Abstract: Described herein are systems and methods for the generation of bio-based plasticizers from lignin from 4-hydroxybenzoic acid (H), vanillic acid (G) and syringic acid (S) obtained via oxidative depolymerization of lignin substrates. Chemical and electrochemical methods are described for catalytic reductive coupling of sulfonate derivatives of H, G and S to generate all possible homo- and cross-coupling products. Advantageously, the provided systems and methods allow for the generation of renewable plasticizers that exhibit performance advantages relative to established petroleum-based phthalate ester plasticizers.