The synergistic effect of benzyl benzoate on the selective oxidation of toluene to benzaldehyde
•Noncarboxylic acid solvents are applied for the liquid-phase oxidation of toluene.•Performances of the ester solvents and acetic acid are compared.•The reaction mechanism and the influence of intermediate products are revealed. To resolve the defects of acetic acid solvents for the liquid-phase oxi...
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| Veröffentlicht in: | Chemical engineering research & design 2019-01, Vol.141, p.181-186 |
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| container_title | Chemical engineering research & design |
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| creator | Lu, Chen Hu, Jiaming Meng, Yuning Zhou, Aidong Zhang, Feng Zhang, Zhibing |
| description | •Noncarboxylic acid solvents are applied for the liquid-phase oxidation of toluene.•Performances of the ester solvents and acetic acid are compared.•The reaction mechanism and the influence of intermediate products are revealed.
To resolve the defects of acetic acid solvents for the liquid-phase oxidation of toluene to benzaldehyde with oxygen, a low-corrosive and green method was developed by introducing benzyl benzoate into the reaction. It was found that compared with the case of acetic acid, benzyl benzoate showed gratifying effect on the oxidation of toluene to benzaldehyde. The reaction was more active in the initial stage of oxidation, and the generated benzaldehyde was protected from further oxidation due to the synergistic effect of benzyl benzoate along with toluene-derived products benzyl alcohol and benzyl bromide. Benzyl benzoate inhibited the esterification of benzyl alcohol, while benzyl bromide promoted the formation of benzyl alcohol. Therefore, considerable benzyl alcohol concentration could be maintained and high benzaldehyde selectivity could be achieved under high toluene conversion. |
| doi_str_mv | 10.1016/j.cherd.2018.10.019 |
| format | Article |
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To resolve the defects of acetic acid solvents for the liquid-phase oxidation of toluene to benzaldehyde with oxygen, a low-corrosive and green method was developed by introducing benzyl benzoate into the reaction. It was found that compared with the case of acetic acid, benzyl benzoate showed gratifying effect on the oxidation of toluene to benzaldehyde. The reaction was more active in the initial stage of oxidation, and the generated benzaldehyde was protected from further oxidation due to the synergistic effect of benzyl benzoate along with toluene-derived products benzyl alcohol and benzyl bromide. Benzyl benzoate inhibited the esterification of benzyl alcohol, while benzyl bromide promoted the formation of benzyl alcohol. Therefore, considerable benzyl alcohol concentration could be maintained and high benzaldehyde selectivity could be achieved under high toluene conversion.</description><identifier>ISSN: 0263-8762</identifier><identifier>EISSN: 1744-3563</identifier><identifier>DOI: 10.1016/j.cherd.2018.10.019</identifier><language>eng</language><publisher>Rugby: Elsevier B.V</publisher><subject>Acetic acid ; Benzaldehyde ; Benzyl alcohol ; Benzyl bromide ; Chemical reactions ; Chemicals ; Effects ; Esterification ; Liquid phase oxidation ; Oxidation ; Selectivity ; Solvents ; Synergistic effect ; Toluene</subject><ispartof>Chemical engineering research & design, 2019-01, Vol.141, p.181-186</ispartof><rights>2018 Institution of Chemical Engineers</rights><rights>Copyright Elsevier Science Ltd. Jan 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-c193c3140a7e6c3f19d4e9108ad09353208d4bf127fdc3152b19212018eb13513</citedby><cites>FETCH-LOGICAL-c368t-c193c3140a7e6c3f19d4e9108ad09353208d4bf127fdc3152b19212018eb13513</cites><orcidid>0000-0002-1872-1602</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.cherd.2018.10.019$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Lu, Chen</creatorcontrib><creatorcontrib>Hu, Jiaming</creatorcontrib><creatorcontrib>Meng, Yuning</creatorcontrib><creatorcontrib>Zhou, Aidong</creatorcontrib><creatorcontrib>Zhang, Feng</creatorcontrib><creatorcontrib>Zhang, Zhibing</creatorcontrib><title>The synergistic effect of benzyl benzoate on the selective oxidation of toluene to benzaldehyde</title><title>Chemical engineering research & design</title><description>•Noncarboxylic acid solvents are applied for the liquid-phase oxidation of toluene.•Performances of the ester solvents and acetic acid are compared.•The reaction mechanism and the influence of intermediate products are revealed.
