The Isomerization of Limonene over the Ti-SBA-15 Catalyst—The Influence of Reaction Time, Temperature, and Catalyst Content

Retajczyk, Monika; Wróblewska, Agnieszka

doi:10.3390/catal7090273

Cited by 19 publications

(13 citation statements)

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“…In addition, the yields of the two main isomerization products (terpinolene and pcymene) are similar in the reaction time range studied up to a duration of 4 hours of the process of isomerization ( Figure 6). Extending the time of isomerization causes the differences in p-cymene In our previous studies on the isomerization of limonene, Ti-SBA-15 was used as the catalyst [15]. In the case of the isomerization of limonene carried out over the Ti-SBA-15 catalyst, the main reaction products were α-terpinene and p-cymene.…”

Section: Resultsmentioning

confidence: 99%

“…At the same temperature (160 • C), at the same catalyst content (15 wt%), and after 23 h of the process of limonene performing, the yield of p-cymene was 29 mol% and at the conversion of limonene amounted to 92 mol%, and 56 mol% and at the conversion of limonene amounted to 99 mol%, for Ti-MCM-41 and Ti-SBA-15, respectively. In our previous studies on the isomerization of limonene, Ti-SBA-15 was used as the catalyst [15]. In the case of the isomerization of limonene carried out over the Ti-SBA-15 catalyst, the main reaction products were α-terpinene and p-cymene.…”

Section: Resultsmentioning

confidence: 99%

“…The studies on the influence of reaction time, temperature and Ti-MCM-41 catalyst content on the course of limonene isomerization were performed according to the method showed in our last article [15]. Limonene isomerization's were carried out in a glass reactor with a capacity of 25 cm 3 .…”

Section: The Methods Of the Isomerization Of Limonene Over The Ti-mcm-mentioning

confidence: 99%

“…The conditions under which the highest yield of p-cymene, the product that forms in the follow-up reactions of the primary products of the limonene isomerization process, were also determined. An additional goal of the study was to compare the results obtained on the Ti-MCM-41 catalyst with the results previously described by us for the Ti-SBA-15 catalyst [15]. Both catalysts are titanium-silicate mesoporous catalysts.…”

Section: Introductionmentioning

confidence: 96%

“…The products of this reaction are valuable compounds such as gamma-terpinene, alpha-terpinene and terpinolene. Extending the reaction time also allows the obtaining of p-cymene (dehydroaromatization product formed from limonene isomers) [15]. The advantage of carrying out the R(+)-limonene isomerization process in the presence of titanium-silicate catalysts is that it is carried out without the use of organic solvents and without the need for waste disposal, which is indispensable in the traditional method of obtaining p-cymene by Friedel-Crafts reaction of toluene with isopropene [25].p-cymene is used as a perfume additive for musky perfumes, as well as a masking fragrance in soaps [24].…”

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Isomerization and Dehydroaromatization of R(+)-Limonene Over the Ti-MCM-41 Catalyst: Effect of Temperature, Reaction Time and Catalyst Content on Product Yield

