With the depletion of petroleum, a new source of feedstock chemicals for polymers is needed. The new source should be a renewable source to avoid future depletion and environmental impact. A potential source of new feedstock chemicals is chitin. The use of ionic liquids for the dissolution of chitin has enabled new processing methods for this biopolymer. Recent results demonstrate that chitin can be depolymerizes in ionic liquid. The products of this depolymerization are N-acetylglucosamine and a furfural derivative. This research investigates the use of ionic liquids and various acid catalysts for the depolymerization of chitin into its monomer units. This research evaluates the effects of temperature, the nature of the catalyst, and solvent effects on the depolymerization of chitin.

Molecular clusters of BBr3 were subjected to electron ionization and mass analysis in a reflectron time-of-flight mass spectrometer. Five series of cluster ions were observed, with formulas corresponding to each of the possible fragment ions of BBr3 being solvated by neutral BBr3 molecules. Geometry optimizations on the observed cluster ions using density functional theory (B3LYP/6-31G*) predict that fragment ions smaller than BBr3+ undergo reactions with neutral BBr3 molecules to form covalently bound adduct species that function as core ions within the clusters. Once all boron atoms are saturated, the reactions cease, and larger cluster ions consist of BBr3 molecules loosely bound to the core ions. Divalent bromine atoms are present in at least three of the cluster ions, and most of the intermolecular contact within the clusters is between Br atoms. Enthalpies of formation, addition reactions, and BBr3 elimination from the cluster ions were derived from B3LYP and MP2 calculations at the B3LYP/6-31G* geometries using both the 6-31G* and the 6-311++G(2df,2p) basis sets. The results are compared to limiting expectations based on known bulk thermochemistry.

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