Debugging periodate oxidation of cellulose: Why following the common protocol of quenching excess periodate with glycol is a bad idea

Simon, Jonas; Fliri, Lukas; Drexler, Felix; Bacher, Markus; Sapkota, Janak; Ristolainen, Matti; Hummel, Michael; Potthast, Antje; Rosenau, Thomas

doi:10.1016/j.carbpol.2023.120691

Cited by 16 publications

(2 citation statements)

References 81 publications

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“…Periodate oxidation of softwood kraft pulp was performed according to our previously reported protocol. [47] Briefly, disintegrated softwood kraft pulp was added to deionized water and sodium periodate. The reaction mixture was stirred in the dark to limit photochemical side reactions.…”

Section: Synthesis Of Dialdehyde Cellulosementioning

confidence: 99%

Towards Tailored Dialdehyde Cellulose Derivatives: A Strategy for Tuning the Glass Transition Temperature

Simon,

Schlapp‐Hackl,

Sapkota

et al. 2023

ChemSusChem

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The derivatization of dialdehyde cellulose (DAC) has received increasing attention in the development of sustainable thermoplastics. In this study, a series of dialcohol celluloses were generated by borohydride reduction, which exhibited glass transition temperature (Tg) values ranging from 23 to 109 °C, depending on the initial degree of oxidation (DO) of the DAC intermediate. However, the DAC derivatives did not exhibit thermoplastic behavior when the DO of the modified DAC was below 26 %. The influence of introduced side chains was highlighted by comparing DAC‐based thermoplastic materials obtained by either oximation or borohydride reduction. Our results provide insights into the generation of DAC‐based thermoplastics and highlight a strategy for tailoring the Tg by adjusting the DO during the periodate oxidation step and selecting appropriate substituents in subsequent modifications.

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Section: Synthesis Of Dialdehyde Cellulosementioning

confidence: 99%

Towards Tailored Dialdehyde Cellulose Derivatives: A Strategy for Tuning the Glass Transition Temperature

Simon,

Schlapp‐Hackl,

Sapkota

et al. 2023

ChemSusChem

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“…This selective oxidation agent cleaves the carbon--carbon bond at C2-C3, resulting in the formal generation of two aldehyde groups per anhydroglucose unit, leading to the formation of 2,3-dialdehyde cellulose (DAC) [3]. An important piece of information is that the aldehyde functionalities appear only to a small extent in the free aldehyde form, while most of them are predominantly hydrated or crosslinked to form hemialdals and hemiacetals, both intra-and intermolecularly [4].…”

Section: Introductionmentioning

confidence: 99%

A step towards tuning the jute fiber structure and properties by employing sodium periodate oxidation and coating with alginate

Ivanovska,

Milošević,

Lađarević

et al. 2024

International Journal of Biological Macromolecules

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β-Elimination as major side reaction in periodate-oxidation of cellulosic model mono- and disaccharides

Sasaki,

Kosma

2023

Monatsh Chem

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To structurally characterize periodate-oxidized cellulosic substrates, methyl 4-O-methyl β-d-glucopyranoside and methyl 4’-O-methyl-cellobioside were subjected to periodate treatment at pH 4.8–5.0. Oxidation of the monosaccharide using two molar equivalents of oxidant produced 3-methoxy-2,5-dihydro-2-furanol as main product. To confirm its structure and mode of formation, 6-O-bisdeuteromethyl 4-O-methyl-β-d-glucopyranoside and methyl 4-O-trisdeuteromethyl-β-d-glucopyranoside were synthesized and oxidized to generate 3-methoxy-5-deutero-2-hydro-2-furanol in the former case and 3-trisdeuteromethoxy-2,5-dihydro-2-furanol in the latter case. Oxidation using one molar equivalent of periodate led to preferential formation of hemialdal products and (E)-4-hydroxy-2-methoxy-2-butenal. The latter product was also formed upon end-wise oxidation of methyl 4’-O-methyl-cellobioside, wherein the reducing unit was released as non-oxidized methyl β-d-glucopyranoside. This data indicate that periodate oxidation of cellulosic model substrates might be accompanied by peeling reactions and formation of β-elimination products even under slightly acidic conditions. Graphical abstract

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Debugging periodate oxidation of cellulose: Why following the common protocol of quenching excess periodate with glycol is a bad idea

Cited by 16 publications

References 81 publications

Towards Tailored Dialdehyde Cellulose Derivatives: A Strategy for Tuning the Glass Transition Temperature

Towards Tailored Dialdehyde Cellulose Derivatives: A Strategy for Tuning the Glass Transition Temperature

A step towards tuning the jute fiber structure and properties by employing sodium periodate oxidation and coating with alginate

β-Elimination as major side reaction in periodate-oxidation of cellulosic model mono- and disaccharides

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