Phosphotungstic acid impregnated niobium coated superparamagnetic iron oxide nanoparticles as recyclable catalyst for selective isomerization of terpenes

Name, Luccas L.; Toma, Sérgio Hiroshi; Nogueira, Helton P.; Avanzi, Luis Humberto; Pereira, Rafael dos Santos; Ferreira, Luis Fernando Peffi; Araki, Koji; Cella, Rodrigo; Toyama, Marcos Makoto

doi:10.1039/d1ra00012h

Cited by 9 publications

(2 citation statements)

References 55 publications

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“…It is worth to notice that the conversion observed with the capsule was comparable to that what was frequently observed with typical heterogeneous Lewis or Brønsted catalysts under harsher experimental conditions with T higher than 100 °C in the gas phase [ 61 ]. More importantly, the product distribution observed is rather unusual if compared to many other heterogeneous catalytic systems known in the literature for leading to higher selectivity for camphene [ 62 – 66 ], and less likely to comparable amounts of camphene and limonene [ 67 – 68 ]. The preferential formation of limonene, which compared to camphene is a much more valuable product, has been less frequently observed, for instance in the case of heteropolyacids on SBA-15 [ 69 ].…”

Section: Resultsmentioning

confidence: 86%

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

Lorenzetto¹,

Fabris²,

Scarso³

2022

Beilstein J. Org. Chem.

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The hexameric resorcin[4]arene capsule as a self-assembled organocatalyst promotes a series of reactions like the carbonyl–ene cyclization of (S)-citronellal preferentially to isopulegol, the water elimination from 1,1-diphenylethanol, the isomerization of α-pinene and β-pinene preferentially to limonene and minor amounts of camphene. The role of the supramolecular catalyst consists in promoting the protonation of the substrates leading to the formation of cationic intermediates that are stabilized within the cavity with consequent peculiar features in terms of acceleration and product selectivity. In all cases the catalytic activity displayed by the hexameric capsule is remarkable if compared to many other strong Brønsted or Lewis acids.

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Section: Resultsmentioning

confidence: 86%

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

Lorenzetto¹,

Fabris²,

Scarso³

2022

Beilstein J. Org. Chem.

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“…Other uses are in [3+2+2] cycloaddition [19] and ring-opening polymerization of epoxidized soybean oil. [20] In the context of our ongoing efforts to transform biomass turpentine into valuable chemicals [21][22][23], HSbF 6 was used as catalyst for the direct esterification of turpentine oil with acetic acid as reactant and solvent. Herein, it is shown that this superacid can greatly improve the reaction rate, due to its high acidity, providing excellent conversion and selectivity of the product of interest, i.e., the fraction of terpenyl acetate formed in relation to the total products.…”

Section: Introductionmentioning

confidence: 99%

Superacid Catalysis: Direct Esterification of Turpentine Oil with Acetic Acid

et al. 2022

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Terpenyl acetate, which is used for the production of flavors and fragrances, is industrially prepared from turpentine oil in a two‐step process including hydration and catalytic esterification. Such processes have several shortcomings like too‐large amounts of catalysts, non‐recyclability of catalysts, long reaction times, and serious environmental pollution. Here, a direct one‐step synthesis of terpenyl acetate from a feed mixture of turpentine oil and acetic acid with fluoroantimonic acid as superacid catalyst is described. Only 0.2 mol % of catalyst is necessary for up to 96 % conversion of starting material at room temperature. The desired product was obtained with a selectivity of up to 60 %. Thus, a clean and environmentally friendly strategy for synthesizing α‐terpenyl acetate is provided.

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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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Phosphotungstic acid impregnated niobium coated superparamagnetic iron oxide nanoparticles as recyclable catalyst for selective isomerization of terpenes

Abstract: Conversion efficiency as high as 80–100% and 50% selectivity for camphene and limonene was achieved with low production of polymeric byproducts (18–28%), using a new magnetically recyclable catalyst – SPION-Nb30@HPW.

Cited by 9 publications

References 55 publications

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

Superacid Catalysis: Direct Esterification of Turpentine Oil with Acetic Acid

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

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