A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates

Johari, Suzaimi; Zaharani, Lia; Gorjian, Hayedeh; Johan, Mohd Rafie; Khaligh, Nader Ghaffari

doi:10.1007/s11164-021-04587-4

Cited by 8 publications

(3 citation statements)

References 31 publications

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“…The average position of the asymmetric (ν as(COO−) ), symmetric (ν s(COO−) ) carbonyl bond, and single carboxyl bond (ν C−O ) of the new ionic liquid appeared at 1553, 1412, and 1279 cm −1 , respectively. In addition, the deformation mode of >NH 2 + groups in protonated piperidine rings of TMDP was observed at 1637 cm −1 [29] . As seen in the spectra of the new ionic liquid, the bands at 2103 cm −1 and the range of 2685–2556 cm −1 are absent.…”

Section: Resultsmentioning

confidence: 85%

“…In continuation of our previous works, [28,29] TMDP and glacial acetic acid in a mole ratio of 1 : 2 were stirred at reflux temperature for 12 hours. A pale yellow cream-like liquid was isolated and characterized by FTIR, 1 H and 13 C NMR, and mass spectrum.…”

Section: Resultsmentioning

confidence: 97%

“…In addition, the deformation mode of > NH 2 + groups in protonated piperidine rings of TMDP was observed at 1637 cm À 1 . [29] As seen in the spectra of the new ionic liquid, the bands at 2103 cm À 1 and the range of 2685-2556 cm À 1 are absent.…”

Section: Ftir Analysismentioning

confidence: 87%

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A More Sustainable and Greener Process for Preparing 3,4,5‐Trisubstituted Furan‐2‐one Derivatives

Zaharani,

Ghafarikhaligh,

Khaligh

2023

ChemistrySelect

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Treatment of 4,4′‐trimethylenedipiperidine with two equivalents of glacial acetic acid gave a cream‐like liquid with a pale yellow color. Then, its ionic chemical structure was demonstrated by different spectroscopic techniques. The thermal behavior of the new ionic liquid was also studied by TGA/DTA and DSC techniques to record its phase transitions and thermal stability and compare those with another analog, i. e., 1H,4H‐piperazine‐N,N′‐diium diacetate. Then, the multicomponent condensation of halogen‐substituted benzaldehydes with dimethyl 2‐(phenylamino) fumarate was investigated using the new ionic liquid in ethanol, an eco‐friendly medium. Excellent yield with 100 % conversion was obtained and pure products could be isolated directly from ethanol. After separating pure products, the residue solution was employed in the next run without separation, concentration, purification, or activation. Furthermore, the synthesis of methyl 2‐(4‐chlorophenyl)‐5‐oxo‐4‐(phenylamino)‐2,5‐dihydro‐furan‐3‐carboxylate was carried out on a large scale using the current catalytic process, affording a conversion of 100 % and a high yield of the crystalline product even after ten consecutive runs. Energy efficiency, cost‐ and time‐saving, and waste prevention demonstrate the newly developed metal‐ and halogen‐free catalysis as a more sustainable catalytic process for preparing 3,4,5‐trisubstituted furan‐2‐one derivatives on the laboratory and industrial scale.

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Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 97%