Retajczyk

Wróblewska

2019

Catalysts

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This work describes research on the isomerization of R(+)-limonene over the Ti-MCM-41 catalyst. The studies showed that the Ti-MCM-41 catalyst is an active catalyst in the isomerization of R(+)-limonene. As a result of the isomerization of this compound, it is possible to obtain α-terpinene, γ-terpinene, terpinolene and p-cymene. Terpinolene is the main product of this process, and p-cymene is formed by the alpha-terpinene, gamma-terpinene and terpinolene dehydrogenation. The aforementioned products are of great practical importance. The most favorable reaction conditions leading to the obtaining of limonene isomerization products is the use of the catalyst in an amount of 15 wt% and the temperature of 160 • C. Depending on whether the desired products are the isomers of limonene (γ-terpinene, α-terpinene and terpinolene) or the product of their dehydroaromatization (β-cymene), it is possible to shorten or extend the reaction time. The method for the isomerization of limonene on the Ti-MCM-41 catalyst makes it possible to obtain a significant yield of both the limonene and p-cymene isomers. Longer reaction time is conducive to obtain larger quantities of other reaction products and less desirable products that constitute impurities (oxidized products and polymeric compounds).Currently, among the mesoporous titanium-silicate catalysts, great attention is paid to the Ti-MCM-41 catalyst. This catalyst can be obtained in a simple way. 1) By the hydrothermal method, crystallization of Ti-MCM-41 in the autoclave from the crystallization gel, 2) by the direct precipitation of Ti-MCM-41 from the crystallization gel at ambient temperature without the crystallization in the autoclave, or 3) by the impregnation of the previously obtained MCM-41 structure with an appropriate titanium source [3]. The first two methods allow the introduction of titanium to the entire catalyst structure (including the pores), while the third method allows the introduction of titanium, only on the surface of this material [4].Materials with MCM-41 structure (including Ti-MCM-41) are mesoporous materials having an ordered, two-dimensional structure with hexagonal pores. The MCM-41 structure resembles a honeycomb. These materials have a narrow pore size distribution (1.8 to 10 nm) that have p6mm symmetry. The size of the pores depends on the synthesis conditions, the composition of the crystallization gel, as well as on the length of alkyl chains of the surfactant used in the synthesis. The specific surface area of these materials is well developed and exceeds 1000 m 2 /g. These types of materials have walls with a thickness of 1 nm, which are made of amorphous silica, and their structure is characterized by a close-range order [5][6][7][8][9]. Thanks to this structure, Ti-MCM-41 materials are used as effective catalysts in the processes of epoxidation, oxidation and isomerization of olefins, e.g., allylic compounds (allyl alcohol [10], diallyl ether [11], allyl-glycidyl ether [12], and allyl chloride [13]) or olefins of natural origin (limonene [...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: The Methods Of the Isomerization Of Limonene Over The Ti-mcm-mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

mentioning

confidence: 99%

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Isomerization and Dehydroaromatization of R(+)-Limonene Over the Ti-MCM-41 Catalyst: Effect of Temperature, Reaction Time and Catalyst Content on Product Yield

Retajczyk

Wróblewska

2019

Catalysts

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Heterogeneous catalyzed isomerization of turpentine oil by ordered mesoporous materials like M41S structures

et al. 2022

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Herein, the synthesis of a structure with a porous system similar to that of molecular sieves, MCM‐41 and 48 types, with the incorporation of heteroatoms in their synthesis, is reported. The catalytic activity of these materials was tested in the isomerization reaction of turpentine oil to obtain camphene. The best results were obtained with Zn‐Al‐Si‐MCM, a mesoporous material, with a conversion of up to 96% and selectivities of 31% and 22% to camphene and 4‐carene, respectively, both of which are bicyclic products. The recycling of the catalyst was also tested, and after three cycles, no significant loss of activity was observed.

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Transformation of dl Limonene into Aromatic Compounds Using Supported Heteropolyacid Catalysts

et al. 2018

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The Isomerization of Limonene over the Ti-SBA-15 Catalyst—The Influence of Reaction Time, Temperature, and Catalyst Content

Cited by 19 publications

References 32 publications

Isomerization and Dehydroaromatization of R(+)-Limonene Over the Ti-MCM-41 Catalyst: Effect of Temperature, Reaction Time and Catalyst Content on Product Yield

Isomerization and Dehydroaromatization of R(+)-Limonene Over the Ti-MCM-41 Catalyst: Effect of Temperature, Reaction Time and Catalyst Content on Product Yield

Heterogeneous catalyzed isomerization of turpentine oil by ordered mesoporous materials like M41S structures

Transformation of dl Limonene into Aromatic Compounds Using Supported Heteropolyacid Catalysts

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