Effect of Unsaturation on the Absorption of Ethane and Ethylene in Imidazolium-Based Ionic Liquids
The influence of the presence of imidazolium side chain unsaturation on the solubility of ethane and ethylene was studied in three ionic liquids: 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amidesaturated alkyl side-chain in the cation; 1-methyl-3-(buten-3-yl)imidazolium bis(trifluoros...
Gespeichert in:
| Veröffentlicht in: | The journal of physical chemistry. B 2013-06, Vol.117 (24), p.7416-7425 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 7425 |
|---|---|
| container_issue | 24 |
| container_start_page | 7416 |
| container_title | The journal of physical chemistry. B |
| container_volume | 117 |
| creator | Moura, Leila Mishra, Manas Bernales, Varinia Fuentealba, Patricio Padua, Agilio A.H Santini, Catherine C Costa Gomes, Margarida F |
| description | The influence of the presence of imidazolium side chain unsaturation on the solubility of ethane and ethylene was studied in three ionic liquids: 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amidesaturated alkyl side-chain in the cation; 1-methyl-3-(buten-3-yl)imidazolium bis(trifluorosulfonyl)imidedouble bond in the side-chain of the cation; and 1-methyl-3-benzylimidazolium bis(trifluorosulfonyl)imidebenzyl group in the side-chain of the cation. The solubility of both gases decreases when the side-chain of the cations is functionalized with an unsaturated group. This can be explained by a less favorable enthalpy of solvation. The difference of solubility between ethane and ethylene can be explained from a balance of enthalpic and entropic factors: for the ionic liquid with the saturated alkyl side-chain and the benzyl-substituted side-chain, it is the favorable entropy of solvation that explains the larger ethylene solubility, whereas in the case of the saturated side-chain, it is the more favorable enthalpy of solvation. Molecular simulation allowed the identification of the mechanisms of solvation and the preferential solvation sites for each gas in the different ionic liquids. Simulations have shown that the entropy of solvation is more favorable when the presence of the gas weakens the cation–anion interactions or when the gas can be solvated near different sites of the ionic liquid. |
| doi_str_mv | 10.1021/jp403074z |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_00944585v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1370635665</sourcerecordid><originalsourceid>FETCH-LOGICAL-a513t-1a4e4da95a3b8e6cf91ee3ab4e7ba1f7f302f33032d0023413500f74118f0f793</originalsourceid><addsrcrecordid>eNqFkcFq3DAQhkVJaNK0h75A0CXQHpxqLMmyj5uwTRYWcmnOYmxLrBbb2kh2IHn6arvu5hIISMxo-JiZXz8h34FdA8vh13YnGGdKvH4i5yBzlqWrTua8AFackS8xbhnLZV4Wn8lZzhXwsszPSb201jQj9ZY-DhHHKeDo_EDTGTeGLurow-5QsXQ5bnAwFId2n750Jj3cQFe9a_HVd27qsxuMpqUrP7iGrt3T5Nr4lZxa7KL5NscL8vh7-ef2Pls_3K1uF-sMJfAxAxRGtFhJ5HVpisZWYAzHWhhVI1hlOcst54znbRLCBXDJmFUCoLQpVvyC_Dz03WCnd8H1GF60R6fvF2u9rzFWCSFL-QyJ_XFgd8E_TSaOunexMV2X9PkpalCSSw5lVX2McsUKLotCvm3QBB9jMPa4BjC9d0ofnUrs5dx2qnvTHsn_1iTgagYwNtjZgEPj4hunRCngn-yZwybqrZ_CkD75nYF_AXaLpOE</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1370635665</pqid></control><display><type>article</type><title>Effect of Unsaturation on the Absorption of Ethane and Ethylene in Imidazolium-Based Ionic Liquids</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Moura, Leila ; Mishra, Manas ; Bernales, Varinia ; Fuentealba, Patricio ; Padua, Agilio A.H ; Santini, Catherine C ; Costa Gomes, Margarida F</creator><creatorcontrib>Moura, Leila ; Mishra, Manas ; Bernales, Varinia ; Fuentealba, Patricio ; Padua, Agilio A.H ; Santini, Catherine C ; Costa Gomes, Margarida F</creatorcontrib><description>The influence of the presence of imidazolium side chain unsaturation on the solubility of ethane and