Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope

Autores
Andreatta, Alfonsina Ester; Charnley, Matthew P.; Brennecke, Joan F.
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Systems that form azeotropes or have relative volatilities close to 1.0 represent very little energy and capital intensive separations. Ionic liquids (ILs) can serve as nonvolatile entrainers to break azeotropes and enable a more energy efficient and environmentally friendly process. Here, six ILs have been investigated for their ability to break the ethanol + ethyl acetate azeotrope at 313.15 K. Three of the ILs investigated, 1-ethyl-3-methylimidazolium methanesulfonate [emim][MeSO3], 1-ethyl-3-methyl-imidazolium methylsulfate [emim][MeSO4], and 1-butyl-3-methyl-imidazolium trifluoromethanesulfonate [bmim]- [CF3SO3] are excellent entrainer candidates. In fact, the ethanol + ethyl acetate azeotrope can be broken over the entire composition range by adding as little as 2.5 mol percent of either [emim][MeSO3] or [emim][MeSO4] to the binary organic mixture, which is less IL than what is needed to break any azeotropic system discussed in literature to date. The other three ILs, 1-ethyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide [emim][Tf2N], 1- hexyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide [hmim][Tf2N], and 1-butyl-1- methyl-pyrrolidinium bis(trifluoromethylsulfonyl)imide [bmpyrr][Tf2N], are limited in their ability to break this azeotrope. The difference between these two groups correlates with the infinite dilution activity coefficients of the ethyl acetate and ethanol in each of the ILs. Both polarity and hydrogen bonding are important in determining the preferential affinity of the ethanol for the ILs, which raises the ethyl acetate/ethanol relative volatility. In addition, the experimental binary and ternary vapor−liquid equilibrium data have been fit to the Non Random Two Liquid (NRTL) activity coefficient model, which is able to predict and correlate the amount of IL needed to break the azeotrope in these ternary vapor− liquid equilibrium systems.
Fil: Andreatta, Alfonsina Ester. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina. University of Notre Dame-Indiana; Estados Unidos
Fil: Charnley, Matthew P.. University of Notre Dame-Indiana; Estados Unidos
Fil: Brennecke, Joan F.. University of Notre Dame-Indiana; Estados Unidos
Materia
Energy
Azeotrope Mixture
Ethyl Acetate Ethanol
Ionic Liqui
Entrainers
Extractive Distillation
Headspace Autosampler
Nrtl
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/46186

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network_name_str CONICET Digital (CONICET)
spelling Using Ionic Liquids To Break the Ethanol−Ethyl Acetate AzeotropeAndreatta, Alfonsina EsterCharnley, Matthew P.Brennecke, Joan F.EnergyAzeotrope MixtureEthyl Acetate EthanolIonic LiquiEntrainersExtractive DistillationHeadspace AutosamplerNrtlhttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2Systems that form azeotropes or have relative volatilities close to 1.0 represent very little energy and capital intensive separations. Ionic liquids (ILs) can serve as nonvolatile entrainers to break azeotropes and enable a more energy efficient and environmentally friendly process. Here, six ILs have been investigated for their ability to break the ethanol + ethyl acetate azeotrope at 313.15 K. Three of the ILs investigated, 1-ethyl-3-methylimidazolium methanesulfonate [emim][MeSO3], 1-ethyl-3-methyl-imidazolium methylsulfate [emim][MeSO4], and 1-butyl-3-methyl-imidazolium trifluoromethanesulfonate [bmim]- [CF3SO3] are excellent entrainer candidates. In fact, the ethanol + ethyl acetate azeotrope can be broken over the entire composition range by adding as little as 2.5 mol percent of either [emim][MeSO3] or [emim][MeSO4] to the binary organic mixture, which is less IL than what is needed to break any azeotropic system discussed in literature to date. The other three ILs, 1-ethyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide [emim][Tf2N], 1- hexyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide [hmim][Tf2N], and 1-butyl-1- methyl-pyrrolidinium bis(trifluoromethylsulfonyl)imide [bmpyrr][Tf2N], are limited in their ability to break this azeotrope. The difference between these two groups correlates with the infinite dilution activity coefficients of the ethyl acetate and ethanol in each of the ILs. Both polarity and hydrogen bonding are important in determining the preferential affinity of the ethanol for the ILs, which raises the ethyl acetate/ethanol relative volatility. In addition, the experimental binary and ternary vapor−liquid equilibrium data have been fit to the Non Random Two Liquid (NRTL) activity coefficient model, which is able to predict and correlate the amount of IL needed to break the azeotrope in these ternary vapor− liquid equilibrium systems.Fil: Andreatta, Alfonsina Ester. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina. University of Notre Dame-Indiana; Estados UnidosFil: Charnley, Matthew P.. University of Notre Dame-Indiana; Estados UnidosFil: Brennecke, Joan F.. University of Notre Dame-Indiana; Estados UnidosAmerican Chemical Society2015-11-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/46186Andreatta, Alfonsina Ester; Charnley, Matthew P.; Brennecke, Joan F.; Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope; American Chemical Society; Sustainable Chemistry & Engineering; 3; 12; 5-11-2015; 3435-34442168-0485CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01175info:eu-repo/semantics/altIdentifier/doi/10.1021/acssuschemeng.5b01175info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:09:09Zoai:ri.conicet.gov.ar:11336/46186instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:09:09.45CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope
title Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope
spellingShingle Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope
Andreatta, Alfonsina Ester
Energy
Azeotrope Mixture
Ethyl Acetate Ethanol
Ionic Liqui
Entrainers
Extractive Distillation
Headspace Autosampler
Nrtl
title_short Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope
title_full Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope
title_fullStr Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope
title_full_unstemmed Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope
title_sort Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope
dc.creator.none.fl_str_mv Andreatta, Alfonsina Ester
Charnley, Matthew P.
