0000000000214343
AUTHOR
Andreas Stenglein
Sustainable access to biobased biphenol epoxy resins by electrochemical dehydrogenative dimerization of eugenol
Limited fossil resources require innovative monomers and polymers derived from renewable feedstocks such as plant biomass. Thermosetting epoxy resins largely rely on petrochemical bisphenol-type monomers, which give high performance materials but are controversial due to their effects on human health. Herein, we present two biobased epoxy resins by direct dehydrogenative dimerization of eugenol, the main component of clove oil. Taking the Principles of Green Chemistry into account, we developed electrochemical dehydrodimerization at reticulated vitreous carbon (RVC) electrodes using methanol as environmentally benign solvent. Thus, fluorinated solvents such as 1,1,1,3,3,3-hexafluoroisopropa…
Large, Highly Modular Narrow-Gap Electrolytic Flow Cell and Application in Dehydrogenative Cross-Coupling of Phenols
The successive scale-up of electrochemical reactions is crucial with regard to the implementation of technical electro-organic syntheses. Therefore, we developed a scalable modular parallel-plate e...
High-Temperature Electrolysis of Kraft Lignin for Selective Vanillin Formation
Lignin represents the largest renewable resource of aromatic moieties on earth and harbors a huge potential as a sustainable feedstock for the synthesis of biobased aromatic fine chemicals. Due to the complex, heterogeneous, and robust chemical structure of the biopolymer, the valorization is associated with significant challenges. Unfortunately, technical lignins, which are a large side stream of the pulp and paper industries, are mainly thermally exploited. In this study, technical Kraft lignin was selectively electrochemically depolymerized to the aroma chemical vanillin. Using electricity, toxic and/or expensive oxidizers could be replaced. The electrodegradation of Kraft lignin was per…
Highly Modular Flow Cell for Electroorganic Synthesis
A highly modular electrochemical flow cell and its application in electroorganic synthesis is reported. This innovative setup facilitates many aspects: an easy adjustment of electrode distance, quick exchange of electrode material, and the possibility to easily switch between a divided or undivided cell. However, the major benefit of the cell is the exact thermal positioning of the electrode material into a Teflon piece. Thereby, the application of expensive and nonmachinable electrode materials like boron-doped diamond or glassy carbon can easily be realized in flow cells. By this geometry, the maximum surface of such valuable electrode materials is exploited. The cell size can compete wit…
Electrosynthesis of 3,3′,5,5’-tetramethyl-2,2′-biphenol in flow
Abstract3,3′,5,5’-Tetramethyl-2,2′-biphenol is well known as an outstanding building block for ligands in transition-metal catalysis and is therefore of particular industrial interest. The electro-organic method is a powerful, sustainable, and efficient alternative to conventional synthetic approaches to obtain symmetric and non-symmetric biphenols. Here, we report the successive scale-up of the dehydrogenative anodic homocoupling of 2,4-dimethylphenol (4) from laboratory scale to the technically relevant scale in highly modular narrow gap flow electrolysis cells. The electrosynthesis was optimized in a manner that allows it to be easily adopted to different scales such as laboratory, semit…