ethylene was studied in three ionic liquids: 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amidesaturated alkyl side-chain in the cation; 1-methyl-3-(buten-3-yl)imidazolium bis(trifluorosulfonyl)imidedouble bond in the side-chain of the cation; and 1-methyl-3-benzylimidazolium bis(trifluorosulfonyl)imidebenzyl group in the side-chain of the cation. The solubility of both gases decreases when the side-chain of the cations is functionalized with an unsaturated group. This can be explained by a less favorable enthalpy of solvation. The difference of solubility between ethane and ethylene can be explained from a balance of enthalpic and entropic factors: for the ionic liquid with the saturated alkyl side-chain and the benzyl-substituted side-chain, it is the favorable entropy of solvation that explains the larger ethylene solubility, whereas in the case of the saturated side-chain, it is the more favorable enthalpy of solvation. Molecular simulation allowed the identification of the mechanisms of solvation and the preferential solvation sites for each gas in the different ionic liquids. Simulations have shown that the entropy of solvation is more favorable when the presence of the gas weakens the cation–anion interactions or when the gas can be solvated near different sites of the ionic liquid.</description><identifier>ISSN: 1520-6106</identifier><identifier>EISSN: 1520-5207</identifier><identifier>DOI: 10.1021/jp403074z</identifier><identifier>PMID: 23713882</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Cations ; Chemistry ; Entropy ; Ethane ; Ethane - chemistry ; Ethylene ; Ethylenes - chemistry ; Exact sciences and technology ; General and physical chemistry ; Imidazoles - chemistry ; Ionic liquids ; Ionic Liquids - chemistry ; Molecular Dynamics Simulation ; Simulation ; Solubility ; Solutions ; Solvation ; Viscosity</subject><ispartof>The journal of physical chemistry. B, 2013-06, Vol.117 (24), p.7416-7425</ispartof><rights>Copyright © 2013 American Chemical Society</rights><rights>2014 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a513t-1a4e4da95a3b8e6cf91ee3ab4e7ba1f7f302f33032d0023413500f74118f0f793</citedby><cites>FETCH-LOGICAL-a513t-1a4e4da95a3b8e6cf91ee3ab4e7ba1f7f302f33032d0023413500f74118f0f793</cites><orcidid>0000-0002-7641-6526 ; 0000-0001-8637-6057 ; 0000-0002-7938-5892</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/jp403074z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jp403074z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=27484179$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23713882$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00944585$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Moura, Leila</creatorcontrib><creatorcontrib>Mishra, Manas</creatorcontrib><creatorcontrib>Bernales, Varinia</creatorcontrib><creatorcontrib>Fuentealba, Patricio</creatorcontrib><creatorcontrib>Padua, Agilio A.H</creatorcontrib><creatorcontrib>Santini, Catherine C</creatorcontrib><creatorcontrib>Costa Gomes, Margarida F</creatorcontrib><title>Effect of Unsaturation on the Absorption of Ethane and Ethylene in Imidazolium-Based Ionic Liquids</title><title>The journal of physical chemistry. B</title><addtitle>J. Phys. Chem. B</addtitle><description>The influence of the presence of imidazolium side chain unsaturation on the solubility of ethane and ethylene was studied in three ionic liquids: 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amidesaturated alkyl side-chain in the cation; 1-methyl-3-(buten-3-yl)imidazolium bis(trifluorosulfonyl)imidedouble bond in the side-chain of the cation; and 1-methyl-3-benzylimidazolium bis(trifluorosulfonyl)imidebenzyl group in the side-chain of the cation. The solubility of both gases decreases when the side-chain of the cations is functionalized with an unsaturated