p-Sulfonic acid calix[n]arenes as organocatalysts for the transesterification reaction of Passiflora seed oil

Almeida, Camila G. de; Souza, Isabella F. de; Liberto, Natália A.; Silva, Márcio José da; Fernandes, Sérgio Antônio; Hyaric, Mireille Le

doi:10.1007/s00706-015-1546-0

Cited by 9 publications

(12 citation statements)

References 42 publications

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“…For the synthesis of the novel MOF, ZrCl 4 was dissolved in dimethylformamide (DMF) in the presence of formic, acetic, or propionic acid as modulating agents . After addition of the calixarene linker H 4 cal (Figure a), the crystallization took place in a preheated oven at 120 °C (see the Experimental Section and the Supporting Information for further details) . From a synthesis with 500 equiv of formic acid we obtained crystals suitable for single‐crystal X‐ray diffraction (see Figure S1 in the Supporting Information) and elucidated the crystal structure (Figure b).…”

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confidence: 99%

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A Calixarene‐Based Metal–Organic Framework for Highly Selective NO₂ Detection

et al. 2018

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A calixarene-based metal-organic framework (Zr-cal, [Zr O (OH) (FA) ] (cal) ], FA=formate, cal=1,3-alt-25,26,27,28-tetrakis[(carboxy)methoxy]calixarene) was synthesized and characterized by single-crystal X-ray diffraction. The three-dimensional framework is a 4,6-connected network of gar topology and exhibits two equal but nonintersecting three-dimensional pore systems. It has a specific BET surface area of 670 m g , and the calixarene cavities are accessible through the pore systems. The exposed calixarenes can be used for the visual detection and encapsulation of NO through the formation of deeply colored charge-transfer complexes inside the MOF. The highly selective complexation was analyzed by UV/Vis and IR spectroscopy, and the stability of the material was confirmed by powder X-ray diffraction and H NMR spectroscopy. Finally, the MOF was used as a sensor material in a home-made sensor cell and showed high sensitivity for NO .

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Section: Figurementioning

confidence: 99%

“…The compound H 4 cal was synthesized according to literature procedures (see the Supporting Information) …”

Section: Figurementioning

confidence: 99%

A Calixarene‐Based Metal–Organic Framework for Highly Selective NO₂ Detection

et al. 2018

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“…Further modification of calixarene has been conducted through a sulfonation reaction that yields acid organocatalysts called p-sulfonic acid calixarenes due to Bronsted acid sites. 14,20 According to a previous study, p-sulfonic acid calixarenes can produce methyl palmitate of up to 91.0% yield. 14 Our previous work showed that calix [4]pyrogallolarene sulfonic acids due to 12 hydroxyl groups could have higher catalytic activity than calix [4]arene sulfonic acids.…”

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confidence: 99%

Preliminary Investigation of Organocatalyst Activity Based on C‐Arylcalix[4]‐2‐Methylresorcinarene Sulfonic Acid Materials for Biodiesel Production

Jumina

Amalina

Triono

et al. 2021

Bulletin Korean Chem Soc

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At present, biodiesel remains an untapped fuel source while crude oil reserves are being depleted. Extensive efforts are necessary to achieve efficient biodiesel production, but catalytic activity in methyl palmitate production remains unsatisfactory. In this study, we report the synthesis and organocatalyst activity of C‐arylcalix[4]‐2‐methylresorcinarene sulfonic acids for biodiesel production. The presence of a methyl group on an aromatic ring is expected to disturb the intramolecular hydrogen bonds; thus, each hydroxyl group could be utilized for the catalytic process. C‐arylcalix[4]‐2‐methylresorcinarene sulfonic acids were prepared from cyclocondensation and sulfonation reactions yielding compounds 1–6 at rates of 66.7%–86.6%. By evaluating the organocatalytic activity of the C‐arylcalix[4]‐2‐methylresorcinarene sulfonic acids, we found that 4 mol% of compound 5 exhibited the highest yield (97.8%) of methyl palmitate at 338 K for 6‐h reaction time, which is remarkable. These findings show that C‐arylcalix[4]‐2‐methylresorcinarene sulfonic acids are promising heterogeneous catalyst materials for biodiesel production.

