Preparation of Nitrogen‐Doped Carbon from Polyacrylonitrile and its Application as a Solid‐Base Catalyst

Fujita, Shin‐ichiro; Katagiri, Ayaka; Watanabe, Hiroyuki; Asano, Sayaka; Yoshida, Hiroshi; Arai, Masahiko

doi:10.1002/cctc.201500337

Cited by 25 publications

(12 citation statements)

References 36 publications

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“…The present authors prepared nitrogen-doped carbon materials by a simple method in which an activated carbon (AC) was treated by a mixture of ammonia and air at temperatures of 400 -800ºC. Those nitrogen-doped AC materials were shown to catalyze different types of organic reactions including Knoevenagel condensation [8,9], transesterification [8], reduction [10], and oxidation [11,12]. One of interesting results obtained is chemoselectivity in the reduction of aromatic substrates by hydrazine [10].…”

Section: Introductionmentioning

confidence: 99%

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

Fujita¹,

Asano²,

Arai³

2016

Journal of Molecular Catalysis A: Chemical

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A nitrogen-doped activated carbon (AC) can catalyze the reduction of nitrobenzene with hydrazine but not phenylacetylene. When nitrobenzene coexists in the reaction mixture, however, phenylacetylene can also be reduced. Nitrobenzene is likely to assist the adsorption of phenylacetylene on the surface of AC catalyst through molecular interactions between the two substrates, allowing their simultaneous reduction to aniline and styrene. For these interactions to occur, nitrogen and/or oxygen species doped on the surface of AC are involved. The results demonstrate a new interesting catalytic function of nitrogen-and oxygen-doped metal-free carbon materials.

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Section: Introductionmentioning

confidence: 99%

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

Fujita¹,

Asano²,

Arai³

2016

Journal of Molecular Catalysis A: Chemical

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“…Then, the carbocation attacks the carbon atom of the carbonyl group of benzaldehyde, producing ECC through the dehydration of an alcohol intermediate compound. It was also reported that, for the Knoevenagel reaction, the catalytic performances of the most active N-AC and N-PAN were comparable with, or higher than those of some solid base catalysts reported so far [25]. Thus, N-AC and N-PAN could be alternatives to conventional solid base catalysts.…”

Section: Use Of Nitrogen-doped Activated Carbon For Base Catalyzed Rementioning

confidence: 71%

“…However, similar to the case of Knoevenagel reaction, liquid pyridine molecules had no activity for the oxidation reaction. The significance of the presence of pyridine-type nitrogen atoms It was also reported that, for the Knoevenagel reaction, the catalytic performances of the most active N-AC and N-PAN were comparable with, or higher than those of some solid base catalysts reported so far [25]. Thus, N-AC and N-PAN could be alternatives to conventional solid base catalysts.…”

Section: Use Of Nitrogen-doped Activated Carbon For Aerobic Oxidationmentioning

confidence: 91%

“…N-AC was also active for butyraldehyde, but inactive for the ketones, because of lower reactivities of ketones than those of aldehydes. In a following study [25], our group also prepared nitrogen-doped carbon materials from polyacrylonitrile (PAN) and used them for the same Knoevenagel reaction. Nitrogen-doped carbon (N-PAN) was obtained by calcination of PAN in air at a few hundred degrees centigrade, and In a following study [25], our group also prepared nitrogen-doped carbon materials from polyacrylonitrile (PAN) and used them for the same Knoevenagel reaction.…”

Section: Use Of Nitrogen-doped Activated Carbon For Base Catalyzed Rementioning

confidence: 99%

“…In a following study [25], our group also prepared nitrogen-doped carbon materials from polyacrylonitrile (PAN) and used them for the same Knoevenagel reaction. Nitrogen-doped carbon (N-PAN) was obtained by calcination of PAN in air at a few hundred degrees centigrade, and In a following study [25], our group also prepared nitrogen-doped carbon materials from polyacrylonitrile (PAN) and used them for the same Knoevenagel reaction. Nitrogen-doped carbon (N-PAN) was obtained by calcination of PAN in air at a few hundred degrees centigrade, and subsequent ammoxidation at higher temperatures.…”

Section: Use Of Nitrogen-doped Activated Carbon For Base Catalyzed Rementioning

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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Unraveling Surface Basicity and Bulk Morphology Relationship on Covalent Triazine Frameworks with Unique Catalytic and Gas Adsorption Properties

Tuci

Pilaski

et al. 2017

Adv Funct Materials

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This paper describes the exohedral N-decoration of multi-walled carbon nanotubes (MWCNTs) with NH-aziridine groups via [2+1] cycloaddition of a tert-butyl-oxycarbonyl nitrene followed by controlled thermal decomposition of the cyclization product. The chemical grafting with Ncontaining groups deeply modifies the properties of the starting MWCNTs, generating new surface microenvironments with specific base (Brønsted) and electronic properties. Both these features translate into a highly versatile single-phase heterogeneous catalyst (MW@N Az ) with remarkable chemical and electrochemical performance. Its surface base character promotes the Knoevenagel condensation with superior activity to that of related N-doped and N-decorated carbon nanomaterials of the state-of-the-art; the N-induced electronic surface redistribution drives the generation of high energy surface "C" sites suitable for O2 activation and its subsequent electrochemical reduction (ORR).

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Preparation of Nitrogen‐Doped Carbon from Polyacrylonitrile and its Application as a Solid‐Base Catalyst

Cited by 25 publications

References 36 publications

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

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

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

Unraveling Surface Basicity and Bulk Morphology Relationship on Covalent Triazine Frameworks with Unique Catalytic and Gas Adsorption Properties

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