Facile esterification of carboxylic acid using amide functionalized benzimidazolium dicationic ionic liquids
•Amide functionalized dicationic benzimidazolium based ionic liquids were synthesized.•Their efficacy as catalysts for esterification has been demonstrated.•Catalytic activity attributed to the amide functionality of ILs via hydrogen bonding.•Catalysts were recyclable for seven runs without signific...
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Veröffentlicht in: | Applied catalysis. A, General General, 2014-07, Vol.482, p.214-220 |
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container_title | Applied catalysis. A, General |
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creator | Muskawar, Prashant Narayan Thenmozhi, K. Gajbhiye, Jayant M. Bhagat, Pundlik Rambhau |
description | •Amide functionalized dicationic benzimidazolium based ionic liquids were synthesized.•Their efficacy as catalysts for esterification has been demonstrated.•Catalytic activity attributed to the amide functionality of ILs via hydrogen bonding.•Catalysts were recyclable for seven runs without significant loss in activity.
Herein, we report the synthesis of a new series of amide functionalized dicationic benzimidazolium based ionic liquids (DBimILs) and appraised their efficacy towards perceptive esterification of carboxylic acids with alkyl/allyl/aryl halides in presence of triethylamine. The amide groups present in this new series of DBimILs are expected to form hydrogen bonding with the carboxylic acids and this could facilitate the esterification reactions under mild conditions devoid of any added catalyst or organic solvent. The plausible mechanism for the enhanced catalytic activity in presence of this new series of ILs has been proposed. The corresponding alkyl/allyl/aryl esters isolated from this reaction were of high purity after simple extraction, which wipe out the necessity for further purification. This protocol addresses clean methodology and the efficient recyclability as well as reusability of the catalyst. |
doi_str_mv | 10.1016/j.apcata.2014.06.004 |
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Herein, we report the synthesis of a new series of amide functionalized dicationic benzimidazolium based ionic liquids (DBimILs) and appraised their efficacy towards perceptive esterification of carboxylic acids with alkyl/allyl/aryl halides in presence of triethylamine. The amide groups present in this new series of DBimILs are expected to form hydrogen bonding with the carboxylic acids and this could facilitate the esterification reactions under mild conditions devoid of any added catalyst or organic solvent. The plausible mechanism for the enhanced catalytic activity in presence of this new series of ILs has been proposed. The corresponding alkyl/allyl/aryl esters isolated from this reaction were of high purity after simple extraction, which wipe out the necessity for further purification. This protocol addresses clean methodology and the efficient recyclability as well as reusability of the catalyst.</description><identifier>ISSN: 0926-860X</identifier><identifier>EISSN: 1873-3875</identifier><identifier>DOI: 10.1016/j.apcata.2014.06.004</identifier><language>eng</language><publisher>Kidlington: Elsevier B.V</publisher><subject>Amides ; Aromatic compounds ; Benzimidazolium ; Carboxylic acids ; Catalysis ; Catalysts ; Chemistry ; Dicationic ionic liquids ; Esterification ; Exact sciences and technology ; Extraction ; General and physical chemistry ; Homogenous catalysis ; Ionic liquids ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry ; Triethylamine</subject><ispartof>Applied catalysis. A, General, 2014-07, Vol.482, p.214-220</ispartof><rights>2014 Elsevier B.V.</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c439t-96c9c6128920748eaf48c514678af92725e98953c047ffaf735b0d1d1ed331ee3</citedby><cites>FETCH-LOGICAL-c439t-96c9c6128920748eaf48c514678af92725e98953c047ffaf735b0d1d1ed331ee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.apcata.2014.06.004$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=28640463$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Muskawar, Prashant Narayan</creatorcontrib><creatorcontrib>Thenmozhi, K.</creatorcontrib><creatorcontrib>Gajbhiye, Jayant M.</creatorcontrib><creatorcontrib>Bhagat, Pundlik Rambhau</creatorcontrib><title>Facile esterification of carboxylic acid using amide functionalized benzimidazolium dicationic ionic liquids</title><title>Applied catalysis. A, General</title><description>•Amide functionalized dicationic benzimidazolium based ionic liquids were synthesized.•Their efficacy as catalysts for esterification has been demonstrated.•Catalytic activity attributed to the amide functionality of ILs via hydrogen bonding.•Catalysts were recyclable for seven runs without significant loss in activity.
