Monoglyceride Synthesis by Heterogeneous Catalysis Using MCM-41 Type Silicas Functionalized with Amino Groups

Cauvel, Anne; Renard, Gilbert; Brunel, Daniel

doi:10.1021/jo9614001

Cited by 343 publications

(178 citation statements)

References 14 publications

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“…[15][16][17][18][19] Recently, the heterogenization of organic bases has become an interesting subject owing to a variety of basic compounds showing unusual performance for different catalytic reactions. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] For example, amino-functionalized mesoporous materials have attracted much attention for their wide applications in Knoevenagel condensation, aldol reaction, nitroaldol reaction, Michael additions, and epoxide ring-opening reactions. [27][28][29][30][31][32][33] Notably, it was reported that some amino-functionalized materials were efficient catalysts for the transesterification reactions of esters (i.e., ethylene carbonate, diethylmalonate and β-ketoester) with alcohols.…”

Section: Introductionmentioning

confidence: 99%

“…[20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] For example, amino-functionalized mesoporous materials have attracted much attention for their wide applications in Knoevenagel condensation, aldol reaction, nitroaldol reaction, Michael additions, and epoxide ring-opening reactions. [27][28][29][30][31][32][33] Notably, it was reported that some amino-functionalized materials were efficient catalysts for the transesterification reactions of esters (i.e., ethylene carbonate, diethylmalonate and β-ketoester) with alcohols. [34][35][36][37] During the past few years, our group has also carried out some work on developing novel heterogeneous catalysts for the transesterification of phenol with DMO, 15,18,38 and we just reported recently that cyclopentadienylfunctionalized mesoporous MCM-41 materials bearing weak basic sites were active catalysts for this reaction.…”

Section: Introductionmentioning

confidence: 99%

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Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Liu¹,

Zhao²,

Zhu³

et al. 2010

J. Braz. Chem. Soc.

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Uma série de materiais híbridos mesoporos MCM-41, contendo diferentes grupos amino (como 3-aminopropila (AP-), (2-aminoetilamino)propila (AAP-), ou [2-(2-aminoetilamino) etilamino]propila (AEP-)) foi preparada pelo método de pós-enxertia e caracterizada por difração de raio X de pó (XRD), adsorção de N 2 , espectroscopia de infravermelho com transformada de Fourier (FT-IR) e dessorção de CO 2 com temperatura controlada (CO 2 -TPD). As propriedades catalíticas destes materiais híbridos para a reação de transesterificação de dimetil oxalato com fenol foram investigadas. Verificou-se que todos são ativos, particularmente o AEP-MCM-41, que apresentou a maior atividade dentre eles. Apenas um pequeno decréscimo na atividade foi observado após vários ensaios catalíticos sucessivos utilizando o mesmo catalisador, indicando uma boa reciclabilidade do mesmo. Notavelmente, a atividade do catalisador pode ser regenerado por simples tratamento com base, sob condições brandas. Além disso, os efeitos da densidade e da força básica dos grupos amino sobre as propriedades catalíticas foram exploradas na proposição do mecanismo de reação, incluindo a provável rota que leva à formação do subproduto anisol.A series of hybrid mesoporous MCM-41 materials containing different amino groups (such as 3-aminopropyl (AP-), (2-aminoethylamino)propyl (AAP-), or [2-(2-aminoethylamino)ethylamino] propyl (AEP-) group) were prepared by a post-grafting method, and characterized by means of X-ray powder diffraction (XRD), N 2 adsorption, Fourier transform-infrared spectroscopy (FT-IR) and temperature-programmed desorption of CO 2 (CO 2 -TPD). The catalytic properties of these hybrid materials were investigated for the transesterification of dimethyl oxalate with phenol. All the samples were active for the transesterification. Among them, the sample AEP-MCM-41 exhibited the highest activity under test conditions. And only a slight decrease in activity could be observed after few runs, indicating the good recyclability of this catalyst. Notably, the activity of the used catalyst could be regenerated by simple treatment with diluted basic agents under mild conditions. Moreover, effects of the density and the basic strength of the amino groups on the catalytic properties were taken into consideration for understanding the reaction mechanism and the possible formation route of the by-product anisole.Keywords: amino-functionalized, MCM-41, dimethyl oxalate, transesterification, recyclability IntroductionDiphenyl carbonate (DPC) is an industrially important intermediate for the production of several organic chemicals, especially as the precursor for the synthesis of polycarbonates (PCs), which have been used in many fields due to excellent mechanical, optical, electrical and heatresistance properties. 1,2 So far, various approaches for DPC synthesis have been reported, including phosgene route, oxidative carbonylation of phenol and transesterification reaction. 1,[3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Among them, transesterification...

