Synthesis of Purine-Based Ionic Liquids and Their Applications

Bio-based ionic liquids (ILs) are being increasingly sought after, as they are more sustainable and eco-friendly. Purines are the most widely distributed, naturally occurring <i>N</i>-heterocycles, but their low water-solubility limits their application. In this work, four purines (theob...

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Autores principales:	Ana R. F. Carreira, Telma Veloso, Nicolas Schaeffer, Joana L. Pereira, Sónia P. M. Ventura, Cécile Rizzi, Juliette Sirieix Plénet, Helena Passos, João A. P. Coutinho
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	synthesis ecotoxicity solubility liquid–liquid equilibrium thermoresponsive systems Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/5352d8fdd9c44f088659bba2ac82b8de
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spelling	oai:doaj.org-article:5352d8fdd9c44f088659bba2ac82b8de2021-11-25T18:28:43ZSynthesis of Purine-Based Ionic Liquids and Their Applications10.3390/molecules262269581420-3049https://doaj.org/article/5352d8fdd9c44f088659bba2ac82b8de2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6958https://doaj.org/toc/1420-3049Bio-based ionic liquids (ILs) are being increasingly sought after, as they are more sustainable and eco-friendly. Purines are the most widely distributed, naturally occurring <i>N</i>-heterocycles, but their low water-solubility limits their application. In this work, four purines (theobromine, theophylline, xanthine, and uric acid) were combined with the cation tetrabutylammonium to synthesize bio-based ILs. The physico–chemical properties of the purine-based ILs were characterized, including their melting and decomposition temperatures and water-solubility. The ecotoxicity against the microalgae <i>Raphidocelis subcapitata</i> was also determined. The ILs show good thermal stability (>457 K) and an aqueous solubility enhancement ranging from 53- to 870-fold, in comparison to their respective purine percursors, unlocking new prospects for their application where aqueous solutions are demanded. The ecotoxicity of these ILs seems to be dominated by the cation, and it is similar to chloride-based IL, emphasizing that the use of natural anions does not necessarily translate to more benign ILs. The application of the novel ILs in the formation of aqueous biphasic systems (ABS), and as solubility enhancers, was also evaluated. The ILs were able to form ABS with sodium sulfate and tripotassium citrate salts. The development of thermoresponsive ABS, using sodium sulfate as a salting-out agent, was accomplished, with the ILs having different thermosensitivities. In addition, the purine-based ILs acted as solubility enhancers of ferulic acid in aqueous solution.Ana R. F. CarreiraTelma VelosoNicolas SchaefferJoana L. PereiraSónia P. M. VenturaCécile RizziJuliette Sirieix PlénetHelena PassosJoão A. P. CoutinhoMDPI AGarticlesynthesisecotoxicitysolubilityliquid–liquid equilibriumthermoresponsive systemsOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6958, p 6958 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	synthesis ecotoxicity solubility liquid–liquid equilibrium thermoresponsive systems Organic chemistry QD241-441
spellingShingle	synthesis ecotoxicity solubility liquid–liquid equilibrium thermoresponsive systems Organic chemistry QD241-441 Ana R. F. Carreira Telma Veloso Nicolas Schaeffer Joana L. Pereira Sónia P. M. Ventura Cécile Rizzi Juliette Sirieix Plénet Helena Passos João A. P. Coutinho Synthesis of Purine-Based Ionic Liquids and Their Applications
description	Bio-based ionic liquids (ILs) are being increasingly sought after, as they are more sustainable and eco-friendly. Purines are the most widely distributed, naturally occurring <i>N</i>-heterocycles, but their low water-solubility limits their application. In this work, four purines (theobromine, theophylline, xanthine, and uric acid) were combined with the cation tetrabutylammonium to synthesize bio-based ILs. The physico–chemical properties of the purine-based ILs were characterized, including their melting and decomposition temperatures and water-solubility. The ecotoxicity against the microalgae <i>Raphidocelis subcapitata</i> was also determined. The ILs show good thermal stability (>457 K) and an aqueous solubility enhancement ranging from 53- to 870-fold, in comparison to their respective purine percursors, unlocking new prospects for their application where aqueous solutions are demanded. The ecotoxicity of these ILs seems to be dominated by the cation, and it is similar to chloride-based IL, emphasizing that the use of natural anions does not necessarily translate to more benign ILs. The application of the novel ILs in the formation of aqueous biphasic systems (ABS), and as solubility enhancers, was also evaluated. The ILs were able to form ABS with sodium sulfate and tripotassium citrate salts. The development of thermoresponsive ABS, using sodium sulfate as a salting-out agent, was accomplished, with the ILs having different thermosensitivities. In addition, the purine-based ILs acted as solubility enhancers of ferulic acid in aqueous solution.
format	article
author	Ana R. F. Carreira Telma Veloso Nicolas Schaeffer Joana L. Pereira Sónia P. M. Ventura Cécile Rizzi Juliette Sirieix Plénet Helena Passos João A. P. Coutinho
author_facet	Ana R. F. Carreira Telma Veloso Nicolas Schaeffer Joana L. Pereira Sónia P. M. Ventura Cécile Rizzi Juliette Sirieix Plénet Helena Passos João A. P. Coutinho
author_sort	Ana R. F. Carreira
title	Synthesis of Purine-Based Ionic Liquids and Their Applications
title_short	Synthesis of Purine-Based Ionic Liquids and Their Applications
title_full	Synthesis of Purine-Based Ionic Liquids and Their Applications
title_fullStr	Synthesis of Purine-Based Ionic Liquids and Their Applications
title_full_unstemmed	Synthesis of Purine-Based Ionic Liquids and Their Applications
title_sort	synthesis of purine-based ionic liquids and their applications
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/5352d8fdd9c44f088659bba2ac82b8de
work_keys_str_mv	AT anarfcarreira synthesisofpurinebasedionicliquidsandtheirapplications AT telmaveloso synthesisofpurinebasedionicliquidsandtheirapplications AT nicolasschaeffer synthesisofpurinebasedionicliquidsandtheirapplications AT joanalpereira synthesisofpurinebasedionicliquidsandtheirapplications AT soniapmventura synthesisofpurinebasedionicliquidsandtheirapplications AT cecilerizzi synthesisofpurinebasedionicliquidsandtheirapplications AT juliettesirieixplenet synthesisofpurinebasedionicliquidsandtheirapplications AT helenapassos synthesisofpurinebasedionicliquidsandtheirapplications AT joaoapcoutinho synthesisofpurinebasedionicliquidsandtheirapplications
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Synthesis of Purine-Based Ionic Liquids and Their Applications

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