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Sustainable, Efficient Approaches to Renewable Platform Chemicals and Polymers

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Sustainable, Efficient Approaches to Renewable Platform Chemicals and Polymers Sustainable, efficient approaches to renewable platform chemicals and polymers Zur Erlangung des akademischen Grades eines DOKTORS DER NATURWISSENSCHAFTEN (Dr. rer. nat.) Fakultät für Chemie und Biowissenschaften Karlsruher Institut für Technologie (KIT) – Universitätsbereich Genehmigte DISSERTATION von M.Sc. Hatice Mutlu aus Kircali, Bulgaria Dekan: Prof. Dr. M. Bastmeyer Referent: Prof. Dr. M. A. R. Meier Korreferent: Prof. Dr. C. Barner-Kowollik Tag der mündlichen Prüfung: 19.04.2012 Die vorliegende Arbeit wurde von Juli 2008 bis Februar 2012 unter Anleitung von Prof. Dr. Michael A. R. Meier an der Hochschule Emden/Leer (von Juli 2008 bis August 2009), der Universität Potsdam (von September 2009 bis Dezember 2011) und am Karlsruher Institut für Technologie (KIT, von January 2011 bis Februar 2012) - Universitätsbereich angefertigt. SevdiklerimeSevdiklerime…… Abstract Environmental concerns, such as pollution and decreases in natural resources, have led to an increased demand for renewable materials in recent years. Adoption of efficient approaches, like metal-free organocatalysis, olefin metathesis and thiol-ene coupling, both in academic and industrial research, offers the potential of increased sustainability, comparatively lower production costs (besides olefin metathesis), and more environmentally benign processes. Thus, the following work is performed with the attempt to meet both, making use of oils as renewable feedstock, in this case mainly plant oil derived platform chemicals, and using sustainable, efficient approaches as valuable synthetic tools. Kurzzusammenfassung Ökologische Bedenken, wie Umweltverschmutzung und der Rückgang der natürlichen Ressourcen, haben in den letzten Jahren zu einer gestiegenen Nachfrage nach nachwachsenden Rohstoffen geführt. Die Anwendung effizienter synthetischer Methoden, wie etwa metallfreie Organokatalyse, Olefinmetathese und Thiol-En- Kupplung, sowohl in akademischer als auch industrieller Forschung, haben das Potenzial zu mehr Nachhaltigkeit, vergleichsweisen niedrigeren Produktionskosten und umweltfreundlicheren Prozessen beizutragen. Aus diesem Grund hat die vorliegende Arbeit als Ziel sowohl die Nutzung nachwachsender Rohstoffe, in diesem Fall vor allem von Pflanzenöl und davon abgeleiteten Plattform Chemikalien, als auch der Anwendung nachhaltiger und effizienter Methoden als wertvolle synthetische Werkzeuge zu veranschaulichen. Content Content.....................................................................................................................i 1 Introduction ..........................................................................................................1 2 Bio-based resources and their efficient utilization: Plant oils as alternative to crude oil ............................................................................................................................9 3 Efficient approaches for carbon-carbon and carbon-hetero atom bond formations .............................................................................................................................. 25 3.1 Olefin metathesis .............................................................................................................. 27 3.2 Guanidines as efficient and promising organocatalysts.................................................... 43 3.3 Thiol-ene reaction ............................................................................................................. 50 4 Main Part ............................................................................................................ 57 4.1 Acyclic Triene Metathesis (ATMET) Polymerization of plukenetia conophora oil : branched polymers by direct polymerization of renewable resources .................................................. 58 Introduction ........................................................................................................................ 58 Results and discussion......................................................................................................... 60 Conclusions ......................................................................................................................... 75 4.2 Acyclic Triene Metathesis (ATMET) polymerization of soybean oil modified with 4- vinylbenzene sulfonic acid ...................................................................................................... 76 Introduction ........................................................................................................................ 76 Result and discussion .......................................................................................................... 78 Conclusions ......................................................................................................................... 81 i 4.3 Living Ring-Opening Metathesis Polymerization (ROMP) of fatty acid derived monomers ................................................................................................................................................. 82 Introduction ........................................................................................................................ 82 Results and discussion......................................................................................................... 83 Monomers synthesis ....................................................................................................... 83 ROMP of monomers M1-M7........................................................................................... 84 Thermal properties.......................................................................................................... 92 Conclusions ......................................................................................................................... 93 4.4 Studies on the activity and selectivity of indenylidene-based metathesis catalysts during ADMET polymerization ........................................................................................................... 94 Introduction ........................................................................................................................ 94 Results and discussion......................................................................................................... 97 Conclusion......................................................................................................................... 106 4.5 Synthesis of castor oil-derived unsaturated PA X,20 via metathesis and catalytic amidation .............................................................................................................................. 108 Introduction ...................................................................................................................... 108 Results and discussion....................................................................................................... 110 Conclusion......................................................................................................................... 118 4.6 Synthesis of carbonate-based polymers and building blocks ......................................... 119 Introduction ...................................................................................................................... 119 Results and discussion....................................................................................................... 121 Unsymmetric organic carbonate synthesis................................................................... 121 Polycarbonate synthesis via TBD mediated polycondensation .................................... 128 Symmetric organic carbonate synthesis and subsequent ADMET studies of representative monomers ............................................................................................ 135 Conclusions ....................................................................................................................... 142 4.7 On the polymerization behavior of telomers: Metathesis versus thiol-ene chemistry .. 143 Introduction ...................................................................................................................... 143 Results and discussion....................................................................................................... 144 ii ADMET Polymerizations................................................................................................ 145 Thiol-ene polymerizations............................................................................................. 155 Conclusions ....................................................................................................................... 165 5 Experimental section ......................................................................................... 166 5.1 Characterization methods............................................................................................... 166 Thin layer chromatography (TLC)...................................................................................... 166 Nuclear magnetic resonance (NMR) spectroscopy........................................................... 166 Gas chromatography (GC)................................................................................................. 167 Gas chromatography-Mass spectroscopy (GC-MS)........................................................... 167 Mass spectrometry (MS)..................................................................................................
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