Role of Alkyl Group in the Aromatic Extraction Using Pyridinium-Based Ionic Liquids
The performance of N-alkylpyridinium-based ionic liquids with a SCN anion (PyILs) was evaluated for the selective extraction of aromatics from aliphatic hydrocarbons. The aromatic extraction ability of PyILs was greatly enhanced by the presence of a methyl group on the pyridinium ring at the 3- or 4...
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| Veröffentlicht in: | The journal of physical chemistry. B 2013-11, Vol.117 (47), p.14827-14834 |
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| container_end_page | 14834 |
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| container_issue | 47 |
| container_start_page | 14827 |
| container_title | The journal of physical chemistry. B |
| container_volume | 117 |
| creator | Kim, Min Ji Shin, Seung Hoon Kim, Young Jin Cheong, Minserk Lee, Je Seung Kim, Hoon Sik |
| description | The performance of N-alkylpyridinium-based ionic liquids with a SCN anion (PyILs) was evaluated for the selective extraction of aromatics from aliphatic hydrocarbons. The aromatic extraction ability of PyILs was greatly enhanced by the presence of a methyl group on the pyridinium ring at the 3- or 4-position, whereas the solubility of the aromatics in the PyILs decreased with increasing the number of methyl groups on the benzene ring. The FT-IR studies revealed that the solubility of an aromatic compound in a PyIL is closely correlated with the degree of aromatic C–H bending frequency shift observed during the dissolution of the aromatic compound in the PyIL: the larger the shift, the higher the solubility. The computational calculations on the dispersion interactions between aromatics and PyILs demonstrated that the anion–aromatic interaction is much more important than the cation–aromatic interaction in determining the aromatic solubility in PyILs, and such anion–aromatic interaction can be enhanced by introducing a methyl group at the carbon atom of the pyridinium ring. |
| doi_str_mv | 10.1021/jp409117j |
| format | Article |
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The aromatic extraction ability of PyILs was greatly enhanced by the presence of a methyl group on the pyridinium ring at the 3- or 4-position, whereas the solubility of the aromatics in the PyILs decreased with increasing the number of methyl groups on the benzene ring. The FT-IR studies revealed that the solubility of an aromatic compound in a PyIL is closely correlated with the degree of aromatic C–H bending frequency shift observed during the dissolution of the aromatic compound in the PyIL: the larger the shift, the higher the solubility. The computational calculations on the dispersion interactions between aromatics and PyILs demonstrated that the anion–aromatic interaction is much more important than the cation–aromatic interaction in determining the aromatic solubility in PyILs, and such anion–aromatic interaction can be enhanced by introducing a methyl group at the carbon atom of the pyridinium ring.</description><identifier>ISSN: 1520-6106</identifier><identifier>EISSN: 1520-5207</identifier><identifier>DOI: 10.1021/jp409117j</identifier><identifier>PMID: 24180561</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Applied sciences ; Aromatic compounds ; Carbon ; Cations ; Chemical engineering ; Dispersions ; Exact sciences and technology ; Extraction ; Ionic liquids ; Liquid-liquid extraction ; Rings (mathematics) ; Solubility</subject><ispartof>The journal of physical chemistry. 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The computational calculations on the dispersion interactions between aromatics and PyILs demonstrated that the anion–aromatic interaction is much more important than the cation–aromatic interaction in determining the aromatic solubility in PyILs, and such anion–aromatic interaction can be enhanced by introducing a methyl group at the carbon atom of the pyridinium ring.