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Statements

Subject Item
n2:RIV%2F61388955%3A_____%2F13%3A00392934%21RIV14-GA0-61388955
rdf:type
skos:Concept n8:Vysledek
dcterms:description
In the present study we have selected three different condensation reactions as model reactions, namely the hydroxylalkylation of anisole by paraformaldehyde to bis(methoxyphenyl)- methane, the Pechmann condensation of phenols with ethyl acetoacetate (EAA) to coumarins and the Knoevenagel condensation of two aldehydes with three active methylene compounds to form a,b-unsaturated esters and nitriles, using two related Fe-containing metal–organic frameworks (MOFs), namely commercial Fe(BTC) (BTC: 1,3,5-benzenetricarboxylate) and synthetic MIL-100(Fe) as the catalysts. The main aim of this study was to determine the nature of the poisons, the MOF structural stability in connection with the substrate, and the variations in the product selectivity. We have found that undesired intermediates (bisarylmethyl cation in the case of hydroxyalkylation) or byproducts (benzoic acid in the case of Knoevenagel condensation) can poison the MOF by being strongly adsorbed within the MOFs and blocking the pores. In the Pechmann condensation, besides pore blocking, a low structural stability of Fe(BTC) was reflected in the collapse of the crystal structure, while using polyhydroxy aromatic compounds because of their ability to act as ligands for Fe3+, replacing trimesate ligand. MIL-100(Fe) was considerably more robust for this reaction. In the present study we have selected three different condensation reactions as model reactions, namely the hydroxylalkylation of anisole by paraformaldehyde to bis(methoxyphenyl)- methane, the Pechmann condensation of phenols with ethyl acetoacetate (EAA) to coumarins and the Knoevenagel condensation of two aldehydes with three active methylene compounds to form a,b-unsaturated esters and nitriles, using two related Fe-containing metal–organic frameworks (MOFs), namely commercial Fe(BTC) (BTC: 1,3,5-benzenetricarboxylate) and synthetic MIL-100(Fe) as the catalysts. The main aim of this study was to determine the nature of the poisons, the MOF structural stability in connection with the substrate, and the variations in the product selectivity. We have found that undesired intermediates (bisarylmethyl cation in the case of hydroxyalkylation) or byproducts (benzoic acid in the case of Knoevenagel condensation) can poison the MOF by being strongly adsorbed within the MOFs and blocking the pores. In the Pechmann condensation, besides pore blocking, a low structural stability of Fe(BTC) was reflected in the collapse of the crystal structure, while using polyhydroxy aromatic compounds because of their ability to act as ligands for Fe3+, replacing trimesate ligand. MIL-100(Fe) was considerably more robust for this reaction.
dcterms:title
Deactivation Pathways of the Catalytic Activity of Metal– Organic Frameworks in Condensation Reactions Deactivation Pathways of the Catalytic Activity of Metal– Organic Frameworks in Condensation Reactions
skos:prefLabel
Deactivation Pathways of the Catalytic Activity of Metal– Organic Frameworks in Condensation Reactions Deactivation Pathways of the Catalytic Activity of Metal– Organic Frameworks in Condensation Reactions
skos:notation
RIV/61388955:_____/13:00392934!RIV14-GA0-61388955
n8:predkladatel
n9:ico%3A61388955
n3:aktivita
n10:I n10:P
n3:aktivity
I, P(GBP106/12/G015)
n3:cisloPeriodika
6
n3:dodaniDat
n4:2014
n3:domaciTvurceVysledku
Opanasenko, Maksym n18:7016662
n3:druhVysledku
n14:J
n3:duvernostUdaju
n17:S
n3:entitaPredkladatele
n12:predkladatel
n3:idSjednocenehoVysledku
68050
n3:idVysledku
RIV/61388955:_____/13:00392934
n3:jazykVysledku
n6:eng
n3:klicovaSlova
aldehydes; CC coupling; heterogeneous catalysis
n3:klicoveSlovo
n16:CC%20coupling n16:aldehydes n16:heterogeneous%20catalysis
n3:kodStatuVydavatele
DE - Spolková republika Německo
n3:kontrolniKodProRIV
[DE17602820DD]
n3:nazevZdroje
ChemCatChem
n3:obor
n19:CF
n3:pocetDomacichTvurcuVysledku
2
n3:pocetTvurcuVysledku
4
n3:projekt
n15:GBP106%2F12%2FG015
n3:rokUplatneniVysledku
n4:2013
n3:svazekPeriodika
5
n3:tvurceVysledku
Dhakshinamoorthy, A. Čejka, Jiří Garcia, H. Opanasenko, Maksym
n3:wos
000319680800044
s:issn
1867-3880
s:numberOfPages
9
n13:doi
10.1002/cctc.201200643