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Max-Planck-Institut Für Kohlenforschung Report for The Max-Planck-Institut für Kohlenforschung Report for the Period of January 2008 – December 2010 Printed December 2010 Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 1 45470 Mülheim an der Ruhr, Germany Tel. +49 208 3 06 1 Fax +49 208 3 06 29 80 http://www.mpi-muelheim.mpg.de Managing Director Professor Dr. Alois Fürstner Director of the Department of Synthetic Organic Chemistry Professor Dr. Manfred T. Reetz Tel. +49 208 3 06 20 00 Fax +49 208 3 06 29 85 E-mail: [email protected] Philipps-Universität Marburg Faculty of Chemistry Hans-Meerwein-Straße 35032 Marburg Tel. +49 6421 28 25 500 Director of the Department of Homogeneous Catalysis Professor Dr. Benjamin List Tel. +49 208 3 06 24 10 Fax +49 208 3 06 29 99 E-mail: [email protected] Director of the Department of Heterogeneous Catalysis Professor Dr. Ferdi Schüth Tel. +49 208 3 06 23 73 Fax +49 208 3 06 29 95 E-mail: [email protected] Director of the Department of Organometallic Chemistry Professor Dr. Alois Fürstner Tel. +49 208 3 06 23 42 Fax +49 208 3 06 29 94 E-mail: [email protected] Director of the Department of Theory Professor Dr. Walter Thiel Tel. +49 208 3 06 21 50 Fax +49 208 3 06 29 96 E-mail: [email protected] Emeritus Scientific Members of the Max-Planck-Institut für Kohlenforschung Professor Dr. Günther Wilke Professor Dr. Roland Köster (deceased, June 2009) External Scientific Members of the Max-Planck-Institut für Kohlenforschung Professor Dr. Alois Haas Medonstraße 17 14532 Kleinmachnow Germany Professor Dr. Jack Halpern University of Chicago Department of Chemistry 5735 South Ellis Avenue Chicago, Illinois 60637 USA Professor Dr. Walter Leitner Lehrstuhl für Technische Chemie und Petrolchemie Institut für Technische und Makromolekulare Chemie Rheinisch-Westfälische Technische Hochschule Aachen Worringer Weg 1 52074 Aachen Germany Members of the Scientific Council of the Max Planck Society, Section of Chemistry, Physics and Technology Dr. Wolfgang Schmidt (August 2003 – July 2009) Dr. Claudia Weidenthaler (since July 2009) Table of Contents 1 The Max-Planck-Institut für Kohlenforschung 9 1.1 History 11 1.2 Current Research Areas 14 1.3 Organigram 2010 16 1.4 Members of the Scientific Advisory Board 17 1.5 Members of the Board of Governors 19 2 Research Programs 21 2.1 Department of Synthetic Organic Chemistry 23 2.1.1 Methodology Development in Directed Evolution (M. T. REETZ) 28 2.1.2 Methods for Enzyme Screening/Selection (M. T. REETZ) 32 2.1.3 Learning from Directed Evolution (M. T. REETZ) 36 2.1.4. Transition Metal Catalysis (M. T. REETZ) 40 2.1.5 Solid-State Hydrogenation / Hydrogenolysis of Coals with Gaseous Catalysts (M. W. HAENEL) 44 2.1.6 Development of Thermostable Homogeneous Catalysts (M. W. HAENEL) 48 2.1.7 Synthesis of Nanocatalysts by Chemical Fluid Deposition and their Application in the Transformation of Biomass (W. LEITNER / N. THEYSSEN) 52 2.2 Department of Homogeneous Catalysis 55 2.2.1 Crystal Structures of Proline Derived Enamines (B. LIST) 60 2.2.2 Catalytic Asymmetric Epoxidation of Electron-Deficient Olefins (B. LIST) 65 2.2.3 Asymmetric Counteranion-Directed Transition Metal Catalysis (B. LIST) 70 2.2.4 Lewis Acid Organocatalysis (B. LIST) 74 2.2.5 Catalytic Asymmetric Acetalizations (B. LIST) 80 2.2.6 Oxidative Coupling Reactions for the Formation of Carbon-Carbon Bonds (M. KLUSSMANN) 85 2.2.7 Electrophilic Activation of Amides / Pericyclic Reactions of Keteniminium Derivatives (N. MAULIDE) 88 2.2.8 Stereoselective Synthesis of Cyclobutenes (N. MAULIDE) 91 2.2.9 Sulfur Chemistry Revisited / New Ylide Transfer Reactions (N. MAULIDE) 94 2.2.10 Immobilization of Bispidine Complexes (K.-R. PÖRSCHKE) 97 2.2.11 NHC-modified Ni(II) Complexes (K.-R. PÖRSCHKE) 100 2.3 Department of Heterogeneous Catalysis 103 2.3.1 Understanding the Synthesis of Solid Catalysts (F. SCHÜTH) 112 2.3.2 High Surface Area Materials (F. SCHÜTH) 116 2.3.3 Nanoengineered Catalysts (F. SCHÜTH / A.-H. LU) 121 2.3.4 Hydrides for Hydrogen and Energy Storage (F. SCHÜTH) 127 2.3.5 Nanostructured Optical Materials (F. MARLOW) 130 2.3.6 Solid Catalysts and Reaction Systems for Utilization of Cellulose and Sugars (R. PALKOVITS) 132 2.3.7 Depolymerization of Cellulose in Ionic Liquids (R. RINALDI / F. SCHÜTH) 136 2.3.8 Exploration of Nanoporous Solids (W. SCHMIDT) 139 2.3.9 High-Throughput Multiplexing Chromatography (O. TRAPP) 145 2.3.10 High-Throughput Dynamic Chromatography and On-column Reaction Chromatography (O. TRAPP) 147 2.4 Department of Organometallic Chemistry 151 2.4.1 -Acid Catalysis (A. FÜRSTNER) 157 2.4.2 Metathesis (A. FÜRSTNER) 162 2.4.3 Iron Catalysis (A. FÜRSTNER) 167 2.4.4 Novel Donor Ligands (A. FÜRSTNER) 171 2.4.5 Catalysis-Based Syntheses and Evaluation of Bioactive Natural Products (A. FÜRSTNER) 175 2.4.6 Design, Synthesis and Applications