Influence of Technological Parameters on the Isomerization of Geraniol Using Sepiolite

Fajdek-Bieda, Anna; Wróblewska, Agnieszka; Miądlicki, Piotr; Szymańska, Alicja; Dzięcioł, Małgorzata; Booth, Andy M.; Michalkiewicz, Beata

doi:10.1007/s10562-019-02987-1

Cited by 20 publications

(11 citation statements)

References 22 publications

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“…This trend also applies to catalysts, because a lot of research shows that porous materials of natural origin (minerals) can also be active catalysts for isomerization and oxidation processes. The use of reagents of natural origin (obtained from plant material) and minerals as catalysts often reduces the costs of running the process and perfectly fits the idea of sustainable development in the organic industry [1][2][3][4][5].…”

Section: Introductionmentioning

confidence: 91%

The isomerization of S-carvone over the natural clinoptilolite as the catalyst: the influence of reaction time, temperature and catalyst content

Wróblewska

Retajczyk

2020

Reac Kinet Mech Cat

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This work describes the isomerization of S-carvone using a natural zeolite-clinoptilolite as the catalyst. The isomerization of S-carvone was carried out at the catalyst content in the reaction mixture from 5 to 15 wt%, in a temperature range of 190-210 °C and for the reaction time from 60 to 300 min. The main product of the isomerization of S-carvone was aromatic alcohol with many practical applicationscarvacrol. The use of the most favorable reaction conditions (the reaction time of 3 h, the temperature of 210 °C and the catalyst content 15 wt%) allowed to obtain this compound with high yield amounted to about 90 mol%. The S-carvone isomerization is an example of environmentally friendly process because it does not use any solvents, S-carvone can be separated from cheap cumin waste (renewable biomass) and a cheap zeolite of natural origin-clinoptilolite can be is used as the catalyst.

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Section: Introductionmentioning

confidence: 91%

The isomerization of S-carvone over the natural clinoptilolite as the catalyst: the influence of reaction time, temperature and catalyst content

Wróblewska

Retajczyk

2020

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“…Although the conversion was influenced by reaction temperatures, the selectivity towards linalool required specific tuning of the porosity and surface morphology of catalysts. 43 The mechanism of linalool isomerization to geraniol or nerol occurred via similar six-membered ring intermediates due to the C = C double bond polarization and the increased electron density of the metal catalysts. Isomerization of linalool from geraniol is a complex reaction, due to further conversion to different products, such as β-pinene, nerol, the ocimenes and also citral.…”

Section: Synthe S Is Of Fr Ag R An Ce Molecule S Via Isomeriz Ationmentioning

confidence: 99%

“…Isomerization of linalool from geraniol is a complex reaction, due to further conversion to different products, such as β-pinene, nerol, the ocimenes and also citral. 43 In the isomerization of linalool to form geraniol, Beta-type zeolite with mesoporosity was preferred to enhance the accessibility of geraniol molecules. 44 Meanwhile, the…”

Section: Synthe S Is Of Fr Ag R An Ce Molecule S Via Isomeriz Ationmentioning

confidence: 99%

“…Isomerization of linalool was a reversible process, therefore, the kinetic of isomerization was influenced by the temperature of the reaction. Although the conversion was influenced by reaction temperatures, the selectivity towards linalool required specific tuning of the porosity and surface morphology of catalysts 43 . The mechanism of linalool isomerization to geraniol or nerol occurred via similar six‐membered ring intermediates due to the C = C double bond polarization and the increased electron density of the metal catalysts.…”

Section: Synthesis Of Fragrance Molecules Via Isomerizationmentioning

confidence: 99%

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Review on heterogeneous catalysts for the synthesis of perfumery chemicals via isomerization, acetalization and hydrogenation

Hartati

Firda

Bahruji

et al. 2021

Flavour & Fragrance J

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Synthetic fragrance has dominated the perfumery industry in recent decades due to the ability to produce perfumery ingredients on a large scale at a low cost. Extensive research in the field of synthetic perfumery chemical involved the utilization of catalysts to improve the productivity. This review will discuss recent advances of heterogeneous catalysts for the synthesis of perfumery chemicals as fragrance ingredients. Transition from homogeneous to heterogeneous catalysts will be included in order to provide insight into the benefits of heterogeneous catalysts to overcome the limitation of homogeneous reaction. Isomerization, acetalization and hydrogenation were identified as three main reactions for the synthesis of perfumery chemicals based on the number of reported work since 2000. This review will focus on α‐pinene and α‐pinene oxide as the main molecular substrates, however, different molecules, for example, linalool, citronellal and cinnamaldehyde will also be included. The synthesis, modification and possible mechanisms for the reactions involving zeolite, aluminosilicate, metal oxides, metal organic framework, monometallic and bimetallic nanoparticles as heterogeneous catalysts will be discussed. Discussion on isomerization and acetalization reactions will focus on the acidity and the porosity of the catalysts as the two main factors that determine the conversion and selectivity. For perfumery chemicals produced via hydrogenation reaction, the role of monometallic and bimetallic nanoparticles catalysts will be discussed in the chemoselective reduction of cinnamaldehyde and citronellal.

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“…Fajdek-Bieda et al [9] described the process of isomerization of geraniol using clay mineral-sepiolite as the catalyst. The research included the influence of such parameters as: temperature, catalyst content and reaction time.…”

Section: Introductionmentioning

confidence: 99%

Clinoptilolite as a natural, active zeolite catalyst for the chemical transformations of geraniol

Fajdek-Bieda

Wróblewska

Miądlicki

et al. 2021

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This work presented the studies with the natural zeolite—clinoptilolite as the catalyst for the isomerization of geraniol. During the research, it turned out that the studied process is much more complicated, and not only isomerization takes place in it, but also dehydration, oxidation, dimerization, cyclization and fragmentation of the carbon chain. Geraniol is an organic raw material which can be obtained not only by a chemical synthesis but also from plants (renewable biomass) by distillation or extraction method, for example a source of geraniol can be a plant—geranium. Before catalytic tests clinoptilolite was characterized by the instrumental methods, such as: XRD, porosity studies—nitrogen adsorption at 77 K, SEM, EDXRF, and FT-IR. Gas chromatography analyses showed that the main products of geraniol isomerization process were 6,11-dimethyl-2,6,10-dodecatrien-1-ol and thumbergol. The selectivity of 6,11-dimethyl-2,6,10-dodecatrien-1-ol and thumbergol depended on the temperature, catalyst content and reaction time. These parameters were changed in the following ranges: 80–150 °C (temperature), 5–15 wt% (catalyst content) and 15–1440 min. (reaction time). The most favorable conditions for 6,11-dimethyl-2,6,10-dodecatrien-1-ol and thumbergol obtaining were: temperature 140 ºC, catalyst content 12.5 wt% and reaction time 180 min. At these conditions, the conversion of geraniol amounted to 98 mol%, and the selectivities of 6,11-dimethyl-2,6,10-dodecatrien-1-ol and thumbergol amounted to 14 and 47 mol%, respectively.

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Influence of Technological Parameters on the Isomerization of Geraniol Using Sepiolite

Cited by 20 publications

References 22 publications

The isomerization of S-carvone over the natural clinoptilolite as the catalyst: the influence of reaction time, temperature and catalyst content

The isomerization of S-carvone over the natural clinoptilolite as the catalyst: the influence of reaction time, temperature and catalyst content

Review on heterogeneous catalysts for the synthesis of perfumery chemicals via isomerization, acetalization and hydrogenation

Clinoptilolite as a natural, active zeolite catalyst for the chemical transformations of geraniol

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