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

Abstract

A unique, bulk-scale lignin-to-chemicals valorisation chain converts economically feasible 4-n-propylsyringol into low-oestrogenic bisphenols suitable for aromatic polyesters.

Shape selectivity vapor-phase conversion of lignin-derived 4-ethylphenol to phenol and ethylene over acidic aluminosilicates: Impact of acid properties and pore constraint

“…Among others, ethyl-(EPs) and propylphenols (PPs) are common aromatics derived from lignin depolymerization and the gasification of coal [3,6,[21][22][23][24][25][26]. Alkylphenols have interesting application themselves like solvents, fuel and rubber additives, and thermosets [27][28][29][30][31]. Valorization of these alkylphenols into base chemicals like phenol and olefins is also relevant when they become abundantly available, but this synthetic pathway is underexplored.…”

BioLogicTool: A Simple Visual Tool for Assisting in the Logical Selection of Pathways from Biomass to Products

“…[31][32][33][34][35][36][37] Yet, to the best of our knowledge, there is only one example where an actual lignin-derived monomer (4-npropylsyringnol, Figure 10C) was used. 38 Moreover, the authors conducted an early-stage economic assessment which showed that the scale-up of the bissyringol (Figure 10C) could be economically feasible. The comparison of BPA with the lignin-based BPA replacement shows two interesting features.…”

Regioselective synthesis, isomerisation, in vitro oestrogenic activity, and copolymerisation of bisguaiacol F (BGF) isomers

“…This allowed more adequate benchmarking as thermal properties of PCs correlate with M w . 48 Strikingly, although previous reports revealed bimodal M w distributions for 4-alkylated poly(m,m′-BGF carbonate) that were hypothesised to be related to macrocycle formation, 34,35 here monomodal distributions were observed for all BGF-PCs, including homopolymeric m,p′-BGF-PC. Further research should unravel if this was indeed connected to m,m′-regioisomerism, or due to the type of phase-transfer catalyst used.…”

“…Firstly, as bio-based p,p′-BGF does only differ from petro-based p,p′-BPF in terms of its o-methoxy groups, these groups can be unambiguously identified as the root cause for the significant drop in in vitro oestrogenic activity, reducing both potency (by about two orders) and efficacy (by >50%). Noticeably, lower in vitro oestrogenic activities were already reported for 4-alkylated m,m′-BGFs and m,m′bissyringol Fs (BSFs), 34,35 although the hypothesised link with the methoxy groups could then not be unambiguously established due to the inaccessibility of non-methoxylated analogues. Taken together, these results clearly illustrate the positive effect of incorporating o-methoxy moieties into bisphenol scaffolds on lowering in vitro oestrogenic transactivation, both in terms of potency and efficacy.…”