Solvent Influence on Selectivity in α-Pinene Oxide Isomerization Using MoO3-Modified Zeolite BETA

Vrbková, Eva; Vyskočilová, Eliška; Lhotka, Miloslav; Červený, Libor

doi:10.3390/catal10111244

Cited by 14 publications

(12 citation statements)

References 36 publications

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“…Moreover, high selectivity to TCV can be linked to an easier proton transfer to the tertiary cation in the presence of a basic solvent, such as N , N -dimethylacetamide applied in the current work. On the contrary, for nonpolar and nonbasic solvents, selectivity to campholenic aldehyde is elevated …”

Section: Resultssupporting

confidence: 93%

“…It was suggested that the formation of trans -carveol over Lewis acid sites (Scheme ) occurs through formation of a tertiary cation C′, similar to cation C in Scheme , which was supposed to be more stable than a secondary cation of type A′. Moreover, high selectivity to TCV can be linked to an easier proton transfer to the tertiary cation in the presence of a basic solvent, such as N , N -dimethylacetamide applied in the current work. On the contrary, for nonpolar and nonbasic solvents, selectivity to campholenic aldehyde is elevated …”

Section: Resultsmentioning

confidence: 99%

“…On the contrary, for nonpolar and nonbasic solvents, selectivity to campholenic aldehyde is elevated. 72 The highest yield of TCV (39−42% after 3 h, Table 4, Figure S9) was achieved over low crystalline micromesoporous materials (MZ-4 and MZ-5). These materials have (1) welldeveloped mesoporosity and (2) an increased fraction of weakto-medium Brønsted acid sites among the total concentration of these sites and are characterized by (3) the low BAS/LAS ratio (Table 4).…”

Section: Acs Sustainable Chemistry and Engineeringmentioning

confidence: 95%

“…Subsequently formation of TCV is more thermodynamically controlled, while CA formation is kinetically controlled requiring a more efficient catalysts for its generation with, for example, stronger Brønsted acid sites. 72 Kinetic Modeling of α-Pinene Oxide Isomerization. The applicability of the proposed mechanism (Scheme 2) of αpinene oxide isomerization was elucidated by comparison of the estimated parameters in kinetic model for the case of transcarveol formation through pinocarveol (Scheme 1) and parallel routes of trans-carveol and pinocarveol formation (Scheme S1).…”

Section: Acs Sustainable Chemistry and Engineeringmentioning

confidence: 99%

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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%

Section: Resultsmentioning

confidence: 99%

Section: Acs Sustainable Chemistry and Engineeringmentioning

confidence: 95%

Section: Acs Sustainable Chemistry and Engineeringmentioning

confidence: 99%

See 2 more Smart Citations

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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“…Solvent influence on the course of any reaction can be crucial [36]. The solvent influence on our reaction is visible in Table 6, rows 6-10.…”

Section: Influence Of the Solventmentioning

confidence: 99%

Acid Treated Montmorillonite—Eco-Friendly Clay as Catalyst in Carvone Isomerization to Carvacrol

et al. 2021

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Acid-treated montmorillonites (MMT) were used as catalysts of carvone isomerization to carvacrol. Mineral acids—sulfuric, hydrochloric, nitric acids and organic acids (acetic and chloroacetic)—were used for the acid treatment. Prepared materials were characterized by available characterization methods, namely XRD, EA, TPD, TPO, UV-Vis, laser light scattering and nitrogen physisorption. The structure of montmorillonite remained intact after treatment. However, TPD proved the increase of acidity of acid-treated materials comparing pure montmorillonite. All materials were tested in the isomerization of carvone, producing carvacrol as the desired product. The initial reaction rate increased using the materials in the row MMT-COOH < MMT-HNO3 < MMT-ClCOOH < MMT-H2SO4 < MMT-HCl, which is in accordance with the pKa of acids used for the treatment. The number of weak acid sites strongly influenced the selectivity to carvacrol. The optimal solvent for the reaction was toluene. Total conversion of carvone and the selectivity to carvacrol 95.5% was achieved within 24 h under 80 °C, with toluene as solvent and montmorillonite treated by chloroacetic acid as catalyst. The catalyst may be reused after calcination with only a low loss of activity.

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Recent Advances and Challenges in the Valorization of α‐Pinene toward Value‐Added Chemicals

Naikwadi,

Dabas,

Ravi

et al. 2023

Advanced Sustainable Systems

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The transformation of abundantly available bioresources into specialty chemicals, particularly as consumer products, remains an important pursuit in chemical research. In this sense, the valorization of bio‐oil strategies that utilize stable and easy‐to‐handle chemical entity not only creates application‐oriented products but also helps in avoiding the usage of toxic and hazardous chemical sources. Recently, the valorization of α‐pinene (readily/naturally available terpenic compounds) has been explored to prepare a wide range of processes to access perfumery products and remains fast‐growing research for industrial and societal applications. Considering the valorization of α‐pinene, challenges for the synthetic and selective preparation of perfumery chemicals are centered around the design of the catalyst and the setting up of the precise reaction conditions. Extensive research is employed using diverse catalytic approaches to utilize α‐pinene to prepare important perfumery intermediates. In this review, the state‐of‐the‐art, recent advances and challenges in the utilization of α‐pinene are reviewed, emphasizing two main products, i.e., α‐campholenic aldehyde and carveol via α‐pinene oxide isomerization, and discussed the pertinent role of various homogeneous and heterogeneous catalytic systems.

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Solvent Influence on Selectivity in α-Pinene Oxide Isomerization Using MoO3-Modified Zeolite BETA

Cited by 14 publications

References 36 publications

Hierarchical Beta Zeolites As Catalysts in α-Pinene Oxide Isomerization

Hierarchical Beta Zeolites As Catalysts in α-Pinene Oxide Isomerization

Acid Treated Montmorillonite—Eco-Friendly Clay as Catalyst in Carvone Isomerization to Carvacrol

Recent Advances and Challenges in the Valorization of α‐Pinene toward Value‐Added Chemicals

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