Selectivity Engineered Friedel–Crafts Acylation of Guaiacol with Vinyl Acetate to Acetovanillone over Cesium-Modified Heteropolyacid Supported on K‑10 Clay
Acetovanillone or apocynin (4-hydroxy-3-methoxyacetophenone) is an effective natural drug. It is typically synthesized by using unsafe and expensive methods. The current paper deals with Friedel–Crafts acylation of guaiacol using several solid acids including modified heteropolyacids (HPA) and modif...
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| Veröffentlicht in: | Industrial & engineering chemistry research 2013-08, Vol.52 (31), p.10627-10636 |
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| creator | Yadav, Ganapati D Yadav, Akhilesh R |
| description | Acetovanillone or apocynin (4-hydroxy-3-methoxyacetophenone) is an effective natural drug. It is typically synthesized by using unsafe and expensive methods. The current paper deals with Friedel–Crafts acylation of guaiacol using several solid acids including modified heteropolyacids (HPA) and modified forms of sulfated zirconia, such as 20% w/w Cs2.5H0.5PW12O40/K-10, 20% w/w H3PW12O40/hexagonal mesoporous silica (HMS), K-10 clay, UDCaT-5, UDCaT-6, and UDCaT-4. Among these, 20% w/w cesium modified dodecatungstophosphoric acid supported on K-10 clay (Cs2.5H0.5PW12O40/K-10) was found to be the best. Vinyl acetate was the best acylating agent. The effects of various factors affecting rate of reaction were studied to establish kinetics and mechanism of reaction. A mathematical model is built to interpret the kinetic data and develop a mechanism. The reaction is intrinsic kinetically controlled and the apparent energy of activation was found to be 15.46 kcal/mol. |
| doi_str_mv | 10.1021/ie401260a |
| format | Article |
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Eng. Chem. Res</addtitle><description>Acetovanillone or apocynin (4-hydroxy-3-methoxyacetophenone) is an effective natural drug. It is typically synthesized by using unsafe and expensive methods. The current paper deals with Friedel–Crafts acylation of guaiacol using several solid acids including modified heteropolyacids (HPA) and modified forms of sulfated zirconia, such as 20% w/w Cs2.5H0.5PW12O40/K-10, 20% w/w H3PW12O40/hexagonal mesoporous silica (HMS), K-10 clay, UDCaT-5, UDCaT-6, and UDCaT-4. Among these, 20% w/w cesium modified dodecatungstophosphoric acid supported on K-10 clay (Cs2.5H0.5PW12O40/K-10) was found to be the best. Vinyl acetate was the best acylating agent. The effects of various factors affecting rate of reaction were studied to establish kinetics and mechanism of reaction. A mathematical model is built to interpret the kinetic data and develop a mechanism. The reaction is intrinsic kinetically controlled and the apparent energy of activation was found to be 15.46 kcal/mol.</description><subject>Acylation</subject><subject>Clay (material)</subject><subject>Industrial engineering</subject><subject>Mathematical models</subject><subject>Reaction kinetics</subject><subject>Silicon dioxide</subject><subject>Vinyl acetate</subject><subject>Zirconium dioxide</subject><issn>0888-5885</issn><issn>1520-5045</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNptkU1O3TAUha2qSH2FDroDTyrBIK2d2IkzRBE_FVQMaDuN7rOvWyO_ONjOQ5mxhYoFdG-spKEPMWJ0rnQ-naujQ8hHzj5zVvIvDgXjZc3gDVlxWbJCMiHfkhVTShVSKfmOvE_phjEmpRAr8vcaPersti7P9GT45QbEiIaeRocG_eP9QxfB5kSP9ewhuzDQYOnZBA508PTO5d_0pxtmvwCYISPN4f8ZtjA478OANGwx0g6TmzbFt2CcXaLpOWaMYQx-Bu0MvZ7GMcS8GMuHi8f7P5zRzsN8QPYs-IQfnnWf_Dg9-d6dF5dXZ1-748sCqrLNRd3A2oKySrZL0ZLppq5Fq5lhvKmM1ev12rTMGtlqbAS0WiioZCOYbevaNKbaJ4e73DGG2wlT7jcuafQeBgxT6nndlpWqy0Ys6NEO1TGkFNH2Y3QbiHPPWf80Qv8ywsJ-2rGgU38TpjgsJV7h_gEvgYpQ</recordid><startdate>20130807</startdate><enddate>20130807</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>20130807</creationdate><title>Selectivity Engineered Friedel–Crafts Acylation of Guaiacol with Vinyl Acetate to Acetovanillone over Cesium-Modified Heteropolyacid Supported on K‑10 Clay</title><author>Yadav, Ganapati D ; Yadav, Akhilesh R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a329t-67abfa8f85988820c76649c0d0173dfcbbbd90fd59ce74a9c48a35740f966d7d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Acylation</topic><topic>Clay (material)</topic><topic>Industrial engineering</topic><topic>Mathematical models</topic><topic>Reaction kinetics</topic><topic>Silicon dioxide</topic><topic>Vinyl acetate</topic><topic>Zirconium dioxide</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>Selectivity Engineered Friedel–Crafts Acylation of Guaiacol with Vinyl Acetate to Acetovanillone over Cesium-Modified Heteropolyacid Supported on K‑10 Clay</atitle><jtitle>Industrial & engineering chemistry research</jtitle><addtitle>Ind. Eng. Chem. Res</addtitle><date>2013-08-07</date><risdate>2013</risdate><volume>52</volume><issue>31</issue><spage>10627</spage><epage>10636</epage><pages>10627-10636</pages><issn>0888-5885</issn><eissn>1520-5045</eissn><abstract>Acetovanillone or apocynin (4-hydroxy-3-methoxyacetophenone) is an effective natural drug. It is typically synthesized by using unsafe and expensive methods. The current paper deals with Friedel–Crafts acylation of guaiacol using several solid acids including modified heteropolyacids (HPA) and modified forms of sulfated zirconia, such as 20% w/w Cs2.5H0.5PW12O40/K-10, 20% w/w H3PW12O40/hexagonal mesoporous silica (HMS), K-10 clay, UDCaT-5, UDCaT-6, and UDCaT-4. Among these, 20% w/w cesium modified dodecatungstophosphoric acid supported on K-10 clay (Cs2.5H0.5PW12O40/K-10) was found to be the best. Vinyl acetate was the best acylating agent. The effects of various factors affecting rate of reaction were studied to establish kinetics and mechanism of reaction. A mathematical model is built to interpret the kinetic data and develop a mechanism. The reaction is intrinsic kinetically controlled and the apparent energy of activation was found to be 15.46 kcal/mol.</abstract><pub>American Chemical Society</pub><doi>10.1021/ie401260a</doi><tpages>10</tpages></addata></record> |
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| ispartof | Industrial & engineering chemistry research, 2013-08, Vol.52 (31), p.10627-10636 |
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| language | eng |
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| source | American Chemical Society Journals |
| subjects | Acylation Clay (material) Industrial engineering Mathematical models Reaction kinetics Silicon dioxide Vinyl acetate Zirconium dioxide |
| title | Selectivity Engineered Friedel–Crafts Acylation of Guaiacol with Vinyl Acetate to Acetovanillone over Cesium-Modified Heteropolyacid Supported on K‑10 Clay |
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