Selective Green Synthesis of 1,5-Benzodiazepine over Modified Heteropolyacid as Nanocatalyst: Kinetics and Mechanism
The present work deals with synthesis of 2,3-dihydro-1H-1,5-benzodiazepine from o-phenylenediamine and acetophenone at 100 °C using a variety of solid acid catalysts, among which 20% w/w Cs2.5H0.5PW12O40 (Cs-DTP)/K-10 clay was the best. The effects of various parameters such as speed of agitation, c...
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Veröffentlicht in: | Industrial & engineering chemistry research 2013-12, Vol.52 (50), p.17812-17820 |
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creator | Yadav, Ganapati D Yadav, Akhilesh R |
description | The present work deals with synthesis of 2,3-dihydro-1H-1,5-benzodiazepine from o-phenylenediamine and acetophenone at 100 °C using a variety of solid acid catalysts, among which 20% w/w Cs2.5H0.5PW12O40 (Cs-DTP)/K-10 clay was the best. The effects of various parameters such as speed of agitation, catalyst loading, mole ratio of 1,2-diamine to acetophenone, and temperature were studied with 20%w/w Cs-DTP/K-10 to establish kinetics of the reaction. The catalyst was found highly active, robust and reusable. The reaction follows Langmuir–Hinshelwood–Hougen–Watson type of mechanism with weak adsorption of all species. The apparent energy of activation is 9.39 kcal/mol. The studies were extended to synthesis of various derivatives of benzodiazepines, which are biologically active. |
doi_str_mv | 10.1021/ie402654u |
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The effects of various parameters such as speed of agitation, catalyst loading, mole ratio of 1,2-diamine to acetophenone, and temperature were studied with 20%w/w Cs-DTP/K-10 to establish kinetics of the reaction. The catalyst was found highly active, robust and reusable. The reaction follows Langmuir–Hinshelwood–Hougen–Watson type of mechanism with weak adsorption of all species. The apparent energy of activation is 9.39 kcal/mol. The studies were extended to synthesis of various derivatives of benzodiazepines, which are biologically active.</description><identifier>ISSN: 0888-5885</identifier><identifier>EISSN: 1520-5045</identifier><identifier>DOI: 10.1021/ie402654u</identifier><language>eng</language><publisher>American Chemical Society</publisher><subject>Acetophenone ; Catalysis ; Catalysts ; Derivatives ; Industrial engineering ; Nanostructure ; Reaction kinetics ; Synthesis</subject><ispartof>Industrial & engineering chemistry research, 2013-12, Vol.52 (50), p.17812-17820</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a292t-83f1b0c7bceebc94fbba48e25b25205f8f484235aa57c5736c9d7ee706729e2f3</citedby><cites>FETCH-LOGICAL-a292t-83f1b0c7bceebc94fbba48e25b25205f8f484235aa57c5736c9d7ee706729e2f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ie402654u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ie402654u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids></links><search><creatorcontrib>Yadav, Ganapati D</creatorcontrib><creatorcontrib>Yadav, Akhilesh R</creatorcontrib><title>Selective Green Synthesis of 1,5-Benzodiazepine over Modified Heteropolyacid as Nanocatalyst: Kinetics and Mechanism</title><title>Industrial & engineering chemistry research</title><addtitle>Ind. Eng. Chem. Res</addtitle><description>The present work deals with synthesis of 2,3-dihydro-1H-1,5-benzodiazepine from o-phenylenediamine and acetophenone at 100 °C using a variety of solid acid catalysts, among which 20% w/w Cs2.5H0.5PW12O40 (Cs-DTP)/K-10 clay was the best. The effects of various parameters such as speed of agitation, catalyst loading, mole ratio of 1,2-diamine to acetophenone, and temperature were studied with 20%w/w Cs-DTP/K-10 to establish kinetics of the reaction. The catalyst was found highly active, robust and reusable. The reaction follows Langmuir–Hinshelwood–Hougen–Watson type of mechanism with weak adsorption of all species. The apparent energy of activation is 9.39 kcal/mol. The studies were extended to synthesis of various derivatives of benzodiazepines, which are biologically active.