Selective hydrogenation of the CC bond of α,β-unsaturated carbonyl compounds over PdNPs–SBA-15 in a water medium

Ganji, Saidulu; Mutyala, Suresh; Neeli, Chinna Krishna Prasad; Rao, K. Srinivasa; Burri, David Raju

doi:10.1039/c3ra41966e

Cited by 52 publications

(25 citation statements)

References 58 publications

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“…Among the investigated catalysts, the Pd/C catalyst has the highest activity and selectivity for the hydrogenation of isophorone to 3,3,5-trimethylcyclohexanone. Over this catalyst, high carbon yield of compound 2 (99.0%) was achieved after the reaction was carried out at 298 K for 1 h. According to literature 31 , 32 , this result can be explained because Pd is more active and selective than Ir, Pt, Ru for the hydrogenation of C = C bond in unsaturated carbonyl compounds. The higher activity Pd for the hydrogenation of C = C bond can be explained by the stronger H 2 /metal interactions accompanied by a preferred formation of surface hydrogen atoms 33 .…”

Section: Resultsmentioning

confidence: 54%

Synthesis of renewable high-density fuel with isophorone

Wang

Liu

et al. 2017

Sci Rep

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1,1,3-Trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane, a renewable high density fuel, was first produced in a high overall carbon yield (~70%) with isophorone which can be derived from hemicellulose. The synthetic route used this work contains three steps. In the first step, 3,3,5-trimethylcyclohexanone was synthesized by the selective hydrogenation of isophorone. Among the investigated catalysts, the Pd/C exhibited the highest activity and selectivity. Over this catalyst, a high carbon yield (99.0%) of 3,3,5-trimethylcyclohexanone was achieved under mild conditions (298 K, 2 MPa H2, 1 h). In the second step, 3,5,5-trimethyl-2-(3,3,5-trimethylcyclohexylidene)cyclohexanone was produced in a high carbon yield (76.4%) by the NaOH catalyzed self-aldol condensation of 3,3,5-trimethylcyclohexanone which was carried out in a round bottom flask attached to the Dean–Stark apparatus. In the third step, the 3,5,5-trimethyl-2-(3,3,5-trimethylcyclohexylidene)cyclohexanone was hydrodeoxygenated under solvent-free conditions. High carbon yield (93.4%) of 1,1,3-trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane was obtained over the Ni/SiO2 catalyst. The 1,1,3-trimethyl-5-(2,4,4-trimethylcyclohexyl)cyclohexane as obtained has a density of 0.858 g mL−1 and a freezing point of 222.2 K. As a potential application, it can be blended into conventional fuels (such as RP-1, RG-1, etc.) for rocket propulsion.

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Section: Resultsmentioning

confidence: 54%

Synthesis of renewable high-density fuel with isophorone

Wang

Liu

et al. 2017

Sci Rep

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“…A considerable number of recent studies have focussed on developing supported metal catalysts with mono and bimetallic combinations of transition metals, and through optimisation of the materials and reaction conditions, extremely high yields of FA are obtainable. [21][22][23][24] Particle size effects are also known to have a profound effect on chemoselectivity, with an example being the hydrogenation of , -unsaturated aldehydes, [25][26][27] an effect which is likely to be due to an alteration of the substrates mode of adsorption. 28 Whilst a substantial amount of literature reports highly effective systems for the selective hydrogenation and transfer hydrogenation of FF to FA, a much smaller quantity of publications focus on the total hydrogenation of FF to THFA.…”

Section: Introductionmentioning

confidence: 99%

The selective hydrogenation of furfural over supported palladium nanoparticle catalysts prepared by sol-immobilisation: effect of catalyst support and reaction conditions

Albilali

Douthwaite

et al. 2018

Catal. Sci. Technol.

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“…In contrast, the hydrogenation of carbonyl group will stop the condensation. Due to its special electron structure, Pd is very good catalyst for the selective hydrogenation of C=C bond in α,β‐unsaturated carbonyl compound especially when it was loaded on basic supports, which may be the reason why Pd demonstrated the best promotion effect among the investigated noble metals.…”

Section: Resultsmentioning

confidence: 99%

Dual‐bed catalyst system for the direct synthesis of high density aviation fuel with cyclopentanone from lignocellulose

Sheng

Wang

et al. 2016

AIChE Journal

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In this article, we demonstrated an integrated process for the direct production of tri(cyclopentane) with cyclopentanone which can be obtained from lignocellulose. The reaction was carried out in a dual-bed continuous flow reactor. In the first bed, cyclopentanone was selectively converted to 2,5-dicyclopentylcyclopentanol over the Pd-MgAl-HT (hydrotalcite) catalyst. Under solvent-free and mild conditions (443 K, 0.1 MPa H 2 ), high carbon yield (81.2%) of 2,5-dicyclopentylcyclopentanol was achieved. Subsequently, the 2,5-dicyclopentylcyclopentanol was further hydrodeoxygenated to tri(cyclopentane) in the second bed. Among the investigated catalysts, the Ni-Hb-DP prepared by deposition-precipitation (DP) method exhibited the highest activity for the hydrodeoxygenation step. By using Pd-MgAl-HT as the first bed catalyst and Ni-Hb-DP as the second bed catalyst, tri(cyclopentane) was directly produced at high carbon yield (80.0%) with cyclopentanone as feedstock. This polycycloalkane has high density (0.91 kg/L) and can be used as additive to improve the density and volumetric heating value of bio-jet fuel.

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Selective hydrogenation of the CC bond of α,β-unsaturated carbonyl compounds over PdNPs–SBA-15 in a water medium

Cited by 52 publications

References 58 publications

Synthesis of renewable high-density fuel with isophorone

Synthesis of renewable high-density fuel with isophorone

The selective hydrogenation of furfural over supported palladium nanoparticle catalysts prepared by sol-immobilisation: effect of catalyst support and reaction conditions

Dual‐bed catalyst system for the direct synthesis of high density aviation fuel with cyclopentanone from lignocellulose

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