Herein, we report the synthesis of a new series of amide functionalized dicationic benzimidazolium based ionic liquids (DBimILs) and appraised their efficacy towards perceptive esterification of carboxylic acids with alkyl/allyl/aryl halides in presence of triethylamine. The amide groups present in this new series of DBimILs are expected to form hydrogen bonding with the carboxylic acids and this could facilitate the esterification reactions under mild conditions devoid of any added catalyst or organic solvent. The plausible mechanism for the enhanced catalytic activity in presence of this new series of ILs has been proposed. The corresponding alkyl/allyl/aryl esters isolated from this reaction were of high purity after simple extraction, which wipe out the necessity for further purification. This protocol addresses clean methodology and the efficient recyclability as well as reusability of the catalyst.</description><subject>Amides</subject><subject>Aromatic compounds</subject><subject>Benzimidazolium</subject><subject>Carboxylic acids</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Dicationic ionic liquids</subject><subject>Esterification</subject><subject>Exact sciences and technology</subject><subject>Extraction</subject><subject>General and physical chemistry</subject><subject>Homogenous catalysis</subject><subject>Ionic liquids</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><subject>Triethylamine</subject><issn>0926-860X</issn><issn>1873-3875</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqNkU-LFDEQxYMoOK77DTz0RfDSbaU7nT8XQRbXFRa8KOwtZJKK1JDpnk2mxZ1Pb4YePC5eqg71e6-oeoy949Bx4PLjrnMH746u64GLDmQHIF6wDddqaAetxpdsA6aXrZbw8Jq9KWUHAL0w44alW-cpYYPliJkiVRuap2aOjXd5O_95SuSbioRmKTT9atyeAjZxmfyZc4lOGJotTieqA3eaEy37JlxsqnStiR4XCuUtexVdKnh96Vfs5-2XHzd37f33r99uPt-3Xgzm2BrpjZe816YHJTS6KLQfuZBKu2h61Y9otBkHD0LF6KIaxi0EHjiGYeCIwxX7sPoe8vy41NPsnorHlNyE81Isr07AFTfwH2gPILVSsqJiRX2eS8kY7SHT3uUny8Gec7A7u-ZgzzlYkLbmUGXvLxtc8S7F7CZP5Z-211KAkEPlPq0c1s_8Jsy2eMLJY6CM_mjDTM8v-gtCQaFQ</recordid><startdate>20140722</startdate><enddate>20140722</enddate><creator>Muskawar, Prashant Narayan</creator><creator>Thenmozhi, K.</creator><creator>Gajbhiye, Jayant M.</creator><creator>Bhagat, Pundlik Rambhau</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20140722</creationdate><title>Facile esterification of carboxylic acid using amide functionalized benzimidazolium dicationic ionic liquids</title><author>Muskawar, Prashant Narayan ; Thenmozhi, K. ; Gajbhiye, Jayant M. ; Bhagat, Pundlik Rambhau</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c439t-96c9c6128920748eaf48c514678af92725e98953c047ffaf735b0d1d1ed331ee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amides</topic><topic>Aromatic compounds</topic><topic>Benzimidazolium</topic><topic>Carboxylic acids</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Dicationic ionic liquids</topic><topic>Esterification</topic><topic>Exact sciences and technology</topic><topic>Extraction</topic><topic>General and physical chemistry</topic><topic>Homogenous catalysis</topic><topic>Ionic liquids</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><topic>Triethylamine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Muskawar, Prashant Narayan</creatorcontrib><creatorcontrib>Thenmozhi, K.</creatorcontrib><creatorcontrib>Gajbhiye, Jayant M.</creatorcontrib><creatorcontrib>Bhagat, Pundlik Rambhau</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</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>Applied catalysis. A, General</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Muskawar, Prashant Narayan</au><au>Thenmozhi, K.</au><au>Gajbhiye, Jayant M.</au><au>Bhagat, Pundlik Rambhau</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile esterification of carboxylic acid using amide functionalized benzimidazolium dicationic ionic liquids</atitle><jtitle>Applied catalysis. A, General</jtitle><date>2014-07-22</date><risdate>2014</risdate><volume>482</volume><spage>214</spage><epage>220</epage><pages>214-220</pages><issn>0926-860X</issn><eissn>1873-3875</eissn><abstract>•Amide functionalized dicationic benzimidazolium based ionic liquids were synthesized.•Their efficacy as catalysts for esterification has been demonstrated.•Catalytic activity attributed to the amide functionality of ILs via hydrogen bonding.•Catalysts were recyclable for seven runs without significant loss in activity.
Herein, we report the synthesis of a new series of amide functionalized dicationic benzimidazolium based ionic liquids (DBimILs) and appraised their efficacy towards perceptive esterification of carboxylic acids with alkyl/allyl/aryl halides in presence of triethylamine. The amide groups present in this new series of DBimILs are expected to form hydrogen bonding with the carboxylic acids and this could facilitate the esterification reactions under mild conditions devoid of any added catalyst or organic solvent. The plausible mechanism for the enhanced catalytic activity in presence of this new series of ILs has been proposed. The corresponding alkyl/allyl/aryl esters isolated from this reaction were of high purity after simple extraction, which wipe out the necessity for further purification. This protocol addresses clean methodology and the efficient recyclability as well as reusability of the catalyst.</abstract><cop>Kidlington</cop><pub>Elsevier B.V</pub><doi>10.1016/j.apcata.2014.06.004</doi><tpages>7</tpages></addata></record> |
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subjects | Amides Aromatic compounds Benzimidazolium Carboxylic acids Catalysis Catalysts Chemistry Dicationic ionic liquids Esterification Exact sciences and technology Extraction General and physical chemistry Homogenous catalysis Ionic liquids Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Triethylamine |
title | Facile esterification of carboxylic acid using amide functionalized benzimidazolium dicationic ionic liquids |
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