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“…[16] Die Porosität, die kontrollierbare Funktionalitätdes Porensystems und die große Zahl an mçglichen Strukturen führt zu MOFs,d ie genau auf ihre potentielle Anwendung zugeschnitten werden kçnnen. [26,29] Ause iner Synthese mit einem Zusatz von 500 ¾quiv.A meisensäure wurden Einkristalle erhalten, die fürd ie Rçntgeneinkristalldiffraktometrie geeignet waren, (vgl. [19,20] Auch kçnnen diese Materialien als Medikamenten-Freisetzungssysteme genutzt werden [21] oder um NO als Neurotransmitter in biomedizinischen Anwendungen freizusetzen.…”

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“…Experimenteller Te il und die Hintergrundinformationen (SI) fürw eitere Details). [26,29] [19,32] Durch die Adsorption von Aceton im Gerüst und der Untersuchung dieser Proben mittels IR-Spektroskopie konnten diese Überlegung überprüft werden (vgl. Abbildung S9).…”

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Eine Calixaren‐basierte Metall‐organische Gerüstverbindung für den hoch selektiven NO₂‐Nachweis

et al. 2018

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Eine Calixaren-basierte Metall-organische Gerüstverbindung (Zr-cal, [Zr 6 O 4 (OH) 4 (FA) 6 ] 2 (cal) 3 ], FA = Formiat, cal = 1,3-alt-25,26,27,28-Tetrakis-[(carboxy)methoxy]-calixaren) wurde synthetisiert und ihre Struktur über Einkristallrçntgendiffraktometrie bestimmt. Das dreidimensionale Gerüst kristallisiert in einem 4,6-verbundenen Netzwerk in der gar-Topologie und weist zwei identische, nichtm iteinander verbundene Porensysteme auf.D ie spezifische BET-Oberflächeb eträgt 670 m 2 g À1 und die Kavitäten der Calixarene sind über das Porensystem zugänglich. Bei der Exposition mit NO 2 bilden die Calixarene stark gefärbte Charge-Transfer-Komplexe im MOF,wodurch das Material zur visuellen Detektion und zur Einlagerung von NO 2 genutzt werden kann. Die hohe Selektivitätd ieser Komplexierung wurde mittels IR-und UV/ Vis-Spektroskopie und die Stabilitätd es Materials mit Rçntgenpulverdiffraktometrie und 1 H-NMR-Spektroskopie überprüft. Schließlich wurded as MOF als Sensormaterial in einer selbstgebauten Messzelle verwendet, wo es eine hohe Sensitivitätgegenüber NO 2 aufwies.

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p-Sulfonic acid calix[n]arenes as organocatalysts for the transesterification reaction of Passiflora seed oil

Cited by 9 publications

References 42 publications

A Calixarene‐Based Metal–Organic Framework for Highly Selective NO₂ Detection

A Calixarene‐Based Metal–Organic Framework for Highly Selective NO₂ Detection

Preliminary Investigation of Organocatalyst Activity Based on C‐Arylcalix[4]‐2‐Methylresorcinarene Sulfonic Acid Materials for Biodiesel Production

Eine Calixaren‐basierte Metall‐organische Gerüstverbindung für den hoch selektiven NO₂‐Nachweis

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p-Sulfonic acid calix[n]arenes as organocatalysts for the transesterification reaction of Passiflora seed oil

Cited by 9 publications

References 42 publications

A Calixarene‐Based Metal–Organic Framework for Highly Selective NO2 Detection

A Calixarene‐Based Metal–Organic Framework for Highly Selective NO2 Detection

Preliminary Investigation of Organocatalyst Activity Based on C‐Arylcalix[4]‐2‐Methylresorcinarene Sulfonic Acid Materials for Biodiesel Production

Eine Calixaren‐basierte Metall‐organische Gerüstverbindung für den hoch selektiven NO2‐Nachweis

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A Calixarene‐Based Metal–Organic Framework for Highly Selective NO₂ Detection

A Calixarene‐Based Metal–Organic Framework for Highly Selective NO₂ Detection

Eine Calixaren‐basierte Metall‐organische Gerüstverbindung für den hoch selektiven NO₂‐Nachweis