The Selective Oxidation Of Methyl-alpha;-D-Glucoside On A Carbon Supported Pt Catalyst

Schuurman, Y.; Kuster, B.F.M.; Wiele, K. van der; Marin, Guy

doi:10.1016/s0167-2991(08)61657-2

Cited by 13 publications

(4 citation statements)

References 16 publications

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“…2,2,6,6-Tetramethyl-1-piperidinyloxyl (TEMPO) and related compounds can be used in conjunction with sodium hypobromite, , sodium hypochlorite, − or a peracid , to obtain uronic acid derivatives. Alternatively, primary OH groups can be oxidized to carboxylic acids in the presence of platinum(0) on carbon or Al 2 O 3 under an oxygen atmosphere, − or by employment of a rhodium(I) complex …”

Section: Oxidationmentioning

confidence: 99%

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

2018

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Methods for site-selective transformations of hydroxyl groups in carbohydrate derivatives are reviewed. The construction of oligosaccharides of defined connectivity hinges on such transformations, which are also needed for the preparation of modified or non-natural sugar derivatives, the installation of naturally occurring postglycosylation modifications, the selective labeling or conjugation of carbohydrate derivatives, and the preparation of therapeutic agents or research tools for glycobiology. The review begins with a discussion of intrinsic factors and processes that can influence selectivity in reactions of unprotected or partially protected carbohydrate derivatives, followed by a description of transformations that engage two OH groups in cyclic adducts (acetals, ketals, boronic esters, and related species). An overview of the various classes of site-selective transformations of OH groups in sugars is then provided: the reactions discussed include esterification, thiocarbonylation, alkylation, glycosylation, arylation, silylation, phosphorylation, sulfonylation, sulfation, and oxidation. Emphasis is placed on recently developed methods that employ reagent or catalyst control to achieve otherwise challenging transformations or site-selectivities.

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Section: Oxidationmentioning

confidence: 99%

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

2018

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“…The reactor is operated at a maximum MGP conversion of 10% because, at this conversion, the selectivity toward NaMG is about 95%. At higher conversions, the production of MGP suffers from the formation of side products resulting from the oxidation of secondary alcoholic groups and from the rupture of C−C bonds . The liquid feed stream contains 1000 mol m -3 of MGP.…”

Section: Reactor Design Considerationsmentioning

confidence: 99%

Design of an Industrial-Size Airlift Loop Redox Cycle (ALRC) Reactor for Catalytic Alcohol Oxidation and Catalyst Reactivation

Kluytmans

Wachem

Kuster

et al. 2003

Ind. Eng. Chem. Res.

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An industrial-size airlift loop redox cycle (ALRC) reactor has been designed for the selective oxidation of alcohols. Selective catalytic alcohol oxidation can produce valuable products for fine chemistry applications. However, the catalyst undergoes a factor of 10 loss in activity within hours as a result of overoxidation. The catalyst can be reactivated by contacting it with a reducing environment. This modeling and reactor design study shows that the ALRC reactor is a suitable option for achieving alternating contact of the catalyst with a reducing and oxidizing environment. It is shown that the superficial slurry velocity and the inlet partial pressure of oxygen mainly determine the reactor performance. A reactor design is developed on the basis of kinetic, hydrodynamic, and economic considerations, in which the catalyst activity remains high during its presence in the reactor. Finally, the ALRC reactor is compared with a stirred-tank reactor process involving alternating gas feed streams. It is shown that the ALRC reactor is much cheaper in terms of reactor operation than the stirred-tank reactor process and, thus, this type of reactor can feasibly be used in the selective oxidation of alcohols while maintaining a high catalyst activity.

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“…The exact process by which the aldehyde forms is not known. Under basic conditions, it has been proposed that the alcohol becomes deprotonated in solution and undergoes hydride elimination on the catalyst surface to form the aldehyde. , This hypothesis has been disputed on the basis of the observation that oxidation also occurs under acidic conditions, and it has been proposed instead that the alkoxide is formed on the catalyst surface. , Other authors have suggested that it is the C–H bond that is broken first because of its lower bond strength. , …”

Section: Introductionmentioning

confidence: 99%

Mechanistic Insights into Solution-Phase Oxidative Esterification of Primary Alcohols on Pd(111) from First-Principles Microkinetic Modeling

2017

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We present an ab initio microkinetic model for the oxidative esterification of 1-propanol to methyl propionate over Pd(111). The model fully accounts for solvation of solution-phase species and added catalytic base and provides key insights into the factors that limit the activity of unpromoted Pd aerobic oxidation catalysts. In particular, we find that the activity is limited by the large steady-state surface H coverage, which destabilizes other adsorbed intermediates via lateral interactions, and substantial barriers governing the formation of O−H bonds, which is required for the reduction of O 2 and removal of H byproducts from the catalyst surface.

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The Selective Oxidation Of Methyl-alpha;-D-Glucoside On A Carbon Supported Pt Catalyst

Cited by 13 publications

References 16 publications

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives

Design of an Industrial-Size Airlift Loop Redox Cycle (ALRC) Reactor for Catalytic Alcohol Oxidation and Catalyst Reactivation

Mechanistic Insights into Solution-Phase Oxidative Esterification of Primary Alcohols on Pd(111) from First-Principles Microkinetic Modeling

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