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Grafting of model primary amine compounds to cellulose nanowhiskers through periodate oxidation

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Abstract

This study demonstrates regioselective oxidation of cellulose nanowhiskers using 2.80–10.02 mmols of sodium periodate per 5 g of whiskers followed by grafting with methyl and butyl amines through a Schiff base reaction to obtain their amine derivatives in 80–90 % yield. We found a corresponding increase in carbonyl content (0.06–0.14 mmols/g) of the dialdehyde cellulose nanowhiskers with the increase in oxidant as measured by titrimetric analysis and this was further evidenced by FT-IR spectroscopy. Grafting of amine compounds to the oxidized cellulose nanowhiskers resulted in their amine derivatives, which are found to be partially soluble in DMSO. Therefore, the reduction reaction between amines and carbonyl groups was confirmed through 13C NMR spectra, which was also supported by copper titration, XPS, and FT-IR spectroscopy. Morphological integrity and crystallinity of the nanowhiskers was maintained after the chemical modification as studied by AFM and solid-state 13C NMR, respectively.

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Acknowledgments

The authors thank DOE (DE-EE0003144) for the support of this study.

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Authors and Affiliations

  1. School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA, 30332, USA

    Rajalaxmi Dash & Arthur J. Ragauskas

  2. USDA-Forest Service, Pineville, LA, 71360, USA

    Thomas Elder

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  1. Rajalaxmi Dash
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Correspondence to Arthur J. Ragauskas.

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Dash, R., Elder, T. & Ragauskas, A.J. Grafting of model primary amine compounds to cellulose nanowhiskers through periodate oxidation. Cellulose 19, 2069–2079 (2012). https://doi.org/10.1007/s10570-012-9769-2

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  • DOI: https://doi.org/10.1007/s10570-012-9769-2

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