Nitrobenzene-assisted reduction of phenylacetylene with hydrazine over nitrogen-doped metal-free activated carbon catalyst: Significance of interactions among substrates and catalyst

Fujita, Shin‐ichiro; Asano, Sayaka; Arai, Masahiko

doi:10.1016/j.molcata.2016.06.022

Cited by 12 publications

(12 citation statements)

References 15 publications

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“…The enhancement in the selectivity is explained by interactions between the modifiers and the substrates on the surface of supported Pt particles, similar to our case in which interactions between CAL and a product of HCAL on the surface of PdZn catalyst are responsible for the increase in the COL selectivity during the reaction. Recently, the present authors reported a similar phenomenon for the reduction of nitrobenzene and phenylacetylene with hydrazine over a nitrogen-and oxygen-doped metal-free activated carbon (AC) catalyst [39].…”

Section: Surface Properties Of Pdzn and Pd Catalystssupporting

confidence: 56%

Pd and PdZn supported on ZnO as catalysts for the hydrogenation of cinnamaldehyde to hydrocinnamyl alcohol

Fujita

Mitani

Zhang

et al. 2017

Molecular Catalysis

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Liquid phase selective hydrogenation of cinnamaldehyde (CAL) was investigated over ZnO-supported Pd and PdZn catalysts different in the Pd loading. The former monometallic catalyst was less selective to the formation of cinnamyl alcohol (COL) irrespective of the Pd loading (5 and 30 wt.-% Pd). When the Pd loading was small (5 wt.-%), PdZn catalyst (PdZn-5) indicated similar catalytic actions. However, PdZn catalyst containing Pd in a larger content of 30 wt.-% (PdZn-30) showed different results: the COL selectivity was about 20% at low conversion but it increased with CAL conversion, reaching to > 50% at a conversion of 60%. The COL selectivity was likely to change depending on the concentration of a product of hydrocinnamaldehyde (HCAL). The coadsorption of HCAL should control the orientation of CAL molecules adsorbed on the PdZn-30 catalyst. This may assist the adsorption of CAL via its aldehyde group on the surface of catalyst, resulting in an increase in the COL selectivity. Unique catalysis of PdZn-30 may result from structural features of the surface of its large PdZn particles, which are different from those of PdZn-5 having smaller PdZn particles.

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Section: Surface Properties Of Pdzn and Pd Catalystssupporting

confidence: 56%

Pd and PdZn supported on ZnO as catalysts for the hydrogenation of cinnamaldehyde to hydrocinnamyl alcohol

Fujita

Mitani

Zhang

et al. 2017

Molecular Catalysis

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“…The promotional effect of the nitro group was further investigated for the hydrogenation of the ethynyl group of phenylacetylene (PA) (Scheme 7d) by using one selected N-OAC [15]. In the absence of catalyst, the hydrogenation of PA alone occurred at a small extent (4%).…”

Section: Use Of Nitrogen-doped Activated Carbon For Transfer Hydrogenmentioning

confidence: 99%

“…It is highly probable that interactions between PA and NB occur, allowing PA to be adsorbed and reduced on the surface of N-OAC. Possible interactions were proposed to occur between C≡C bond and O-N bonds (Scheme 9) [15], in which O and N could originate from both NB and the surface species on N-OAC. Interactions between PA and adsorbed hydrazine might also contribute to the PA hydrogenation assisted by NB.…”

Section: Use Of Nitrogen-doped Activated Carbon For Transfer Hydrogenmentioning

confidence: 99%

“…The present authors doped nitrogen to an activated carbon (AC) by treating in a mixture of ammonia and air at temperatures of 400-800 °C. The nitrogen-doped AC (N-AC) materials, so prepared, are active for such several liquid phase reactions as Knoevenagel condensation [11], transesterification [11], aerobic oxidation of xanthene [12] and alcohols [13], and chemo-selective reduction of nitrobenzene, styrene, 3-nitrostyrene, and phenylacetylene with hydrazine [14,15], which are ordinarily catalyzed by bases, metals, and metal oxides [16][17][18][19][20][21][22]. X-ray photoelectron spectroscopy (XPS) surface analysis indicates that different types of nitrogen dopants are involved in the formation of catalytically active sites for those different reactions.…”

Section: Introductionmentioning

confidence: 99%

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Nitrogen-Doped Activated Carbon as Metal-Free Catalysts Having Various Functions

