Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates

Liu, Fei; Audemar, Maïté; Vigier, Karine De Oliveira; Clacens, Jean‐Marc; Campo, Floryan De; Jérôme, François

doi:10.1002/cssc.201402221

Cited by 84 publications

(81 citation statements)

References 26 publications

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“…After further optimization, the best results were obtained with I (0.5 mol %) with 10 bar H 2 at 120 °C in water and HHD was isolated in 69 % yield (Table , entry 1). The major byproduct was found to be an insoluble polymeric solid, presumably humins, which is consistent with the observations of other groups . In addition, the utilization of a phosphoric acid/sodium phosphate buffer solution allowed processing with lower catalyst loading (0.075 mol %), albeit with no improvement in yield.…”

Section: Methodssupporting

confidence: 89%

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

Woźniak

Spannenberg

et al. 2017

ChemSusChem

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Section: Methodssupporting

confidence: 89%

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

Woźniak

Spannenberg

et al. 2017

ChemSusChem

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“…[47][48][49] Hydrogenation/hydrolytic ring opening of 5-HMF to the corresponding 10 diketones was reported by Au nanoparticles in the presence of H 3 PO 4 . 32 Ebitani et al studied hydrogenolytic ring opening of 5-HMF to 1, [6][7][8][9][10][11][12][13] hexanediol over Pd/ZrP at 140 °C using formic acid as a hydrogen source. 32 Ebitani et al studied hydrogenolytic ring opening of 5-HMF to 1, [6][7][8][9][10][11][12][13] hexanediol over Pd/ZrP at 140 °C using formic acid as a hydrogen source.…”

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confidence: 99%

Catalytic transformation of bio-derived furans to valuable ketoacids and diketones by water-soluble ruthenium catalysts

et al. 2015

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9Bio-derived furans such as 2-furfural (furfural), 5-hydroxymethyl-2-furfual (5-HMF) and 10 5-methyl-2-furfural (5-MF) was successfully transformed to ketoacid, levulinic acid 11 (LA), and diketones, 1-hydroxyhexane-2,5-dione (1-HHD), 3-hydroxyhexane-2,5-dione 12 (3-HHD) and hexane-2,5-dione (HD), at moderate reaction conditions using water 13 soluble and recyclable 8-aminoquinoline coordinated arene-ruthenium(II) complexes. At 14 the optimized condition using 1 mol % catalyst in the presence of 12 equivalent formic 15 acid at 80 ~ 100 °C, complete conversion of furfural to LA with high selectivity was 16 achieved. Several experiments along with 1 H NMR spectral studies are described which 17 provide more insights into the mechanism of the transformation of furans to open ring 18 components. Experiment performed using structural analogues of active catalyst inferred 19 a structural-activity relationship for the observed superior catalytic activity of the 8-20 aminoquinoline coordinated arene-ruthenium(II) complex. Furthermore, due to high 21 aqueous solubility of the studied complexes, high recyclability, up to 4 catalytic runs, 22 was achieved without any significant loss of activity. Molecular identities of the studied 23 8-aminoquinoline coordinated arene-ruthenium(II) complex was also confirmed by 24 single-crystal X-ray diffraction studies. Development of new methodologies and catalysts for the transformation of biomass and 2 biomass derived compounds into biofuel components are highly desirable to reduce the 3 global dependence on the fossil fuel resources. Moreover, these transformations of 4 biomass can also produce several value added chemicals for potential applications in 5 chemical industries. However, direct usage of biomass is unsuitable so far. 1-7 In this 6 regard, furans, an important feedstock of biomass obtained by selective dehydration of 7 hexose and pentose sugar, are considered as an important resource for the production of 8 bio-based chemicals. 8-19 Furan derivatives such as 5-HMF, furfural and 5-MF are being 9 used as valuable C5/C6 resources for the synthesis of value added chemicals and biofuel 10 components based on LA, succinic acid, ketones, 1,6-hexanediol, cyclopentanone, adipic 11 acid, caprolactam, caprolactone, furoic acid and so on. 20-36 Moreover, C5-C9 alkane can 12 also be produced by the hydrolytic ring opening and complete hydrogenation of furans 13 and its aldol adducts. 36-38 14 Ketoacids and diketones have been successfully used to produce several value 15 added fine chemicals such as esters, alcohols, lactones, amines and cycloketones. 39-41 16 According to US-DOE, LA (ketoacid) has been identified as one of the 12 important 17 target chemicals in their biomass program. 41 Due to the presence of carbonyl group, 18 carboxylic group and α-H in LA, various sorts of compounds can be synthesized by 19 different type of reactions like halogenation, esterification, hydrogenation, condensation 20 etc. that can be used in drugs, agriculture, food, cosmetics and spice industry (...

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“…There were several reports on the conversion of HMF to HHD. Supported Pd, Pt and Au catalysts were proved to be effective for this conversion . Mentech and their group reported this conversion with 60% yield of HHD using Pt/C by the addition of oxalic acid for the first time .…”

Section: Introductionmentioning

confidence: 95%

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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Palladium/Carbon Dioxide Cooperative Catalysis for the Production of Diketone Derivatives from Carbohydrates

Cited by 84 publications

References 26 publications

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

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

Catalytic transformation of bio-derived furans to valuable ketoacids and diketones by water-soluble ruthenium catalysts

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

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