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Microwave-Assisted Synthesis of Cinnamyl Long Chain Aroma Esters

Cinnamyl long chain aroma esters were prepared by using the conventional and microwave-assisted methods. The esterification reaction of naturally occurring 3-phenyl-prop-2-en-1-ol and different chain lengths acidic and diol reagents was carried out at the temperature of 140 °C under solvent free con...

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Autor principal: Worzakowska, Marta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272307/
https://www.ncbi.nlm.nih.gov/pubmed/26060921
http://dx.doi.org/10.3390/molecules200610594
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author Worzakowska, Marta
author_facet Worzakowska, Marta
author_sort Worzakowska, Marta
collection PubMed
description Cinnamyl long chain aroma esters were prepared by using the conventional and microwave-assisted methods. The esterification reaction of naturally occurring 3-phenyl-prop-2-en-1-ol and different chain lengths acidic and diol reagents was carried out at the temperature of 140 °C under solvent free conditions. As acidic reagents, oxolane-2,5-dione, oxane-2,6-dione, hexanedioic acid and decanedioic acid were applied. Ethane-1,2-diol and 2,2ʹ-[oxybis(2,1-ethandiyloxy)]diethanol were used as diol reagents. The synthesis of high molecular mass cinnamyl esters under conventional method conditions requires a long time to obtain high yields. The studies confirm that by using microwave irradiation, it is possible to reduce the reaction times to only 10–20 min. The structures of prepared esters were confirmed on the basis of FTIR, (1)H-NMR and (13)C-NMR. In addition, the newly obtained cinnamyl long chain esters were tested for their thermal properties. The TG studies proved the high thermal resistance of the obtained esters under inert and oxidative conditions.
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spelling pubmed-62723072018-12-31 Microwave-Assisted Synthesis of Cinnamyl Long Chain Aroma Esters Worzakowska, Marta Molecules Article Cinnamyl long chain aroma esters were prepared by using the conventional and microwave-assisted methods. The esterification reaction of naturally occurring 3-phenyl-prop-2-en-1-ol and different chain lengths acidic and diol reagents was carried out at the temperature of 140 °C under solvent free conditions. As acidic reagents, oxolane-2,5-dione, oxane-2,6-dione, hexanedioic acid and decanedioic acid were applied. Ethane-1,2-diol and 2,2ʹ-[oxybis(2,1-ethandiyloxy)]diethanol were used as diol reagents. The synthesis of high molecular mass cinnamyl esters under conventional method conditions requires a long time to obtain high yields. The studies confirm that by using microwave irradiation, it is possible to reduce the reaction times to only 10–20 min. The structures of prepared esters were confirmed on the basis of FTIR, (1)H-NMR and (13)C-NMR. In addition, the newly obtained cinnamyl long chain esters were tested for their thermal properties. The TG studies proved the high thermal resistance of the obtained esters under inert and oxidative conditions. MDPI 2015-06-08 /pmc/articles/PMC6272307/ /pubmed/26060921 http://dx.doi.org/10.3390/molecules200610594 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Worzakowska, Marta
Microwave-Assisted Synthesis of Cinnamyl Long Chain Aroma Esters
title Microwave-Assisted Synthesis of Cinnamyl Long Chain Aroma Esters
title_full Microwave-Assisted Synthesis of Cinnamyl Long Chain Aroma Esters
title_fullStr Microwave-Assisted Synthesis of Cinnamyl Long Chain Aroma Esters
title_full_unstemmed Microwave-Assisted Synthesis of Cinnamyl Long Chain Aroma Esters
title_short Microwave-Assisted Synthesis of Cinnamyl Long Chain Aroma Esters
title_sort microwave-assisted synthesis of cinnamyl long chain aroma esters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272307/
https://www.ncbi.nlm.nih.gov/pubmed/26060921
http://dx.doi.org/10.3390/molecules200610594
work_keys_str_mv AT worzakowskamarta microwaveassistedsynthesisofcinnamyllongchainaromaesters