Lignin, the second most abundant biopolymer on earth, is potentially a replaceable source for bulky fuels and chemical feedstocks. There have been numerous reports on methods for the oxidative cleavage of β-O-4 linkages but relatively few reports of how those methods affect other linkages that are present in lignin. We investigated how the β-1 and β-5 linkages respond under oxidative conditions proposed for lignin deconstruction based on their effect on β-O-4 linkages. Mechanochemical treatment of lignin can greatly improve the yield of monomer products and we applied a mechanochemical approach, using powerful ring-and-puck milling to promote lignin degradation. Along with similar production of monomers in a much shorter period than what we observed in previous ball-milling process, much more unexpected reactions were taking place during the current mechanochemical process. Lignin is a promising feedstock for epoxy resins since lignin-derived aromatic monomers usually bear hydroxyl and carboxyl groups. We are working on utilizing these mono-aromatic compounds and highly-functionalized-lignin as precursors for preparation of epoxy thermosets. We are interested in investigating the properties of thermosets by utilizing the actual isolated monomer streams from raw lignin. We expect to observe attractive thermal and mechanical properties from these lignin-derived epoxy thermosets compare to that of the commercialized but currently limited-used BPA-based epoxy resins.