Photooxidation of Cyclohexane by Visible and Near-UV Light Catalyzed by Tetraethylammonium Tetrachloroferrate
Tetraethylammonium tetrachloroferrate catalyzes the photooxidation of cyclohexane heterogeneously, exhibiting significant photocatalysis even in the visible portion of the spectrum. The photoproducts, cyclohexanol and cyclohexanone, initially develop at constant rates, implying that the ketone and t...
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| Veröffentlicht in: | Catalysts 2018-09, Vol.8 (9), p.403 |
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| creator | Fahy, Kira M. Liu, Adam C. Barnard, Kelsie R. Bright, Valerie R. Enright, Robert J. Hoggard, Patrick E. |
| description | Tetraethylammonium tetrachloroferrate catalyzes the photooxidation of cyclohexane heterogeneously, exhibiting significant photocatalysis even in the visible portion of the spectrum. The photoproducts, cyclohexanol and cyclohexanone, initially develop at constant rates, implying that the ketone and the alcohol are both primary products. The yield is improved by the inclusion of 1% acetic acid in the cyclohexane. With small amounts of catalyst, the reaction rate increases with the amount of catalyst employed, but then passes through a maximum and decreases, due to increased reflection of the incident light. The reaction rate also passes through a maximum as the percentage of dioxygen above the sample is increased. This behavior is due to quenching by oxygen, which at the same time is a reactant. Under one set of reaction conditions, the photonic efficiency at 365 nm was 0.018 mol/Einstein. Compared to TiO2 as a catalyst, Et4N[FeCl4] generates lower yields at wavelengths below about 380 nm, but higher yields at longer wavelengths. Selectivity for cyclohexanol is considerably greater with Et4N[FeCl4], and oxidation does not proceed past cyclohexanone. |
| doi_str_mv | 10.3390/catal8090403 |
| format | Article |
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The photoproducts, cyclohexanol and cyclohexanone, initially develop at constant rates, implying that the ketone and the alcohol are both primary products. The yield is improved by the inclusion of 1% acetic acid in the cyclohexane. With small amounts of catalyst, the reaction rate increases with the amount of catalyst employed, but then passes through a maximum and decreases, due to increased reflection of the incident light. The reaction rate also passes through a maximum as the percentage of dioxygen above the sample is increased. This behavior is due to quenching by oxygen, which at the same time is a reactant. Under one set of reaction conditions, the photonic efficiency at 365 nm was 0.018 mol/Einstein. Compared to TiO2 as a catalyst, Et4N[FeCl4] generates lower yields at wavelengths below about 380 nm, but higher yields at longer wavelengths. Selectivity for cyclohexanol is considerably greater with Et4N[FeCl4], and oxidation does not proceed past cyclohexanone.</description><identifier>ISSN: 2073-4344</identifier><identifier>EISSN: 2073-4344</identifier><identifier>DOI: 10.3390/catal8090403</identifier><language>eng</language><publisher>Basel: MDPI AG</publisher><subject>Acetic acid ; Acids ; Catalysis ; Catalysts ; Chemical reactions ; Chlorine ; Cyclohexane ; Cyclohexanone ; Experiments ; Green chemistry ; Hydrocarbons ; Incident light ; Light reflection ; Oxidation ; Photocatalysis ; Photonics ; Photooxidation ; Product development ; Titanium ; Titanium dioxide ; Wavelengths ; Zeolites</subject><ispartof>Catalysts, 2018-09, Vol.8 (9), p.403</ispartof><rights>2018. This work is licensed under https://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c301t-fcb480f0cd0fc0d03e011f707d63c56d57f37fbedf7a5fb038e0c609557c65e3</citedby><cites>FETCH-LOGICAL-c301t-fcb480f0cd0fc0d03e011f707d63c56d57f37fbedf7a5fb038e0c609557c65e3</cites><orcidid>0000-0003-3086-8751 ; 0000-0001-6490-3004</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Fahy, Kira M.</creatorcontrib><creatorcontrib>Liu, Adam C.</creatorcontrib><creatorcontrib>Barnard, Kelsie R.</creatorcontrib><creatorcontrib>Bright, Valerie R.</creatorcontrib><creatorcontrib>Enright, Robert J.</creatorcontrib><creatorcontrib>Hoggard, Patrick E.