Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake

This study reports the synthesis and comprehensive characterization of five fluorinated ionic liquids (FILs), each composed of an imidazolium cation of varied fluoroalkyl chain lengths paired with a fluorinated anion: a newly developed aromatic sulfonamide, bistriflimide (Tf2N), or iodide. The relat...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Industrial & engineering chemistry research 2024-05, Vol.63 (19), p.8761-8771
Hauptverfasser: Pulukkody, Randinu, Baca, Kalin R., Lak, Sarah N., Butler-Christodoulou, Athena, Shiflett, Mark B., Pentzer, Emily B.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 8771
container_issue 19
container_start_page 8761
container_title Industrial & engineering chemistry research
container_volume 63
creator Pulukkody, Randinu
Baca, Kalin R.
Lak, Sarah N.
Butler-Christodoulou, Athena
Shiflett, Mark B.
Pentzer, Emily B.
description This study reports the synthesis and comprehensive characterization of five fluorinated ionic liquids (FILs), each composed of an imidazolium cation of varied fluoroalkyl chain lengths paired with a fluorinated anion: a newly developed aromatic sulfonamide, bistriflimide (Tf2N), or iodide. The relationship between molecular structure and physical properties, including thermal behavior, density, and viscosity, is reported. The identity of the anion has the strongest effect on both thermal stability and thermal behavior, whereas elongation of the fluorinated alkyl chain of the cation more strongly influences density and viscosity. These observations suggest nanosegregation within the liquid and the formation of three microphases (polar, nonpolar, and fluorous). We then evaluate the solubilities of commonly used hydrofluorocarbon refrigerant gases, HFC-32 (difluoromethane) and HFC-125 (pentafluoroethane), in the neat and encapsulated FILs, comparing their performance against commercially available ionic liquids (ILs). We find higher solubilities of HFC-32 in the FILs relative to nonfluorinated commercial ILs that exhibited greater solubility of HFC-125, highlighting selective gas absorption. Additionally, we observe that encapsulated FILs exhibit trends in gas uptake analogous to those of neat FILs. This work not only contributes to a deeper understanding of the structure–property relationships in FILs but also presents promising avenues for their utilization in HFC gas uptake and separation processes, emphasizing the potential of encapsulated FILs as a viable technology to overcome challenges associated with high viscosities of ILs in bulk processing.
doi_str_mv 10.1021/acs.iecr.4c00370
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_iecr_4c00370</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c49699643</sourcerecordid><originalsourceid>FETCH-LOGICAL-a233t-9011538b874c17d5ce2defc141f836e0790732cffc06d3c66de0da43333617c03</originalsourceid><addsrcrecordid>eNp1kE1PwzAMhiMEEmNw55gfQIfTJG12nCb2IU3iwHauMifRMkbTJd1h_HpadVd8seTXj2U9hLwymDDI2bvGNPEW40QgAC_hjoyYzCGTIOQ9GYFSKpNKyUfylNIRAKQUYkTOX9e6PdjkE9W1ofODjhpbG_2vbn2oaXB0cbqE6GvdWkPXofZIN_588WYgtgfrI501zcnjgPiarq4mBtdzAXXcd8OlTnTXtPrbPpMHp0_Jvtz6mOwWH9v5Ktt8Ltfz2SbTOedtNgXGJFd7VQpkpZFoc2MdMsGc4oWFcgolz9E5hMJwLApjwWjBuypYicDHBIa7GENK0bqqif5Hx2vFoOqVVZ2yqldW3ZR1yNuA9MkxXGLdPfj_-h8HnHGc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake</title><source>American Chemical Society Journals</source><creator>Pulukkody, Randinu ; Baca, Kalin R. ; Lak, Sarah N. ; Butler-Christodoulou, Athena ; Shiflett, Mark B. ; Pentzer, Emily B.</creator><creatorcontrib>Pulukkody, Randinu ; Baca, Kalin R. ; Lak, Sarah N. ; Butler-Christodoulou, Athena ; Shiflett, Mark B. ; Pentzer, Emily B.</creatorcontrib><description>This study reports the synthesis and comprehensive characterization of five fluorinated ionic liquids (FILs), each composed of an imidazolium cation of varied fluoroalkyl chain lengths paired with a fluorinated anion: a newly developed aromatic sulfonamide, bistriflimide (Tf2N), or iodide. The relationship between molecular structure and physical properties, including thermal behavior, density, and viscosity, is reported. The identity of the anion has the strongest effect on both thermal stability and thermal behavior, whereas elongation of the fluorinated alkyl chain of the cation more strongly influences density and viscosity. These observations suggest nanosegregation within the liquid and the formation of three microphases (polar, nonpolar, and fluorous). We then evaluate the solubilities of commonly used hydrofluorocarbon refrigerant gases, HFC-32 (difluoromethane) and HFC-125 (pentafluoroethane), in the neat and