Subramaniam and Daryle H. Busch
Center for Environmentally Beneficial Catalysis, University of Kansas, Lawrence, KS 66047
VII. Symposium on Other Topics in Catalysis 453
50. catASium® M: A New Family of Chiral Bisphospholanes and their Application in Enantioselective Hydrogenations
455
Thomas H. Riermeier,(a) Axel Monsees,a Jens Holz,(b) Armin Börner(b) and John Tarabocchia(c)
a Degussa AG, Degussa Homogeneous Catalysts, Rodenbacher Chaussee 4, 63457 Hanau-Wolfgang, Germany
b Leibniz-Institut for Organische Katalyse an der Universitdt Rostock e. V., Buchbinderstr. 5/6, 18055 Rostock, Germany
c Degussa Corporation, 379 Interpace Parkway, Parsippany, NJ 07054
51. Synthesis of Chiral 2-Amino-1-Phenylethanol
463
Robert Augustine, Setrak Tanielyan, Norman Marin and Gabriela Alvez
Center for Applied Catalysis, Seton Hall University, South Orange, NJ 07079
52. Selective Tertiary-Butanol Dehydration to lsobutylene via Reactive Distillation and Solid Acid Catalysis
469
John F. Knifton(a) and John R. Sanderson(b)
a Consultant; P.O. Box 200333, Austin, TX 78720
b Retired
53. Leaching Resistance of Precious Metal Powder Catalysts - Part 2
475
Tim Pohlmann, Kimberly Humphries, Jaime Morrow, Tracy Dunn, Marisa Cruz, Konrad Möbus and Baoshu Chen
Degussa Corporation, 5150 Gilbertsville Highway, Calvert City, KY 42029
54. Optimization of Reductive Alkylation Catalysts by Experimental Design
481
Venu Arunajatesan, Marisa Cruz, Konrad Möbus and Baoshu Chen
Degussa Corporation, 5150 Gilbertsville Hwy, Calvert City, KY 42029
55. Accelerated Identification of the Preferred Precious Metal Powder Catalysts for Selective Hydrogenation of Multi-functional Substrates
487
Dorit Wolf, Steffen Seebald and Thomas Tacke
Degussa AG, Exclusive Synthesis & Catalysts, EC-KA-RD-WG Rodenbacher Chaussee4 D-63457 Hanau (Wolfgang), Germany
56. Transition Metal Removal from Organic Media by Deloxan® Metal Scavengers
493
Jaime B. Woods¹, Robin Spears¹, Jurgen Krauter², Tim McCarthy³, Micheal Murphy³, Lee Hord4, Peter Doorley4 and Baoshu Chen¹
¹Degussa Corporation, Business Line Catalysts, 5150 Gilbertsville Hwy., Calvert City, KY 42029;
²Degussa AG, Business Line Catalysts, Rodenbacher Chaussee 4, D-63457, Hanau, Germany;
³Degussa Corporation, Business Line Catalysts, 379 Interpace Parkway, Parsippany, NJ, 07054;
4Mobile Process Technology, 2070 Airways Boulevard, Memphis, TN, 38114
57. Electroreductive Pd-Catalyzed Ullmann Reactions in Ionic Liquids
501
Laura Durán Pachón and Gadi Rothenberg
Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands
Author Index 507
Keyword Index 513

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