</creatorcontrib><title>Photooxidation of Cyclohexane by Visible and Near-UV Light Catalyzed by Tetraethylammonium Tetrachloroferrate</title><title>Catalysts</title><description>Tetraethylammonium tetrachloroferrate catalyzes the photooxidation of cyclohexane heterogeneously, exhibiting significant photocatalysis even in the visible portion of the spectrum. The photoproducts, cyclohexanol and cyclohexanone, initially develop at constant rates, implying that the ketone and the alcohol are both primary products. The yield is improved by the inclusion of 1% acetic acid in the cyclohexane. With small amounts of catalyst, the reaction rate increases with the amount of catalyst employed, but then passes through a maximum and decreases, due to increased reflection of the incident light. The reaction rate also passes through a maximum as the percentage of dioxygen above the sample is increased. This behavior is due to quenching by oxygen, which at the same time is a reactant. Under one set of reaction conditions, the photonic efficiency at 365 nm was 0.018 mol/Einstein. Compared to TiO2 as a catalyst, Et4N[FeCl4] generates lower yields at wavelengths below about 380 nm, but higher yields at longer wavelengths. Selectivity for cyclohexanol is considerably greater with Et4N[FeCl4], and oxidation does not proceed past cyclohexanone.</description><subject>Acetic acid</subject><subject>Acids</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Chlorine</subject><subject>Cyclohexane</subject><subject>Cyclohexanone</subject><subject>Experiments</subject><subject>Green chemistry</subject><subject>Hydrocarbons</subject><subject>Incident light</subject><subject>Light reflection</subject><subject>Oxidation</subject><subject>Photocatalysis</subject><subject>Photonics</subject><subject>Photooxidation</subject><subject>Product development</subject><subject>Titanium</subject><subject>Titanium dioxide</subject><subject>Wavelengths</subject><subject>Zeolites</subject><issn>2073-4344</issn><issn>2073-4344</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>BENPR</sourceid><recordid>eNpNkF9LwzAUxYMoOHRvfoCAr1ZvmqZpH6X4D4b6MPda0uTGZrTNTDNY_fRuzIedl3s4_LgHDiE3DO45L-FBq6i6AkrIgJ-RWQqSJxnPsvMTf0nm47iGvUrGCyZmpP9sffR-54yKzg_UW1pNuvMt7tSAtJnoyo2u6ZCqwdB3VCH5WtGF-24jrQ6N0y-aA7bEGBTGdupU3_vBbftjpNvOB28xBBXxmlxY1Y04_79XZPn8tKxek8XHy1v1uEg0BxYTq5usAAvagNVggCMwZiVIk3MtciOk5dI2aKxUwjbACwSdQymE1LlAfkVuj283wf9scYz12m_DsG-sU5aKNBe8kHvq7kjp4McxoK03wfUqTDWD-jBpfTop_wNyeWvo</recordid><startdate>20180919</startdate><enddate>20180919</enddate><creator>Fahy, Kira M.</creator><creator>Liu, Adam C.</creator><creator>Barnard, Kelsie R.</creator><creator>Bright, Valerie R.</creator><creator>Enright, Robert J.</creator><creator>Hoggard, Patrick E.</creator><general>MDPI AG</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><orcidid>https://orcid.org/0000-0003-3086-8751</orcidid><orcidid>https://orcid.org/0000-0001-6490-3004</orcidid></search><sort><creationdate>20180919</creationdate><title>Photooxidation of Cyclohexane by Visible and Near-UV Light Catalyzed by Tetraethylammonium Tetrachloroferrate</title><author>Fahy, Kira M. ; 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The photoproducts, cyclohexanol and cyclohexanone, initially develop at constant rates, implying that the ketone and the alcohol are both primary products. The yield is improved by the inclusion of 1% acetic acid in the cyclohexane. With small amounts of catalyst, the reaction rate increases with the amount of catalyst employed, but then passes through a maximum and decreases, due to increased reflection of the incident light. The reaction rate also passes through a maximum as the percentage of dioxygen above the sample is increased. This behavior is due to quenching by oxygen, which at the same time is a reactant. Under one set of reaction conditions, the photonic efficiency at 365 nm was 0.018 mol/Einstein. Compared to TiO2 as a catalyst, Et4N[FeCl4] generates lower yields at wavelengths below about 380 nm, but higher yields at longer wavelengths. 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| subjects | Acetic acid Acids Catalysis Catalysts Chemical reactions Chlorine Cyclohexane Cyclohexanone Experiments Green chemistry Hydrocarbons Incident light Light reflection Oxidation Photocatalysis Photonics Photooxidation Product development Titanium Titanium dioxide Wavelengths Zeolites |
| title | Photooxidation of Cyclohexane by Visible and Near-UV Light Catalyzed by Tetraethylammonium Tetrachloroferrate |
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