Isomerization of c is -2,5-Di(hydroxymethyl)tetrahydrofuran to its t rans -Isomer and the Effect of the c is /t rans Ratio on the Properties of its Polyester with 1,12-Dodecanedioic Acid
Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide 2,5-Di(hydroxymethyl)tetrahydrofuran (DHMTHF) was prepared by the Raney-nickel-catalyzed hydrogenation of biobased 5-hydroxymethylfurfural. It was obtained as mainly the cis isomer which could be partially converted to its trans isomer via a ruthenium-catalyzed borrowing hydrogen-type reaction. After acetylation of the cis / trans -DHMTHF mixture, the trans isomer was found to selectively precipitate from a diethyl ether solution at −15 °C. DHMTHF was used as a polyol building block, and the influence of its stereochemistry on the properties of polyester polyols and polyurethanes (PUs) that are suitable for adhesive applications was investigated. A polyester polyol derived from 100% biobased material was prepared using dodecanedioic acid. The polymer with a high trans isomer content (85%) exhibited a higher crystallinity than the two polyester polyols containing a lower amount of the trans isomer. In contrast, the PU synthesized from the cis / trans (57/43) DHMTHF-derived polyester polyol showed superior mechanical properties as compared to those of the corresponding PUs containing cis- and trans -enriched analogues.
Authors: Brian Spiegelberg, Claas Schünemann, Alexander Kux, Adrian Brandt, Andreas Taden, Horst Beck, Christian Hering-Junghans, Sergey Tin, Johannes G. de Vries
Institutions: Leibniz Institute for Catalysis, Henkel (Germany)
Language: English
Subfield: Biomaterials
Field: Materials Science
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Award: G7452063831
OpenAlex ID: W4411140717