Rapid synthesis of unsaturated alcohols under mild conditions by highly selective hydrogenation

Tamura, Masazumi; Tokonami, Kensuke; Nakagawa, Yoshinao; Tomishige, Keiichi

doi:10.1039/c3cc41526k

Cited by 207 publications

(167 citation statements)

References 30 publications

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“…15 In a recent report, Tamura et al applied a Ir-ReO x catalyst for the hydrogenation of HMF and obtained a 99% yield of BHMF after 6 h of reaction at 30°C and a hydrogen pressure of 0.8 MPa. 16 While preparing this manuscript another group detected a 99% yield of BHMF at 100°C after 3 h of reaction in ethanol over a copper-doped porous metal oxide prepared by the calcination of hydrotalcite. 17 Thus, in most of the cases, higher hydrogen pressure, longer reaction time, organic solvents or additional metal oxide additive were used to achieve a high yield of BHMF.…”

Section: Introductionmentioning

confidence: 98%

Selective hydrogenation of 5-hydroxymethylfurfural to 2,5-bis-(hydroxymethyl)furan using Pt/MCM-41 in an aqueous medium: a simple approach

2014

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The hydrogenation of HMF has been conducted in a neutral aqueous medium. Without any additive, HMF was hydrogenated to 2,5-bis-(hydroxymethyl)furan (BHMF) with complete conversion and selectivity (98.9%) using Pt/MCM-41 as catalyst. A very low temperature of 35°C and 0.8 MPa of hydrogen pressure was used to accomplish the highest selectivity of BHMF within a reaction time of 2 h. Different reaction parameters such as reaction time, hydrogen pressure and the amount of water was optimized to achieve the highest catalytic activity. In particular, the presence or absence of water and the amount of water played an important role to determine the conversion and product distribution of the reaction. For instance, in the absence of water or a large excess of water, the selectivity of BHMF was decreased. In addition, instead of water the influence of three different groups of organic solvent were also explored to obtain BHMF under the studied reaction conditions. It has been observed that the studied organic solvents strongly influenced the catalytic performance, such as solvents with a negative δ value, which followed a clear trend with the substrate conversion, whereas no impact was observed for solvents with a positive δ value. Catalyst recycling experiments revealed that the catalyst could be recycled several times without any significant loss of catalytic activity.

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Section: Introductionmentioning

confidence: 98%

Selective hydrogenation of 5-hydroxymethylfurfural to 2,5-bis-(hydroxymethyl)furan using Pt/MCM-41 in an aqueous medium: a simple approach

2014

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“…Furthermore, BHMTHF is the preferred product when Ru is supported on ceria, magnesia‐zirconia, and γ‐alumina, whereas Pt and Pd are less selective than Ru . While Pd promotes the formation of 5‐methyl furfural , Pt and Ir‐Re catalysts are selective to BHMF .…”

Section: Introductionmentioning

confidence: 99%

Kinetics of Catalytic Hydrogenation of 5-Hydroxymethylfurfural to 2,5-bis-Hydroxymethylfuran in Aqueous Solution over Ru/C

Jain

Vaidya

2016

Int. J. Chem. Kinet.

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5‐Hydroxymethylfurfural (5‐HMF) is a cellulosic product of the hydrolysis of biomass, and it is widely considered for the production of several interesting chemicals and derivatives. In the present work, catalytic hydrogenation of 5‐hydroxymethylfurfural to 2,5‐bis‐hydroxymethylfuran was investigated using 5% Ru/C in the aqueous phase. Kinetic data were experimentally obtained over a wide range of temperatures (313–343 K), H2 partial pressure (0.69–2.07 MPa), initial HMF concentration (19.8–59.5 mM), and catalyst loading (0.3–0.7 kg/m3) in a three‐phase slurry reactor. Disappearance of initial 5‐HMF concentrations was modeled using the power law and Langmuir–Hinshelwood–Hougen–Watson models. A model based on the competitive adsorption of molecular H2 and HMF was proposed. It is presumed that surface reaction between nondissociatively chemisorbed H2 and 5‐HMF was rate determining. This model provided the best fit for the kinetic data. From the Arrhenius equation, the activation energy for the surface reaction was found to be 104.9 kJ/mol.

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“…For DHMF synthesis, Alamillo et al 10 studied supported Ru, Pd and Pt catalysts for HMF hydrogenation, of which Ru was the most active metal with a yield of 81-94%. 13 For DMF production, Dumesic et al 7 reported for the first time a Ru-Cu catalyst with a yield of 76-79%. 11 Other catalysts were also reported, including Pt/MCM-41, 6 Pd/C 12 and Ir-ReO x /SiO 2 .…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of 2,5-dihydroxymethylfuran and 2,5-dimethylfuran from 5-hydroxymethylfurfural using mineral-derived Cu catalysts as versatile catalysts

Zhu

Kong

Zheng

et al. 2015

Catal. Sci. Technol.

141

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Selective conversion of 5-hydroxymethylfurfural (HMF) can produce sustainable fuels and chemicals.Herein, Cu-ZnO catalysts derived from minerals (malachite, rosasite and aurichalcite) were employed for selective hydrogenation of HMF for the first time. High yields of 2,5-dihydroxymethylfuran (~99.1%) and 2,5-dimethylfuran (~91.8%) were obtained tunably over the catalyst with a Cu/Zn molar ratio of 2, due to the well-dispersed metal sites tailored by mineral precursors, well-controlled surface sites and optimized reaction conditions. The relationship between catalytic performance and catalyst properties was elucidated by characterization based on the composition and the structural and surface properties, and catalytic tests.The catalyst can also be extended to selective hydrogenation of other bio-derived molecules (furfural and 5-methylfurfural) to target products. The construction of mineral-derived Cu-ZnO catalysts and the revelation of the structure-performance relationship can be applied to further rational design and functionalization of non-noble Cu catalysts for selective conversion of bio-derived compounds.Catal. Sci. Technol. This journal is

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Rapid synthesis of unsaturated alcohols under mild conditions by highly selective hydrogenation

Abstract: Ir-ReOx/SiO2 acted as a highly active and selective heterogeneous catalyst for the hydrogenation of unsaturated aldehydes to unsaturated alcohols in water at low H2 pressure (0.8 MPa) and low temperature (303 K). The catalysis is derived from the synergy between Ir metal and ReOx.

Cited by 207 publications

References 30 publications

Selective hydrogenation of 5-hydroxymethylfurfural to 2,5-bis-(hydroxymethyl)furan using Pt/MCM-41 in an aqueous medium: a simple approach

Selective hydrogenation of 5-hydroxymethylfurfural to 2,5-bis-(hydroxymethyl)furan using Pt/MCM-41 in an aqueous medium: a simple approach

Kinetics of Catalytic Hydrogenation of 5-Hydroxymethylfurfural to 2,5-bis-Hydroxymethylfuran in Aqueous Solution over Ru/C

Efficient synthesis of 2,5-dihydroxymethylfuran and 2,5-dimethylfuran from 5-hydroxymethylfurfural using mineral-derived Cu catalysts as versatile catalysts

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