Cyclopentanone Derivatives from 5‐Hydroxymethylfurfural via 1‐Hydroxyhexane‐2,5‐dione as Intermediate

Woźniak, Bartosz; Spannenberg, Anke; Li, Yuehui; Hinze, Sandra; Vries, Johannes G. de

doi:10.1002/cssc.201702100

Cited by 49 publications

(60 citation statements)

References 36 publications

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“…The hydrogenation of another biosourced compound, namely 5-hydroxymethylfurfural (HMF), into 1hydroxyhexane-2,5-dione (HHD) was reported by de Vries (Figure 12). 21 Among five catalysts evaluated, the iridium-dpa C19 furnished the highest yield of 76%. Notably, the well-know and efficient Ru-pincer catalyst C28 led to high conversion but poor selectivity for the desired product isolated in only 5%.…”

Section: Scheme 2 Reductive Amination Of Levulinic Acidmentioning

confidence: 99%

2,2′-Dipyridylamines: more than just sister members of the bipyridine family. Applications and achievements in homogeneous catalysis and photoluminescent materials

et al. 2019

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HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés. 2,2'-Dipyridylamines more than just sister members of the bipyridine family. Applications and achievements in homogeneous catalysis and photoluminescent materialsAbstract 2,2'-Dipyridylamine (dpa) and related compounds belong to the family of polydentate nitrogen ligands. More than a century has passed since its first report but new complexes and applications have been emerging in the recent years owing to the versatility of dpa-based architectures. This review aims to present and highlight the main achievements attained with dpa-containing metal complexes in the domains of homogeneous catalysis and luminescent materials.

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Section: Scheme 2 Reductive Amination Of Levulinic Acidmentioning

confidence: 99%

2,2′-Dipyridylamines: more than just sister members of the bipyridine family. Applications and achievements in homogeneous catalysis and photoluminescent materials

et al. 2019

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“…Recently, our group had realized the preparation of 2‐hydroxy‐3‐methyl‐2‐cyclopenten‐1‐one (MCP), a precious edible essence, from HMF with 58% yield via a two‐step procedure . The same procedure was also reported by de Vries et al shortly later . The first step in this procedure was the conversion of HMF to 1‐hydroxy‐2,5‐hexanedione (HHD) on Pd catalysts.…”

Section: Introductionmentioning

confidence: 99%

Highly Selective Conversion of HMF to 1‐hydroxy‐ 2,5‐hexanedione on Pd/MIL‐101(Cr)

et al. 2019

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Saturated cyclohexene water was used as the reductant for the preparation of Pd/MIL‐101(Cr). The catalysts were characterized by XRD, N2 adsorption/desorption isotherms, XPS, TEM, FTIR, ICP‐AES and in‐situ FTIR spectra of adsorbed pyridine. The water saturated by cyclohexene was proved to be an effective reductant to produce metallic Pd catalyst. The texture of MIL‐101(Cr) was kept well after the introduction of Pd to MIL‐101(Cr). The hydrogenation of HMF to 1‐hydroxy‐2,5‐hexanedione (HHD) was conducted in water using Pd/MIL‐101(Cr) as catalyst. After reacted for 6 h at 413 K 4 MPa H2, up to 82% yield of HHD was achieved without acid additives. The MIL‐101(Cr) acted both as support and acid catalyst generated from the open Cr3+. The stability of the catalyst was investigated to find that the TOFs decreased slightly after the catalyst was used. The decline in the catalytic activity was discussed and ascribed to the condensation of intermediates on the active sites and the partly aggregate of Pd.

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“…Furaldehydes are known as key platform compounds for biomass transformations in lignocellulosic biomass resources. In particular, 5-hydroxymethyl-2-furaldehyde (HMF) is the most important furaldehyde: it possesses two functionalities of formyl and hydroxyl groups on a furan ring at the second and fifth positions and this character enables various successive transformations to afford 2,5-furandicarboxylic acid [7,8], 2,5-diformylfuran [9,10], 2,5-bis(hydroxymethyl)furan (BHMF) [11,12], 2,5-dimethylfuran [13][14][15], 5-hydroxymethylfurfurylamine (HMFA) [16], 1,6-hexanediol [17], levulinic acid [18,19], aldol-adducts [20], and so on [21][22][23]. On the other hand, 2-furaldehyde (furfural), an abundant furaldehyde which is producible at the plant scale with a large quantity, has also permitted many conversions towards furoic acid [24,25], furfuryl alcohol [26,27], 2-methylfuran [28,29], furfuriyamine [30,31], 1,5-pentandiol [32,33], succinic acid [34], condensation products [35][36][37], cyclopentenones [38][39][40] and so on [41], as well as HMF reaction protocols.…”

Section: Introductionmentioning

confidence: 99%

Hydroxymethylation of Furfural to HMF with Aqueous Formaldehyde over Zeolite Beta Catalyst

Nishimura

Shibata

2019

Catalysts

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Hydroxymethylation of 2-furaldehyde (furfural) toward 5-hydroxymethyl-2-furaldehyde (HMF) was examined in this work among various zeolites with an aqueous formaldehyde as a reagent in a batch and a flow reactor system. It was found that the zeolite beta gave high activity and good reusability with calcination treatment before each run for the target reaction in the batch system. The unique stability of the HMF yield in the liquid-flow system was also observed only in the case of zeolite beta. The effect of the SiO2/Al2O3 ratio in the zeolite beta suggested that hydrophobicity would be an important factor in faster hydroxymethylation with an aqueous formaldehyde reagent. The highest turnover frequency (TOF) for HMF production was found to be 2.4 h−1 in the case of zeolite beta with SiO2/Al2O3 = 440 in the batch reactor system. An approximately 30% yield for HMF was achieved under optimum conditions for zeolite beta catalysts.

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Cyclopentanone Derivatives from 5‐Hydroxymethylfurfural via 1‐Hydroxyhexane‐2,5‐dione as Intermediate

Cited by 49 publications

References 36 publications

2,2′-Dipyridylamines: more than just sister members of the bipyridine family. Applications and achievements in homogeneous catalysis and photoluminescent materials

2,2′-Dipyridylamines: more than just sister members of the bipyridine family. Applications and achievements in homogeneous catalysis and photoluminescent materials

Highly Selective Conversion of HMF to 1‐hydroxy‐ 2,5‐hexanedione on Pd/MIL‐101(Cr)

Hydroxymethylation of Furfural to HMF with Aqueous Formaldehyde over Zeolite Beta Catalyst

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