(703d) Production of Neo Acids from Biomass-Derived Monomers

Neo acids are highly branched carboxylic acids currently produced from fossil fuels. The high steric hindrance due to their structure imparts excellent thermal and hydrolytic stability, and resistance to chemicals and oxidative compounds. Depending on the chemistry applied to the carboxylic functional group, derivatives with diverse applications can be obtained. Neo acids are commercially manufactured from petroleum-derived olefins (isobutene and mixed nonenes) through the Koch synthesis, such as neopentanoic acid and neodecanoic acid (ExxonMobil) and versatic acid (Hexion). However, the process involves harsh reaction conditions, such as high temperatures and pressures and strong acids, and toxic substances, which cause environmental concerns. Additionally, multi-step purifications are needed to separate dimeric and trimeric isobutene by-products. Thus, there remains a need for sustainable and environmentally friendly alternatives to produce neo acids from renewable resources, such as biomass. In this work, we produce renewable neo acids from lignocellulosic biomass-derived furan via C-C coupling through hydroxyalkylation/alkylation (HAA), followed by ring-opening of furans through hydrodeoxygenation (HDO). Catalyst screening and multi-parameter optimization using machine learning optimize the yield and elucidate the correlation between variables and outcomes. We demonstrate selective furan ring-opening without affecting the carboxylic acid to make neo acids.