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

A novel sublimable organic salt was synthesized, and its chemical structure was characterized by FTIR, 1D NMR, 2D NMR, and elemental analysis. In addition, the thermal phase transitions and thermal stability of new organic salt were investigated. The DSC and TGA results showed that the organic salt...

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Main Authors: Johari, Suzaimi, Zaharani, Lia, Gorjian, Hayedeh, Johan, Mohd Rafie, Khaligh, Nader Ghaffari
Format: Article
Published: Springer Verlag 2022
Subjects:
QD Chemistry
Online Access:http://eprints.um.edu.my/33772/
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spelling my.um.eprints.337722022-04-28T07:34:38Z http://eprints.um.edu.my/33772/ 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 QD Chemistry A novel sublimable organic salt was synthesized, and its chemical structure was characterized by FTIR, 1D NMR, 2D NMR, and elemental analysis. In addition, the thermal phase transitions and thermal stability of new organic salt were investigated. The DSC and TGA results showed that the organic salt could convert into constituent molecules at < 145 degrees C before decomposition temperature (T-dec. similar to 200 degrees C) under atmospheric pressure without forming the liquid phase. Then, it was recondensed to regenerate the initial organic salt in the cool part of the vial. Therefore, it can be a promising organic salt towards the regeneration of spent catalyst from synthesis processes when the reaction mixture contains poorly volatile components and includes its use in gas-phase procedures. Also, the catalytic efficiency of new organic salt was investigated in the Knoevenagel condensation reaction. A variety of substituted arylidene and alkylidene malonates were isolated in 78-95% yield within six hours.(sic) Under the optimized reaction conditions, the current catalytic procedure exhibited superiority compared to the mixed piperazine/acetic acid, piperidine/acetic acid, and piperidinium acetate. There were no significant changes in the new organic salt chemical structure and catalytic activity even after the 5th run. This work revealed the importance of the existence of simultaneous hydrogen bond acceptor/donor groups in our environmentally friendly catalyst to promote the Knoevenagel condensation reaction without the use of metal-containing catalysts. Springer Verlag 2022-01 Article PeerReviewed Johari, Suzaimi and Zaharani, Lia and Gorjian, Hayedeh and Johan, Mohd Rafie and Khaligh, Nader Ghaffari (2022) A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates. Research on Chemical Intermediates, 48 (1). pp. 361-377. ISSN 0922-6168, DOI https://doi.org/10.1007/s11164-021-04587-4 <https://doi.org/10.1007/s11164-021-04587-4>. 10.1007/s11164-021-04587-4
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QD Chemistry
spellingShingle QD Chemistry
Johari, Suzaimi
Zaharani, Lia
Gorjian, Hayedeh
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates
description A novel sublimable organic salt was synthesized, and its chemical structure was characterized by FTIR, 1D NMR, 2D NMR, and elemental analysis. In addition, the thermal phase transitions and thermal stability of new organic salt were investigated. The DSC and TGA results showed that the organic salt could convert into constituent molecules at < 145 degrees C before decomposition temperature (T-dec. similar to 200 degrees C) under atmospheric pressure without forming the liquid phase. Then, it was recondensed to regenerate the initial organic salt in the cool part of the vial. Therefore, it can be a promising organic salt towards the regeneration of spent catalyst from synthesis processes when the reaction mixture contains poorly volatile components and includes its use in gas-phase procedures. Also, the catalytic efficiency of new organic salt was investigated in the Knoevenagel condensation reaction. A variety of substituted arylidene and alkylidene malonates were isolated in 78-95% yield within six hours.(sic) Under the optimized reaction conditions, the current catalytic procedure exhibited superiority compared to the mixed piperazine/acetic acid, piperidine/acetic acid, and piperidinium acetate. There were no significant changes in the new organic salt chemical structure and catalytic activity even after the 5th run. This work revealed the importance of the existence of simultaneous hydrogen bond acceptor/donor groups in our environmentally friendly catalyst to promote the Knoevenagel condensation reaction without the use of metal-containing catalysts.
format Article
author Johari, Suzaimi
Zaharani, Lia
Gorjian, Hayedeh
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
author_facet Johari, Suzaimi
Zaharani, Lia
Gorjian, Hayedeh
Johan, Mohd Rafie
Khaligh, Nader Ghaffari
author_sort Johari, Suzaimi
title A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates
title_short A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates
title_full A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates
title_fullStr A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates
title_full_unstemmed A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates
title_sort novel sublimable organic salt: synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates
publisher Springer Verlag
publishDate 2022
url http://eprints.um.edu.my/33772/
_version_ 1735409589386477568
score 13.211869

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