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ISBN 978-3-8439-2872-4

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978-3-8439-2872-4, Reihe Technische Chemie

Thomas Seidensticker
Development of Catalytic Tandem Reaction Systems in the Context of Green Chemistry

254 Seiten, Dissertation Technische Universität Dortmund (2016), Softcover, A5

Zusammenfassung / Abstract

Catalysis represents one of the central principles of Green Chemistry. Hence, the merger of two or more catalyzed transformations into a single operative step clearly features decisive advantages; saving resources by not isolating Intermediates, for example. Such reaction systems are referred to as tandem catalysis. Due to their major benefit in contrast to the iterative synthesis of products within a value chain, they recently gained much attention. However, catalysis is only one principle of Green Chemistry fulfilled by tandem reactions; a more general assessment of their potential within the context of Green Chemistry is not reported to date.

In the present thesis, different innovative tandem catalytic reaction systems have been developed, each focusing on additional principles of Green Chemistry in order to increase the impact on Green Chemistry and sustainability in general. The developed reaction systems are based on the carbonylation of olefins, linking two essential aspects of this thesis: technical relevance and recent research trends. Technical relevance was additionally tackled by focusing on the synthesis of linear bifunctional molecules, which are of high industrial importance for producing polymers.

Four new tandem reactions were established within this thesis: By incorporating coproducts by formate alkoxycarbonylation into the target molecule, thereby effectively minimizing the waste produced, two essential principles of Green Chemistry were addressed in an innovative synthesis of adipic esters. The implementation of lesshazardous CO substitutes represents a major trend in carbonylation reaction and has been extended within this thesis to enable amide synthesis from inexpensive substrates. A bifunctional, industrially readily available compound was efficiently converted into a linear C10-diester by merging two individual carbonylations at two distinct reactive sites of the molecule. Taking inspiration from this approach, the reaction of a bifunctional amine with two equivalents of olefin has been optimized and enabled for the linear linkage of renewable substrates. For this specific example, a process was designed under consideration of Green Chemistry principles: Starting from the functionalized, renewable substrates, the effective isolation of desired products from the reaction mixture by retaining the active precious metal catalyst was successful and allowed finally for the synthesis of a polyester from renewable substrates.