Hydrophobic Deep eutectic Solvents based on cineole and organic acids

The hydrophobic Natural Deep Eutectic Solvent formed by the combination of cineole and decanoic acid (capric acid) was studied using a combined experimental and computational approach. Experimental study was carried considering relevant physicochemical properties as density, viscosity, refraction in...

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Detalhes bibliográficos
Autores: Trenzado, José Luis, Benito, Cristina, Atilhan, Mert, Aparicio Martínez, Santiago
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:2023
País:España
Recursos:Universidad de Burgos (UBU)
Repositório:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/9256
Acesso em linha:http://hdl.handle.net/10259/9256
Access Level:Acceso aberto
Palavra-chave:Deep eutectic solvents
Hydrophobic
Natural
Thermophysics
COSMO
Molecular dynamics
Química física
Chemistry, Physical and theoretical
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spelling Hydrophobic Deep eutectic Solvents based on cineole and organic acidsTrenzado, José LuisBenito, CristinaAtilhan, MertAparicio Martínez, SantiagoDeep eutectic solventsHydrophobicNaturalThermophysicsCOSMOMolecular dynamicsQuímica físicaChemistry, Physical and theoreticalThe hydrophobic Natural Deep Eutectic Solvent formed by the combination of cineole and decanoic acid (capric acid) was studied using a combined experimental and computational approach. Experimental study was carried considering relevant physicochemical properties as density, viscosity, refraction index and thermal conductivity as a function of temperature, as well as Raman spectra for 785 nm excitation wavelength. Thermophysical properties measured showed a low -viscous low-dense fluid, which is of great relevance for its technological application, as well as the Raman spectra confirmed the formation of hydrogen bonding. The analysis of nanoscopic properties and structuring was carried out using theoretical method as the Density Functional Theory (BP86/def2-TZVP plus Grimme’s D3 theoretical level) and classical Molecular Dynamics simulation (using AMOEBA polarizable force field). Molecular modelling studies using quantum chemistry and classical molecular dynamics methods allowed a nanoscopic characterization of the fluid as well as of its intermolecular forces (hydrogen bonding). Phase equilibria were predicted using COSMO method considered solid–liquid (melting behavior) and vapor – liquid (evaporation), as well as excess properties. The COSMO results showed a low volatile, wide liquid range fluid, characterized by non-ideality because of the formation of hydrogen bonding. Likewise, the interaction of the considered material with POPC lipid was studied using COSMOperm method to analyze its behavior at lipid bilayers as models of cell membranes for the consideration of its possible toxicological effects, showing how the considered molecules are able to penetrate and disrupt the model membranes because of the lipophilic nature of the considered molecules.We acknowledge SCAYLE (Supercomputación Castilla y León, Spain) for providing supercomputing facilities. The statements made herein are solely the responsibility of the authors.Elsevier202420242023info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10259/9256reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)instname:Universidad de Burgos (UBU)InglésJournal of Molecular Liquids. 2023, V. 377, 121322https://doi.org/10.1016/j.molliq.2023.121322Attribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:riubu.ubu.es:10259/92562026-05-28T07:56:11Z
dc.title.none.fl_str_mv Hydrophobic Deep eutectic Solvents based on cineole and organic acids
title Hydrophobic Deep eutectic Solvents based on cineole and organic acids
spellingShingle Hydrophobic Deep eutectic Solvents based on cineole and organic acids
Trenzado, José Luis
Deep eutectic solvents
Hydrophobic
Natural
Thermophysics
COSMO
Molecular dynamics
Química física
Chemistry, Physical and theoretical
title_short Hydrophobic Deep eutectic Solvents based on cineole and organic acids
title_full Hydrophobic Deep eutectic Solvents based on cineole and organic acids
title_fullStr Hydrophobic Deep eutectic Solvents based on cineole and organic acids
title_full_unstemmed Hydrophobic Deep eutectic Solvents based on cineole and organic acids
title_sort Hydrophobic Deep eutectic Solvents based on cineole and organic acids
dc.creator.none.fl_str_mv Trenzado, José Luis
Benito, Cristina
Atilhan, Mert
Aparicio Martínez, Santiago
author Trenzado, José Luis
author_facet Trenzado, José Luis
Benito, Cristina
Atilhan, Mert
Aparicio Martínez, Santiago
author_role author
author2 Benito, Cristina
Atilhan, Mert
Aparicio Martínez, Santiago
author2_role author
author
author
dc.subject.none.fl_str_mv Deep eutectic solvents
Hydrophobic
Natural
Thermophysics
COSMO
Molecular dynamics
Química física
Chemistry, Physical and theoretical
topic Deep eutectic solvents
Hydrophobic
Natural
Thermophysics
COSMO
Molecular dynamics
Química física
Chemistry, Physical and theoretical
description The hydrophobic Natural Deep Eutectic Solvent formed by the combination of cineole and decanoic acid (capric acid) was studied using a combined experimental and computational approach. Experimental study was carried considering relevant physicochemical properties as density, viscosity, refraction index and thermal conductivity as a function of temperature, as well as Raman spectra for 785 nm excitation wavelength. Thermophysical properties measured showed a low -viscous low-dense fluid, which is of great relevance for its technological application, as well as the Raman spectra confirmed the formation of hydrogen bonding. The analysis of nanoscopic properties and structuring was carried out using theoretical method as the Density Functional Theory (BP86/def2-TZVP plus Grimme’s D3 theoretical level) and classical Molecular Dynamics simulation (using AMOEBA polarizable force field). Molecular modelling studies using quantum chemistry and classical molecular dynamics methods allowed a nanoscopic characterization of the fluid as well as of its intermolecular forces (hydrogen bonding). Phase equilibria were predicted using COSMO method considered solid–liquid (melting behavior) and vapor – liquid (evaporation), as well as excess properties. The COSMO results showed a low volatile, wide liquid range fluid, characterized by non-ideality because of the formation of hydrogen bonding. Likewise, the interaction of the considered material with POPC lipid was studied using COSMOperm method to analyze its behavior at lipid bilayers as models of cell membranes for the consideration of its possible toxicological effects, showing how the considered molecules are able to penetrate and disrupt the model membranes because of the lipophilic nature of the considered molecules.
publishDate 2023
dc.date.none.fl_str_mv 2023
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10259/9256
url http://hdl.handle.net/10259/9256
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Journal of Molecular Liquids. 2023, V. 377, 121322
https://doi.org/10.1016/j.molliq.2023.121322
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)
instname:Universidad de Burgos (UBU)
instname_str Universidad de Burgos (UBU)
reponame_str Repositorio Institucional de la Universidad de Burgos (RIUBU)
collection Repositorio Institucional de la Universidad de Burgos (RIUBU)
repository.name.fl_str_mv
repository.mail.fl_str_mv
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