Fujita¹,

Yoshida²,

Arai³

2017

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Nitrogen-doped carbon materials have been gaining increasing interest as metal-free catalysts. In this article, the authors have briefly introduced their recent studies on the utilization of nitrogen-doped activated carbon (N-AC) for several organic synthesis reactions, which include base catalyzed reactions of Knoevenagel condensation and transesterification, aerobic oxidation of xanthene and alcohols, and transfer hydrogenation of nitrobenzene, 3-nitrostyrene, styrene, and phenylacetylene with hydrazine. Doped-nitrogen species existed on the AC surface in different structures. For example, pyridine-type nitrogen species appear to be involved in the active sites for Knoevenagel condensation and for the oxidation of xanthene, while graphite-type nitrogen species appear to be involved for the oxidation of alcohols. Being different from these reactions, both surface nitrogen and oxygen species are involved in the active sites for the hydrogenation of nitrobenzene. N-AC was practically inactive for the transfer hydrogenation of vinyl and ethynyl groups, but it can catalyze those hydrogenation reactions assisted by co-existing nitrobenzene. Comparison of N-AC with conventional catalysts shows that N-AC can alternate with conventional solid base catalysts and supported metal catalysts for the Knoevenagel condensation and oxidation reactions.Keywords: activated carbon; ammoxidation; solid base; aerobic oxidation; transfer hydrogenation IntroductionVarious catalysts are used in industry [1], in which suitable active components are selected and tailored into an effective catalyst for a target reaction under optimized conditions. That is, different catalyst components are selected and used according to target production processes. It is interesting to design and prepare a catalyst, single or multi-component, that can have different active sites on its surface and act as a multifunctional catalyst: the same catalyst can be effectively used for different types of synthetic reaction. One of potential components for such a multifunctional catalyst may be carbon.Carbon is an interesting material, due to its physicochemical and electrochemical properties and has been used as one of the industrial functional materials. It is also important as either a carrier or a catalyst in the field of catalysis. The carbon materials have a few different functional groups on their surface, depending on their sources and carbonization processes, and these are catalytically active in chemical reactions like oxidation [2]. Their surface functionalization can further be made by doping foreign species, such as nitrogen [3]. Nitrogen-doped carbon and carbon nitride would be interesting functional materials. Those modified carbon materials are prepared by different methods, including chemical vapor deposition, well-designed organic synthesis, and doping of nitrogen to parent bulk carbon materials (say, activated carbon). In addition to their effectiveness in electrochemical applications, those carbon-based materials will serve as metal-fr...

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“…As catalyst supports, NCMs can improve the sur-face charge density of metal particles, such as: Co [6] and Ru [7], which facilitates the catalytic activity. Recent studies indicate that NCMs can be directly used as catalysts for some heterogeneous catalytic reactions, such as: dehydrogenation of ethylbenzene [8], the catalytic reductions of nitrobenzene [9] or phenylacetylene [10], catalytic oxidation of ethylbenzene to acetophenone [11], and catalytic hydrogen chlorination of acetylene [12]. Compared with metal-loaded NCMs, metal-free NCMs would not suffer from the aggregation and loss of metal particles, which are certain disadvantages for metallic catalysts [13].…”

Section: Introductionmentioning

confidence: 99%

Preparation of Metal-Free Nitrogen-Doped Carbon Material and Its Catalytic Performance

Wang¹,

Yang²,

Cai³

et al. 2018

Bull. Chem. React. Eng. Catal.

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Nitrogen-doped carbon materials (NCMs) were prepared via hydrothermal treatment together with pyrolysis under nitrogen atmosphere by using melamine as nitrogen source and sucrose as carbon source. The NCMs were characterized by X-ray diffraction (XRD), laser Raman spectroscopy and X-ray photoelectron spectroscopy (XPS). The results showed that nitrogen species were successfully doped into NCMs in the form of pyridinic N, pyrrolic N, graphitic N, and oxidized N. With the temperature of pyrolysis increasing, the total amount of nitrogen species decreased, while the proportion of graphitic N increased. The catalytic performance was investigated by the reduction of p-nitrophenol with excessive KBH4 at 30 ℃. The reaction rate constant can reach 1.06 min -1 for NCM-800. The NCM-800 has good stability, which can be used for 8 cycles without obvious deactivation.

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Nitrobenzene-assisted reduction of phenylacetylene with hydrazine over nitrogen-doped metal-free activated carbon catalyst: Significance of interactions among substrates and catalyst

Cited by 12 publications

References 15 publications

Pd and PdZn supported on ZnO as catalysts for the hydrogenation of cinnamaldehyde to hydrocinnamyl alcohol

Pd and PdZn supported on ZnO as catalysts for the hydrogenation of cinnamaldehyde to hydrocinnamyl alcohol

Nitrogen-Doped Activated Carbon as Metal-Free Catalysts Having Various Functions

Preparation of Metal-Free Nitrogen-Doped Carbon Material and Its Catalytic Performance

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