encapsulated FILs, comparing their performance against commercially available ionic liquids (ILs). We find higher solubilities of HFC-32 in the FILs relative to nonfluorinated commercial ILs that exhibited greater solubility of HFC-125, highlighting selective gas absorption. Additionally, we observe that encapsulated FILs exhibit trends in gas uptake analogous to those of neat FILs. This work not only contributes to a deeper understanding of the structure–property relationships in FILs but also presents promising avenues for their utilization in HFC gas uptake and separation processes, emphasizing the potential of encapsulated FILs as a viable technology to overcome challenges associated with high viscosities of ILs in bulk processing.</description><identifier>ISSN: 0888-5885</identifier><identifier>EISSN: 1520-5045</identifier><identifier>DOI: 10.1021/acs.iecr.4c00370</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>Separations</subject><ispartof>Industrial &amp; engineering chemistry research, 2024-05, Vol.63 (19), p.8761-8771</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a233t-9011538b874c17d5ce2defc141f836e0790732cffc06d3c66de0da43333617c03</cites><orcidid>0000-0003-1266-5918 ; 0000-0002-7496-5011 ; 0000-0002-7292-8698 ; 0000-0001-6187-6135 ; 0000-0001-8744-7769 ; 0000-0002-8934-6192</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.iecr.4c00370$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.iecr.4c00370$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Pulukkody, Randinu</creatorcontrib><creatorcontrib>Baca, Kalin R.</creatorcontrib><creatorcontrib>Lak, Sarah N.</creatorcontrib><creatorcontrib>Butler-Christodoulou, Athena</creatorcontrib><creatorcontrib>Shiflett, Mark B.</creatorcontrib><creatorcontrib>Pentzer, Emily B.</creatorcontrib><title>Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake</title><title>Industrial &amp; engineering chemistry research</title><addtitle>Ind. Eng. Chem. Res</addtitle><description>This study reports the synthesis and comprehensive characterization of five fluorinated ionic liquids (FILs), each composed of an imidazolium cation of varied fluoroalkyl chain lengths paired with a fluorinated anion: a newly developed aromatic sulfonamide, bistriflimide (Tf2N), or iodide. The relationship between molecular structure and physical properties, including thermal behavior, density, and viscosity, is reported. The identity of the anion has the strongest effect on both thermal stability and thermal behavior, whereas elongation of the fluorinated alkyl chain of the cation more strongly influences density and viscosity. These observations suggest nanosegregation within the liquid and the formation of three microphases (polar, nonpolar, and fluorous). We then evaluate the solubilities of commonly used hydrofluorocarbon refrigerant gases, HFC-32 (difluoromethane) and HFC-125 (pentafluoroethane), in the neat and encapsulated FILs, comparing their performance against commercially available ionic liquids (ILs). We find higher solubilities of HFC-32 in the FILs relative to nonfluorinated commercial ILs that exhibited greater solubility of HFC-125, highlighting selective gas absorption. Additionally, we observe that encapsulated FILs exhibit trends in gas uptake analogous to those of neat FILs. This work not only contributes to a deeper understanding of the structure–property relationships in FILs but also presents promising avenues for their utilization in HFC gas uptake and separation processes, emphasizing the potential of encapsulated FILs as a viable technology to overcome challenges associated with high viscosities of ILs in bulk processing.</description><subject>Separations</subject><issn>0888-5885</issn><issn>1520-5045</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kE1PwzAMhiMEEmNw55gfQIfTJG12nCb2IU3iwHauMifRMkbTJd1h_HpadVd8seTXj2U9hLwymDDI2bvGNPEW40QgAC_hjoyYzCGTIOQ9GYFSKpNKyUfylNIRAKQUYkTOX9e6PdjkE9W1ofODjhpbG_2vbn2oaXB0cbqE6GvdWkPXofZIN_588WYgtgfrI501zcnjgPiarq4mBtdzAXXcd8OlTnTXtPrbPpMHp0_Jvtz6mOwWH9v5Ktt8Ltfz2SbTOedtNgXGJFd7VQpkpZFoc2MdMsGc4oWFcgolz9E5hMJwLApjwWjBuypYicDHBIa7GENK0bqqif5Hx2vFoOqVVZ2yqldW3ZR1yNuA9MkxXGLdPfj_-h8HnHGc</recordid><startdate>20240515</startdate><enddate>20240515</enddate><creator>Pulukkody, Randinu</creator><creator>Baca, Kalin R.</creator><creator>Lak, Sarah N.</creator><creator>Butler-Christodoulou, Athena</creator><creator>Shiflett, Mark B.</creator><creator>Pentzer, Emily B.