A metal-free, high nitrogen-doped nanoporous graphitic carbon catalyst for an effective aerobic HMF-to-FDCA conversion

Nguyen, Chi Van; Liao, Ying‐Chih; Kang, Ting-Cih; Chen, Jeffrey E.; Yoshikawa, Takuya; Nakasaka, Yuta; Masuda, Toshio; Wu, Kevin C.‐W.

doi:10.1039/c6gc02118b

Cited by 134 publications

(88 citation statements)

References 48 publications

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“…Although the polymer framework did not comprise nitrogen‐containing units, the nitrogen atoms in the nickel ammine complexes during the pyrolysis process were introduced in the carbon layer of the MC/Ni catalyst. Typically, three peaks were fitted to the N 1s XPS spectra of the MC/Ni catalyst with binding energies at 398.5, 399.5, and 400.8 eV, which were assigned to pyridinic N (N‐1), pyrrolic N (N‐2), and graphitic N (N‐3), respectively (Figure ) . As shown in Figure , the C 1s XPS spectra of the MC/Ni catalyst had one main peak at 284.6 eV, corresponding to sp 2 ‐hybridized graphitic carbon (C=C).…”

Section: Resultsmentioning

confidence: 99%

Nitrogen‐Doped Carbon‐Supported Nickel Nanoparticles: A Robust Catalyst to Bridge the Hydrogenation of Nitriles and the Reductive Amination of Carbonyl Compounds for the Synthesis of Primary Amines

et al. 2019

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An efficient method was developed for the synthesis of primary amines either from the hydrogenation of nitriles or reductive amination of carbonyl compounds. The reactions were catalyzed by nitrogen‐doped mesoporous carbon (MC)‐supported nickel nanoparticles (abbreviated as MC/Ni). The MC/Ni catalyst demonstrated high catalytic activity for the hydrogenation of nitriles into primary amines in high yields (81.9–99 %) under mild reaction conditions (80 °C and 2.5 bar H2). The MC/Ni catalyst also promoted the reductive amination of carbonyl compounds for the synthesis of primary amines at 80 °C and 1 bar H2. The hydrogenation of nitriles and the reductive amination proceeded through the same intermediates for the generation of the primary amines. To the best of our knowledge, no other heterogeneous non‐noble metal catalysts have been reported for the synthesis of primary amines under mild conditions, both from the hydrogenation of nitriles and reductive amination.

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Section: Resultsmentioning

confidence: 99%

Nitrogen‐Doped Carbon‐Supported Nickel Nanoparticles: A Robust Catalyst to Bridge the Hydrogenation of Nitriles and the Reductive Amination of Carbonyl Compounds for the Synthesis of Primary Amines

et al. 2019

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“…Thus, high selectivity to DFF (over 90 %) can be achieved from HMF or through the one‐pot conversion of fructose . FFCA, through further oxidation of DFF or HMFCA, is a main chain of FDCA production and is also the rate‐limiting step . To eliminate these intermediates, high temperatures (over 120 °C) and pressures (over 2 MPa) are usually applied in closed systems to increase the solubility of gaseous oxygen.…”

Section: Methodsmentioning

confidence: 99%

Hydrogen Peroxide Assisted Selective Oxidation of 5‐Hydroxymethylfurfural in Water under Mild Conditions

et al. 2017

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What was the biggest surprise?It would be the controllable selectivity to 5-formyl-2-furoic acid (FFCA) and2 ,5-furandicarboxylic acid (FDCA). Selectivity to the desired product is alwaysaproblem in the oxidation of 5-hydroxymethylfurfural (HMF), not only because HMF is easily converted to other chemicals, but also because there are several intermediate stages duringt he sequential oxidationp rocess. However,o wing to the different reactionr ates of each intermediate, we found that we are ablet oc ontrol the reaction product to be either FFCA or FDCA by simply adjusting the ratio between HMF and the catalyst.

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“…Both of them demonstrated the pivotal active site role of graphitic N species. While the ZIF‐8‐derived N‐doped nanoporous carbon (denoted as NNC) turned the aerobic oxidation of HMF into another important product, 2,5‐furandicarboxylic acids (FDCA) (Figure ) . In comparison to conventional nitrogen‐doped carbons, the resulting NNC derived from ZIF‐8 owns enhanced loading amount of nitrogen.…”

Section: Oxidationmentioning

confidence: 99%

“…While the ZIF-8-derived N-doped nanoporous carbon (denoted as NNC) turned the aerobic oxidation of HMF into another important product, 2,5-furandicarboxylic acids (FDCA) ( Figure 10). [73] In comparison to conventional nitrogen-doped carbons, the resulting NNC derived from ZIF-8 owns enhanced loading amount of nitrogen. As the calcination temperature increased from 600 to 900°C, the total nitrogen content decreased from 29.4 to 15.3 wt%; while the amount of graphitic nitrogen (NÀ Q) was found to increased from 4 % to 25 %.…”

Section: Oxidation Of 5-hydroxymethylfrufural (Hmf)mentioning

confidence: 99%

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Heteroatom‐Enhanced Metal‐Free Catalytic Performance of Carbocatalysts for Organic Transformations

Shang

Gao

2019

ChemCatChem

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The exploitation and design of metal‐free catalysts for chemical transformation is always a fascinating theme from the prospective of fundamental and applied research. In addition to their distinct advantages such as lower cost, higher biocompatibility and reliability and thus higher sustainability, metal‐free materials often unexpectedly render different reaction pathway or mechanism from conventional metal catalysts. As a consequence, metal‐free catalysts have revolutionized and expanded the platform of catalysis. Among them, carbons are a typical class of nonmetallic materials. To date, a series of elements (e. g., B, N, P or S) as heteroatom dopants have equipped pristine carbons with enhanced performance and even new chemical functionality. It was proposed to attribute to modulated electrical properties and surface physicochemical features originated from structural distortions and changes of charge densities. In this minireview, we overviewed the catalytic application of heteroatom‐doped carbocatalysts in oxidation, oxidative coupling, reduction and hydrogenation reactions with special emphasis on the role of heteroatoms and consequently enhanced performance. This minireview highlights the structure‐activity correlations, thereby directing the rational design of advanced metal‐free catalysts for organic synthesis. Some controversies about active sites and challenges in catalyst design are also discussed here.

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A metal-free, high nitrogen-doped nanoporous graphitic carbon catalyst for an effective aerobic HMF-to-FDCA conversion

Abstract: Nanoporous carbon nanoparticles with high graphitic nitrogen amounts were synthesized and used as a metal free catalyst for effective HMF-to-FDCA conversion.

Cited by 134 publications

References 48 publications

Nitrogen‐Doped Carbon‐Supported Nickel Nanoparticles: A Robust Catalyst to Bridge the Hydrogenation of Nitriles and the Reductive Amination of Carbonyl Compounds for the Synthesis of Primary Amines

Nitrogen‐Doped Carbon‐Supported Nickel Nanoparticles: A Robust Catalyst to Bridge the Hydrogenation of Nitriles and the Reductive Amination of Carbonyl Compounds for the Synthesis of Primary Amines

Hydrogen Peroxide Assisted Selective Oxidation of 5‐Hydroxymethylfurfural in Water under Mild Conditions

Heteroatom‐Enhanced Metal‐Free Catalytic Performance of Carbocatalysts for Organic Transformations

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