(632d) Bio-Based Amines Production Via Selective Deoxygenation of N-Containing Biomass

Today, industrial amines are synthesized from ammonia, which is produced on a large scale by the highly energy-intensive Haber-Bosch process. In contrast, the production of bio-based amines from the abundant N-containing bio-based feedstock is attractive and can save a lot of energy. Two types of biobased amines sources could be highlighted; the first one is proteins or amino acids, and the second one has functions with nitrogen, such as chitin. Lysine is the second most-produced amino acid in industry, next to glutamic acid. Lysine has two amino groups and one carboxylic group. Hence, to maximize the production yield of diamine from lysine, the oxygen in lysine must be removed, while two amino groups being kept intact. Bio-based diamines, such as pentamethylene diamine (cadaverine), are the key building block monomers to synthesize bio-based polyamides, such as Nylon 5.6, 5.10, etc. While cellulose is the most abundant polysaccharide in nature, chitin is the second most abundant and a major component of the exoskeletons of insects and crustaceans. As one of three main components in those shells, chitin is a polymer of the amino sugar N-acetylglucosamine (NAG). Besides protein or its derivatives, chitin is the most important organic substance having amino groups on their polysaccharide backbones. Utilization of the ocean fixed nitrogen made a greener production of N-containing chemicals since industrial ammonia/amines synthesis is energy-intensive and consumes more than 1% of the total energy generated in the world. Through the selective deoxygenation of chitin monomers/L-lysine over Ru/C in acidic solutions, bio-based amines/diamines were obtained respectively in one-pot reactions, in which the critical step is to protect the amino group against deamination.