Heteropoly acid catalysts in Prins cyclization for the synthesis of Florol®

Meireles, Augusto L.P. de; Rocha, Kelly A. da Silva; Kozhevnikova, Elena F.; Kozhevnikov, Ivan V.; Gusevskaya, Elena V.

doi:10.1016/j.mcat.2020.111382

Cited by 5 publications

(5 citation statements)

References 31 publications

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“…Based on the previous papers considering the mechanism of the Prins cyclization reaction [24,31] and the obtained dependencies of selectivity on isoprenol conversion over hierarchical beta zeolites, the reaction pathways presented in Scheme 2 can be suggested for the studied catalysts.…”

Section: Kinetic Analysismentioning

confidence: 99%

“…Application of heteropoly acids per se and immobilized on silica MCM-41 afforded 96% selectivity (at 70% conversion of isovaleraldehyde) towards the desired tetrahydropyranol at 80 • C in water as a solvent [23]. 80% yield of Florol was reported over a silica-supported heteropoly acid under mild conditions using green solvents (dimethylcarbonate or diethylcarbonate) [24]. Deposition of MoO 3 onto silicas [25] or alumosilicates [26] providing a higher dispersion of the active phase resulted in ca.…”

Section: Introductionmentioning

confidence: 99%

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Florol synthesis via Prins cyclization over hierarchical beta zeolites

Shcherban

Barakov²,

Lasne³

et al. 2022

Molecular Catalysis

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Section: Kinetic Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Florol synthesis via Prins cyclization over hierarchical beta zeolites

Shcherban

Barakov²,

Lasne³

et al. 2022

Molecular Catalysis

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“…The affections of acid type, acid strength and acid concentration on the catalytic activity for this reaction were investigated. On the basis of these experiments, we choose phosphotungstic acid (HPW), a solid acid with super strong B acidity (Alazman et al, 2019;Meireles et al, 2021), as the catalyst for the conversion of sesamin to asarinin for the first time. The effect of various conditions, such as catalyst amount, reaction time, reaction temperature and initial sesamin concentration was investigated.…”

Section: Studies On the Highly Efficient Catalyzation Of Sesamin To A...mentioning

confidence: 99%

Studies on the highly efficient catalyzation of sesamin to asarinin by phosphotungstic acid

Shen

et al. 2023

Food Sci. Technol

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The conversion of sesamin to asarinin is a promising route for the production of asarinin. This work reports the affection of acid type and strength of the catalyst on the conversion of sesamin to asarinin and the effect of various reaction conditions in anhydrous ethanol using phosphotungstic acid (HPW) as catalyst. The experimental results indicate that the activity of sesamin conversion is determined by strong B acids. L acids are not active for the reaction, and do not show synergy with B acids for the formation of asarinin. Reaction time, HPW dosage and temperature have significant effects on sesamin conversion. A maximum asarinin yield of 57.93% was achieved. The reaction kinetics in the temperature range 55-75 °C were studied. The kinetic curves can be successfully fitted with an opposing first-order reaction model. The activation energy (Ea) for this reaction is found to be 105.2 ± 0.4 kJ/mol.

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“…Compared with conventional alkylation approaches using Lewis acids or protonic acids as catalysts, , the employment of heteropoly acids (HPAs) for alkylation is attractive from both cost and sustainability viewpoints. , Due to their strong and uniform Brønsted acid sites, − Keggin type HPAs exhibit high activity in a wide variety of Friedel–Crafts alkylation reactions. − The most typical Keggin HPAs are H 3 PW 12 O 40 (HPW), H 4 SiW 12 O 40 (HSiW), H 3 PMo 12 O 40 (HPMo), and H 4 SiMo 12 O 40 (HSiMo), and HPW is reported as the most acidic HPA. − Frédéric Richard showed that MgF 2 -supported HPW is an efficient catalyst for the alkylation of benzothiophene with 2-methyl-1-pentene under mild conditions . However, part of HPW loss in organic media, agglomeration of active species, and small surface area restrict its application. ,,, Gan Ye realized the combination of HPW and UiO-66(Zr) and found that polyoxometalate encapsulated in UiO-66(Zr) possesses good stability in the oxidative desulfurization reaction . Zeolites, with a regularly distributed supercage structure, can be used as hosts for exquisitely anchored HPW .…”

Section: Introductionmentioning

confidence: 99%

“…25 However, part of HPW loss in organic media, agglomeration of active species, and small surface area restrict its application. 15,21,28,29 Gan Ye realized the combination of HPW and UiO-66(Zr) and found that polyoxometalate encapsulated in UiO-66(Zr) possesses good stability in the oxidative desulfurization reaction. 30 Zeolites, with a regularly distributed supercage structure, can be used as hosts for exquisitely anchored HPW.…”

Section: Introductionmentioning

confidence: 99%

Identification of the Encapsulation Effect of Heteropolyacid in the Si–Al Framework toward Benzene Alkylation

Liu

Sun

et al. 2022

ACS Catal.

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Heterogenization of homogeneous catalysts is a long-term pursuit in the field of catalysis application. Traditional alkylation of arenes with olefins is usually achieved using acid catalysts in a homogeneous system, with high catalytic activity and selectivity but difficulty in catalyst separation and reusability. Herein, H3PW12O40 (HPW), an excellent homogeneous Brønsted acid catalyst, was anchored to the faujasite (FAU) cage of ultrastable Y (USY) zeolite with high dispersion (HPW@USY). 100% conversion of cyclohexene (CHE) with 99.9% yield of cyclohexylbenzene was obtained by the alkylation of benzene (C6H6) and CHE (V C6H6 /VCHE= 7:1). No obvious deactivation was observed over HPW@USY after eight cycles. Our experimental and theoretical results demonstrated that W–OH exposed in HPW, encapsulated in the FAU cage, is the active site for alkylation. The excellent performance of the HPW@USY catalyst was attributed to the homogeneous chemical environment and stability of the encapsulated HPW. Benefiting from the formation and stabilization of a reaction intermediate (C6H11 •) during the CHE activation, the encapsulation effect of HPW in the Si–Al framework played a significant role in the alkylation between CHE and other aromatic hydrocarbons with high yields of alkylated products. This work provides a promising heterogeneous catalyst strategy, making the alkylation efficiency of aromatics and olefins as high as that of homogeneous catalysts.

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Heteropoly acid catalysts in Prins cyclization for the synthesis of Florol®

Cited by 5 publications

References 31 publications

Florol synthesis via Prins cyclization over hierarchical beta zeolites

Florol synthesis via Prins cyclization over hierarchical beta zeolites

Studies on the highly efficient catalyzation of sesamin to asarinin by phosphotungstic acid

Identification of the Encapsulation Effect of Heteropolyacid in the Si–Al Framework toward Benzene Alkylation

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