Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14740%2F20%3A00121454" target="_blank" >RIV/00216224:14740/20:00121454 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/70883521:28610/20:63526508

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0144861719311713?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0144861719311713?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.carbpol.2019.115503" target="_blank" >10.1016/j.carbpol.2019.115503</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides

Popis výsledku v původním jazyce

Oxidation of polysaccharides to 2,3-dicarboxypolysaccharides is a two-stage process, where selective oxidation by periodate is followed by secondary oxidation by chlorite. Addition of sulfamic acid before the secondary oxidation influences the molecular weight and degree of oxidation of the product. Here, mechanism of sulfamic acid-catalysed chain scission is elucidated for selectively oxidized cellulose and dextrin. Initially, sulfamic acid sulfonates the aldehyde groups of 2,3-dialdehydepolysaccharide. Introduced -SO3H groups are in ideal position to protonate the oxygen atom of 1-4' glycosidic bond and to trigger acidic hydrolysis. This can be used to obtain a direct control over the molecular weight of the product. Observed slightly lower degree of oxidation was ascribed to the ability of sulfamic acid to scavenge the hypochlorite and thus protect the intermolecular hemiacetals from oxidation. Usually undesirable hypochlorite thus seems to be necessary for preparation of selectively oxidized polysaccharides with degree of oxidation above 90%.

Název v anglickém jazyce

Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides

Popis výsledku anglicky

Oxidation of polysaccharides to 2,3-dicarboxypolysaccharides is a two-stage process, where selective oxidation by periodate is followed by secondary oxidation by chlorite. Addition of sulfamic acid before the secondary oxidation influences the molecular weight and degree of oxidation of the product. Here, mechanism of sulfamic acid-catalysed chain scission is elucidated for selectively oxidized cellulose and dextrin. Initially, sulfamic acid sulfonates the aldehyde groups of 2,3-dialdehydepolysaccharide. Introduced -SO3H groups are in ideal position to protonate the oxygen atom of 1-4' glycosidic bond and to trigger acidic hydrolysis. This can be used to obtain a direct control over the molecular weight of the product. Observed slightly lower degree of oxidation was ascribed to the ability of sulfamic acid to scavenge the hypochlorite and thus protect the intermolecular hemiacetals from oxidation. Usually undesirable hypochlorite thus seems to be necessary for preparation of selectively oxidized polysaccharides with degree of oxidation above 90%.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10400 - Chemical sciences

Projekt

—

Návaznosti

—

Rok uplatnění

2020

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Carbohydrate Polymers

ISSN

0144-8617

e-ISSN

—

Svazek periodika

229

Číslo periodika v rámci svazku

FEB

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

10

Strana od-do

115503

Kód UT WoS článku

000501796600076

EID výsledku v databázi Scopus

2-s2.0-85075346483