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Liu¹,

Zhao²,

Zhu³

et al. 2010

J. Braz. Chem. Soc.

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“…We report herein the preparation of two different organic bases anchored on silica gel (KG-NEt 2 and KG-TBD - Figure 1) pivoting on literature procedures [23][24] and their use as catalysts in the reaction between an α,β-unsaturated compound and an active methylene reagent. Remarkably, it is possible to steer the selectivity towards either mono-alkylated products 3 or bis-alkylated adducts 4 depending on the strength of the basic catalyst (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Triethylamine and TBD supported on silica: useful heterogeneous catalysts for the reaction of β-dicarbonyl derivatives with α,β-unsaturated compounds under batch and continuous flow conditions

Maggi¹,

Piscopo²,

Maestri³

2015

Arkivoc

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The synthesis of either mono-or bis-adducts via Michael reaction between active methylene compounds and α,β-unsaturated reagents is reported. These processes are catalyzed by two heterogeneous basic catalysts, namely KG-NEt 2 and KG-TBD. Both catalysts show good catalytic efficiency and can be reused several times fully preserving their efficiency. The process could be efficiently performed under continuous flow conditions obtaining promising results in term of yield and selectivity.

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“…Com relação à síntese de MCM-41 contendo metais, vários métodos são descritos na literatura e esses materiais são utilizados principalmente como catalisadores em diversos tipos de reações (Cauvel et al, 1997;Corma et al, 1997). Outro material de particular interesse é a peneira molecular Al-MCM-41 [Naik et al, 2010] a qual apresenta propriedades bastante distintas tais como suas propriedades ácido-base, a relação entre o tamanho dos poros e o conteúdo de Al e a estabilidade térmica.…”

Section: Introductionunclassified

Síntese E Caracterização De Peneiras Moleculares Mesoporosas

Salvia

Valença²,

Anjos³

2015

Anais Do XX Congresso Brasileiro De Engenharia Química

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RESUMO -No início dos anos 90, cientistas da Mobil Oil Corporation sintetizaram um material com estrutura mesoporosa ordenada, chamada MCM-41. Peneiras moleculares mesoporosas, do tipo MCM-41 foram preparadas com e sem a adição de alumínio estrutural e posteriormente foram caracterizadas por Fisissorção de N 2 , DRX, RMN, TPD-NH 3 , Quimissorção de CO 2 , AAS e TGA. As técnicas analíticas comprovaram a correta adição do metal, ou seja, o alumínio foi incorporado à rede de sílica e também apresentaram propriedades típicas de sólidos do tipo MCM-41. As peneiras moleculares apresentaram área superficial e fases típicas desse tipo de material. A quantidade de sítios ácidos e básicos aumentou com a introdução e com o aumento do Al estrutural.

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Monoglyceride Synthesis by Heterogeneous Catalysis Using MCM-41 Type Silicas Functionalized with Amino Groups

Cited by 343 publications

References 14 publications

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Comparative study on the catalytic properties of amino-functionalized silica materials for the transesterification of dimethyl oxalate with phenol

Triethylamine and TBD supported on silica: useful heterogeneous catalysts for the reaction of β-dicarbonyl derivatives with α,β-unsaturated compounds under batch and continuous flow conditions

Síntese E Caracterização De Peneiras Moleculares Mesoporosas

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