To resolve the defects of acetic acid solvents for the liquid-phase oxidation of toluene to benzaldehyde with oxygen, a low-corrosive and green method was developed by introducing benzyl benzoate into the reaction. It was found that compared with the case of acetic acid, benzyl benzoate showed gratifying effect on the oxidation of toluene to benzaldehyde. The reaction was more active in the initial stage of oxidation, and the generated benzaldehyde was protected from further oxidation due to the synergistic effect of benzyl benzoate along with toluene-derived products benzyl alcohol and benzyl bromide. Benzyl benzoate inhibited the esterification of benzyl alcohol, while benzyl bromide promoted the formation of benzyl alcohol. Therefore, considerable benzyl alcohol concentration could be maintained and high benzaldehyde selectivity could be achieved under high toluene conversion.</description><subject>Acetic acid</subject><subject>Benzaldehyde</subject><subject>Benzyl alcohol</subject><subject>Benzyl bromide</subject><subject>Chemical reactions</subject><subject>Chemicals</subject><subject>Effects</subject><subject>Esterification</subject><subject>Liquid phase oxidation</subject><subject>Oxidation</subject><subject>Selectivity</subject><subject>Solvents</subject><subject>Synergistic effect</subject><subject>Toluene</subject><issn>0263-8762</issn><issn>1744-3563</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kEtPwzAQhC0EEqXwC7hE4pzgtfM8cEAVL6kSl3K2EntNHYW42C4i_HqcljOnkWZndrUfIddAM6BQ3vaZ3KJTGaNQRyej0JyQBVR5nvKi5KdkQVnJ07oq2Tm58L6nlMZpvSBis8XETyO6d-ODkQlqjTIkVicdjj_TcBDbBkzsmIQ5jEMMmK9ofBvVBhP9mA522OOIUQ-NdlC4nRRekjPdDh6v_nRJ3h4fNqvndP369LK6X6eSl3VIJTRccshpW2EpuYZG5dgArVtFG15wRmuVdxpYpVXMFayDhsH8LnbAC-BLcnPcu3P2c48-iN7u3RhPCgZ1TjljEcSS8GNKOuu9Qy12zny0bhJAxUxS9OJAUsyrZzOSjK27YwvjA18GnfDS4ChRGRdRCGXNv_1fh619Nw</recordid><startdate>201901</startdate><enddate>201901</enddate><creator>Lu, Chen</creator><creator>Hu, Jiaming</creator><creator>Meng, Yuning</creator><creator>Zhou, Aidong</creator><creator>Zhang, Feng</creator><creator>Zhang, Zhibing</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-1872-1602</orcidid></search><sort><creationdate>201901</creationdate><title>The synergistic effect of benzyl benzoate on the selective oxidation of toluene to benzaldehyde</title><author>Lu, Chen ; Hu, Jiaming ; Meng, Yuning ; Zhou, Aidong ; Zhang, Feng ; Zhang, Zhibing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-c193c3140a7e6c3f19d4e9108ad09353208d4bf127fdc3152b19212018eb13513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Acetic acid</topic><topic>Benzaldehyde</topic><topic>Benzyl alcohol</topic><topic>Benzyl bromide</topic><topic>Chemical reactions</topic><topic>Chemicals</topic><topic>Effects</topic><topic>Esterification</topic><topic>Liquid phase oxidation</topic><topic>Oxidation</topic><topic>Selectivity</topic><topic>Solvents</topic><topic>Synergistic effect</topic><topic>Toluene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lu, Chen</creatorcontrib><creatorcontrib>Hu, Jiaming</creatorcontrib><creatorcontrib>Meng, Yuning</creatorcontrib><creatorcontrib>Zhou, Aidong</creatorcontrib><creatorcontrib>Zhang, Feng</creatorcontrib><creatorcontrib>Zhang, Zhibing</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemical engineering research & design</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lu, Chen</au><au>Hu, Jiaming</au><au>Meng, Yuning</au><au>Zhou, Aidong</au><au>Zhang, Feng</au><au>Zhang, Zhibing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The synergistic effect of benzyl benzoate on the selective oxidation of toluene to benzaldehyde</atitle><jtitle>Chemical engineering research & design</jtitle><date>2019-01</date><risdate>2019</risdate><volume>141</volume><spage>181</spage><epage>186</epage><pages>181-186</pages><issn>0263-8762</issn><eissn>1744-3563</eissn><abstract>•Noncarboxylic acid solvents are applied for the liquid-phase oxidation of toluene.•Performances of the ester solvents and acetic acid are compared.•The reaction mechanism and the influence of intermediate products are revealed.
To resolve the defects of acetic acid solvents for the liquid-phase oxidation of toluene to benzaldehyde with oxygen, a low-corrosive and green method was developed by introducing benzyl benzoate into the reaction. It was found that compared with the case of acetic acid, benzyl benzoate showed gratifying effect on the oxidation of toluene to benzaldehyde. The reaction was more active in the initial stage of oxidation, and the generated benzaldehyde was protected from further oxidation due to the synergistic effect of benzyl benzoate along with toluene-derived products benzyl alcohol and benzyl bromide. Benzyl benzoate inhibited the esterification of benzyl alcohol, while benzyl bromide promoted the formation of benzyl alcohol. Therefore, considerable benzyl alcohol concentration could be maintained and high benzaldehyde selectivity could be achieved under high toluene conversion.</abstract><cop>Rugby</cop><pub>Elsevier B.V</pub><doi>10.1016/j.cherd.2018.10.019</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-1872-1602</orcidid></addata></record> |
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| ispartof | Chemical engineering research & design, 2019-01, Vol.141, p.181-186 |
| issn | 0263-8762 1744-3563 |
| language | eng |
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| source | Elsevier ScienceDirect Journals Complete |
| subjects | Acetic acid Benzaldehyde Benzyl alcohol Benzyl bromide Chemical reactions Chemicals Effects Esterification Liquid phase oxidation Oxidation Selectivity Solvents Synergistic effect Toluene |
| title | The synergistic effect of benzyl benzoate on the selective oxidation of toluene to benzaldehyde |
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