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Promising bulk production of a potentially benign bisphenol A replacement from a hardwood lignin platform

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Abstract

A full lignin-to-chemicals valorisation chain – from hardwood over bissyringols to aromatic polyesters (APEs) – is established for renewable 4-n-propylsyringol (PS), the main product from catalytic hydrogenolysis of (native) hardwood lignin. To do so, reagent-grade PS was produced from birch wood via reductive catalytic fractionation (RCF) and isolated in 34 wt% yield on lignin basis. Additional early-stage theoretical calculations, based on both relative volatility (α) and distillation resistance (Ω) as well as Aspen Plus® simulations, predict that the isolation of PS by means of distillation is economically feasible at industrial scales ($85–95 per ton of propylphenolics at 200–400 kt a−1 scale). Subsequent stoichiometric acid-catalysed condensation with formaldehyde unveils a remarkably high 92 wt% selectivity towards the dimer 3,3′-methylenebis(4-n-propylsyringol) (m,m′-BSF-4P), which is isolated in >99% purity by facile single-step crystallisation. The striking dimer selectivity is ascribed to the synergetic interplay between the activating methoxy groups and the oligomerisation-inhibiting propyl chain. Next, an in vitro human oestrogen receptor α (hERα) assay was performed to ensure safe(r) chemical design. The bissyringyl scaffold displays reduced potency (∼19–45-times lower affinity than bisphenol A) and lower efficacy (∼36–45% of BPA's maximum activity). Lastly, to assess the functionality of the safe(r) bissyringol scaffold, it was converted into an APE. The APE displays a Mw = 43.0 kDa, Mn = 24.4 kDa, Tg = 157 °C and Td,5% = 345 °C. In short, (i) the feasibility and scalability of the feedstock, (ii) the simplified process conditions, (iii) the reduced in vitro oestrogenicity, and (iv) the functionality towards polymerisation, make this bissyringol a renewable and potentially benign bisphenol replacement, capable for production at bulk scale.

Graphical abstract: Promising bulk production of a potentially benign bisphenol A replacement from a hardwood lignin platform

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Publication details

The article was received on 03 Oct 2017, accepted on 23 Jan 2018 and first published on 01 Feb 2018


Article type: Paper
DOI: 10.1039/C7GC02989F
Citation: Green Chem., 2018, Advance Article
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    Promising bulk production of a potentially benign bisphenol A replacement from a hardwood lignin platform

    S.-F. Koelewijn, C. Cooreman, T. Renders, C. Andecochea Saiz, S. Van den Bosch, W. Schutyser, W. De Leger, M. Smet, P. Van Puyvelde, H. Witters, B. Van der Bruggen and B. F. Sels, Green Chem., 2018, Advance Article , DOI: 10.1039/C7GC02989F

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