Photocatalytic degradation of paracetamol: Intermediates and total reaction mechanism
[Display omitted] ► The advanced oxidation of paracetamol with TiO2/UV was investigated. ► HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol. ► IR studies indicated that p-nitrophenol and p-aminophenol are also produced. ► PAM photocatalytic reaction mechani...
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| Veröffentlicht in: | Journal of hazardous materials 2012-12, Vol.243, p.130-138 |
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| creator | Moctezuma, Edgar Leyva, Elisa Aguilar, Claudia A. Luna, Raúl A. Montalvo, Carlos |
| description | [Display omitted]
► The advanced oxidation of paracetamol with TiO2/UV was investigated. ► HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol. ► IR studies indicated that p-nitrophenol and p-aminophenol are also produced. ► PAM photocatalytic reaction mechanism includes an alternative deacylation pathway.
The advanced oxidation of paracetamol (PAM) promoted by TiO2/UV system in aqueous medium was investigated. Monitoring this reaction by HPLC and TOC, it was demonstrated that while oxidation of paracetamol is quite efficient under these conditions, its mineralization is not complete. HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol in the reaction mixtures. Further evidence of p-nitrophenol formation was obtained following the reaction by UV–vis spectroscopy. Continuous monitoring by IR spectroscopy demonstrated the breaking of the aromatic amide present in PAM and subsequent formation of several aromatic intermediate compounds such as p-aminophenol and p-nitrophenol. These aromatic compounds were eventually converted into trans-unsaturated carboxylic acids. Based on these experimental results, an alternative deacylation mechanism for the photocatalytic oxidation of paracetamol is proposed. Our studies also demonstrated IR spectroscopy to be a useful technique to investigate oxidative mechanisms of pharmaceutical compounds. |
| doi_str_mv | 10.1016/j.jhazmat.2012.10.010 |
| format | Article |
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► The advanced oxidation of paracetamol with TiO2/UV was investigated. ► HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol. ► IR studies indicated that p-nitrophenol and p-aminophenol are also produced. ► PAM photocatalytic reaction mechanism includes an alternative deacylation pathway.
The advanced oxidation of paracetamol (PAM) promoted by TiO2/UV system in aqueous medium was investigated. Monitoring this reaction by HPLC and TOC, it was demonstrated that while oxidation of paracetamol is quite efficient under these conditions, its mineralization is not complete. HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol in the reaction mixtures. Further evidence of p-nitrophenol formation was obtained following the reaction by UV–vis spectroscopy. Continuous monitoring by IR spectroscopy demonstrated the breaking of the aromatic amide present in PAM and subsequent formation of several aromatic intermediate compounds such as p-aminophenol and p-nitrophenol. These aromatic compounds were eventually converted into trans-unsaturated carboxylic acids. Based on these experimental results, an alternative deacylation mechanism for the photocatalytic oxidation of paracetamol is proposed. Our studies also demonstrated IR spectroscopy to be a useful technique to investigate oxidative mechanisms of pharmaceutical compounds.</description><identifier>ISSN: 0304-3894</identifier><identifier>EISSN: 1873-3336</identifier><identifier>DOI: 10.1016/j.jhazmat.2012.10.010</identifier><identifier>PMID: 23123003</identifier><identifier>CODEN: JHMAD9</identifier><language>eng</language><publisher>Kidlington: Elsevier B.V</publisher><subject>Acetaminophen - chemistry ; Acetaminophen - radiation effects ; Applied sciences ; Carbon - analysis ; Carboxylic Acids - chemistry ; Catalysis ; Catalytic reactions ; Chemical engineering ; Chemistry ; Chromatography, High Pressure Liquid ; Exact sciences and technology ; General and physical chemistry ; Hydrogen-Ion Concentration ; Oxidation-Reduction ; Paracetamol ; Photocatalytic degradation ; Photochemistry ; Pollution ; Reaction mechanism ; Reactors ; Spectrophotometry, Infrared ; Spectrophotometry, Ultraviolet ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry ; Titanium - chemistry ; Ultraviolet Rays</subject><ispartof>Journal of hazardous materials, 2012-12, Vol.243, p.130-138</ispartof><rights>2012 Elsevier B.V.</rights><rights>2014 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c461t-e3a377d6ac0bf191d6e0344fbe4b9de6f8ed14986eab280fa5dae08d2118b2223</citedby><cites>FETCH-LOGICAL-c461t-e3a377d6ac0bf191d6e0344fbe4b9de6f8ed14986eab280fa5dae08d2118b2223</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0304389412010151$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26735750$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23123003$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Moctezuma, Edgar</creatorcontrib><creatorcontrib>Leyva, Elisa</creatorcontrib><creatorcontrib>Aguilar, Claudia A.</creatorcontrib><creatorcontrib>Luna, Raúl A.</creatorcontrib><creatorcontrib>Montalvo, Carlos</creatorcontrib><title>Photocatalytic degradation of paracetamol: Intermediates and total reaction mechanism</title><title>Journal of hazardous materials</title><addtitle>J Hazard Mater</addtitle><description>[Display omitted]
► The advanced oxidation of paracetamol with TiO2/UV was investigated. ► HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol. ► IR studies indicated that p-nitrophenol and p-aminophenol are also produced. ► PAM photocatalytic reaction mechanism includes an alternative deacylation pathway.
