Highly efficient liquid-phase oxidation of primary alcohols to aldehydes with oxygen catalysed by Ru–Co oxide

Musawir, Mehdi; Davey, Paul N.; Kelly, Gordon; Kozhevnikov, Ivan V.

doi:10.1039/b212585b

Cited by 118 publications

(63 citation statements)

References 18 publications

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“…In addition, from a series of different bases, including LiOH, NaOH, KOH, Ca(OH) 2 , Ba(OH) 2 and t-BuOK, NaOH turned out to be the most efficient. Due to the fact that the CuSO 4 /phen/TEMPO/NaOH combination provides high activity and selectivity, and because it is a halogen-free system, it was chosen for further studies.…”

Section: Resultsmentioning

confidence: 96%

“…Apparently, the most effective system is achieved with rather high pH (12)(13)(14) and with a 1:1 ligand/ metal ratio. Interestingly, for the CuA C H T U N G T R E N N U N G (phen) n systems without TEMPO the optimised ligand to metal ratio was 2:1, which leads to pentacoordinated Cu(II) complexes of the type CuA C H T U N G T R E N N U N G (phen)(OH) 2 .…”

Section: Resultsmentioning

confidence: 98%

“…[1] Selective oxidation of benzylic alcohols to aldehydes is a particularly useful chemical transformation, as these aldehydes are important intermediates in the synthesis of other organic compounds, ranging from pharmaceuticals to plastic additives as well as in the processing of perfume and flavouring compounds and in the preparation of certain aniline dyes in the textile industry. [2] Many stoichiometric oxidants are known for the oxidation of alcohols such as chromates, hypochlorite, permanganates, and others, [3] however their main disadvantage is that most of them are toxic and produce large amounts of waste. In this respect, non-waste-producing oxidants such as air, dioxygen or hydrogen peroxide, provide a base for more enviromentally friendly and relatively cheap systems but activation of these oxidants with catalysts is needed.…”

Section: Introductionmentioning

confidence: 99%

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TEMPO‐Copper(II) Diimine‐Catalysed Oxidation of Benzylic Alcohols in Aqueous Media

2007

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In situ generated copper(II)-diimine complexes combined with TEMPO (2,2,6,6-tetramethylpiperidinyl-1-oxyl radical) were studied in the oxidation of benzylic alcohols, the focus being on enviromentally benign reaction conditions. In this respect, reactions were studied in aqueous alkaline solutions and dioxygen was used as an end oxidant. This simple catalytic system turned out to be highly efficient and selective in the oxidation of primary and secondary benzylic alcohols to their corresponding carbonyl compounds. Under optimised reaction conditions [5 mol % of TEMPO, 3 mol % of copper (II) diimine, pH 12.6-13.5, 80 8C, 10 bar O 2 ] benzyl alcohol was quantitatively and selectively oxidised to benzaldehyde. According to ESI-MS studies, coordination of TEMPO, as well as deprotonated benzyl alcohol to the parent copper-diimine complex in aqueous solutions is feasible. Supported by these observations a plausible reaction mechanism is proposed for the oxidation reaction.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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TEMPO‐Copper(II) Diimine‐Catalysed Oxidation of Benzylic Alcohols in Aqueous Media

2007

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“…A considerable effort was devoted to develop bicomponent and multi Ru-containing oxide catalysts, such as Ru − Co-oxide [156], Ru − Co − Ce-oxide [157], and Ru − Mn − Fe − Cu-oxides [158,159]. On the basis of the TOF values, none of these was more active than hydrated ruthenium oxide, but there were significant differences in selectivities and in the synthetic potential of the mixed oxides.…”

Section: Zeolitesmentioning

confidence: 99%

Oxidation of Alcohols with Molecular Oxygen

Mallát

Baiker

2008

Handbook of Heterogeneous Catalysis

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The sections in this article are Introduction Oxidation in the Gas Phase Metals Oxides Phosphates Zeolites Oxidation in the Liquid Phase Platinum‐Group Metals Gold Oxides Molecular Sieves Hydrotalcites Phosphates and Apatites Heterogenized Metal Complexes Summary