group. This can be explained by a less favorable enthalpy of solvation. The difference of solubility between ethane and ethylene can be explained from a balance of enthalpic and entropic factors: for the ionic liquid with the saturated alkyl side-chain and the benzyl-substituted side-chain, it is the favorable entropy of solvation that explains the larger ethylene solubility, whereas in the case of the saturated side-chain, it is the more favorable enthalpy of solvation. Molecular simulation allowed the identification of the mechanisms of solvation and the preferential solvation sites for each gas in the different ionic liquids. Simulations have shown that the entropy of solvation is more favorable when the presence of the gas weakens the cation–anion interactions or when the gas can be solvated near different sites of the ionic liquid.</description><subject>Cations</subject><subject>Chemistry</subject><subject>Entropy</subject><subject>Ethane</subject><subject>Ethane - chemistry</subject><subject>Ethylene</subject><subject>Ethylenes - chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Imidazoles - chemistry</subject><subject>Ionic liquids</subject><subject>Ionic Liquids - chemistry</subject><subject>Molecular Dynamics Simulation</subject><subject>Simulation</subject><subject>Solubility</subject><subject>Solutions</subject><subject>Solvation</subject><subject>Viscosity</subject><issn>1520-6106</issn><issn>1520-5207</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFq3DAQhkVJaNK0h75A0CXQHpxqLMmyj5uwTRYWcmnOYmxLrBbb2kh2IHn6arvu5hIISMxo-JiZXz8h34FdA8vh13YnGGdKvH4i5yBzlqWrTua8AFackS8xbhnLZV4Wn8lZzhXwsszPSb201jQj9ZY-DhHHKeDo_EDTGTeGLurow-5QsXQ5bnAwFId2n750Jj3cQFe9a_HVd27qsxuMpqUrP7iGrt3T5Nr4lZxa7KL5NscL8vh7-ef2Pls_3K1uF-sMJfAxAxRGtFhJ5HVpisZWYAzHWhhVI1hlOcst54znbRLCBXDJmFUCoLQpVvyC_Dz03WCnd8H1GF60R6fvF2u9rzFWCSFL-QyJ_XFgd8E_TSaOunexMV2X9PkpalCSSw5lVX2McsUKLotCvm3QBB9jMPa4BjC9d0ofnUrs5dx2qnvTHsn_1iTgagYwNtjZgEPj4hunRCngn-yZwybqrZ_CkD75nYF_AXaLpOE</recordid><startdate>20130620</startdate><enddate>20130620</enddate><creator>Moura, Leila</creator><creator>Mishra, Manas</creator><creator>Bernales, Varinia</creator><creator>Fuentealba, Patricio</creator><creator>Padua, Agilio A.H</creator><creator>Santini, Catherine C</creator><creator>Costa Gomes, Margarida F</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-7641-6526</orcidid><orcidid>https://orcid.org/0000-0001-8637-6057</orcidid><orcidid>https://orcid.org/0000-0002-7938-5892</orcidid></search><sort><creationdate>20130620</creationdate><title>Effect of Unsaturation on the Absorption of Ethane and Ethylene in Imidazolium-Based Ionic Liquids</title><author>Moura, Leila ; Mishra, Manas ; Bernales, Varinia ; Fuentealba, Patricio ; Padua, Agilio A.H ; Santini, Catherine C ; Costa Gomes, Margarida F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a513t-1a4e4da95a3b8e6cf91ee3ab4e7ba1f7f302f33032d0023413500f74118f0f793</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Cations</topic><topic>Chemistry</topic><topic>Entropy</topic><topic>Ethane</topic><topic>Ethane - chemistry</topic><topic>Ethylene</topic><topic>Ethylenes - chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Imidazoles - chemistry</topic><topic>Ionic liquids</topic><topic>Ionic Liquids - chemistry</topic><topic>Molecular Dynamics Simulation</topic><topic>Simulation</topic><topic>Solubility</topic><topic>Solutions</topic><topic>Solvation</topic><topic>Viscosity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moura, Leila</creatorcontrib><creatorcontrib>Mishra, Manas</creatorcontrib><creatorcontrib>Bernales, Varinia</creatorcontrib><creatorcontrib>Fuentealba, Patricio</creatorcontrib><creatorcontrib>Padua, Agilio A.H</creatorcontrib><creatorcontrib>Santini, Catherine C</creatorcontrib><creatorcontrib>Costa Gomes, Margarida