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Homogeneous Catalysis in Industry Tantárgyfelelős: Dr. Joó Ferenc A tárgy oktatója: Dr. Bogár Krisztián (University of Bergen, Norvégia; meghívott előadó) Óraszám/hét: 2 Kreditszám: 2 Számonkérés módja: kollokvium Előfeltétel: felvétel a PhD képzésbe Tematika: I. Introduction Industry as a profit-oriented organization, Law, Intellectual Property, Patent Research and development (R&D) Production and waste-handling Resource, Outsource Green chemistry – Why and how? Catalysis: definition, classification with examples, selectivity issues a) Homogeneous and heterogeneous catalysis b) Gas phase-, liquid phase-, biphasic catalysis, phase-transfer catalysis c) Metal catalysis, biocatalysis, organocatalysis Safety issues: risk and safety analysis, oxygen balance II. Process chemistry: Scale-up of laboratory syntheses for industrial processes Choice of starting materials and reagents Solvent choice Synthetic route choice for scale-up Running the reaction (tank reactor, flow chemistry, microwave reactor) Monitoring the reaction Quenching and work-up Purification Methods for removal of residual metal, scavengers Characterization Packaging, storage, shipping, delivery Recycling, reusing, dumping III. Frequently used processes in industry a) Reduction Olefin hydrogenation reactions Imine hydrogenation reactions Carbonyl hydrogenation reactions 1 Selective hydrogenation reactions Reduction of nitroarenes to aniline derivatives b) Oxidation Alcohol oxidation reactions Oxidation of heteroatoms: Sulfoxidation (Kagan oxidation) Baeyer-Villiger reaction c) Friedel-Crafts reaction Alkylation and acylation reactions Diarylketones via other methods d) Carbonylation, Cyanation and Sandmeyer reaction e) Olefin chemistry Olefination reactions Wacker oxidation Oxidative olefin bond cleavage Acetoxylation and diacetoxylation of olefins Epoxidation, aziridination, cyclopropanation reactions Dihydroxylation Metathesis reactions Allylic substitution and conjugate addition reactions Alternative synthetic routes to profens Hydroamination Hydroacylation f) Alcohols for C-C, C-N and C-X bond formations Isomerization reactions The “borrowing hydrogen” strategy g) Reductive amination h) Cross-coupling reactions Wurtz reaction Glaser coupling Ullmann reaction Gomberg-Bachmann reaction Cadiot-Chodkiewicz coupling Castro-Stephens coupling Gilman reagent coupling Cassar reaction Kumada-Corriu reaction Heck reaction and double Heck reaction Sonogashira reaction Negishi reaction and ZACA Stille reaction Suzuki-Miyaura reaction Hiyama coupling Buchwald-Hartwig amination 2 Etherification Fukuyama reaction Liebeskind-Strogl reaction Decarboxylative cross-coupling reactions Chan-Lam coupling reaction Choice of catalyst precursor, ligand, base and solvent, cesium-effect i) C-H actication, direct arylation, trifluoromethylation -Arylation of ketones Allylic C-H activation Fluorination and trifluoromethylation reactions Direct arylation of activated and unactivated arenes j) Biocatalysis Enzyme classification, enzyme catalysis, enzyme kinetics Whole cell catalysis Industrial catalysis using free enzymes Immobilized enzyme catalysis in industrial syntheses k) Combined metal and enzyme catalysis Dynamic kinetic resolution (DKR): Large-scale application Dynamic kinetic asymmetric transformation (DYKAT) Literature: Mathias Christmann, Stefan Bräse (Eds.), Asymmetric Synthesis – The Essentials, Wiley, 2008. Robert E. Gawley; Jeffrey Aubé, Principle of Asymmetric Synthesis; Pergamon, 1996. Robert B. Grossmann, The Art of Writing Reasonable Organic Reaction Mechanisms; Springer, 2003. Matthias Beller; Albert Renken; Rutger A. van Santen (Eds.), Catalysis – From Principles to Applications; Wiley, 2012. Matthias Beller, Carsten Bolm (Eds.), Transition Metals for Organic Synthesis, Wiley, 2008. John F. Hartwig, Organotransition Metal Chemistry – From Bonding to Catalysis; University Science Books, Mill Valley, California, USA, 2010. Francois Diederich; Peter J. Stang (Eds.), Metal-catalyzed Cross-coupling Reactions; Wiley, 1998. Norbert Krause (Ed.), Modern Organocopper Chemistry, Wiley, 2002. Alfredo Ricci (Ed.), Modern Amination Methods; Wiley 2000. 3 Christian Bruneau; Pierre H. Dixneuf (Eds.), Ruthenium Catalysts and Fine Chemistry, Topics in Organometallic Chemistry, Vol. 11.; Springer, 2004. Jan-Erling Bäckvall (Ed.), Modern Oxidation Methods; Wiley, 2010. Jason P. Tierney; Pelle Lindström, Microwave Assisted Organic Synthesis; Blackwell Publishing Ltd., 2005. Antonio de la Hoz; André Loupy (Eds.), Microwaves in Organic Synthesis; Wiley, 2012. Neal G. Anderson, Practical Process Research & Development – A Guide for Organic Chemists; Academic Press, 2012. Nobuyoshi Yosuda, The Art of Process Chemistry; Wiley, 2011. Peter J. Harrington, Pharmaceutical Process Chemistry for Synthesis – Rethinking the Routes to Scale-Up; Wiley, 2011. Hans-Ulrich Blaser; Jans-Jürgen Federsel, Asymmetric Catalysis on Industrial Scale – Challenges, Approaches and Solutions; Wiley, 2010. Kurt Faber, Biotransformations in Organic Chemistry; Springer, 2004. Karlheinz Drauz, Herbert Waldmann (Eds.), Enzyme Catalysis in Organic Synthesis, Wiley, 1995. Uwe T. Bornscheuer, Romas J. Kazlauskas, Hydrolases in Organic Synthesis – Regio- and Stereoselective Biotransformations, Wiley, 1999. Vincente Gotor, Ignacio Alfonso, Eduardo García-Urdiales (Eds.), Asymmetric Organic Synthesis with Enzymes, Wiley, 2008. Giacomo Carrea, Sergio Riva (Eds.), Organic Synthesis with Enzymes in Non-Aqueous Media, Wiley, 2008. Rolf D. Schmid, Vlada B. Urlacher (Eds.), Modern Biooxidation – Enzymes, Reactions and Applications, Wiley, 2007. Richard B. Silverman, The Organic Chemistry of Enzyme-Catalyzed Reactions, Academic Press, 2002. Daniela Gamenara; Gustavo A. Seoane; Patricia Saenz-Méndez; Pablo Domínguez de María, Redox Biocatalysis – Fundamentals ans Applications; Wiley, 2013. Roger A. Sheldon, Chirotechnology – Industrial Synthesis of Optically Active Compounds; Marcel Dekker Inc., 1993. Ramesh N. Patel (Ed.), Biocatalysis in the Pharmaceutical and Biotechnological Industries; CRC Press, 2007. 4