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Ring‐Opening Terpolymerisation of Elemental Sulfur Waste with Propylene Oxide and Carbon Disulfide via Lithium Catalysis

Title data

Gallizioli, Cesare ; Battke, David ; Schlaad, Helmut ; Deglmann, Peter ; Plajer, Alex:
Ring‐Opening Terpolymerisation of Elemental Sulfur Waste with Propylene Oxide and Carbon Disulfide via Lithium Catalysis.
In: Angewandte Chemie International Edition. Vol. 63 (2024) Issue 17 . - e202319810.
ISSN 1521-3773
DOI: https://doi.org/10.1002/anie.202319810

Abstract in another language

Elemental sulfur, a waste product of the oil refinement process, represents a promising raw material for the synthesis of degradable polymers. We show that simple lithium alkoxides facilitate the polymerisation of elemental sulfur S8 with industrially relevant propylene oxide (PO) and CS2 (a base chemical sourced from waste S8 itself) to give poly(monothiocarbonate-alt-Sx) in which x can be controlled by the amount of supplied sulfur. The in situ generation of thiolate intermediates obtained by a rearrangement, which follows CS2 and PO incorporation, allows to combine S8 and epoxides into one polymer sequence that would otherwise not be possible. Mechanistic investigations reveal that alkyl oligosulfide intermediates from S8 ring opening and sulfur chain length equilibration represent the better nucleophiles for inserting the next PO if compared to the trithiocarbonates obtained from the competing CS2 addition, which causes the sequence selectivity. The polymers can be crosslinked in situ with multifunctional thiols to yield reprocessable and degradable networks. Our report demonstrates how mechanistic understanding allows to combine intrinsically incompatible building blocks for sulfur waste utilisation.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Junior Professor Polymers for Electrooptical and Sensory Applications > Junior Professor Polymers for Electrooptical and Sensory Applications - Juniorprof. Dr. Alex Johannes Plajer
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Junior Professor Polymers for Electrooptical and Sensory Applications
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 19 Mar 2024 10:54
Last Modified: 03 May 2024 06:31
URI: https://eref.uni-bayreuth.de/id/eprint/88942