The synthesis of o-cyclohexylphenol in supercritical carbon dioxide: towards a continuous two-step reaction

Amandi, Rodrigo; Scovell, Katherine; Licence, Peter; Lotz, T. J.; Poliakoff, Martyn

doi:10.1039/b618727g

Cited by 25 publications

(12 citation statements)

References 22 publications

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“…For many years, chemists at Nottingham have been developing continuous reactors to carry out simple chemical transformations 2 -including hydrogenation 3,4 , alkylation 5,6 and etherification 7,8 -as cleanly as possible. For nearly a decade, the reactors have been automated so that more tedious experiments, such as studying the effect of ramping up the temperature of the reactor, can be performed under full computer control 3 .…”

Section: Reactors At the Readymentioning

confidence: 99%

Remote-controlled experiments with cloud chemistry

et al. 2014

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Section: Reactors At the Readymentioning

confidence: 99%

Remote-controlled experiments with cloud chemistry

et al. 2014

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“…In contrast, bicyclic compounds, such as cyclohexylphenol, can be formed and diffuse within the larger micropores (12‐membered rings) of the BEA zeolitic structure. In this way, it must be highlighted that the formation of cyclohexylphenol in significant amounts over the Co 2 P/h‐beta catalyst is an interesting finding due to its commercial application for the manufacture of dyes, resins, and biocides …”

Section: Resultsmentioning

confidence: 99%

“…In this way, it must be highlighted that the formation of cyclohexylphenol in significant amounts over the Co 2 P/h-beta catalyst is an interesting finding due to its commercial application for the manufacture of dyes, resins, and biocides. [32]…”

Section: Cp-cyclopentane Mcp-methylcyclopentane Mcpe-methylcyclopenmentioning

confidence: 99%

On the Feasibility of Using Hierarchical ZSM‐5 and Beta Zeolites as Supports of Metal Phosphides for Catalytic Hydrodeoxygenation of Phenol

et al. 2019

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Hierarchical ZSM‐5 and beta zeolites are assessed and compared as supports for the preparation of Ni and Co phosphide‐based hydrodeoxygenation (HDO) catalysts. Zeolites are first impregnated with the metals and P precursors, followed by temperature‐programmed reduction, to obtain the corresponding Ni2P and Co2P phases. In the HDO tests, phenol is used as a model compound typically present in pyrolysis bio‐oils. Me2P deposition affects the textural and acidic properties of the zeolitic supports, especially in the case of h‐beta, because a collapse of its mesoporosity and the formation of aluminophosphate species are observed. For both zeolites, Ni2P is the most active phosphide phase. In particular, Ni2P/h‐ZSM‐5 exhibits outstanding results (almost full phenol conversion, complete deoxygenation, and narrower compound yield distribution), even when compared with other Ni2P‐supported materials reported in the literature. Moreover, this catalyst can be effectively regenerated by calcination and subsequent reduction treatment, so that the catalytic performance remains hardly unaltered. The superior catalytic activity for phenol HDO of the h‐ZSM‐5 support is assigned mainly to the preservation of the secondary mesoporosity, which provides a good dispersion of the Ni2P nanoparticles and a good accessibility to the zeolite acid sites.

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“…Alkylation of phenol with cyclohexene has attracted considerable interest because of its industrial and academic relevance [13][14][15][16][17][18][19][20][21]. This reaction leads to a variety of products such as 4-cyclohexylphenol, 2-cyclohexylphenol, and cyclohexyl phenyl ether depending on both the catalyst and the reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Acid catalyzed alkylation of phenols with cyclohexene: Comparison between homogeneous and heterogeneous catalysis, influence of cyclohexyl phenyl ether equilibrium and of the substituent on reaction rate and selectivity

Ronchin

Vavasori

Toniolo

2012

Journal of Molecular Catalysis A: Chemical

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a b s t r a c tThe reactivity of several phenols toward liquid phase alkylation with cyclohexene in the presence of heterogeneous and homogeneous acid catalyst at 358 K is studied. The comparison between Amberlyst 15 and CH 3 SO 3 H, as examples of heterogeneous and homogeneous systems, shows a higher activity of the former with different behavior of selectivity between the two systems, anyway, in both systems O-alkylation and ring alkylations occur. A remarkable difference in the selectivity of the ring alkylation between heterogeneous and homogeneous systems is observed: Amberlyst 15 shows a constant ortho/para ratio close to 2, while in the presence of CH 3 SO 3 H ortho/para is variable from 3 to 5, suggesting an involvement of the cyclohexyl phenyl ether rearrangement. This is proved also by a direct relationship between the ortho/para ratio and the concentration of the cyclohexyl phenyl ether when CH 3 SO 3 H is used as a catalyst. The formation of cyclohexyl aryl ethers is reversible; on the contrary, ring alkylation appears irreversible. The reactivity of the dimethylphenols shows a strong influence of the steric hindrance of the substituent on the electrophilic attack of the cyclohexyl cation, which is poorly influenced by the inductive effect of the methyl group.

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The synthesis of o-cyclohexylphenol in supercritical carbon dioxide: towards a continuous two-step reaction

Cited by 25 publications

References 22 publications

Remote-controlled experiments with cloud chemistry

Remote-controlled experiments with cloud chemistry

On the Feasibility of Using Hierarchical ZSM‐5 and Beta Zeolites as Supports of Metal Phosphides for Catalytic Hydrodeoxygenation of Phenol

Acid catalyzed alkylation of phenols with cyclohexene: Comparison between homogeneous and heterogeneous catalysis, influence of cyclohexyl phenyl ether equilibrium and of the substituent on reaction rate and selectivity

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