Traditional lignin pyrolysis generates a bio-oil with a complex mixture of alkyl-functionalized guaiacol and syringol monomers that have limited utility to completely replace phenol in resins. In this work, formate assisted fast pyrolysis (FAsP) of lignin yielded a bio-oil consisting of alkylated phenol compounds, due to deoxyhydrogenation, that was used to synthesize phenol/formaldehyde resins. A solvent extraction method was developed to concentrate the phenolics in the extract to yield a phenol rich monomer mixture. Phenolic resins were synthesized using phenol (phenol resin), FAsP bio-oil (oil resin), and an extract mimic (mimic resin) that was prepared to resemble the extract after further purification. All three phenolic sources could synthesize novolac resins with reactive sites remaining for subsequent resin curing. Differential scanning calorimetry and thermogravimetric analysis of the three resins revealed similar thermal and decomposition behavior of phenol and the mimic resins, while the oil resin was less stable. Resins were cured with hexamethylenetetramine and the mimic resin demonstrated improved curing energies compared to the oil resin. The adhesive strength of the mimic resin was found to be superior to that of the oil resins. These results confirmed that extracting a mixture of substituted aromatics from FAsP bio-oil could synthesize resins with properties similar to those from phenol and improved over the parent bio-oil.

Building on previous work where 5-hydroxymethylfurfural (HMF) was selectively functionalized by etherification with phenols, we demonstrated that the oxidized versions of these HMF ethers can be converted to functionalized δ-hexalactones...