Issue 6, 2023

Controlling selectivity for dechlorination of poly(vinyl chloride) with (xantphos)RhCl

Abstract

Reaction of poly(vinyl chloride) (PVC) with 5 equiv. of triethyl silane in THF, in the presence of in situ generated (xantphos)RhCl catalyst, results in partial reduction of PVC via hydrodechlorination to yield poly(vinyl chloride-co-ethylene). Increasing catalyst loading or using N,N-dimethylacetamide (DMA) as a solvent both diminished selectivity for hydrodechlorination, promoting competitive dehydrochlorination reactions. Reaction of PVC with 2 equiv. of sodium formate in THF in the presence of (xantphos)RhCl affords excellent selectivity for hydrodechlorination along with complete PVC dechlorination, yielding polyethylene-like polymers. Higher catalyst loadings were necessary to activate PVC towards reduction in this case. In contrast, reaction of PVC with 1 equiv. of NaH in DMA, in the presence of (xantphos)RhCl, exhibited good selectivity for dehydrochlorination, as well as much higher reaction rates. These results combined shed light on the interplay between critical reaction parameters that control PVC's mode of reactivity.

Graphical abstract: Controlling selectivity for dechlorination of poly(vinyl chloride) with (xantphos)RhCl

Supplementary files

Article information

Article type
Communication
Submitted
18 okt 2022
Accepted
03 apr 2023
First published
11 apr 2023

Mater. Horiz., 2023,10, 2047-2052

Author version available

Controlling selectivity for dechlorination of poly(vinyl chloride) with (xantphos)RhCl

N. G. Bush, M. K. Assefa, S. Bac, S. Mallikarjun Sharada and M. E. Fieser, Mater. Horiz., 2023, 10, 2047 DOI: 10.1039/D2MH01293F

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