The non-renewable and endocrine disrupting nature of conventional petro-based bisphenols, like bisphenol A (BPA) and F (BPF), has sparked the quest for bio-based and oestrogen inactive bisphenol replacements, used for the production of aromatic polycarbonate (PC) and epoxy resins. A promising BPA/bisphenol replacement, is para,para’-bisguaiacol F (p,p’-BGF), a condensation product of lignin-derivable vanillyl alcohol (VA) and guaiacol. In this master thesis, the potential of p,p’-BGF as a green and safe(r) building block for PCs is examined. Special attention is given to the integrated and simultaneous valorisation of meta,para’-bisguaiacol F (m,p’-BGF), a significant side product inherently linked to p,p’-BGF synthesis. In a new and successful approach, both BGF regioisomers are selectively synthesised by acid-catalysed condensation of guaiacol with commercially available VA regioisomers. For p,p’-BGF (from VA), optimisation leads to a chemo- and regioselectivity of 56 wt% and 73%, respectively. Similar values (58 wt% and 72%) are obtained for m,p’-BGF (from isovanillyl alcohol). Preliminary results indicate the existence of acid-catalysed isomerisation for p,p’-BGF (to o,p’-BGF), but it seems to lacks for m,p’- and o,p’-isomers. Subsequent purification by column chromatography and successive (re)crystallisation yields isomerically pure (p,p’- and m,p’-)BGF (>99.5%). Before polymerisation, to ensure safer chemical design, their estrogenic activity (EA) is tested in an in vitro luciferase assay, and found to be significantly lower compared to BPA and BPF. p,p’- and m,p’-BGF display reduced potencies (84 and 89 times lower affinity than BPA) and lowered efficacies (52% and 38% of BPA’s maximum effect), respectively. One-on-one comparison of p,p’-BPF and p,p’-BGF demonstrates the direct link between lower EA and the presence of ortho-methoxy groups. Next, homo- and copolymers (25:75, 50:50 and 75:25) of p,p’- and m,p’-BGF are successfully prepared by interfacial polymerisation (in >80% yield) with in situ generated phosgene (from triphosgene), as unambiguously proven by (1H and 13C) NMR, FTIR and GPC. All BGF-based PCs (BGF-PCs) display nearly identical thermal and physicochemical properties, having Mw = 20.0-26.2 kDa, Mn = 5.5-6.2 kDa, Tg = 102-111 °C and Td;max = 417-419 °C, of which the latter two properties are almost similar to petro-based BPF-PC (Tg = 119 °C, Td;max= 447 °C), regardless of their different Mw.