of Organic Frustrated Lewis Pairs (M. ALCARAZO) 179 2.4.7 Design and Synthesis of Unconventional Ligands (M. ALCARAZO) 183 2.5 Department of Theory 187 2.5.1 Ab Initio Methods (W. THIEL) 192 2.5.2 Density Functional Methods (W. THIEL) 197 2.5.3 Semiempirical Methods (W. THIEL) 200 2.5.4 Combined Quantum Mechanical / Molecular Mechanical Methods (W. THIEL) 204 2.5.5 Simulations of Photoexcited Molecules and Dynamical Processes (M. BARBATTI) 211 3 Scientific Service Units 213 3.1 Technical Laboratories (N. THEYSSEN) 216 3.2 Chromatography and Separation Science (P. SCHULZE) 218 3.3 Mass Spectrometry (W. SCHRADER) 220 3.4 Nuclear Magnetic Resonance (R. MYNOTT / C. FARÈS) 223 3.5 Electron Microscopy and Chemical Crystallography (C. W. LEHMANN) 226 3.6 Library and Information Management (P. FISCHER / R. BARABASCH) 230 3.7 Computer Group (P. FISCHER) 232 4 The Training of Young Scientists 235 5 Equal Opportunities 245 6 Technology Transfer 249 7 Appendices 255 7.1 List of Publications 257 7.2 List of Invited Talks Given by Members of the Institute 303 7.3 Scientific Honors, Name Lectureships, Awards 324 7.4 Contacts with Universities 328 7.5 Special Events and Activities 332 7.5.1 Symposia Organized by the Institute 336 7.6 List of Talks Given by Guests 344 7.7 Local Activities of the Young Chemists Forum (JCF) of the German Chemical Society (GDCh) 362 7.8 Public Relations 364 7.9 Special Equipment 369 7.10 How to Reach the Institute 379 CHAPTER 1 The Max-Planck-Institut für Kohlenforschung 9 10 History 1.1 History The decision to found a Kaiser-Wilhelm-Institut für Kohlenforschung (coal research) in Mülheim/Ruhr was taken in 1912 by the Kaiser Wilhelm Society, representatives of the coal industry and the town of Mülheim/Ruhr. In 1913 Franz Fischer (1877-1947), who in 1911 had been appointed professor for electrochemistry at the Technical University in Berlin-Charlottenburg, was chosen as the first Director. Franz Fischer and his co-workers carried out basic research in a number of areas concerning the formation and chemical composition of coal as well as on its conversion into solid, liquid and gaseous products. The most important contribution culminated in the so-called Fischer-Tropsch process for coal liquefaction. In 1925, Franz Fischer and the group leader Hans Tropsch reported that liquid hydrocarbons (alkanes) can be produced from carbon monoxide and hydrogen in the presence of solid metal catalysts. The mixture of the two gases (synthesis gas) necessary for this new process was prepared by the “gasification” of coal with steam and oxygen at 900°C. In 1925 the “Studien- und Verwertungsgesellschaft mbH” was founded for the purpose of exploiting the patents. By the early 1940s nine industrial plants were operating in Germany producing ca. 600 000 tons of liquid hydrocarbons per year. Today there is a renewed interest in Fischer-Tropsch technology with plants in Sasolburg/South Africa, Malaysia, and Qatar (using natural gas instead of coal). In 1939 Franz Fischer instigated a change in the status of the Institute; it became a foundation of private law with the objective of supporting the scientific investigation of coal for the public benefit. Following Fischer’s retirement in 1943 Karl Ziegler (1898-1973) was appointed Director of the Institute. After the founding of the Max Planck Society as the successor of the Kaiser Wilhelm Society in 1948, the Institute obtained its present name in 1949. As a consequence of Ziegler’s appointment, the main research efforts shifted to organometallic chemistry. Based upon his earlier experience with the organic compounds of the alkali metals, Ziegler and his co-workers turned their attention to aluminum. In 1949 they reported the multiple addition of ethylene to aluminum alkyls which became known as the “Aufbau” reaction. The product of this oligomerization was a mixture of aluminum alkyls having long, linear alkyl chains attached to the metal; these compounds could be converted into -olefins or primary alcohols, the latter being important for the production of biodegradable detergents. An unexpected observation during the systematic investigation of this reaction led to the discovery that transition metals have a dramatic effect on the “Aufbau” reaction; in particular, the addition of 11 History compounds of titanium or zirconium led to the coupling of up to 100 000 ethylene molecules at normal pressure and temperature. The optimized process employed the so- called organometallic “Mischkatalysatoren” consisting of an aluminum alkyl and a transition metal salt. It was patented in 1953 and led to a dramatic development of the industrial production of polyethylene and polypropylene as cheap and versatile polymers. The licensing of the patents enabled the Institute to be operated on an independent financial basis for nearly 40 years.
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