The advanced oxidation of paracetamol (PAM) promoted by TiO2/UV system in aqueous medium was investigated. Monitoring this reaction by HPLC and TOC, it was demonstrated that while oxidation of paracetamol is quite efficient under these conditions, its mineralization is not complete. HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol in the reaction mixtures. Further evidence of p-nitrophenol formation was obtained following the reaction by UV–vis spectroscopy. Continuous monitoring by IR spectroscopy demonstrated the breaking of the aromatic amide present in PAM and subsequent formation of several aromatic intermediate compounds such as p-aminophenol and p-nitrophenol. These aromatic compounds were eventually converted into trans-unsaturated carboxylic acids. Based on these experimental results, an alternative deacylation mechanism for the photocatalytic oxidation of paracetamol is proposed. Our studies also demonstrated IR spectroscopy to be a useful technique to investigate oxidative mechanisms of pharmaceutical compounds.</description><subject>Acetaminophen - chemistry</subject><subject>Acetaminophen - radiation effects</subject><subject>Applied sciences</subject><subject>Carbon - analysis</subject><subject>Carboxylic Acids - chemistry</subject><subject>Catalysis</subject><subject>Catalytic reactions</subject><subject>Chemical engineering</subject><subject>Chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Oxidation-Reduction</subject><subject>Paracetamol</subject><subject>Photocatalytic degradation</subject><subject>Photochemistry</subject><subject>Pollution</subject><subject>Reaction mechanism</subject><subject>Reactors</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><subject>Titanium - chemistry</subject><subject>Ultraviolet Rays</subject><issn>0304-3894</issn><issn>1873-3336</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1P3DAQhq2qFSyUn1CUSyUu2Y7txEm4oArRFgkJDuVsTexJ16skXmwvEv31eLvb9shppNHzzsfD2CcOSw5cfVkv1yv8PWFaCuAi95bA4R1b8LaRpZRSvWcLkFCVsu2qY3YS4xoAeFNXR-xYSC4kgFywx4eVT95gwvElOVNY-hXQYnJ-LvxQbDCgoYSTHy-L2zlRmMg6TBQLnG2RfM4VgdD8CUxkVji7OH1kHwYcI50d6il7_Hbz8_pHeXf__fb6611pKsVTSRJl01iFBvqBd9wqAllVQ09V31lSQ0uWV12rCHvRwoC1RYLWCs7bXgghT9nFfu4m-KctxaQnFw2NI87kt1FzkVFZq67JaL1HTfAxBhr0JrgJw4vmoHdG9VofjOqd0V07G82588OKbZ9__5f6qzADnw8ARoPjEHA2Lv7nVCPrpt4NutpzlIU8Owo6GkezyT4DmaStd2-c8gpv75g9</recordid><startdate>20121201</startdate><enddate>20121201</enddate><creator>Moctezuma, Edgar</creator><creator>Leyva, Elisa</creator><creator>Aguilar, Claudia A.</creator><creator>Luna, Raúl A.</creator><creator>Montalvo, Carlos</creator><general>Elsevier B.V</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20121201</creationdate><title>Photocatalytic degradation of paracetamol: Intermediates and total reaction mechanism</title><author>Moctezuma, Edgar ; Leyva, Elisa ; Aguilar, Claudia A. ; Luna, Raúl A. ; Montalvo, Carlos</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c461t-e3a377d6ac0bf191d6e0344fbe4b9de6f8ed14986eab280fa5dae08d2118b2223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acetaminophen - chemistry</topic><topic>Acetaminophen - radiation effects</topic><topic>Applied sciences</topic><topic>Carbon - analysis</topic><topic>Carboxylic Acids - chemistry</topic><topic>Catalysis</topic><topic>Catalytic reactions</topic><topic>Chemical engineering</topic><topic>Chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Oxidation-Reduction</topic><topic>Paracetamol</topic><topic>Photocatalytic degradation</topic><topic>Photochemistry</topic><topic>Pollution</topic><topic>Reaction mechanism</topic><topic>Reactors</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><topic>Titanium - chemistry</topic><topic>Ultraviolet Rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moctezuma, Edgar</creatorcontrib><creatorcontrib>Leyva, Elisa</creatorcontrib><creatorcontrib>Aguilar, Claudia A.