Biomimetic conversion of α-pinene with H2O2 to sobrerol over V2O5: Dihydroxylation by a peroxo vanadium peracid vectoring gentle synergistic oxidation

Liu, Qiang; Huang, Guohong; He, Huiting; Xu, Qiong; Li, Hui; Liu, Jian; Liu, Xianxiang; Mao, Liang; Kirk, Steven R.; Su, Shengpei; Yin, Daqiang

doi:10.1016/j.catcom.2020.106041

Cited by 6 publications

(4 citation statements)

References 33 publications

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“…Figure a reveals the UV–vis DRS spectra of the prepared catalysts. A distinct absorption band can be found at 425 nm, which can be designated as vanadium (V 5+ ) existing as VO 2 + in an acidic solution (pH ≤ 2). − The wide absorption range of FeV 3 O 8 nanorods can be extended to the visible-light region, indicating that it has a strong response to visible light. Normally, the band-gap energy of FeV 3 O 8 was computed using the typical Tauc equation α h ν = A ( h ν – E g ) n /2 , where α, ν, A , and E g are ascribed to the absorptance, light frequency, proportionality constant, and value of the band gap, respectively.…”

Section: Resultsmentioning

confidence: 99%

FeV₃O₈ Nanorods for Photodegrading Multiple Dyes

Lin

Huang

Zhao

et al. 2023

ACS Appl. Nano Mater.

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nanostructures have attracted considerable attention in the field of environmental purification and energy conversion. In this paper, 1D FeV 3 O 8 nanorods with 100 nm diameter and about 1 μm length were synthesized via a facile benign route without any surfactants. The crystal structure morphology and chemical composition of the samples were characterized by powder X-ray diffraction, fieldemission scanning electron microscopy, X-ray photoelectron spectroscopy, transmission electron microscopy, Brunauer−Emmett−Teller, and UV−vis and Raman spectroscopy. According to the results, the monoclinic phase of FeV 3 O 8 nanorods is a narrow band gap of 2.38 eV (HOMO, 0.81 eV; LUMO, −1.57 eV). The as-prepared FeV 3 O 8 nanorod has a large specific surface area of 20.006 m 2 g −1 . It could degrade 100% of Rhodamine B (RhB, 25 mg L −1 ) and 99% of Methylene blue (MB, 20 mg L −1 ) within 25 min and still can achieve 98% after four catalytic cycles, which is far better than a commercial TiO 2 catalyst (P25). A nucleation− nanoparticle−nanoflower−nanorod growth mechanism (4N mechanism) for the FeV 3 O 8 nanocrystals was proposed. Moreover, on the basis of the radical quenching and electron paramagnetic resonance tests, a possible photo-Fenton degradation mechanism was proposed. • OH was found to be the best active species during the degradation reactions. Results from this work show that the FeV 3 O 8 catalyst exhibited an excellent photocatalytic performance and durability toward the degradation of multiple organic pollutants in a neutral system.

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Section: Resultsmentioning

confidence: 99%

FeV₃O₈ Nanorods for Photodegrading Multiple Dyes

Lin

Huang

Zhao

et al. 2023

ACS Appl. Nano Mater.

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“…It is difficult to catalyze the conversion of αpinene in a solvent with small polarity such as dichloromethane or ethyl acetate, whose solubility in water is also poor so that it is also difficult to improve the reaction substrate H 2 O 2 transport to the catalytic active site in AC-COIMI-NH 4 PW. Unlike the isomerization of α-pinene, which might takes place in the presence of water or wet raw materials, over heterogeneous sol-gel Sn/SiO 2 or Ce/SiO 2 catalysts to give mainly sobrerol, using a weakly basic acetone as solvent [20], acetonitrile as a stronger basic solvent, in which the lone pair electrons on the nitrogen atom determine its Lewis basicity, is more conducive to selectively promote the tandem epoxidation-hydration of α-pinene and hydrogen peroxide aqueous solution on the surface of AC-COIMI-NH 4 PW to sobrerol, which essentially seems to be due to the dihydroxylation of α-pinene with H 2 O 2 in acetone by the soluble peroxo-vanadium acid as catalyst [25]. Notably, the allylic oxidation of α-pinene by oxygenfunctionalizing of C2 is promoted on [NH 4 PW] sites in several oxygenated solvents with ester or ether bonds.…”

Section: Solvent Modification Of Catalytic Performancementioning

confidence: 99%

“…Compared with the catalytic systems studied in the literature using α-pinene and hydrogen peroxide as raw materials, the reaction temperature is 25 • C by V 2 O 5 as catalyst [25], and the catalytic active species is peroxyvanadate, which is dissolved in the reaction system. The treatments of precipitation and washing are required at the end of the reaction, so the catalyst has no reusability, and its selectivity also is slightly lower than the nitrogen-doped activated-carbon-supported ammonium-phosphotungstate catalyst AC-COIMI-NH 4 PW in our this work.…”

