Selective reduction of unsaturated aldehydes to unsaturated alcohols using supercritical 2-propanol

Daimon, Atsushi; Kamitanaka, Takashi; Kishida, Nobuhiro; Matsuda, Tomoko; Harada, Tadao

doi:10.1016/j.supflu.2005.09.001

Cited by 26 publications

(16 citation statements)

References 6 publications

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“…Alcohol 15 should be produced by Meerwein-Ponndorf-Verley (MPV) reduction of aldehyde 1a in the presence of a large excess amount of benzyl alcohol because the reaction conditions were the variant of representative non-catalytic MPV reduction [19]. Thus, it is truly noteworthy that the ester was obtained as a main product from aldehyde directly even though under MPV reduction conditions.…”

Section: Methodsmentioning

confidence: 99%

“…In contrast, much attention has been paid to superheated fluids such as subcritical water (sub-CW) [17], supercritical water (SCW) [17], and supercritical alcohols [18,19] from the perspective of green reactions because of their unique properties. For example, extremely strong complexation effect under high pressure produces solvent clusters around the solute molecules, which leads to strong interactions between the solute and solvent molecules.…”

Section: Introductionmentioning

confidence: 99%

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One-step and non-catalytic intramolecular redox reactions of conjugated all E-dienals to non-conjugated Z-enoic acids in subcritical water

Chen

Sumoto

Mitani

et al. 2012

The Journal of Supercritical Fluids

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Hightlights1. Non-conjugated unsaturated acid derivatives are obtained by treating conjugated dienals in superheated fluids in one-step.2. Simple treatment of all E-dienals in superheated fluids produces thermodynamically less-stable Z unsaturated acid derivatives.3. The obtained non-conjugated unsaturated acid is converted to biologically active -lactone with a hydroxyl group by hydrogen peroxide in one step.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One-step and non-catalytic intramolecular redox reactions of conjugated all E-dienals to non-conjugated Z-enoic acids in subcritical water

Chen

Sumoto

Mitani

et al. 2012

The Journal of Supercritical Fluids

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“…108 Harada et al also reported a catalyst-free carbonyl reduction process in supercritical iPrOH (508 K, 48 bar). [109][110] Scheme 10. sCO2 for: A) citral C=O reduction B) Zn/H2O-induced carbonyl reduction.…”

Section: Supercritical Carbon Dioxidementioning

confidence: 99%

Carbonyl Reduction and Biomass: A Case Study of Sustainable Catalysis

Moores

2019

ACS Sustainable Chem. Eng.

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Catalysis plays a major role at mitigating the environmental impact of the chemical industry, drastically cutting its energy and material consumption. For this perspective, we have chosen C=O reduction in the context of biomass as a benchmark reaction to introduce and illustrate essential aspects of green catalysis. We first covered the most used C=O hydrogenation substrates made from biomass. Then, we looked at alternative energy sources to convective heating, discussed the use of greener solvents and reductants, and listed a few precious metalfree catalytic systems. Finally we looked at various hydrogen sources, including bio-sourced ones. In particular, we emphasized the use of metrics in order to quantify the actual impact of these innovations.

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“…Image J software was used to calculate the crystallite sizes. Based on the mean crystallite size measured from TEM data, Ni metal dispersion () was calculated using the formula (2) (2) where M is the molecular weight of metal in case, a is the atomic surface area (3.8×10 -20 m 2 /atom for Ni), ρ is the metal density (8.9 g/cm 3 of Ni),…”

Section: 1mentioning

confidence: 99%

“…2 Conventionally, hydrogenation of C=O bond in CAL is achieved by reduction with various hydride donors, such as LiAlH4 and NaBH4. [3][4][5] Development of non-noble metal catalysts with high activity and selectivity towards COL remains a challenge. 6,7 Supported noble metal (Pt, Pd, & Ir) catalysts have been studied extensively for this reaction.…”

Section: Introductionmentioning

confidence: 99%

Nickel Based Catalysts for Selective Hydrogenation of Cinnamaldehyde- Influence of Support Phases

Prakash¹,

Mahalakshmy²,

Krishnamurthy³

et al. 2017

ECB

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of supports; polymorphs of titania; nickel at interface Ni (15% w/w) supported on alumina, silica, and titania (P-25, anatase and rutile phases) have been investigated for the liquid phase hydrogenation of cinnamaldehyde. XRD, TPR and XPS data (binding energy shifts for Ni2p) indicate metal-support interactions in all supported catalysts. Weaker binding of H2 on Ni/TiO2 (H2-TPD) improves activity. Ni/TiO2 phases display higher cinnamaldehyde conversion and selectivity to cinnamyl alcohol compared to the catalysts supported on alumina and silica. Amongst the three polymorphs of titania, the maximum activity, and selectivity displayed by Ni/ TiO2-P-25, is attributed to the active Ni crystallites located at the interface between anatase and rutile phases in titania P-25 matrix (HRTEM). Though Ni crystallites on alumina and silica are relatively smaller (compared to those on the three TiO2 phases) in size, their activity vis-à-vis for those supported on titania phases is less, implying that factors other than crystallite size influence the performance.

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Selective reduction of unsaturated aldehydes to unsaturated alcohols using supercritical 2-propanol

Cited by 26 publications

References 6 publications

One-step and non-catalytic intramolecular redox reactions of conjugated all E-dienals to non-conjugated Z-enoic acids in subcritical water

One-step and non-catalytic intramolecular redox reactions of conjugated all E-dienals to non-conjugated Z-enoic acids in subcritical water

Carbonyl Reduction and Biomass: A Case Study of Sustainable Catalysis

Nickel Based Catalysts for Selective Hydrogenation of Cinnamaldehyde- Influence of Support Phases

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