Brennecke, Joan F.
author Andreatta, Alfonsina Ester
author_facet Andreatta, Alfonsina Ester
Charnley, Matthew P.
Brennecke, Joan F.
author_role author
author2 Charnley, Matthew P.
Brennecke, Joan F.
author2_role author
author
dc.subject.none.fl_str_mv Energy
Azeotrope Mixture
Ethyl Acetate Ethanol
Ionic Liqui
Entrainers
Extractive Distillation
Headspace Autosampler
Nrtl
topic Energy
Azeotrope Mixture
Ethyl Acetate Ethanol
Ionic Liqui
Entrainers
Extractive Distillation
Headspace Autosampler
Nrtl
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Systems that form azeotropes or have relative volatilities close to 1.0 represent very little energy and capital intensive separations. Ionic liquids (ILs) can serve as nonvolatile entrainers to break azeotropes and enable a more energy efficient and environmentally friendly process. Here, six ILs have been investigated for their ability to break the ethanol + ethyl acetate azeotrope at 313.15 K. Three of the ILs investigated, 1-ethyl-3-methylimidazolium methanesulfonate [emim][MeSO3], 1-ethyl-3-methyl-imidazolium methylsulfate [emim][MeSO4], and 1-butyl-3-methyl-imidazolium trifluoromethanesulfonate [bmim]- [CF3SO3] are excellent entrainer candidates. In fact, the ethanol + ethyl acetate azeotrope can be broken over the entire composition range by adding as little as 2.5 mol percent of either [emim][MeSO3] or [emim][MeSO4] to the binary organic mixture, which is less IL than what is needed to break any azeotropic system discussed in literature to date. The other three ILs, 1-ethyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide [emim][Tf2N], 1- hexyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide [hmim][Tf2N], and 1-butyl-1- methyl-pyrrolidinium bis(trifluoromethylsulfonyl)imide [bmpyrr][Tf2N], are limited in their ability to break this azeotrope. The difference between these two groups correlates with the infinite dilution activity coefficients of the ethyl acetate and ethanol in each of the ILs. Both polarity and hydrogen bonding are important in determining the preferential affinity of the ethanol for the ILs, which raises the ethyl acetate/ethanol relative volatility. In addition, the experimental binary and ternary vapor−liquid equilibrium data have been fit to the Non Random Two Liquid (NRTL) activity coefficient model, which is able to predict and correlate the amount of IL needed to break the azeotrope in these ternary vapor− liquid equilibrium systems.
Fil: Andreatta, Alfonsina Ester. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina. University of Notre Dame-Indiana; Estados Unidos
Fil: Charnley, Matthew P.. University of Notre Dame-Indiana; Estados Unidos
Fil: Brennecke, Joan F.. University of Notre Dame-Indiana; Estados Unidos
description Systems that form azeotropes or have relative volatilities close to 1.0 represent very little energy and capital intensive separations. Ionic liquids (ILs) can serve as nonvolatile entrainers to break azeotropes and enable a more energy efficient and environmentally friendly process. Here, six ILs have been investigated for their ability to break the ethanol + ethyl acetate azeotrope at 313.15 K. Three of the ILs investigated, 1-ethyl-3-methylimidazolium methanesulfonate [emim][MeSO3], 1-ethyl-3-methyl-imidazolium methylsulfate [emim][MeSO4], and 1-butyl-3-methyl-imidazolium trifluoromethanesulfonate [bmim]- [CF3SO3] are excellent entrainer candidates. In fact, the ethanol + ethyl acetate azeotrope can be broken over the entire composition range by adding as little as 2.5 mol percent of either [emim][MeSO3] or [emim][MeSO4] to the binary organic mixture, which is less IL than what is needed to break any azeotropic system discussed in literature to date. The other three ILs, 1-ethyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide [emim][Tf2N], 1- hexyl-3-methyl-imidazolium bis(trifluoromethylsulfonyl)imide [hmim][Tf2N], and 1-butyl-1- methyl-pyrrolidinium bis(trifluoromethylsulfonyl)imide [bmpyrr][Tf2N], are limited in their ability to break this azeotrope. The difference between these two groups correlates with the infinite dilution activity coefficients of the ethyl acetate and ethanol in each of the ILs. Both polarity and hydrogen bonding are important in determining the preferential affinity of the ethanol for the ILs, which raises the ethyl acetate/ethanol relative volatility. In addition, the experimental binary and ternary vapor−liquid equilibrium data have been fit to the Non Random Two Liquid (NRTL) activity coefficient model, which is able to predict and correlate the amount of IL needed to break the azeotrope in these ternary vapor− liquid equilibrium systems.
publishDate 2015
dc.date.none.fl_str_mv 2015-11-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/46186
Andreatta, Alfonsina Ester; Charnley, Matthew P.; Brennecke, Joan F.; Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope; American Chemical Society; Sustainable Chemistry & Engineering; 3; 12; 5-11-2015; 3435-3444
2168-0485
CONICET Digital
CONICET
url http://hdl.handle.net/11336/46186
identifier_str_mv Andreatta, Alfonsina Ester; Charnley, Matthew P.; Brennecke, Joan F.; Using Ionic Liquids To Break the Ethanol−Ethyl Acetate Azeotrope; American Chemical Society; Sustainable Chemistry & Engineering; 3; 12; 5-11-2015; 3435-3444
2168-0485
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/acssuschemeng.5b01175
info:eu-repo/semantics/altIdentifier/doi/10.1021/acssuschemeng.5b01175
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
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instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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