Efficient Isomerization of α-Pinene Oxide to Campholenic Aldehyde Promoted by a Mixed-Ring Analogue of Molybdenocene

Bruno, Sofia M.; Valente, Anabela A.; Pillinger, Martyn; Amelse, Jeffrey; Romão, Carlos C.; Gonçalves, Isabel S.

doi:10.1021/acssuschemeng.9b03087

Cited by 13 publications

(6 citation statements)

References 39 publications

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“…Molybdenum modified materials are active acid catalysts (because of material Lewis acidity enhancement due MoO 3 content [25,26]) and may serve as catalysts in alkane isomerization [27][28][29][30][31]. Usage of molybdenum-based catalyst in α-pinene oxide is also reported [32]. Based on these facts, we decided to prepare several types of molybdenum modified zeolites BETA and test a large number of different solvents concerning campholenic aldehyde and trans-carveol selectivity.…”

Section: Materials Preparation and Characterizationmentioning

confidence: 99%

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

et al. 2020

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Natural source turpentine is an available source of α-pinene oxide. This compound’s value is especially given by the possibility of producing important compounds campholenic aldehyde and trans-carveol. In this work, we would like to present the usage of MoO3-modified zeolite BETA in α-pinene oxide isomerization concerning campholenic aldehyde and trans-carveol formation using a wide range of solvents. Catalyst calcination temperature also influenced the reaction course (selectivity to desired compounds and reaction rate). MoO3-zeolite BETA was prepared by the wet impregnation method and characterized by different techniques. The use of polar aprotic solvents had the most positive effect on the reaction course. Solvent basicity and polarity considerably influenced the reaction rate and selectivity to particular products. The combination of high basicity and the high polarity was the most suitable for the studied reaction from the reaction rate point of view. Selectivity to campholenic aldehyde and trans-carveol was the most influenced by solvent basicity. Higher solvent basicity caused the preferential formation of trans–carveol, influence on selectivity to campholenic aldehyde formation was the opposite. The described catalyst may be used for α-pinene oxide rearrangement to both desired products dependently on the used solvent. Molybdenum offers an exciting alternative for previously described modifications of zeolites for this reaction.

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Section: Materials Preparation and Characterizationmentioning

confidence: 99%

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

et al. 2020

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“…Together with its structural isomer α-pinene, β-pinene is the major component of turpentine oil obtained from conifers, mainly pine tree. , Turpentine oil represents a readily available co-product in the paper industry, reaching 360,000 tons per year (2015), and this production is expected to increase in the future with the evolution of biorefineries. Therefore, practical uses for these terpenes are actively being sought. − Natural deep eutectic solvents were also evaluated here as reaction media but proved unsuccessful (Supporting Information Discussion 2).…”

Section: Resultsmentioning

confidence: 99%

Utilization of Plant-Based Wastes for a Sustainable Preparation of Xanthophyll Esters via Acid Anhydrides Using β-Pinene as a Bio-Derived Solvent

Metličar

Kranjc

Albreht

2021

ACS Sustainable Chem. Eng.

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A new valorization strategy for selected plant-based waste materials has been put forward. We have shown that avocado peels (fruit waste) and green leaves of Japanese knotweed (plant waste) are good sources of free xanthophylls such as antheraxanthin (9 mg/100 g dry weight) and lutein (106 mg/100 g dry weight), respectively, which can be converted into xanthophyll esters, a process inspired by nature to regulate the physicochemical properties of these bioactive species such as solubility and chemical stability. To this end, we developed the first environmentally friendly and economically viable synthetic platform and critically evaluated it by preparing 55 different xanthophyll esters (combining 5 model xanthophylls with 11 structurally and electronically distinct acid anhydrides). These esters were synthesized using β-pinene as a bio-derived solvent at ambient temperature and pressure with excellent selectivity (median 97%) and finally isolated in high yields (median 81%) and with high purities (median 97%). The integration of this technology with xanthophyll-containing wastes contributes to the zero-waste principle, and new valorization pathways for invasive alien plant species (such as Japanese knotweed) are particularly welcome as they help to control their rapid spread which causes great economic damage and loss of biodiversity around the globe.

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“…36 Interestingly, IL media have not yet been explored in this regard. In order to efficiently isomerize APO to CA with an 87% yield, Bruno et al 37 employed the IL [choline][NTf 2 ] as a co-solvent along with a molybdenum-based catalyst. The function of the IL was restricted to solubilizing the catalyst.…”

Section: Introductionmentioning

confidence: 99%

Selective isomerization of α-pinene oxide totrans-carveol by task-specific ionic liquids: mechanistic insightsviaphysicochemical studies

et al. 2023

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Efficient Isomerization of α-Pinene Oxide to Campholenic Aldehyde Promoted by a Mixed-Ring Analogue of Molybdenocene

Cited by 13 publications

References 39 publications

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

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

Utilization of Plant-Based Wastes for a Sustainable Preparation of Xanthophyll Esters via Acid Anhydrides Using β-Pinene as a Bio-Derived Solvent

Selective isomerization of α-pinene oxide totrans-carveol by task-specific ionic liquids: mechanistic insightsviaphysicochemical studies

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