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Preparation of amidated derivatives of monocarboxy cellulose

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Abstract

Amidated derivatives of monocarboxy cellulose (MCC), the product of cellulose oxidation, containing carboxyl groups only at C-6 position, were prepared and characterised. Two-step way of amidation was based on the esterification of C-6 carboxyls in MCC by reaction with methanol at 60 °C for 72 h and further amino-de-alkoxylation (aminolysis) of the obtained methyl ester with n-alkylamines, hydrazine and hydroxylamine in the N,N-dimethylformamide medium. Purity and substitution degree of the products were monitored by vibration spectroscopic methods (FTIR and FT Raman) and organic elemental analysis. Analytical methods confirmed the preparation of highly or moderately substituted N-alkylamides, hydrazide and hydroxamic acid of MCC.

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Abbreviations

DA:

Degree of amidation

DM:

Degree of methylation

DMF:

N,N-Dimethylformamide

DO:

Degree of C-6 oxidation

FT:

Fourier-transform

FTIR:

Fourier-transform infrared spectroscopy

MCC:

Monocarboxy cellulose

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Acknowledgments

This work was supported by the Ministry of Industry and Trade (project No 2A-1TP1/041), Ministry of Education, Youth and Sport (project No CEZ MSM 6046137305), Czech Science Foundation (project No 503/11/2479) and IGA (project No A1_FPBT_2013_010, A2_FPBT_2013_004, financial support from specific university research MSMT No 20/2013).

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Authors and Affiliations

  1. Department of Carbohydrates and Cereals, ICT Prague, Technická 1905, 166 28, Prague 6, Czech Republic

    Tomáš Taubner, Jana Čopíková & Andriy Synytsya

  2. VUOS a.s., Rybitví 296, 533 54, Pardubice-Rybitví, Czech Republic

    Pavel Havelka

Authors
  1. Tomáš Taubner
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  2. Jana Čopíková
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  3. Pavel Havelka
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  4. Andriy Synytsya
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Correspondence to Tomáš Taubner.

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Taubner, T., Čopíková, J., Havelka, P. et al. Preparation of amidated derivatives of monocarboxy cellulose. Cellulose 20, 2045–2055 (2013). https://doi.org/10.1007/s10570-013-9938-y

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  • DOI: https://doi.org/10.1007/s10570-013-9938-y

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