Over five million metric tons of bisphenol A (BPA) are produced annually for the synthesis of plastics such as epoxy resins vinyl ester resins and polycarbonates. BPA is a known endocrine disruptor and can cause adverse health effects at doses lower than the safety exposure limit of 50 µg/kg body weight/day. This invention describes a process to synthesize renewable BPA alternatives and novel polymer systems derived from substituted phenolic compounds. These BPA alternatives can be derived from renewable resources such as those obtained from lignin and are designed to reduce endocrine disruption relative to BPA. The substituted phenols derived from lignin via fast pyrolysis include vanillin vanillyl alcohol creosol guaiacol and cresol. Bisguaiacol compounds are synthesized through the reaction of vanillyl alcohol with other substituted phenols using a solid acid catalyst in a biphasic system. The feed composition can be varied to provide control over the production of isomers. Pure bisguaiacol components are recovered by extraction and recrystallization from hexanes. An example of synthesizing bisguaiacol F (BGF) from vanillyl alcohol and guaiacol is shown in the figure below. Applications: BPA is used in the synthesis and manufacturing of epoxy coatings and resins vinyl ester resins polycarbonates and aromatic polyether and polyesters.
1) Cost effective alternative. 2) Synthesized from renewable resources such as lignin a renewable waste stream from the paper and pulping industry. 3) Reduced endocrine effects while maintaining similar thermo mechanical properties imparted by BPA in thermoplastic and thermoset applications. 4) Substantially reduced environmental and human health impact.