F</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>The journal of physical chemistry. B</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moura, Leila</au><au>Mishra, Manas</au><au>Bernales, Varinia</au><au>Fuentealba, Patricio</au><au>Padua, Agilio A.H</au><au>Santini, Catherine C</au><au>Costa Gomes, Margarida F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effect of Unsaturation on the Absorption of Ethane and Ethylene in Imidazolium-Based Ionic Liquids</atitle><jtitle>The journal of physical chemistry. B</jtitle><addtitle>J. Phys. Chem. B</addtitle><date>2013-06-20</date><risdate>2013</risdate><volume>117</volume><issue>24</issue><spage>7416</spage><epage>7425</epage><pages>7416-7425</pages><issn>1520-6106</issn><eissn>1520-5207</eissn><abstract>The influence of the presence of imidazolium side chain unsaturation on the solubility of ethane and ethylene was studied in three ionic liquids: 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)amidesaturated alkyl side-chain in the cation; 1-methyl-3-(buten-3-yl)imidazolium bis(trifluorosulfonyl)imidedouble bond in the side-chain of the cation; and 1-methyl-3-benzylimidazolium bis(trifluorosulfonyl)imidebenzyl group in the side-chain of the cation. The solubility of both gases decreases when the side-chain of the cations is functionalized with an unsaturated group. This can be explained by a less favorable enthalpy of solvation. The difference of solubility between ethane and ethylene can be explained from a balance of enthalpic and entropic factors: for the ionic liquid with the saturated alkyl side-chain and the benzyl-substituted side-chain, it is the favorable entropy of solvation that explains the larger ethylene solubility, whereas in the case of the saturated side-chain, it is the more favorable enthalpy of solvation. Molecular simulation allowed the identification of the mechanisms of solvation and the preferential solvation sites for each gas in the different ionic liquids. Simulations have shown that the entropy of solvation is more favorable when the presence of the gas weakens the cation–anion interactions or when the gas can be solvated near different sites of the ionic liquid.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>23713882</pmid><doi>10.1021/jp403074z</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-7641-6526</orcidid><orcidid>https://orcid.org/0000-0001-8637-6057</orcidid><orcidid>https://orcid.org/0000-0002-7938-5892</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1520-6106 |
| ispartof | The journal of physical chemistry. B, 2013-06, Vol.117 (24), p.7416-7425 |
| issn | 1520-6106 1520-5207 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_00944585v1 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Cations Chemistry Entropy Ethane Ethane - chemistry Ethylene Ethylenes - chemistry Exact sciences and technology General and physical chemistry Imidazoles - chemistry Ionic liquids Ionic Liquids - chemistry Molecular Dynamics Simulation Simulation Solubility Solutions Solvation Viscosity |
| title | Effect of Unsaturation on the Absorption of Ethane and Ethylene in Imidazolium-Based Ionic Liquids |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-28T23%3A38%3A58IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Effect%20of%20Unsaturation%20on%20the%20Absorption%20of%20Ethane%20and%20Ethylene%20in%20Imidazolium-Based%20Ionic%20Liquids&rft.jtitle=The%20journal%20of%20physical%20chemistry.%20B&rft.au=Moura,%20Leila&rft.date=2013-06-20&rft.volume=117&rft.issue=24&rft.spage=7416&rft.epage=7425&rft.pages=7416-7425&rft.issn=1520-6106&rft.eissn=1520-5207&rft_id=info:doi/10.1021/jp403074z&rft_dat=%3Cproquest_hal_p%3E1370635665%3C/proquest_hal_p%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1370635665&rft_id=info:pmid/23713882&rfr_iscdi=true |