The conversion of cellulose to dialdehyde cellulose (DAC) by treatment with aqueous periodate was studied by the CCOA method, which is a combination of gel permeation chromatography and carbonyl-selective fluorescence labeling. The beta-alkoxy-elimination reaction under alkaline conditions was used as a diagnostic tool to address the regioselectivity of the oxidation at low degrees of conversion. The oxidation proceeded by random oxidant attack; cluster-like or isolated oxidation patterns were excluded. The beta-alkoxy-elimination proceeded as a competitive process during reduction of DAC by sodium borohydride. Reduction was thus inevitably accompanied by a significant loss in molecular weight. The borohydride treatment decompacted the molecules by reducing the aldehyde groups and destroying hemiacetal crosslinks. As a result, highly flexible chains were produced.
TY - JOUR
AU - Potthast, Antje
AU - Schiehser, Sonja
AU - Rosenau, Thomas
AU - Kostić, Mirjana
PY - 2009
UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1502
AB - The conversion of cellulose to dialdehyde cellulose (DAC) by treatment with aqueous periodate was studied by the CCOA method, which is a combination of gel permeation chromatography and carbonyl-selective fluorescence labeling. The beta-alkoxy-elimination reaction under alkaline conditions was used as a diagnostic tool to address the regioselectivity of the oxidation at low degrees of conversion. The oxidation proceeded by random oxidant attack; cluster-like or isolated oxidation patterns were excluded. The beta-alkoxy-elimination proceeded as a competitive process during reduction of DAC by sodium borohydride. Reduction was thus inevitably accompanied by a significant loss in molecular weight. The borohydride treatment decompacted the molecules by reducing the aldehyde groups and destroying hemiacetal crosslinks. As a result, highly flexible chains were produced.
PB - Walter de Gruyter & Co, Berlin
T2 - Holzforschung
T1 - Oxidative modifications of cellulose in the periodate system - Reduction and beta-elimination reactions
EP - 17
IS - 1
SP - 12
VL - 63
DO - 10.1515/HF.2009.108
ER -
@article{
author = "Potthast, Antje and Schiehser, Sonja and Rosenau, Thomas and Kostić, Mirjana",
year = "2009",
abstract = "The conversion of cellulose to dialdehyde cellulose (DAC) by treatment with aqueous periodate was studied by the CCOA method, which is a combination of gel permeation chromatography and carbonyl-selective fluorescence labeling. The beta-alkoxy-elimination reaction under alkaline conditions was used as a diagnostic tool to address the regioselectivity of the oxidation at low degrees of conversion. The oxidation proceeded by random oxidant attack; cluster-like or isolated oxidation patterns were excluded. The beta-alkoxy-elimination proceeded as a competitive process during reduction of DAC by sodium borohydride. Reduction was thus inevitably accompanied by a significant loss in molecular weight. The borohydride treatment decompacted the molecules by reducing the aldehyde groups and destroying hemiacetal crosslinks. As a result, highly flexible chains were produced.",
publisher = "Walter de Gruyter & Co, Berlin",
journal = "Holzforschung",
title = "Oxidative modifications of cellulose in the periodate system - Reduction and beta-elimination reactions",
pages = "17-12",
number = "1",
volume = "63",
doi = "10.1515/HF.2009.108"
}
Potthast, A., Schiehser, S., Rosenau, T.,& Kostić, M.. (2009). Oxidative modifications of cellulose in the periodate system - Reduction and beta-elimination reactions. in Holzforschung
Walter de Gruyter & Co, Berlin., 63(1), 12-17.
https://doi.org/10.1515/HF.2009.108
Potthast A, Schiehser S, Rosenau T, Kostić M. Oxidative modifications of cellulose in the periodate system - Reduction and beta-elimination reactions. in Holzforschung. 2009;63(1):12-17.
doi:10.1515/HF.2009.108 .
Potthast, Antje, Schiehser, Sonja, Rosenau, Thomas, Kostić, Mirjana, "Oxidative modifications of cellulose in the periodate system - Reduction and beta-elimination reactions" in Holzforschung, 63, no. 1 (2009):12-17,
https://doi.org/10.1515/HF.2009.108 . .
