The effect of the distance between acidic site and basic site immobilized on mesoporous solid on the activity in catalyzing aldol condensation

Yu, Xiaofang; Yu, Xiaobo; Wu, Shujie; Liao, Bo; Liu, Heng; Guan, Jingqi; Kan, Qiubin

doi:10.1016/j.jssc.2010.11.007

Cited by 34 publications

(24 citation statements)

References 40 publications

(49 reference statements)

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“…The distance between the amine and carboxylic acid was recently controlled through amide coupling of lysine onto an organosilane, as shown in Scheme 6 [85]. Lysine has two amines with a different number of carbons between the carboxylic acid and amine (i.e., one and five).…”

Section: Heterogeneous -Acid-base Pairingmentioning

confidence: 99%

Tuning acid–base cooperativity to create next generation silica-supported organocatalysts

Brunelli

Jones

2013

Journal of Catalysis

127

168

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Section: Heterogeneous -Acid-base Pairingmentioning

confidence: 99%

Tuning acid–base cooperativity to create next generation silica-supported organocatalysts

Brunelli

Jones

2013

Journal of Catalysis

127

168

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“…Therefore, optimization of heterogeneous catalysts is often performed by selection or design of supports rather than by modifying the structure of the catalytic groups. [2][3][4][5] In addition, homogeneous catalysts typically exhibit superior selectivity and kinetics. Despite these disadvantages, heterogeneous catalysts are valued because they allow easy separation of products and can be reused for extended periods of time.…”

Section: Introductionmentioning

confidence: 99%

Substrate inhibition in the heterogeneous catalyzed aldol condensation: A mechanistic study of supported organocatalysts

Kandel

Althaus

Peeraphatdit

et al. 2012

Journal of Catalysis

137

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In this study, we demonstrate how materials science can be combined with the established methods of organic chemistry to find mechanistic bottlenecks and redesign heterogeneous catalysts for improved performance. By using solid-state NMR, infrared spectroscopy, surface and kinetic analysis, we prove the existence of a substrate inhibition in the aldol condensation catalyzed by heterogeneous amines. We show that modifying the structure of the supported amines according to the proposed mechanism dramatically enhances the activity of the heterogeneous catalyst. We also provide evidence that the reaction benefits significantly from the surface chemistry of the silica support, which plays the role of a co-catalyst, giving activities up to two orders of magnitude larger than those of homogeneous amines. This study confirms that the optimization of a heterogeneous catalyst depends as much on obtaining organic mechanistic information as it does on controlling the structure of the support. Disciplines Materials Chemistry | Other Chemistry | Physical ChemistryComments NOTICE: this is the author's version of a work that was accepted for publication in Journal of Catalysis. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Catalysis, [291, (2012) AbstractIn this study we demonstrate how materials science can be combined with the established methods of organic chemistry to find mechanistic bottlenecks and redesign heterogeneous catalysts for improved performance. By using solid-state NMR, infrared spectroscopy, surface and kinetic analysis, we prove the existence of a substrate inhibition in the aldol condensation catalyzed by heterogeneous amines. We show that modifying the structure of the supported amines according to the proposed mechanism dramatically enhances the activity of the heterogeneous catalyst. We also provide evidence that the reaction benefits significantly from the surface chemistry of the silica support, which plays the role of a co-catalyst, giving activities up to two orders of magnitude larger than those of homogeneous amines. This study confirms that the optimization of a heterogeneous catalyst depends as much on obtaining organic mechanistic information as it does on controlling the structure of the support.

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“…7, the complexation was clearly indicated by the distinctive absorbance peaks at 1726 cm -1 and 1554 cm -1 . The former wavenumber indicates the presence of -COOH, whereas the latter the formation of -COO --N + bond [9]. These peaks disappeared completely after washing with 0.1 M HCl solution.…”

Section: Key and Lock Behavior Of Pore Windowmentioning

confidence: 96%

“…In particular, a great deal of effort has been made to functionalize ordered mesoporous silica materials (OMS) with various organic functional groups because hybridization of OMS with organic groups could offer remarkable new properties and multifunctional nature [5][6][7][8][9][10]. It is also known that organic groups could be tailored topographically as well as multiply [11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Fabrication of pore window in ordered mesoporous silica by spatial control of functional groups

Park¹,

Kim²,

Shim³

2014

Chemical Engineering Journal

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The effect of the distance between acidic site and basic site immobilized on mesoporous solid on the activity in catalyzing aldol condensation

Cited by 34 publications

References 40 publications

Tuning acid–base cooperativity to create next generation silica-supported organocatalysts

Tuning acid–base cooperativity to create next generation silica-supported organocatalysts

Substrate inhibition in the heterogeneous catalyzed aldol condensation: A mechanistic study of supported organocatalysts

Fabrication of pore window in ordered mesoporous silica by spatial control of functional groups

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