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The Schiff base was synthesized by simultaneous reaction of chitosan a natural polyaminosaccharide with formaldehyde and benzaldehyde. The two imine groups formed were then reduced with NaBH4 to give the corresponding tertiary amine derivative. The reaction mechanism and structure of imine intermediate were identified using some spectroscopic methods. The structure, crystallinity degree and molecular electron spectrum of the main product has been characterized by XRD, UV-Vis and 1H, 13C NMR analyses. It was observed that, N-benzyl N-methyl chitosan has 14-17% more crystallinity than chitosan. Inclusion of hydrophobic methyl and benzyl groups into chitosan macromolecule cause reduction in an intermolecular interaction and hydrogen bonding. This leads to an increase in the polarization degree of the product functional groups in a polar environment and better solubility.

oriental journal of chemistry/oriental journal of chemistry

Synthesis of N-Benzyl N-Methyl chitosan by Simultaneous Alkylation of Formaldehyde and Benzaldehyde: Investigation of Chemical Structure and Composition