H- and Fe-modified zeolite beta catalysts for preparation of trans-carveol from α-pinene oxide

Stekrova, Martina; Kumar, Narendra; Diáz, Sara Faten; Mäki‐Arvela, Päivi; Murzin, Dmitry Yu.

doi:10.1016/j.cattod.2013.12.004

Cited by 42 publications

(44 citation statements)

References 15 publications

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“…The in-depth characterization of some of the tested catalysts (HBeta-25, H-Beta-150, H-Beta-300, Fe-Beta-150, Ce-MCM-41) was carried out using various methods (scanning electron microscopy, X-ray absorption spectroscopy, nitrogen adsorption, FTIR with pyridine as a probe molecule) and was published previously [24,25]. Also the parent material Na-MCM-41 used for Ce-MCM-41 was fully characterized in ref.…”

Section: Catalysts Characterization Resultsmentioning

confidence: 99%

Prins cyclization: Synthesis of compounds with tetrahydropyran moiety over heterogeneous catalysts

Stekrova

Mäki‐Arvela

Kumar

et al. 2015

Journal of Molecular Catalysis A: Chemical

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Section: Catalysts Characterization Resultsmentioning

confidence: 99%

Prins cyclization: Synthesis of compounds with tetrahydropyran moiety over heterogeneous catalysts

Stekrova

Mäki‐Arvela

Kumar

et al. 2015

Journal of Molecular Catalysis A: Chemical

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“…Isomerization of -pinene oxide (97%, Aldrich) was performed in this work with two catalysts, H-Beta-300 and Fe-H-Beta-300. The preparation and characterization of catalysts, H-Beta-300 and Fe-H-Beta-300, used in this work, are reported in [4,5].…”

Section: Methodsmentioning

confidence: 99%

“…Isomerization of -pinene oxide has been intensively studied in the recent years over several homogeneous and heterogeneous catalysts [1][2][3][4][5][6][7][8][9]. The two main valuable products are campholenic aldehyde and trans-carveol finding applications in perfumes and flavors [10].…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, weakly acidic illite clays promoted formation of fencholenic aldehyde at 30 °C in cyclohexane [12]. On the other hand, trans-carveol was produced using a basic solvent, N,N-dimethylacetamide (DMA) at a higher temperature 140 °C [1,4]. A rather selective catalyst for trans-carveol (S = 43%) has been, for example Fe-H-beta exhibiting both Brønsted and Lewis acid sites [4], when the reaction was performed in DMA at 140 °C.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, trans-carveol was produced using a basic solvent, N,N-dimethylacetamide (DMA) at a higher temperature 140 °C [1,4]. A rather selective catalyst for trans-carveol (S = 43%) has been, for example Fe-H-beta exhibiting both Brønsted and Lewis acid sites [4], when the reaction was performed in DMA at 140 °C. On the other hand campholenic aldehyde has been formed on Fe-SiO 2 in toluene as a solvent [6] and on Fe-Y-12 in toluene [7].…”

Section: Introductionmentioning

confidence: 99%

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Isomerization of α-Pinene Oxide: Solvent Effects, Kinetics and Thermodynamics

et al. 2018

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Kinetics and thermodynamics of-pinene oxide isomerization was investigated both theoretically and experimentally in different solvents in the temperature range of 50-140 °C using different zeolites, iron modified zeolites, Fe-H-MCM-41 and micro-mesoporous ZSM-5 derived catalysts. The aim was to elucidate the effect of solvent basicity and polarity on the product distribution in this reaction giving as the main value-added products campholenic aldehyde and trans-carveol, which are used as fragrances and perfumes. A generic kinetic first order model was developed composed of both parallel and consecutive routes. A thermodynamic analysis showed that product selectivity is determined by kinetic control and not by thermodynamics. Formation of campholenic aldehyde was favored in non-polar solvents, whereas basic solvents promoted formation of trans-carveol independent on temperature.

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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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H- and Fe-modified zeolite beta catalysts for preparation of trans-carveol from α-pinene oxide

Cited by 42 publications

References 15 publications

Prins cyclization: Synthesis of compounds with tetrahydropyran moiety over heterogeneous catalysts

Prins cyclization: Synthesis of compounds with tetrahydropyran moiety over heterogeneous catalysts

Isomerization of α-Pinene Oxide: Solvent Effects, Kinetics and Thermodynamics

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

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