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. 2022 Aug 1;61(31):e202203353.
doi: 10.1002/anie.202203353. Epub 2022 May 31.

Towards Upcycling Biomass-Derived Crosslinked Polymers with Light

Ravichandranath Singathi  1 , Ramya Raghunathan  1 , Retheesh Krishnan  2 , Saravana Kumar Rajendran  3 , Sruthy Baburaj  1 , Mukund P Sibi  4 , Dean C Webster  5 , Jayaraman Sivaguru  1
Affiliations

Towards Upcycling Biomass-Derived Crosslinked Polymers with Light

Ravichandranath Singathi et al. Angew Chem Int Ed Engl. .

Abstract

Photodegradable, recyclable, and renewable, crosslinked polymers from bioresources show promise towards developing a sustainable strategy to address the issue of plastics degradability and recyclability. Photo processes are not widely exploited for upcycling polymers in spite of the potential to have spatial and temporal control of the degradation in addition to being a green process. In this report we highlight a methodology in which biomass-derived crosslinked polymers can be programmed to degrade at ≈300 nm with ≈60 % recovery of the monomer. The recovered monomer was recycled back to the crosslinked polymer.

Keywords: Biomass; Photodegradation; Phototriggered Materials; Polymer Degradation; Upcycling.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Upcycling biomass‐derived polymers with light.
Scheme 1
Scheme 1
Photoreaction of phenacyl chromophores and developing a model system.
Scheme 2
Scheme 2
Programmed degradation of biomass‐derived crosslinked polymers 12 a, b.
Figure 2
Figure 2
Attenuated total reflection Fourier transform infra‐red (ATR‐FTIR) spectroscopy of 7, 11 a, 11 b, 12 a, 12 a (resynthesized) and 12 b.
Figure 3
Figure 3
TGA of acrylate polymer 12 a as synthesized from biomass (A) and after photodegradation and resynthesis from recycled monomer (B). PXRD of acrylate polymer 12 a as synthesized (bottom; blue) from biomass and after re‐synthesis (top; red) from recycled monomer (C). DSC analysis of 12 a as synthesized (D) and resynthesized from recycled monomer (E).
Figure 4
Figure 4
A) Absorbance spectra of vanillin 1 (blue), model compound 5 (red) and bis‐ketone derivative 7 (black) at 0.08 mM in MeCN. B) Phosphorescence spectra of vanillin 1 (blue) model compound 5 (red) and bis‐ketone derivative 7 (black) at 77 K in EtOH glass.
Figure 5
Figure 5
Programmed degradation of biomass‐derived insoluble crosslinked polymer 12 b.
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