Section: Comparison Of Catalytic Performance With the Literaturementioning

confidence: 99%

“…It was earlier found that sobrerol can be preciously obtained through biologically converting α-pinene by microorganism Armillariella mellea [24], which was incubated in 0.2% α-pinene for 4-5 days with a yield of sobrerol of 20%. Recently, interesting biomimetic catalytic dihydroxylation of α-pinene with H 2 O 2 to sobrerol in one pot was delivered by a water-soluble peroxo vanadium peracid under benign reaction conditions [25]. There are still no data given on the reuse of catalyst, the separation of the reaction mixture and the purification of the product sobrerol.…”

Section: Introductionmentioning

confidence: 99%

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Selective Catalytic Epoxidation–Hydration of α-Pinene with Hydrogen Peroxide to Sobrerol by Durable Ammonium Phosphotungstate Immobilized on Imidazolized Activated Carbon

Zheng

Xun

et al. 2023

Nanomaterials

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It is presented that the activated carbon was carboxylated with hydrogen peroxide and then acylated with 2-methylimidazole to prepare the porous carbon support with a surface imidazolated modification. Through the adsorption of phosphotungstic acid on the fundamental site of an imidazolyl group and then adjusting the acid strength with the ammonia molecule, a catalytic carbon material immobilized with ammonium phosphotungstate (AC-COIMO-NH4PW) was obtained, which was used to catalyze a one-pot reaction of convenient α-pinene and hydrogen peroxide to sobrerol. The bifunctional active site originated from the dual property of ammonium phosphotungstate, as the oxidant and acid presenting a cooperatively catalytic performance, which effectively catalyzes the tandem epoxidation–isomerization–hydration of α-pinene to sobrerol, in which the solvent effect of catalysis simultaneously exists. The sobrerol selectivity was significantly improved after the acid strength weakening by ammonia. Monomolecular chemical bonding and anchoring of ammonium phosphotungstate at the basic site prevented the loss of the active catalytic species, and the recovered catalyst showed excellent catalytic stability in reuse. Using acetonitrile as the solvent at 40℃ for 4 h, the conversion of α-pinene could reach 90.6%, and the selectivity of sobrerol was 40.5%. The results of five cycles show that the catalyst presents excellent stability due to the tight immobilization of ammonium phosphotungstate bonding on the imidazolized activated carbon, based on which a catalytic-cycle mechanism is proposed for the tandem reaction.

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Synthesis of 2,6‐Dimethoxy‐p‐aminophenol from Hardwood Lignin

Bai

Zhu

et al. 2023

ChemSusChem

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Although the multiple functional groups in biomass offer notable chances for producing high‐value chemicals, most of the current studies focused on the (deep) defunctionalization of biomass and its derivates. Herein, we present a catalytic approach to valorize birch wood lignin with maintaining the methoxy and hydroxy groups in the final product (i.e. 2,6‐dimethoxy‐p‐aminophenol), which has applications in different sectors such as pharmaceuticals. The proved approach involves four steps with a high yield (21.3wt% on the basis of used lignin) to 2,6‐dimethoxy‐p‐aminophenol. The native lignin in birch wood was first converted using alkaline aerobic oxidation in the presence of copper ions toward high‐yield syringaldehyde, which was then selectively oxidized toward 2,6‐dimethoxy‐1,4‐benzoquinone using H2O2 and V2O5. Oximation of 2,6‐dimethoxy‐1,4‐benzoquinone can selectively form 2,6‐dimethoxy‐1,4‐benzoquinone‐4‐oxime, which can be quantitatively hydrogenated toward 2,6‐dimethoxy‐p‐aminophenol. This work highlights the unique potential of biomass and its derivates for the sustainable production of high‐value products with exploring the value of inherent functional groups.

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Biomimetic conversion of α-pinene with H2O2 to sobrerol over V2O5: Dihydroxylation by a peroxo vanadium peracid vectoring gentle synergistic oxidation

Cited by 6 publications

References 33 publications

FeV₃O₈ Nanorods for Photodegrading Multiple Dyes

FeV₃O₈ Nanorods for Photodegrading Multiple Dyes

Selective Catalytic Epoxidation–Hydration of α-Pinene with Hydrogen Peroxide to Sobrerol by Durable Ammonium Phosphotungstate Immobilized on Imidazolized Activated Carbon

Synthesis of 2,6‐Dimethoxy‐p‐aminophenol from Hardwood Lignin

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Biomimetic conversion of α-pinene with H2O2 to sobrerol over V2O5: Dihydroxylation by a peroxo vanadium peracid vectoring gentle synergistic oxidation

Cited by 6 publications

References 33 publications

FeV3O8 Nanorods for Photodegrading Multiple Dyes

FeV3O8 Nanorods for Photodegrading Multiple Dyes

Selective Catalytic Epoxidation–Hydration of α-Pinene with Hydrogen Peroxide to Sobrerol by Durable Ammonium Phosphotungstate Immobilized on Imidazolized Activated Carbon

Synthesis of 2,6‐Dimethoxy‐p‐aminophenol from Hardwood Lignin

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FeV₃O₈ Nanorods for Photodegrading Multiple Dyes

FeV₃O₈ Nanorods for Photodegrading Multiple Dyes