</creatorcontrib><creatorcontrib>Luna, Raúl A.</creatorcontrib><creatorcontrib>Montalvo, Carlos</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of hazardous materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moctezuma, Edgar</au><au>Leyva, Elisa</au><au>Aguilar, Claudia A.</au><au>Luna, Raúl A.</au><au>Montalvo, Carlos</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic degradation of paracetamol: Intermediates and total reaction mechanism</atitle><jtitle>Journal of hazardous materials</jtitle><addtitle>J Hazard Mater</addtitle><date>2012-12-01</date><risdate>2012</risdate><volume>243</volume><spage>130</spage><epage>138</epage><pages>130-138</pages><issn>0304-3894</issn><eissn>1873-3336</eissn><coden>JHMAD9</coden><abstract>[Display omitted]
► The advanced oxidation of paracetamol with TiO2/UV was investigated. ► HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol. ► IR studies indicated that p-nitrophenol and p-aminophenol are also produced. ► PAM photocatalytic reaction mechanism includes an alternative deacylation pathway.
The advanced oxidation of paracetamol (PAM) promoted by TiO2/UV system in aqueous medium was investigated. Monitoring this reaction by HPLC and TOC, it was demonstrated that while oxidation of paracetamol is quite efficient under these conditions, its mineralization is not complete. HPLC indicated the formation of hydroquinone, benzoquinone, p-aminophenol and p-nitrophenol in the reaction mixtures. Further evidence of p-nitrophenol formation was obtained following the reaction by UV–vis spectroscopy. Continuous monitoring by IR spectroscopy demonstrated the breaking of the aromatic amide present in PAM and subsequent formation of several aromatic intermediate compounds such as p-aminophenol and p-nitrophenol. These aromatic compounds were eventually converted into trans-unsaturated carboxylic acids. Based on these experimental results, an alternative deacylation mechanism for the photocatalytic oxidation of paracetamol is proposed. Our studies also demonstrated IR spectroscopy to be a useful technique to investigate oxidative mechanisms of pharmaceutical compounds.</abstract><cop>Kidlington</cop><pub>Elsevier B.V</pub><pmid>23123003</pmid><doi>10.1016/j.jhazmat.2012.10.010</doi><tpages>9</tpages></addata></record> |
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| subjects | Acetaminophen - chemistry Acetaminophen - radiation effects Applied sciences Carbon - analysis Carboxylic Acids - chemistry Catalysis Catalytic reactions Chemical engineering Chemistry Chromatography, High Pressure Liquid Exact sciences and technology General and physical chemistry Hydrogen-Ion Concentration Oxidation-Reduction Paracetamol Photocatalytic degradation Photochemistry Pollution Reaction mechanism Reactors Spectrophotometry, Infrared Spectrophotometry, Ultraviolet Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Titanium - chemistry Ultraviolet Rays |
| title | Photocatalytic degradation of paracetamol: Intermediates and total reaction mechanism |
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