</description><subject>Applied sciences</subject><subject>Aromatic compounds</subject><subject>Carbon</subject><subject>Cations</subject><subject>Chemical engineering</subject><subject>Dispersions</subject><subject>Exact sciences and technology</subject><subject>Extraction</subject><subject>Ionic liquids</subject><subject>Liquid-liquid extraction</subject><subject>Rings (mathematics)</subject><subject>Solubility</subject><issn>1520-6106</issn><issn>1520-5207</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqF0EtLxDAQB_Agiu-DX0ByEfRQzeTZHtfFFywoPs4lSVPN2jZr0oL77a246kXwMMwcfswwf4QOgJwCoXA2X3BSAKj5GtoGQUk2llpfzRKI3EI7Kc0JoYLmchNtUQ45ERK20cN9aBwONZ40r8sGX8UwLLDvcP_i8CSGVvfe4ov3Pmrb-9Dhp-S7Z3y3jL7ynR_a7FwnV-Gb0I1u5t8GX6U9tFHrJrn9Vd9FT5cXj9PrbHZ7dTOdzDLNVN5nAIbWoLihjAhTEw61FpRbWXDJqGNaCmEct4xZXjFa5aYwOTGcFkQLkzu2i46_9i5ieBtc6svWJ-uaRncuDKkEJdj4MFD2P-WSMkWkIiM9-aI2hpSiq8tF9K2OyxJI-Rl3-RP3aA9XawfTuupHfuc7gqMV0Mnqpo66sz79upwoDqr4ddqmch6G2I3B_XHwA0U7kSg</recordid><startdate>20131127</startdate><enddate>20131127</enddate><creator>Kim, Min Ji</creator><creator>Shin, Seung Hoon</creator><creator>Kim, Young Jin</creator><creator>Cheong, Minserk</creator><creator>Lee, Je Seung</creator><creator>Kim, Hoon Sik</creator><general>American Chemical Society</general><scope>IQODW</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></search><sort><creationdate>20131127</creationdate><title>Role of Alkyl Group in the Aromatic Extraction Using Pyridinium-Based Ionic Liquids</title><author>Kim, Min Ji ; Shin, Seung Hoon ; Kim, Young Jin ; Cheong, Minserk ; Lee, Je Seung ; Kim, Hoon Sik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a378t-11b2f174b2305bf041fa524c694632e3a655be4c33c4d32d8b9b80b4290a5b8e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Applied sciences</topic><topic>Aromatic compounds</topic><topic>Carbon</topic><topic>Cations</topic><topic>Chemical engineering</topic><topic>Dispersions</topic><topic>Exact sciences and technology</topic><topic>Extraction</topic><topic>Ionic liquids</topic><topic>Liquid-liquid extraction</topic><topic>Rings (mathematics)</topic><topic>Solubility</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Min Ji</creatorcontrib><creatorcontrib>Shin, Seung Hoon</creatorcontrib><creatorcontrib>Kim, Young Jin</creatorcontrib><creatorcontrib>Cheong, Minserk</creatorcontrib><creatorcontrib>Lee, Je Seung</creatorcontrib><creatorcontrib>Kim, Hoon Sik</creatorcontrib><collection>Pascal-Francis</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><jtitle>The journal of physical chemistry. B</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Min Ji</au><au>Shin, Seung Hoon</au><au>Kim, Young Jin</au><au>Cheong, Minserk</au><au>Lee, Je Seung</au><au>Kim, Hoon Sik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Role of Alkyl Group in the Aromatic Extraction Using Pyridinium-Based Ionic Liquids</atitle><jtitle>The journal of physical chemistry. B</jtitle><addtitle>J. Phys. Chem. B</addtitle><date>2013-11-27</date><risdate>2013</risdate><volume>117</volume><issue>47</issue><spage>14827</spage><epage>14834</epage><pages>14827-14834</pages><issn>1520-6106</issn><eissn>1520-5207</eissn><abstract>The performance of N-alkylpyridinium-based ionic liquids with a SCN anion (PyILs) was evaluated for the selective extraction of aromatics from aliphatic hydrocarbons. The aromatic extraction ability of PyILs was greatly enhanced by the presence of a methyl group on the pyridinium ring at the 3- or 4-position, whereas the solubility of the aromatics in the PyILs decreased with increasing the number of methyl groups on the benzene ring. The FT-IR studies revealed that the solubility of an aromatic compound in a PyIL is closely correlated with the degree of aromatic C–H bending frequency shift observed during the dissolution of the aromatic compound in the PyIL: the larger the shift, the higher the solubility. The computational calculations on the dispersion interactions between aromatics and PyILs demonstrated that the anion–aromatic interaction is much more important than the cation–aromatic interaction in determining the aromatic solubility in PyILs, and such anion–aromatic interaction can be enhanced by introducing a methyl group at the carbon atom of the pyridinium ring.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>24180561</pmid><doi>10.1021/jp409117j</doi><tpages>8</tpages></addata></record> |
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| subjects | Applied sciences Aromatic compounds Carbon Cations Chemical engineering Dispersions Exact sciences and technology Extraction Ionic liquids Liquid-liquid extraction Rings (mathematics) Solubility |
| title | Role of Alkyl Group in the Aromatic Extraction Using Pyridinium-Based Ionic Liquids |
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