Oxidative modifications of cellulose in the periodate system - Reduction and beta-elimination reactions
Само за регистроване кориснике
2009
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
beta-elimination / cellulose / dialdehyde cellulose (DAC) / gel permeation chromatography / oxidation / periodate / reductionИзвор:
Holzforschung, 2009, 63, 1, 12-17Издавач:
- Walter de Gruyter & Co, Berlin
DOI: 10.1515/HF.2009.108
ISSN: 0018-3830
WoS: 000263247700003
Scopus: 2-s2.0-58149096826
Институција/група
Tehnološko-metalurški fakultetTY - 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 . .