</description><subject>Acetophenone</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Derivatives</subject><subject>Industrial engineering</subject><subject>Nanostructure</subject><subject>Reaction kinetics</subject><subject>Synthesis</subject><issn>0888-5885</issn><issn>1520-5045</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNpt0EFLwzAUB_AgCs7pwW-Qi6BgNU2TNvWmQ5246WF6Lmn6wjK6ZCbpoPv0ViaePD14_N6D_x-h85TcpISmtwYYoTln3QEapZyShBPGD9GICCESLgQ_RichrAghnDM2QnEBLahotoCfPYDFi97GJQQTsNM4vebJA9ida4zcwcZYwG4LHs-HhTbQ4ClE8G7j2l4q02AZ8Ju0Tsko2z7EO_w6nESjApa2wXNQS2lNWJ-iIy3bAGe_c4w-nx4_JtNk9v78MrmfJZKWNCYi02lNVFErgFqVTNe1ZAIor-mQjGuhmWA041LyQvEiy1XZFAAFyQtaAtXZGF3u_268--ogxGptgoK2lRZcF6o0L2lWsDwvB3q1p8q7EDzoauPNWvq-Skn102z11-xgL_ZWqlCtXOftEOIf9w0h2Hjp</recordid><startdate>20131218</startdate><enddate>20131218</enddate><creator>Yadav, Ganapati D</creator><creator>Yadav, Akhilesh R</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20131218</creationdate><title>Selective Green Synthesis of 1,5-Benzodiazepine over Modified Heteropolyacid as Nanocatalyst: Kinetics and Mechanism</title><author>Yadav, Ganapati D ; Yadav, Akhilesh R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a292t-83f1b0c7bceebc94fbba48e25b25205f8f484235aa57c5736c9d7ee706729e2f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Acetophenone</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Derivatives</topic><topic>Industrial engineering</topic><topic>Nanostructure</topic><topic>Reaction kinetics</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yadav, Ganapati D</creatorcontrib><creatorcontrib>Yadav, Akhilesh R</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Industrial & engineering chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yadav, Ganapati D</au><au>Yadav, Akhilesh R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Green Synthesis of 1,5-Benzodiazepine over Modified Heteropolyacid as Nanocatalyst: Kinetics and Mechanism</atitle><jtitle>Industrial & engineering chemistry research</jtitle><addtitle>Ind. Eng. Chem. Res</addtitle><date>2013-12-18</date><risdate>2013</risdate><volume>52</volume><issue>50</issue><spage>17812</spage><epage>17820</epage><pages>17812-17820</pages><issn>0888-5885</issn><eissn>1520-5045</eissn><abstract>The present work deals with synthesis of 2,3-dihydro-1H-1,5-benzodiazepine from o-phenylenediamine and acetophenone at 100 °C using a variety of solid acid catalysts, among which 20% w/w Cs2.5H0.5PW12O40 (Cs-DTP)/K-10 clay was the best. The effects of various parameters such as speed of agitation, catalyst loading, mole ratio of 1,2-diamine to acetophenone, and temperature were studied with 20%w/w Cs-DTP/K-10 to establish kinetics of the reaction. The catalyst was found highly active, robust and reusable. The reaction follows Langmuir–Hinshelwood–Hougen–Watson type of mechanism with weak adsorption of all species. The apparent energy of activation is 9.39 kcal/mol. The studies were extended to synthesis of various derivatives of benzodiazepines, which are biologically active.</abstract><pub>American Chemical Society</pub><doi>10.1021/ie402654u</doi><tpages>9</tpages></addata></record> |
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subjects | Acetophenone Catalysis Catalysts Derivatives Industrial engineering Nanostructure Reaction kinetics Synthesis |
title | Selective Green Synthesis of 1,5-Benzodiazepine over Modified Heteropolyacid as Nanocatalyst: Kinetics and Mechanism |
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