</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-1266-5918</orcidid><orcidid>https://orcid.org/0000-0002-7496-5011</orcidid><orcidid>https://orcid.org/0000-0002-7292-8698</orcidid><orcidid>https://orcid.org/0000-0001-6187-6135</orcidid><orcidid>https://orcid.org/0000-0001-8744-7769</orcidid><orcidid>https://orcid.org/0000-0002-8934-6192</orcidid></search><sort><creationdate>20240515</creationdate><title>Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake</title><author>Pulukkody, Randinu ; Baca, Kalin R. ; Lak, Sarah N. ; Butler-Christodoulou, Athena ; Shiflett, Mark B. ; Pentzer, Emily B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a233t-9011538b874c17d5ce2defc141f836e0790732cffc06d3c66de0da43333617c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Separations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pulukkody, Randinu</creatorcontrib><creatorcontrib>Baca, Kalin R.</creatorcontrib><creatorcontrib>Lak, Sarah N.</creatorcontrib><creatorcontrib>Butler-Christodoulou, Athena</creatorcontrib><creatorcontrib>Shiflett, Mark B.</creatorcontrib><creatorcontrib>Pentzer, Emily B.</creatorcontrib><collection>CrossRef</collection><jtitle>Industrial &amp; engineering chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pulukkody, Randinu</au><au>Baca, Kalin R.</au><au>Lak, Sarah N.</au><au>Butler-Christodoulou, Athena</au><au>Shiflett, Mark B.</au><au>Pentzer, Emily B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake</atitle><jtitle>Industrial &amp; engineering chemistry research</jtitle><addtitle>Ind. Eng. Chem. Res</addtitle><date>2024-05-15</date><risdate>2024</risdate><volume>63</volume><issue>19</issue><spage>8761</spage><epage>8771</epage><pages>8761-8771</pages><issn>0888-5885</issn><eissn>1520-5045</eissn><abstract>This study reports the synthesis and comprehensive characterization of five fluorinated ionic liquids (FILs), each composed of an imidazolium cation of varied fluoroalkyl chain lengths paired with a fluorinated anion: a newly developed aromatic sulfonamide, bistriflimide (Tf2N), or iodide. The relationship between molecular structure and physical properties, including thermal behavior, density, and viscosity, is reported. The identity of the anion has the strongest effect on both thermal stability and thermal behavior, whereas elongation of the fluorinated alkyl chain of the cation more strongly influences density and viscosity. These observations suggest nanosegregation within the liquid and the formation of three microphases (polar, nonpolar, and fluorous). We then evaluate the solubilities of commonly used hydrofluorocarbon refrigerant gases, HFC-32 (difluoromethane) and HFC-125 (pentafluoroethane), in the neat and encapsulated FILs, comparing their performance against commercially available ionic liquids (ILs). We find higher solubilities of HFC-32 in the FILs relative to nonfluorinated commercial ILs that exhibited greater solubility of HFC-125, highlighting selective gas absorption. Additionally, we observe that encapsulated FILs exhibit trends in gas uptake analogous to those of neat FILs. This work not only contributes to a deeper understanding of the structure–property relationships in FILs but also presents promising avenues for their utilization in HFC gas uptake and separation processes, emphasizing the potential of encapsulated FILs as a viable technology to overcome challenges associated with high viscosities of ILs in bulk processing.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.iecr.4c00370</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0003-1266-5918</orcidid><orcidid>https://orcid.org/0000-0002-7496-5011</orcidid><orcidid>https://orcid.org/0000-0002-7292-8698</orcidid><orcidid>https://orcid.org/0000-0001-6187-6135</orcidid><orcidid>https://orcid.org/0000-0001-8744-7769</orcidid><orcidid>https://orcid.org/0000-0002-8934-6192</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0888-5885
ispartof Industrial & engineering chemistry research, 2024-05, Vol.63 (19), p.8761-8771
issn 0888-5885
1520-5045
language eng
recordid cdi_crossref_primary_10_1021_acs_iecr_4c00370
source American Chemical Society Journals
subjects Separations
title Synthesis and Characterization of Fluorinated Ionic Liquids and Their Application in Hydrofluorocarbon Gas Uptake
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T13%3A00%3A05IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20Characterization%20of%20Fluorinated%20Ionic%20Liquids%20and%20Their%20Application%20in%20Hydrofluorocarbon%20Gas%20Uptake&rft.jtitle=Industrial%20&%20engineering%20chemistry%20research&rft.au=Pulukkody,%20Randinu&rft.date=2024-05-15&rft.volume=63&rft.issue=19&rft.spage=8761&rft.epage=8771&rft.pages=8761-8771&rft.issn=0888-5885&rft.eissn=1520-5045&rft_id=info:doi/10.1021/acs.iecr.4c00370&rft_dat=%3Cacs_cross%3Ec49699643%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true