Green and low cost synthesis of 3,3',5,5'-azobenzene tetracarboxylic acid

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A rapid increase in natural gas production due to advances in exploitation technologies, such as horizontal drilling and hydraulic fracturing, and its lower emission values for CO, CO2, and NOx make natural gas an economically valid alternative to gasoline. However, the widespread use in light-duty passenger vehicles and small motorized tools and toys is hampered by the low volumetric energy density of natural gas at ambient temperature and pressure (0.04 MJ/L in comparison to 32.4 MJ/L for gasoline). Tanks filled with adsorbents are most promising for a storage and release of natural gas at moderate pressures (35-65 bar) and ambient temperatures. Alternative Fuel Containers, LLC (AFC) is in the process of developing adsorbent filled natural gas tanks for light-duty passenger vehicles, which involves several collaborations with industrial and academic partners to tackle the numerous technical challenges. Objective of this Engage project is the development of a green, low cost, and scalable synthesis of the organic ligand 3,3',5,5'-azobenzene tetracarboxylic acid, which is the organic building block for the metal-organic framework AFC wants to use as adsorbing material in their new generation of natural gas tanks.