Selective aerobic oxidation of toluene to benzaldehyde on immobilized CoOx on SiO2 catalyst in the presence of N-hydroxyphthalimide and hexafluoropropan-2-ol

Shi, Gaoquan; Xu, Sihao; Bao, Yan Ling; Xu, Jinyang; Liang, Yuxin

doi:10.1016/j.catcom.2019.01.017

Cited by 41 publications

(13 citation statements)

References 26 publications

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“…Hence, the autoxidation of benzaldehyde to benzoic acid was unnoticeable in HFIP during the reaction time period. On the basis of this work, an immobilized CoO x /SiO 2 catalyst was reported for the selective oxidation of toluene to benzaldehyde in the presence of NHPI in HFIP . This NHPI/Co(II) system was investigated for the oxidation of ethylbenzene to acetophenone .…”

Section: Oxidations and Reductionsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions. The use of this solvent has exponentially increased in the past decade and has become a solvent of choice in some areas, such as C–H functionalization chemistry. In this review, following a brief history of HFIP in organic synthesis and an overview of its physical properties, literature examples of organic reactions using HFIP as a solvent or an additive are presented, emphasizing the effect of solvent of each reaction.

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Section: Oxidations and Reductionsmentioning

confidence: 99%

HFIP in Organic Synthesis

et al. 2022

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“…Shi and colleagues developed a NHPI-based method for the selective oxidation of toluene to benzaldehyde based on immobilized CoO x on SiO 2 catalyst in the presence of HFIP using molecular oxygen at room temperature. [65] A high toluene conversion of 91 % and a selectivity to benzaldehyde of 68 % were obtained, due to the synergy between the immobilized cobalt oxide on silica and the NHPI in HFIP. The SiO 2 support showed no activity under the reaction conditions whereas the non-supported Co 3 O 4 provided a low reactivity.…”

Section: Silicas As Supports For Heterogeneous N-hydroxyimide-based Systemsmentioning

confidence: 98%

Organocatalysis Meets Hydrocarbon Oxyfunctionalization: the Role of N‐Hydroxyimides

Andrade

Martins

2021

Eur J Org Chem

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The merging of organocatalysis and CÀ H bond oxyfunctionalization has demonstrated to be a powerful approach towards the development of new efficient and selective synthetic protocols. Both research areas have witnessed a tremendous growth over the past two decades, with a high number of studies mainly reporting the use of N-hydroxyphthalimide (NHPI) and related compounds in the selective oxyfunctionaliza-tion of hydrocarbons. Additionally, heterogeneous NHPI-based systems can provide a green and sustainable perspective for oxidation reactions. Nevertheless, reports related to this latter approach are still scarce and need further scouting in terms of types of supports used. This short review accounts for relevant contributions from 2010 onwards on the use of NHPI-based systems for hydrocarbon oxyfunctionalization.

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“…A 91% toluene conversion was observed, but the selectivity to benzaldehyde was found to be as low as 68%. Moreover, this reaction employed N-hydroxyphthalimide and hexafluoropropan-2-ol as promoters, which have to be separated from the product obtained at a later stage [49] [50], which led to a 62.5% benzaldehyde yield. V-Mo-Fe-O mixed oxide yielded a maximum of 40.3% toluene conversion with an 84.5% selectivity towards benzaldehyde.…”

Section: Extended Catalytic Activity Evaluationmentioning

confidence: 99%

Selective Catalytic Oxidation of Toluene to Benzaldehyde: Effect of Aging Time and Calcination Temperature Using CuxZnyO Mixed Metal Oxide Nanoparticles

et al. 2021

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Oxidation is an important organic transformation, and several catalysts have been reported for this conversion. In this study, we report the synthesis of mixed metal oxide CuxZnyO, which is prepared by a coprecipitation method by varying the molar ratio of Cu and Zn in the catalytic system. The prepared mixed metal oxide CuxZnyO was evaluated for catalytic performance for toluene oxidation. Various parameters of the catalytic evaluation were studied in order to ascertain the optimum condition for the best catalytic performance. The results indicate that aging time, calcination temperature, reaction temperature, and feed rate influence catalytic performance. It was found that the catalyst interfaces apparently enhanced catalytic activity for toluene oxidation. The XRD diffractograms reveal the crystalline nature of the mixed metal oxide formed and also confirm the coexistence of hexagonal and monoclinic crystalline phases. The catalyst prepared by aging for 4 h and calcined at 450 °C was found to be the best for the conversion of toluene to benzaldehyde while the reactor temperature was maintained at 250 °C with toluene fed into the reactor at 0.01 mL/min. The catalyst was active for about 13 h.

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Selective aerobic oxidation of toluene to benzaldehyde on immobilized CoOx on SiO2 catalyst in the presence of N-hydroxyphthalimide and hexafluoropropan-2-ol

Cited by 41 publications

References 26 publications

HFIP in Organic Synthesis

HFIP in Organic Synthesis

Organocatalysis Meets Hydrocarbon Oxyfunctionalization: the Role of N‐Hydroxyimides

Selective Catalytic Oxidation of Toluene to Benzaldehyde: Effect of Aging Time and Calcination Temperature Using CuxZnyO Mixed Metal Oxide Nanoparticles

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