I-Corps: Translation Potential of Green Synthesis of Imines and Imine-Related Compounds

The broader impact of this I-Corps project is the development of an environmentally-friendly and economically-compelling alternative chemical synthesis for imines and their derivatives. Imines are organic chemical intermediates with high-value commercial applications in pharmaceutical, agrochemical, and specialty chemical supply chains. This imine synthesis offers chemical manufacturers a solution that produces high-yield, high-purity imines at a fraction of the time, energy, and cost of traditional industry methods. This I-Corps project utilizes experiential learning coupled with a first-hand investigation of the industry ecosystem to assess the translation potential of the technology. This solution is based on the development of a novel green imine synthesis. The technology is an aqueous-based imine manufacturing process that replaces conventional toxic solvents with a renewable, biodegradable solvent that is Food and Drug Administration (FDA)-approved for use as a food additive. This solution allows for imine synthesis under ambient conditions and can be tuned with water as co-solvent to optimize polarity and induce rapid product formation within seconds to minutes. In contrast, conventional methods of imine synthesis often use petroleum-derived solvents that are flammable, explosive, and potentially harmful to workers and the environment, due to emission of fumes at the temperatures required. The new process has been validated to produce over 400 unique imines and dozens of related compound classes including oximes, azines, semicarbazones, pyrazoles, pyrazolones, quinoxalines, and quinoxalin-2(1H)-ones. The technology has also been validated at lab scale and is projected to scale to commercial manufacturing quantities. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.