One-pot myrtenol amination over Au nanoparticles supported on different metal oxides

Demidova, Yu. S.; Simakova, Irina L.; Estrada, Miguel; Beloshapkin, Sergey; Суслов, Е. В.; Корчагина, Д. В.; Волчо, К. П.; Salakhutdinov, N. F.; Simakov, Andrey; Murzin, Dmitry Yu.

doi:10.1016/j.apcata.2013.06.013

Cited by 35 publications

(24 citation statements)

References 32 publications

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“…52% after 16 h [22]. However, in the presence of this catalyst only traces of myrtenal were observed during the reaction, which hinders a more complete kinetic analysis.…”

Section: Kinetic Modelingmentioning

confidence: 80%

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Demidova

Simakova

Wärnå

et al. 2014

Chemical Engineering Journal

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“…52% after 16 h [22]. However, in the presence of this catalyst only traces of myrtenal were observed during the reaction, which hinders a more complete kinetic analysis.…”

Section: Kinetic Modelingmentioning

confidence: 80%

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Demidova

Simakova

Wärnå

et al. 2014

Chemical Engineering Journal

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“…In addition, Al 2 O 3 shows the lowest catalytic activity with the main product of acetal. It was reported that the Au elements on Au/Al 2 O 3 prepared using the deposition/precipitation method mainly existed in the form of Au(OH) 3 and Au 2 O 3 and only a portion of Au 3+ was reduced to metallic state when the calcination temperature was below 200 °C . While the Au 3+ was reduced to Au 0 by NaBH 4 in the preparation process of Au/Al 2 O 3 ‐CP by the colloidal deposition method and finally the metallic Au mainly presented on the catalyst dried at 80−120 °C .…”

Section: Resultsmentioning

confidence: 97%

Structure‐Activity Relationships of Au/Al₂O₃ Catalyst for the Selective Oxidative Esterification of 1,3‐Propanediol and Methanol

et al. 2019

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1.5 wt. % Au/Al2O3 catalysts were prepared using the deposition‐precipitation or colloid‐deposition method and calcined at different temperatures for the selective oxidative esterification reaction of 1,3‐propanediol and methanol to form methyl 3‐hydroxypropionate (3‐HPM). The catalysts were characterized by nitrogen adsorption, transmission electron microscopy (TEM), X‐ray diffraction (XRD), UV‐Vis diffuse reflectance spectroscopy, X‐ray photoelectron spectra (XPS), CO2 temperature‐programmed desorption (CO2‐TPD) and NH3 temperature‐programmed desorption (NH3‐TPD). The effect of the calcination temperature of the catalyst prepared by the deposition‐precipitation method on the catalytic performance for the selective oxidative esterification of 1,3‐propanediol was studied. The results showed that the conversion of 1,3‐propanediol and the selectivity of 3‐HPM increased at first and then decreased with the increase of the calcination temperature of catalyst. The highest conversion of 1,3‐propanediol and selectivity of 3‐HPM at the optimal calcination temperature of 350 °C were 92.0% and 88.5%, respectively. Considering the effects of preparation method and calcination temperature, it could be concluded that the metallic Au nanoparticles with appropriate particle size in coordination with the suitable amount of weak and middle acid and base sites, were favorable to the oxidative esterification of 1,3‐propanediol and methanol to 3‐HPM. Moreover, we found that the 1.5 wt. % Au/Al2O3 catalyst could be effectively recovered without obvious decline of the catalytic properties.

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“…This particular catalyst was considered to be an exception, as in fact the hydrogen borrowing approach rarely results in synthesis of amines and diamines with optimal yields using homogeneous catalysts based on Ru and Ir complexes combined with P-ligands. Some examples of reasonable yields of primary and secondary terpene amines exceeding 80% were reported for such primary and secondary terpene alcohols as myrtenol [123,124], citronellol, nerol, geraniol, farnesol, and fenchol [9,125].…”

Section: Homogeneous Catalystsmentioning

confidence: 99%

“…Schematic view of the one-pot alcohols amination applying "hydrogen borrowing approach", where oxidation in fact stands for dehydrogenation. Reprinted from [123] with permission from Elsevier.…”

Section: Heterogeneous Catalystsmentioning

confidence: 99%

“…First application of typical heterogeneous catalysts in direct terpene alcohol amination was demonstrated in a series of recent studies by Simakova and co-workers [123,[136][137][138][139][140]. Liquid-phase amination of myrtenol [123,[136][137][138][139], nopol, and perillyl alcohol [140] was carried out over supported Au catalysts (Au 1.4 mol% to substrate) in toluene at 180 • C under 9 bar nitrogen pressure using equimolar amounts of substrates without any bases as additives. The reaction network for myrtenol amination is presented in Figure 23.…”

Section: Heterogeneous Catalystsmentioning

confidence: 99%

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Valorization of Biomass Derived Terpene Compounds by Catalytic Amination

2018

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This review fills an apparent gap existing in the literature by providing an overview of the readily available terpenes and existing catalytic protocols for preparation of terpene-derived amines. To address the role of solid catalysts in amination of terpenes the same reactions with homogeneous counterparts are also discussed. Such catalysts can be considered as a benchmark, which solid catalysts should match. Although catalytic systems based on transition metal complexes have been developed for synthesis of amines to a larger extent, there is an apparent need to reduce the production costs. Subsequently, homogenous systems based on cheaper metals operating by nucleophilic substitution (e.g., Ni, Co, Cu, Fe) with a possibility of easy recycling, as well as metal nanoparticles (e.g., Pd, Au) supported on amphoteric oxides should be developed. These catalysts will allow synthesis of amine derivatives of terpenes which have a broad range of applications as specialty chemicals (e.g., pesticides, surfactants, etc.) and pharmaceuticals. The review will be useful in selection and design of appropriate solid materials with tailored properties as efficient catalysts for amination of terpenes.

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One-pot myrtenol amination over Au nanoparticles supported on different metal oxides

Cited by 35 publications

References 32 publications

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Structure‐Activity Relationships of Au/Al₂O₃ Catalyst for the Selective Oxidative Esterification of 1,3‐Propanediol and Methanol

Valorization of Biomass Derived Terpene Compounds by Catalytic Amination

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One-pot myrtenol amination over Au nanoparticles supported on different metal oxides

Cited by 35 publications

References 32 publications

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Kinetic modeling of one-pot myrtenol amination over Au/ZrO2 catalyst

Structure‐Activity Relationships of Au/Al2O3 Catalyst for the Selective Oxidative Esterification of 1,3‐Propanediol and Methanol

Valorization of Biomass Derived Terpene Compounds by Catalytic Amination

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Structure‐Activity Relationships of Au/Al₂O₃ Catalyst for the Selective Oxidative Esterification of 1,3‐Propanediol and Methanol