A series of secondary amines were added to epichlorohydrin under different reaction conditions to synthesize a “ring-open” form chloro-hydroxy-diamine. This ring-open form will then be used in conjunction with lab synthesized azetidinium salts to chemically modify the hydroxide groups on the surface of nanocrystalline cellulose (CNC). The completion of reactions to the “ring-open” forms were verified using NMR techniques. Attachment of the chloro-hydroxy-diamine to the CNC with azetidinium salt was carried out in water. Classification of the success of this reaction was done with FTIR spectroscopy. Much of this study worked with the changing reaction conditions to produce the “ring-open” form. A primary series of tests were done under microwave conditions with Bismuth (III) nitrate pentahydrate. Verification of this reaction used Thin-layer chromatography and H<sup>1</sup>NMR spectroscopy. Formation of azetidinium salts were classified and later used in CNC reactions.  The same secondary amines were run through the same reaction under microwave conditions in and Ethanol solution. Classification of ring open form was found using COSY NMR and HSQC NMR spectroscopy. <br/>

Synthesis of secondary amines with epichlorohydrin for reaction with cellulose to improve hydrophobicity

2019 Spring National Meeting

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