Catalytic Isomerization of α-Pinene Epoxide Over a Natural Zeolite

Sánchez-Velandia, Julián E.; Gelves, J. F.; Márquez, María del Carmen Bellido; Dorkis, Ludovic; Villa, Aída Luz

doi:10.1007/s10562-020-03225-9

Cited by 12 publications

(8 citation statements)

References 46 publications

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“…These values imply diffusional limitations considering that the pore size of beta zeolite is 0.68 nm . The achieved TOF values over investigated catalysts (1.1–3.1 min –1 ) exceed the corresponding value for a natural zeolite (heulandite, chabazite, and clinoptilolite as main crystallographic phases; TOF = 0.12 min –1 ) due to a higher accessibly of the active sites of beta-based catalysts for α-pinene oxide.…”

Section: Resultssupporting

confidence: 93%

Hierarchical Beta Zeolites As Catalysts in α-Pinene Oxide Isomerization

Barakov

Shcherban

Mäki‐Arvela

et al. 2022

ACS Sustainable Chem. Eng.

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Hierarchical beta zeolites obtained in the concentrated reaction mixtures (H 2 O/Si = 2.5) and micromesoporous materials synthesized using a dual-template approach from a zeolite beta precursor were rigorously characterized and tested in a sustainable and environmentally friendly process of α-pinene oxide isomerization. The highest yield of trans-carveol (42%) with chemopreventive activity of mammary carcinogenesis was achieved over low crystalline micromesoporous materials characterized by well-developed mesoporosity, an increased fraction of weak-to-medium Brønsted acid sites and low Brønsted and Lewis acid sites (BAS/LAS) ratio. In turn, highly crystalline hierarchical beta zeolites with a lower mesopore volume and the mesopore surface area, stronger Brønsted acidity, and a higher BAS/LAS ratio favored the formation of campholenic aldehyde (31% yield). The mechanism of the desired product and byproducts formation was discussed and its feasibility was confirmed by kinetic modeling.

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Section: Resultssupporting

confidence: 93%

Hierarchical Beta Zeolites As Catalysts in α-Pinene Oxide Isomerization

Barakov

Shcherban

Mäki‐Arvela

et al. 2022

ACS Sustainable Chem. Eng.

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“…reported that the natural zeolite with varying the Si/Al ratio and identified the lower concentration of Lewis acidic sites favors carveol formation. [ 20 ] All the reported heterogeneous catalyst has required harsh reaction conditions (above 100 °C) and long reaction time (1–7 h) required to achieve 100% conversion with 40–85% selectivity of TC. [ 17–22 ] To overcome these disadvantages of heterogeneous metal and carbon‐based catalysts, very few groups are working under ambient conditions using Ti and P metal‐based catalysts.…”

Section: Methodsmentioning

confidence: 99%

Sustainable Isomerization of α‐Pinene Oxide to trans‐Carveol using Formic Acid/Aniline System at Room Temperature

Ravi

Naikwadi

Biradar

2021

Advanced Sustainable Systems

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trans‐Carveol is an essential and expensive chemical used as valencia orange essence oil in the fragrance industry, and can be obtained through Brønsted acid‐catalyzed isomerization of α‐pinene oxide (APO) using hazardous solvent at higher temperatures. Therefore the development of a simple, metal‐free, and cost‐effective, sustainable method for isomerization of APO at milder conditions is desired. In this study, in situ formed formanilide (IFF) and tetrahydrofuran are used as active solvents and formic acid used as a Brønsted acid catalyst for selective isomerization of APO. Under the optimized conditions, the maximum 80% selectivity of trans‐carveol is achieved with complete APO conversion in 30 min at room temperature. The solvent system's practical utility is demonstrated at a 10 g scale with complete conversion and 76% selectivity at room temperature within 60 min. Furthermore, isotopic labeling experiments show donation of a proton from the IFF solvent.

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“…The largest pore in Heulandite structure is a 10member ring (10MR) with the size of approximately 11 Å which is large enough to host small molecules, such as methanol. Two other pores of 8MR channels have diameter of approximately 7 Å. Heulandite and its isostructural type which is clinoptilolite have been reported for several applications such as adsorption of hydrocarbon [26,27] and water [28,29], cation exchange [30] and catalysis [31].…”

Section: Introductionmentioning

confidence: 99%

Investigating the Interaction between Methanol and the Heulandite-type Zeolite using First Principle Molecular Dynamic

Wulandhani

Pambudi

2022

Bull. Chem. React. Eng. Catal.

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The interaction between methanol and the Heulandite-type zeolite has been unveiled to give an atomic scale detail regarding the catalytic activity of this zeolite for methanol conversion. The study was carried out by first principle molecular dynamics to get an insight into the structure and electronic behaviour of methanol inside the zeolite structure at different temperatures. The behaviour of methanol was studied when the location of the proton of Bronsted acid sites was varied to give both possible direct and less interaction with methanol. The results show that methanol interacts with the proton from zeolite to give a cationic species of [CH3OH2]+ both in 300K and 573K conditions. However, when the proton is located at different location far from possible interaction with methanol, the formation of a cationic species is hindered. This study provides an insight into the design of Heulandite type zeolite to give a catalytic activity toward methanol transformation.

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Catalytic Isomerization of α-Pinene Epoxide Over a Natural Zeolite

Cited by 12 publications

References 46 publications

Hierarchical Beta Zeolites As Catalysts in α-Pinene Oxide Isomerization

Hierarchical Beta Zeolites As Catalysts in α-Pinene Oxide Isomerization

Sustainable Isomerization of α‐Pinene Oxide to trans‐Carveol using Formic Acid/Aniline System at Room Temperature

Investigating the Interaction between Methanol and the Heulandite-type Zeolite using First Principle Molecular Dynamic

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