Acidic properties of sulfonic acid-functionalized FSM-16 mesoporous silica and its catalytic efficiency for acetalization of carbonyl compounds

Shimizu, Ken‐ichi; Hayashi, Eidai; Hatamachi, Tsuyoshi; Kodama, Tetsuya; Higuchi, Tomoya; Satsuma, Atsushi; Kitayama, Yoshie

doi:10.1016/j.jcat.2005.01.017

Cited by 97 publications

(69 citation statements)

References 24 publications

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“…They conclude that the number of acid sites per gram of the catalyst is not necessarily for acetal formation and the high activity of the silica should be due the strong Brønsted acid sites inside the mesopore and higher specific areas. 27 In this work the higher performance of niobium phosphate compared with Amberlyst 35 could be due to the acid strength of the Brønsted acid sites and the higher specific area of the former in accordance with the results reported by Shimizu et al 27 …”

Section: Acetalization Reaction Catalyzed By Niobium Phosphatesupporting

confidence: 89%

“…The protonation of the oxygen atom on the carbonyl group by an acidic site from the catalytic surface of niobium 25 The ion exchange resin present lower acid strength (H 0 ≤ 2.2). 26 Shimizu et al, 27 studied the acetalization of different carbonyl compounds with ethylene glycol over solids acids. They compared the catalytic activity of zeolites, clay, sulfonic acid functionalized mesoporous silica and the sulfonic resin Amberlyst 15.…”

Section: Acetalization Reaction Catalyzed By Niobium Phosphatementioning

confidence: 99%

See 1 more Smart Citation

Acetalization of hexanal with 2-ethyl hexanol catalyzed by solid acids

Barros

Faísca

Lachter

et al. 2011

J. Braz. Chem. Soc.

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A atividade catalítica de sólidos ácidos como o fosfato de nióbio e a Amberlyst 35, uma resina trocadora de íons, foi avaliada na acetalização do hexanal com 2-etil-hexanol. Foram avaliadas a concentração do catalisador e a temperatura de reação na conversão do hexanal. A possibilidade de re-utilização do fosfato de nióbio também foi estudada e evidenciou ser possível re-utilizar este catalisador sem perda da atividade. O rendimento em acetal foi acima de 90% em condições brandas de reação.The catalyst activity of solid acids such as niobium phosphate and Amberlyst 35, an ion exchange resin, was evaluated in the acetalization of hexanal with 2-ethyl-hexanol. The catalyst loading and the reaction temperature were evaluated in the hexanal conversions. The possibility of recycling niobium phosphate was also studied, showing that it was possible to reuse this catalyst without significant loss in its catalytic activity. The yield in acetal was above 90% under mild conditions.

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Section: Acetalization Reaction Catalyzed By Niobium Phosphatesupporting

confidence: 89%

Section: Acetalization Reaction Catalyzed By Niobium Phosphatementioning

confidence: 99%

Acetalization of hexanal with 2-ethyl hexanol catalyzed by solid acids

Barros

Faísca

Lachter

et al. 2011

J. Braz. Chem. Soc.

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“…1.0 µmol/m 2 . Such high initial heats are comparable to that exhibited by the sulpho group anchored to FSM-16 (Shimizu et al 2005). The initial heat of adsorption of C16-MS-SO 3 H-30% was not as great as those of C16-MS-SO 3 H-10 and C16-MS-SO 3 H-20%, but heat evolution persisted to higher adsorbed amounts due to the larger amounts of sulpho groups contained in this sample.…”

Section: Ammonia Adsorptionsupporting

confidence: 56%

Preparation and Characterization of Sulpho-Functionalized Ordered Mesoporous Silica

Yeoh

Matsumoto

Iwase

et al. 2008

Adsorption Science & Technology

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Sulpho groups have been successfully embedded in mesoporous silica with an ordered two-dimensional hexagonal structure. The sulpho-functionalized mesoporous silica was prepared by the oxidation of a thiol-functionalized mesoporous silica which was obtained via the hydrolysis and co-condensation of tetramethoxysilane (TMOS) and mercaptopropyl trimethoxysilane (MPTMS). The samples exhibited an ordered two-dimensional hexagonal pore array up to 30 mol% MPTMS loading. The large surface area of MCM-41 (ca. 1000 m 2 /g) was maintained after incorporation of the mercaptopropyl group and oxidation of its thiol group. Solid-state 29 Si NMR spectra showed the existence a mercaptopropyl group in a silica framework and 13 C NMR studies further proved that treatment with hydrogen peroxide led to oxidation of the sulpho groups. High ammonia uptakes with high differential heats of adsorption revealed the strong acidity of sulpho-functionalized mesoporous silica. The amounts of acid sites may be controlled by regulating the amount of MPTMS employed in the synthesis. The sulpho-functionalized mesoporous silica behaved as an acid catalysis for the isomerization reaction of but-1-ene to cis-and trans-but-2-ene.

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“…Of particular interest for this work, both SiO 2 -SO 3 H 8 and SiO 2 -CH 2 -CH 2 -CH 2 -SO 3 H 6 have been used with success for ketalization reactions using conventional heating with reaction times extending up to 12 h. An example involves the preparation of the cyclohexanone ketal in 90% yield using toluene as the solvent and heating at reflux temperature for 3 h. 6 The same reaction was performed using SiO 2 -SO 3 H as the catalyst in the absence of solvent under low microwave irradiation power (360 W). The temperature of the slurry did not exceed 73 ºC, and a 99.9% yield was obtained in only 2 min (entry 1 in Table 1).…”

Section: General Remarksmentioning

confidence: 99%

“…5 This method is also a form of diminishing the hydrophilicity of the catalyst. 6 We recently developed a mesoporous, sulfonated silica as a Brønsted acid, whose high hydrophilicity made it ideal for the catalysis of waterforming, proton-assisted organic transformations, such as the formation of ethers from alcohols and the esterification of acids with alcohols, equations 1 and 2. 7 SiO 2 -SO 3 H 8 and SiO 2 -(CH 2 ) 3 -SO 3 H 6 have been reported to catalyze ketal formation from ketones and ethylene glycol, which is also a water-forming reaction involving the equilibrium shown in equation 3.…”

Section: Introductionmentioning

confidence: 99%

Ketalization of Ketones to 1,3-Dioxolanes and Concurring Self-Aldolization Catalyzed by an Amorphous, Hydrophilic SiO2-SO3H Catalyst under Microwave Irradiation

Barbosa¹,

Ottone²,

Almeida³

et al. 2018

J. Braz. Chem. Soc.

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The amorphous, mesoporous SiO 2 -SO 3 H catalyst with a surface area of 115 m 2 g -1 and 1.32 mmol H + per g was very efficient for the protonation of ketones on a 10% (m/m) basis, and the catalyst-bound intermediates can be trapped by polyalcohols to produce ketals in high yields or suffer aldol condensations within minutes under low-power microwave irradiation. The same catalyst can easily reverse the ketalization reaction.

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Acidic properties of sulfonic acid-functionalized FSM-16 mesoporous silica and its catalytic efficiency for acetalization of carbonyl compounds

Cited by 97 publications

References 24 publications

Acetalization of hexanal with 2-ethyl hexanol catalyzed by solid acids

Acetalization of hexanal with 2-ethyl hexanol catalyzed by solid acids

Preparation and Characterization of Sulpho-Functionalized Ordered Mesoporous Silica

Ketalization of Ketones to 1,3-Dioxolanes and Concurring Self-Aldolization Catalyzed by an Amorphous, Hydrophilic SiO2-SO3H Catalyst under Microwave Irradiation

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