TEMPO mediated oxidation of carbohydrates using electrochemical methods

Parpot, Píer; Servat, Karine; Bettencourt, Ana Paula; Huser, Hervé; Kokoh, K. Boniface

doi:10.1007/s10570-010-9417-7

Cited by 30 publications

(34 citation statements)

References 13 publications

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“…This means that the electrode materials play two crucial roles: electron conductor (electrochemistry) and catalyst (catalysis). We mostly focus on examples from our groups while other examples of electrosynthesis can be found in literature ,,,,,,…”

Section: Electrochemistry At Work In Organics Synthesissupporting

confidence: 83%

Advances in Electrocatalysis for Energy Conversion and Synthesis of Organic Molecules

et al. 2017

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Ubiquitous electrochemistry is expected to play a major role for reliable energy supply as well as for production of sustainable fuels and chemicals. The fundamental understanding of organics‐based electrocatalysis in alkaline media at the solid–liquid interface involves complex mechanisms and performance descriptors (from the electrolyte and reaction intermediates), which undermine the roads towards advance and breakthroughs. Here, we review and diagnose recently designed strategies for the electrochemical conversion of organics into electricity and/or higher‐value chemicals. To tune the mysterious workings of nanocatalysts in electrochemical devices, we examine the guiding principles by which the performance of a particular electrode material is governed, thus highlighting various tactics for the development of synthesis methods for nanomaterials with specific properties. We end by examining the production of chemicals by using electrochemical methods, from selective oxidation to reduction reactions. The intricate relationship between electrode and selectivity encourages both of the communities of electrocatalysis and organic synthesis to move forward together toward the renaissance of electrosynthesis methods.

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Section: Electrochemistry At Work In Organics Synthesissupporting

confidence: 83%

Advances in Electrocatalysis for Energy Conversion and Synthesis of Organic Molecules

et al. 2017

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“…TEMPO electro-mediated reactions were reported as green chemical processes for selective oxidation of primary hydroxyls of carbohydrates (Schnatbaum and Schäfer 1999;Belgsir and Schäfer 2001;Liaigre et al 2005;Parpot et al 2010;Isogai et al 2010a). When mono-, di-and tri-saccharides were oxidised by electro-mediated reactions with a TEMPO catalyst in carbonate buffers at pH 10, the corresponding C6-carboxylate compounds were obtained in the yields of 22-99% (Schnatbaum and Schäfer 1999;Belgsir and Schäfer 2001;Liaigre et al 2005;Parpot et al 2010). Seventy four and 63% of the C6-primary hydroxyls of b-cyclodextrin and potato stach, respectively, were converted to C6-carboxyl groups by the TEMPO electro-mediated oxidation at pH 10 (Schnatbaum and Schäfer 1999).…”

Section: Introductionmentioning

confidence: 99%

“…Seventy four and 63% of the C6-primary hydroxyls of b-cyclodextrin and potato stach, respectively, were converted to C6-carboxyl groups by the TEMPO electro-mediated oxidation at pH 10 (Schnatbaum and Schäfer 1999). When a mercerized microcrystalline cellulose was oxidized under the above conditions, water-soluble cellouronic acid was obtained (Parpot et al 2010). On the other hand, when curdlan and amylodextrin were oxidized by electro-mediated reaction with 4-acetamido-TEMPO in a buffer at pH 6.8, their C6-primary hydroxyls were mostly converted to C6-carboxyls and molecuar weights of the oxidized products were sufficiently high (Isogai et al 2010a).…”

Section: Introductionmentioning

confidence: 99%

Wood cellulose nanofibrils prepared by TEMPO electro-mediated oxidation

2010

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A softwood bleached kraft pulp (SBKP) was subjected to electro-mediated oxidation in water with TEMPO or 4-acetamido-TEMPO without any chlorine-containing oxidant. Solid recovery ratios of water-insoluble fractions of the oxidized SBKPs were more than 80%, and C6-carboxylate contents increased up to approximately 1 mmol g -1 after oxidation for 48 h. Significant amounts of C6-aldehyde groups (0.17-0.38 mmol g -1 ) were also formed in the oxidized SBKPs. The degree of polymerization decreased from 2,200 to 520 and 1,400 by the oxidation for 48 h with TEMPO at pH 10 and 4-acetamido-TEMPO at pH 6.8, respectively. The original cellulose I crystal structure and crystallinity of SBKP were maintained after the oxidation, indicating that all C6-oxidized groups were selectively formed on crystalline cellulose microfibril surfaces. The oxidized SBKPs with carboxylate contents of more than 0.9 mmol g -1 were convertible to individual cellulose nanofibrils in yields of more than 80% by disintegration in water.

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“…Several other TEMPO‐mediated protocols were also proposed by different research groups, including those using enzymes (lacasse), or even TEMPO‐electromediated oxidation in order to avoid halide‐based activation of the catalyst …”

Section: Resultsmentioning

confidence: 99%

“…[26,29] Several other TEMPO-mediated protocols were also proposed by different research groups, including those using enzymes (lacasse), [30,31] or even TEMPO-electromediated oxidation in order to avoid halide-based activation of the catalyst. [32,33] The purified carboxylated polysaccharides were subsequently used to obtain nanocomposite particles consisting of Figure 2. The difference consists mainly in the agglomeration of the nanoparticles; the particles seem to be interconnected by the organic shell.…”

Section: Resultsmentioning

confidence: 99%

Carboxylated Polysaccharides Decorated with Ultrasmall Magnetic Nanoparticles with Antibacterial and MRI Properties

Biliuță

Săcărescu

Socoliuc

et al. 2017

Macro Chemistry & Physics

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Two natural polymers, namely, cellulose and pullulan, are selectively oxidized employing the well‐established (2,2,6,6‐tetramethylpiperidine‐1‐yl)‐oxyl radical protocol in order to introduce in their structural unit negatively charged carboxylic groups. These newly introduced moieties further serve as efficient matrix for the in situ iron oxide nanoparticles fabrication. The morphology, structure, stability, and magnetic properties of the as‐prepared carboxylated polysaccharides embedded ultrasmall iron oxide nanoparticles are analyzed using various techniques, such as Fourier transform infrared spectroscopy, dynamic light scattering, zeta potential, transmission electron microscopy, energy dispersive X‐ray spectroscopy, thermogravimetric analyses, and vibrating sample magnetometer. The results show that the two used polysaccharides are excellent materials to produce highly uniform shaped nanoparticles with an average size of about 3 nm. Moreover, the nanoparticles have excellent water dispersibility and stability. The prepared magnetic samples show antibacterial effect against Gram‐positive bacteria and also exhibit characteristics as contrasting agent for noninvasive cellular and molecular imaging.

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TEMPO mediated oxidation of carbohydrates using electrochemical methods

Cited by 30 publications

References 13 publications

Advances in Electrocatalysis for Energy Conversion and Synthesis of Organic Molecules

Advances in Electrocatalysis for Energy Conversion and Synthesis of Organic Molecules

Wood cellulose nanofibrils prepared by TEMPO electro-mediated oxidation

Carboxylated Polysaccharides Decorated with Ultrasmall Magnetic Nanoparticles with Antibacterial and MRI Properties

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