The application of TS-1 materials with different titanium contents as catalysts for the autoxidation of α-pinene

Wróblewska, Agnieszka; Tołpa, Jadwiga; Kłosin, Dominika; Miądlicki, Piotr; Koren, Zvi; Michalkiewicz, Beata

doi:10.1016/j.micromeso.2020.110384

Cited by 17 publications

(11 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[ 6 ] Epoxidation of α‐pinene will provides α‐pinene oxide (APO), which can be further transformed into various chemicals like campholenic aldehyde (CA), trans ‐carveol (TC), trans ‐sobrerol, and trans ‐pinocarveol. [ 7,8 ]…”

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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

“…The catalysts obtained in this way were more active in the epoxidation of cyclohexene than TS-1 catalyst [4,5]. Another and very important way of modifying of titanium-silicate catalysts and increasing their activity can be also modification of TS-1 catalyst by the increasing the amount of titanium incorporated into the structure of titanium-silicate catalysts [6].…”

Section: Introductionmentioning

confidence: 94%

“…The TS-1 catalysts were obtained by the hydrothermal method, with different molar ratios of silicon to titanium in the crystallization gel, according to the method described in the literature [6]. The obtained catalysts were marked as: TS-1_1 (titanium content 9.92 wt%), TS-1_2 (titanium content 5.42 wt%), TS-1_3 (titanium content 3.39 wt%), TS-1_4 (titanium content 3.08 wt%).…”

Section: Synthesis Of Ts-1 Catalystsmentioning

confidence: 99%

“…Wróblewska et al [6] described the autoxidation of α-pinene on TS-1 catalysts with different titanium content. Originally, the α-pinene isomerization reaction was investigated.…”

Section: Introductionmentioning

confidence: 99%

“…Based on our results presented in the above-mentioned reference [6], we decided to check how the process of α-pinene oxidation would be affected by introducing the oxidant in the form of oxygen from the cylinder to the reaction environment-such studies on the oxidation of α-pinene have not been described in literature so far. Will it allow to increase the selectivity of the transformation to selected products and increase the conversion of α-pinene, which would be beneficial considering the separation of the post-reaction mixture into pure components (separation of products and their purification is very expensive with a large number of by-products)?…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The Studies on α-Pinene Oxidation over the TS-1. The Influence of the Temperature, Reaction Time, Titanium and Catalyst Content

et al. 2021

Self Cite

View full text Add to dashboard Cite

The work presents the results of studies on α-pinene oxidation over the TS-1 catalysts with different Ti content (in wt%): TS-1_1 (9.92), TS-1_2 (5.42), TS-1_3 (3.39) and TS-1_4 (3.08). No solvent was used in the oxidation studies, and molecular oxygen was used as the oxidizing agent. The effect of titanium content in the TS-1 catalyst, temperature, reaction time and amount of the catalyst in the reaction mixture on the conversion of α-pinene and the selectivities of appropriate products was investigated. It was found that it is most advantageous to carry out the process of α-pinene oxidation in the presence of the TS-1 catalyst with the titanium content of 5.42 wt% (TS-1_2), at the temperature of 85 °C, for 6 h and with the catalyst TS-1 content in the reaction mixture of 1 wt%. Under these conditions the conversion of α-pinene amounted to 34 mol%, and the selectivities of main products of α-pinene oxidation process were: α-pinene oxide (29 mol%), verbenol (15 mol%) and verbenone (12 mol%). In smaller quantities also campholenic aldehyde, trans-pinocarveol, myrtenal, myrtenol, L-carveol, carvone and 1,2-pinanediol were also formed. These products are of great practical importance in food, cosmetics, perfumery and medicine industries. Kinetic studies were also performed for the studied process.

show abstract

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

Naikwadi,

Dabas,

Ravi

et al. 2023

Advanced Sustainable Systems

View full text Add to dashboard Cite

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.

show abstract

The application of TS-1 materials with different titanium contents as catalysts for the autoxidation of α-pinene

Cited by 17 publications

References 43 publications

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

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

The Studies on α-Pinene Oxidation over the TS-1. The Influence of the Temperature, Reaction Time, Titanium and Catalyst Content

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

Contact Info

Product

Resources

About