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“…Figure 5 shows the Raman spectrum of graphene oxide (GO), ZnO x (1%)-MnCO 3 , and ZnO x (1%)-MnCO 3 /(1%)HRG. Raman spectra of ZnO x (1%)-MnCO 3 , and ZnO x (1%)-MnCO 3 /(1%)HRG nanocomposites exhibited two distinct peaks at 724 and 1086 cm −1 which are a finger-print for MnCO 3 . This indicates the existence of MnCO 3 in the nanocomposite consistent with XRD analysis as displayed in Figure 5b,c [86].…”

Section: Scanning Electron Microscopy (Sem) and Elemental Analysis (Edx)mentioning

confidence: 99%

Mixed Zinc/Manganese on Highly Reduced Graphene Oxide: A Highly Active Nanocomposite Catalyst for Aerial Oxidation of Benzylic Alcohols

et al. 2017

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Nanocomposites of highly reduced graphene oxide (HRG) and ZnO x nanoparticles doped manganese carbonate containing different percentages of HRG were prepared via a facile co-precipitation method.The prepared sample calcined at 300 • C yielded i.e., ZnO x (1%)-MnCO 3 /(X%)HRG (where X = 0-7), calcination at 400 • C and 500 • C, yielded different manganese oxides i.e., ZnO x (1%)-MnO 2 /(X%)HRG and ZnO x (1%)-Mn 2 O 3 /(X%)HRG respectively. The prepared catalyst were subjected to catalytic evaluation and a comparative catalytic study between carbonates and oxides for the liquid-phase aerobic oxidation of benzylic alcohols to corresponding aldehydes using molecular oxygen as an eco-friendly oxidant without adding additives or bases. The influence of various parameters such as percentage of HRG, reaction time, catalyst amount, calcination and reaction temperature was systematically examined to optimize reaction conditions using oxidation of benzyl alcohol as a substrate model. It was found that the catalytic performance is remarkably enhanced after using HRG as catalyst co-dopant for the aerobic oxidation of alcohols, possibly owing to the presence of carbon defects and oxygenated functional groups on HRG surface. The as-synthesized catalysts were characterized by SEM, EDX, XRD, Raman, TGA, BET, and FT-IR. Under optimal conditions, the catalyst with composition ZnO x (1%)-MnCO 3 /(1%)HRG calcined at 300 • C exhibited remarkable specific activity (57.1 mmol·g −1 ·h −1 ) with 100% conversion of benzyl alcohol and more than 99% product selectivity within extremely short time (7 min). The as-prepared catalyst was re-used up to five consecutive times without significant decrease in its activity and selectivity. To the best of our knowledge, the achieved specific activity is the highest so far compared to the earlier reported catalysts used for the benzyl alcohol oxidation. A wide range of substituted benzylic and aliphatic alcohols were selectively oxidized into their corresponding aldehydes with complete convertibility and selectivity in short reaction times without over-oxidation to the acids. Due to their significant low cost, superior reproducibility, excellent catalytic efficiency, the ZnO x (1%)-MnCO 3 /(X%)HRG nanocomposites possess several application prospect in other organic chemistry reactions.

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Highly efficient liquid-phase oxidation of primary alcohols to aldehydes with oxygen catalysed by Ru–Co oxide

Abstract: RuIV-CoIII (1:1.5) binary oxide, prepared by co-precipitation, is a highly efficient solid catalyst for the oxidation of primary alcohols to aldehydes with O2 (76-95% selectivity at 54-100% conversion) in a liquid phase under atmospheric pressure.

Cited by 118 publications

References 18 publications

TEMPO‐Copper(II) Diimine‐Catalysed Oxidation of Benzylic Alcohols in Aqueous Media

TEMPO‐Copper(II) Diimine‐Catalysed Oxidation of Benzylic Alcohols in Aqueous Media

Oxidation of Alcohols with Molecular Oxygen

Mixed Zinc/Manganese on Highly Reduced Graphene Oxide: A Highly Active Nanocomposite Catalyst for Aerial Oxidation of Benzylic Alcohols

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